IUPAC-NIST Solubility Data Series. 90. Hydroxybenzoic Acid Derivatives in Binary and Ternary Systems

IUPAC-NIST Solubility Data Series. 90. Hydroxybenzoic Acid Derivatives in Binary and Ternary Systems. Part II. Hydroxybenzoic Acids, Hydroxybenzoates, and Hydroxybenzoic Acid Salts in Nonaqueous Systems

Ayako Gotoa… University of Shizuoka, Shizuoka 422-8526, Japan

Hiroshi Miyamoto Niigata University, Niigata 950-2181, Japan

Mark Salomon MaxPower Inc., 141 Christopher Lane, Harleysville, Pennsylvania 19438

Rensuke Goto University of Shizuoka, Shizuoka 422-8526, Japan

Hiroshi Fukuda Kitasato University, Kanagawa 252-0373, Japan

Erich Königsberger Murdoch University, Murdoch, Western Australia 6150, Australia

Lan-Chi Königsberger Murdoch University, Murdoch, Western Australia 6150, Australia

Pirketta Scharlin University of Turku, FIN-20014 Turku, Finland

͑Received 4 February 2011; accepted 11 February 2011; published online 18 May 2011͒

The solid-liquid solubility data for well deﬁned nonaqueous binary and ternary systems are reviewed. One component includes hydroxybenzoic acid, hydroxybenzoate, and hydroxybenzoic acid salt, and another component includes a variety of organic compounds ͑hydrocarbons, alcohols, halogenated hydrocarbons, carboxylic acids, esters, et al.͒ and carbon dioxide. The ternary systems include mixtures of organic substances of various classes and carbon dioxide. The total number of compilation sheets is 270 for six types of system. Almost all data are expressed as mass percent and mole fraction as well as the originally reported units, while some data are expressed as molar concentration. Critical evaluation was carried out for the binary nonaqueous systems of 2-, 3-, and 4-hydroxybenzoic acids and hydroxybenzoates ͑methylparaben, ethylparaben, propylparaben, and butylparaben͒ in alcohols, 1-heptane, and benzene. © 2011 American Institute of Physics. ͓doi:10.1063/1.3569816͔

Key words: hydroxybenzoic acid; hydroxybenzoic acid salt; nonaqueous systems; paraben; salicylic acid; solubility.

CONTENTS 1.1. Scope of the volume...... 4 1.2. Experimental methods...... 5 1.3. Procedure used in critical evaluation...... 5 1. Preface...... 4 2. Hydroxybenzoic Acids, Parabens, and

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2.1. Hydroxybenzoic acid–organic compound 3.2. Hydroxybenzoic acid–organic compound– systems...... 6 inorganic compound systems...... 112 2.1.1. Critical evaluation of the solubility 3.2.1. Salicylic acid...... 112 of hydroxybenzoic acids in alkanes.. 6 3.2.2. 3-Hydroxybenzoic acid...... 114 2.1.1.1. Salicylic acid...... 6 3.2.3. 4-Hydroxybenzoic acid...... 115 2.1.2. Critical evaluation of the solubility 4. References...... 115 of hydroxybenzoic acids in alcohols...... 8 List of Tables 2.1.2.1. Salicylic acid...... 8 2.1.2.2. 3-Hydroxybenzoic acid. . . . 11 1. List of compiled sheets for solutes in 2.1.2.3. 4-Hydroxybenzoic acid. . . . 13 nonaqueous binary and ternary systems...... 5 2.1.3. Critical evaluation of the solubility 2. Analytical methods of solutes in nonaqueous of hydroxybenzoic acids in systems...... 5 aromatic compounds...... 16 3. List of evaluation sheets for solutes in binary 2.1.3.1. Salicylic acid...... 16 systems of various solvents...... 6 2.1.3.2. 3-Hydroxybenzoic acid. . . . 19 4. Summary of experimental solubility data of 2.1.3.3. 4-Hydroxybenzoic acid. . . . 21 salicylic acid in heptane...... 6 2.1.4. Data for hydroxybenzoic acid– 5. Observed data and recommended values organic compound systems...... 24 calculated according to Eq. ͑1͒ for salicylic 2.1.4.1. Salicylic acid...... 24 acid in heptane...... 7 2.1.4.2. 3-Hydroxybenzoic acid. . . . 40 6. Summary of experimental solubility data of 2.1.4.3. 4-Hydroxybenzoic acid. . . . 43 salicylic acid in ethanol...... 8 2.1.5. Data for hydroxybenzoic acid– 7. Observed data and recommended values inorganic compound systems...... 51 calculated according to Eq. ͑1͒ for salicylic 2.1.5.1. Salicylic acid...... 51 acid in ethanol...... 8 2.1.5.2. 3-Hydroxybenzoic acid. . . . 52 8. Summary of experimental solubility data of 2.1.5.3. 4-Hydroxybenzoic acid. . . . 53 salicylic acid in 1-butanol...... 10 2.2. Paraben–organic compound systems...... 53 9. Observed data and recommended values 2.2.1. Critical evaluation of the solubility calculated according to Eq. ͑1͒ for salicylic of parabens in alcohols...... 53 acid in 1-butanol...... 10 2.2.1.1. Methylparaben...... 53 10. Summary of experimental solubility data of 2.2.1.2. Ethylparaben...... 62 3-hydroxybenzoic acid in ethanol...... 12 2.2.1.3. Propylparaben...... 72 11. Observed data and recommended values 2.2.1.4. Butylparaben...... 83 calculated according to Eq. ͑1͒ for 2.2.2. Data for paraben–organic 3-hydroxybenzoic acid in ethanol...... 12 compound systems...... 93 12. Summary of experimental solubility data of 2.2.2.1. Methylparaben...... 93 4-hydroxybenzoic acid in ethanol...... 13 2.2.2.2. Ethyl-, propyl-, and 13. Observed data and recommended values butylparaben...... 99 calculated according to Eq. ͑1͒ for 2.2.2.3. Hexyl-, heptyl-, octyl-, and 4-hydroxybenzoic acid in ethanol...... 13 decylparaben...... 101 14. Summary of experimental solubility data of 2.2.2.4. Methylpropyl-, pentyl-, 4-hydroxybenzoic acid in 1-butanol...... 14 and benzylparaben...... 104 15. Observed data and recommended values 2.3. Hydroxybenzoic acid salt–organic calculated according to Eq. ͑1͒ for compound systems...... 104 4-hydroxybenzoic acid in 1-butanol...... 15 2.3.1. 2-Hydroxybenzoic acid salt ͑Na͒.... 104 16. Summary of experimental solubility data of 2.3.2. 2-Hydroxybenzoic acid salt ͑Ag͒.... 105 salicylic acid in benzene...... 16 ͑ ͒ 2.3.3. 2-Hydroxybenzoic acid salt NH4 .. 106 17. Observed data and recommended values 2.3.4. 4-Hydroxybenzoic acid salt ͑Ag͒.... 106 calculated according to Eq. ͑1͒ for salicylic 3. Hydroxybenzoic Acids and Parabens in acid in benzene...... 17 Ternary Nonaqueous Systems...... 107 18. Summary of experimental solubility data of 3.1. Hydroxybenzoic acid and paraben– 3-hydroxybenzoic acid in benzene...... 19 organic compound ͑1͒–organic compound 19. Observed data and recommended values ͑2͒ systems...... 107 calculated according to Eq. ͑1͒ for 3.1.1. Salicylic acid...... 107 3-hydroxybenzoic acid in benzene...... 20 3.1.2. Methylparaben...... 111 20. Summary of experimental solubility data of 3.1.3. Propylparaben...... 111 4-hydroxybenzoic acid in benzene...... 21

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21. Observed data and recommended values ethylparaben in 1-hexanol...... 68 calculated according to Eq. ͑1͒ for 44. Summary of experimental solubility data of 4-hydroxybenzoic acid in benzene...... 22 ethylparaben in 1-octanol...... 69 22. Summary of experimental solubility data of 45. Observed data and recommended values methylparaben in methanol...... 53 calculated according to Eq. ͑2͒ for 23. Observed data and recommended values ethylparaben in 1-octanol...... 70 calculated according to Eq. ͑2͒ for 46. Summary of experimental solubility data of methylparaben in methanol...... 54 ethylparaben in 1-decanol...... 71 24. Summary of experimental solubility data of 47. Observed data and recommended values methylparaben in ethanol...... 55 calculated according to Eq. ͑2͒ for 25. Observed data and recommended values ethylparaben in 1-decanol...... 72 calculated according to Eq. ͑2͒ for 48. Summary of experimental solubility data of methylparaben in ethanol...... 55 propylparaben in methanol...... 72 26. Summary of experimental solubility data of 49. Observed data and recommended values methylparaben in 1-propanol...... 56 calculated according to Eq. ͑2͒ for 27. Observed data and recommended values propylparaben in methanol...... 73 calculated according to Eq. ͑2͒ for 50. Summary of experimental solubility data of methylparaben in 1-propanol...... 57 propylparaben in ethanol...... 74 28. Summary of experimental solubility data of 51. Observed data and recommended values methylparaben in 1-butanol...... 58 calculated according to Eq. ͑2͒ for 29. Observed data and recommended values propylparaben in ethanol...... 74 calculated according to Eq. ͑2͒ for 52. Summary of experimental solubility data of methylparaben in 1-butanol...... 58 propylparaben in 1-propanol...... 75 30. Summary of experimental solubility data of 53. Observed data and recommended values methylparaben in 1-hexanol...... 59 calculated according to Eq. ͑2͒ for 31. Observed data and recommended values propylparaben in 1-propanol...... 75 calculated according to Eq. ͑2͒ for 54. Summary of experimental solubility data of methylparaben in 1-hexanol...... 60 propylparaben in 1-butanol...... 76 32. Summary of experimental solubility data of 55. Observed data and recommended values methylparaben in 1-decanol...... 61 calculated according to Eq. ͑2͒ for 33. Observed data and recommended values propylparaben in 1-butanol...... 77 calculated according to Eq. ͑2͒ for 56. Summary of experimental solubility data of methylparaben in 1-decanol...... 61 propylparaben in 1-hexanol...... 78 34. Summary of experimental solubility data of 57. Observed data and recommended values ethylparaben in methanol...... 62 calculated according to Eq. ͑2͒ for 35. Observed data and recommended values propylparaben in 1-hexanol...... 79 calculated according to Eq. ͑2͒ for 58. Summary of experimental solubility data of ethylparaben in methanol...... 63 propylparaben in 1-octanol...... 80 36. Summary of experimental solubility data of 59. Observed data and recommended values ethylparaben in ethanol...... 63 calculated according to Eq. ͑2͒ for 37. Observed data and recommended values propylparaben in 1-octanol...... 80 calculated according to Eq. ͑2͒ for 60. Summary of experimental solubility data of ethylparaben in ethanol...... 64 propylparaben in 1-decanol...... 82 38. Summary of experimental solubility data of 61. Observed data and recommended values ethylparaben in 1-propanol...... 65 calculated according to Eq. ͑2͒ for 39. Observed data and recommended values propylparaben in 1-decanol...... 82 calculated according to Eq. ͑2͒ for 62. Summary of experimental solubility data of ethylparaben in 1-propanol...... 65 butylparaben in methanol...... 83 40. Summary of experimental solubility data of 63. Observed data and recommended values ethylparaben in 1-butanol...... 66 calculated according to Eq. ͑2͒ for 41. Observed data and recommended values butylparaben in methanol...... 83 calculated according to Eq. ͑2͒ for 64. Summary of experimental solubility data of ethylparaben in 1-butanol...... 67 butylparaben in ethanol...... 84 42. Summary of experimental solubility data of 65. Observed data and recommended values ethylparaben in 1-hexanol...... 68 calculated according to Eq. ͑2͒ for 43. Observed data and recommended values butylparaben in ethanol...... 85 calculated according to Eq. ͑2͒ for 66. Summary of experimental solubility data of

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butylparaben in 1-propanol...... 85 16. Fitting curve of Eq. ͑2͒ and the observed data 67. Observed data and recommended values for ethylparaben in methanol...... 62 calculated according to Eq. ͑2͒ for 17. Fitting curve of Eq. ͑2͒ and the observed data butylparaben in 1-propanol...... 86 for ethylparaben in ethanol...... 64 68. Summary of experimental solubility data of 18. Fitting curve of Eq. ͑2͒ and the observed data butylparaben in 1-butanol...... 87 for ethylparaben in 1-propanol...... 65 69. Observed data and recommended values 19. Fitting curve of Eq. ͑2͒ and the observed data calculated according to Eq. ͑2͒ for for ethylparaben in 1-butanol...... 66 butylparaben in 1-butanol...... 87 20. Fitting curve of Eq. ͑2͒ and the observed data 70. Summary of experimental solubility data of for ethylparaben in 1-hexanol...... 68 butylparaben in 1-hexanol...... 88 21. Fitting curve of Eq. ͑2͒ and the observed data 71. Observed data and recommended values for ethylparaben in 1-octanol...... 69 calculated according to Eq. ͑2͒ for 22. Fitting curve of Eq. ͑2͒ and the observed data butylparaben in 1-hexanol...... 89 for ethylparaben in 1-decanol...... 71 72. Summary of experimental solubility data of 23. Fitting curve of Eq. ͑2͒ and the observed data butylparaben in 1-octanol...... 90 for propylparaben in methanol...... 73 73. Observed data and recommended values 24. Fitting curve of Eq. ͑2͒ and the observed data calculated according to Eq. ͑2͒ for for propylparaben in ethanol...... 74 butylparaben in 1-octanol...... 91 25. Fitting curve of Eq. ͑2͒ and the observed data 74. Summary of experimental solubility data of for propylparaben in 1-propanol...... 75 butylparaben in 1-decanol...... 92 26. Fitting curve of Eq. ͑2͒ and the observed data 75. Observed data and recommended values for propylparaben in 1-butanol...... 77 calculated according to Eq. ͑2͒ for 27. Fitting curve of Eq. ͑2͒ and the observed data butylparaben in 1-decanol...... 93 for propylparaben in 1-hexanol...... 78 28. Fitting curve of Eq. ͑2͒ and the observed data List of Figures for propylparaben in 1-octanol...... 80 29. Fitting curve of Eq. ͑2͒ and the observed data 1. Fitting curve of Eq. ͑1͒ and the observed data for propylparaben in 1-decanol...... 82 ͑ ͒ for salicylic acid in heptane...... 7 30. Fitting curve of Eq. 2 and the observed data 2. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in methanol...... 83 ͑ ͒ for salicylic acid in ethanol...... 8 31. Fitting curve of Eq. 2 and the observed data 3. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in ethanol...... 84 ͑ ͒ for salicylic acid in 1-butanol...... 10 32. Fitting curve of Eq. 2 and the observed data 4. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in 1-propanol...... 86 ͑ ͒ for 3-hydroxybenzoic acid in ethanol...... 12 33. Fitting curve of Eq. 2 and the observed data 5. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in 1-butanol...... 87 ͑ ͒ for 4-hydroxybenzoic acid in ethanol...... 13 34. Fitting curve of Eq. 2 and the observed data 6. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in 1-hexanol...... 89 ͑ ͒ for 4-hydroxybenzoic acid in 1-butanol...... 15 35. Fitting curve of Eq. 2 and the observed data 7. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in 1-octanol...... 90 ͑ ͒ for salicylic acid in benzene...... 16 36. Fitting curve of Eq. 2 and the observed data 8. Fitting curve of Eq. ͑1͒ and the observed data for butylparaben in 1-decanol...... 92 for 3-hydroxybenzoic acid in benzene...... 19 9. Fitting curve of Eq. ͑1͒ and the observed data for 4-hydroxybenzoic acid in benzene...... 22 1. Preface 10. Fitting curve of Eq. ͑2͒ and the observed data 1.1. Scope of the volume for methylparaben in methanol...... 53 11. Fitting curve of Eq. ͑2͒ and the observed data We have reported the solubilities of hydroxybenzoic acid for methylparaben in ethanol...... 55 derivatives in aqueous systems as Part 1 of this volume.1 12. Fitting curve of Eq. ͑2͒ and the observed data This Part 2 reviews experimentally determined solubility for methylparaben in 1-propanol...... 57 data of the hydroxybenzoic acid derivatives for well deﬁned 13. Fitting curve of Eq. ͑2͒ and the observed data nonaqueous binary and ternary systems of organic com- for methylparaben in 1-butanol...... 58 pounds. The solutes are as follows: Hydroxybenzoic acid 14. Fitting curve of Eq. ͑2͒ and the observed data corresponds to 2-, 3-, and 4-hydroxbenzoic acids. for methylparaben in 1-hexanol...... 60 4-Hydroxybenzoic acid alkyl ester ͑paraben͒ corresponds to 15. Fitting curve of Eq. ͑2͒ and the observed data methyl-, ethyl-, propyl-, butyl-, hexyl-, heptyl-, octyl-, for methylparaben in 1-decanol...... 61 decyl-, methylpropyl-, pentyl-, and benzyl esters. Monohy-

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droxybenzoic acid salts correspond to sodium, silver, and 284.2 to 486.2 K at atmospheric pressure. Samples of liquid ammonium salts. All of the solutes are in the solid state at phases at equilibrium are analyzed by various methods. Table room temperature. 2 shows the list of various methods for the measurement of As another component, a variety of organic solvents ͑al- the solubilities. The solubility measurements of hydroxyben- cohols, halogenated hydrocarbons, carboxylic acids, amides, esters, etc.͒ were examined, along with supercritical carbon zoic acids for binary and ternary systems are mainly carried dioxide. This volume includes solid-liquid equilibrium of out by UV spectroscopy, titration, gravimetry, and synthetic nonaqueous binary and ternary systems, and the goal of the method. The basic approach to solubility measurement of search of Part 2 is to include all published data for nonaque- hydroxybenzoates for binary and ternary systems is UV ous systems designated in the title. The list of solutes in- spectroscopy, but gravimetry is used in limited systems. cluded is shown in Table 1. Hydroxybenzoic acids and the related compounds are im- TABLE 2. Analytical methods of solutes in nonaqueous systems portant substances closely related to daily life, as described 1 in the previous paper. Recently, hydroxybenzoates ͑para- Binary system Ternary system bens͒ have been widely used as preservatives in the cos- Total Method HAa HAEb HASc HA HAE HAS numberd metic, pharmaceutical, and food industries. Their solubilities in nonaqueous solutions as well as in aqueous solutions are Spectroscopy 46 118͑40͒ 0020 166 important from the viewpoint of their solution states in mi- Titration 22 0 0 5 0 0 27 cellar solutions and the partition coefﬁcients between water Gravimetry 29 56͑40͒ 1900 95 and oil phases, as described by Goto.2–8 Synthetic method 11 0 0 0 0 0 11 e The solubility data for six classes of systems were found Other methods 31 30007 by an exhaustive search of the chemical literature published aHA: Hydroxybenzoic acid. prior to 2001, as shown in Table 1. From these, 270 compi- bHAE: Hydroxybenzoic acid ester. lation sheets were prepared. Most compilations present the cHAS: Hydroxybenzoic acid salt. solubility data for one system as reported in one publication. dThe total number of sheets does not correspond with the sum of the differ- They are the result of an exhaustive search of the chemical ent methods because some sheets contain plural analytical methods and literature using Chemical Abstracts. some sheets for references whose methods are not described clearly are not counted. TABLE 1. List of compiled sheets for solutes in nonaqueous binary and eOther methods include thermometry, and measurement of radioisotopes, ternary systems potential difference, and vapor pressure.

Binary system Ternary system System pressure at the solution temperature is seldom reported because it is assumed that the effect of pressure is Hydroxybenzoic acid ͑HA͒ 136 14 Hydroxybenzoic acid ester ͑HAE͒ 112 2 minor. With the solvent, a correction was made at higher Hydroxybenzoic acid salt ͑HAS͒ 60temperatures for the amount present as vapor in the bulb, and carbon dioxide was also affected by the pressure. Sources of In some original sources, solubility data were reported as error in these methods include gravitational effects and im- incidental or ancillary information to other studies. If, for purities in materials whose solubilities are determined. this or other reasons, details concerning experimental methods, source and purity of materials, or estimated errors were brief or absent, correspondingly short entries appear in the compilations, sometime with the note “No further details were reported” or “Not stated” or “Nothing specified.” 1.3. Procedure used in critical evaluation For convenience of comparison of experimental data, the compilers and evaluators of this volume, as far as possible, Data are recommended if the results of independent expressed all initial results in mass percent and mole fraction groups are in good agreement and the evaluators have no as well as in units reported in the original source. Conver- doubt of the adequacy of the experimental and computational sions, where they were made, are clearly attributed to the compiler. Some units require numerical data for the density procedures used. Data determined by an inadequate or ill- of pure components and/or the mixtures. Definitions of mass defined method are rejected. percent and mole fraction as well as their relation to other Where two or more reliable compilations were found for a units of solubility are given in the Introduction to the Solu- system, a critical evaluation was carried out. This was pos- 9 bility Data Series. sible for 36 systems of hydroxybenzoic acids and parabens ͑methyl-, ethyl-, propyl-, and butylparabens͒ in binary sys- 1.2. Experimental methods tems of alcohols, alkane and benzene, as shown in Table 3. Most solubility measurements of binary and ternary systems containing each solute have been made from

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TABLE 3. List of evaluation sheets for solutes in binary systems of various 2. Hydroxybenzoic Acids, Parabens, and solvents. ᭺: evaluated, —: not evaluated Hydroxybenzoic Acid Salts in Binary Solute Nonaqueous Systems Hydroxybenzoic Acid ͑HA͒ Hydroxybenzoic Acid Estera 2.1. Hydroxybenzoic acid–organic compound Organic solvent 2HA 3HA 4HA MP EP PP BP systems 2.1.1. Critical evaluation of the solubility of Methanol — — — ᭺᭺᭺᭺ Ethanol ᭺᭺᭺᭺᭺᭺᭺ hydroxybenzoic acids in alkanes 1-Propanol — — — ᭺᭺᭺᭺ 2.1.1.1. Salicylic acid 1-Butanol ᭺ — ᭺᭺᭺᭺᭺ 1-Hexanol — — — ᭺᭺᭺᭺ Components: Evaluators: 1-Octanol — — — — ᭺᭺᭺ 1-Decanol — — — ᭺᭺᭺᭺ ͑1͒ Benzoic acid, 2-hydroxy- Ayako Goto, University of 1-Heptane ᭺ ——————͑o-hydroxybenzoic acid, salicylic Shizuoka, Shizuoka, Japan ͒ ͓ ͔ Benzene ᭺᭺᭺———— acid ;C7H6O3; 69-72-7 Rensuke Goto, University of ͑ ͒ ͑ ͒ 2 n-Heptane heptane ;C7H16; Shizuoka, Shizuoka, Japan aMP: methylparaben; EP: ethylparaben; PP: propylparaben; BP: butylpara- ͓142-82-5͔ Hiroshi Fukuda, Kitasato ben. University, Tokyo, Japan The data for the solubility of the hydroxybenzoic acids and the parabens in organic solvents were treated as a func- Critical Evaluation TABLE 4. Summary of experimental solubility data of salicylic acid in tion of absolute temperature. Data for the solubility of the heptane hydroxybenzoic acids and the parabens were fitted to Eq. ͑1͒ 10–12 / / −1 or ͑2͒, T K 100m1 mol kg 100w1 100x1 Analytical method Reference 298.2 0.33 0.048 Spectroscopy 13 365.4 2.09 1.52a Synthetic method 14 385.6 5.37 3.95a Synthetic method 14 ln x = A/T + B ln T + C, ͑1͒ 1 397.9 10.25 7.651a Synthetic method 14 407.5 20.15 1.55a Synthetic method 14 415.2 41.6 3.41a Synthetic method 14 418.7 60.2 5.23a Synthetic method 14 / ͑ ͒ a ln x1 = A T + C. 2 422.7 81.4 7.60 Synthetic method 14 a The equation parameters statistically calculated by the The mole-fraction solubilities were calculated based on w1. Solubilities of salicylic acid in heptane were reported in least squares method are presented in the critical evaluations. two publications. The measurement was carried out from The solubilities calculated by the proposed equations are pre- 298.2 to 422.7 K. The solubilities of salicylic acid in hep- sented in the tables; these values are recommended. tane are shown in Table 4, in which molality, mass percent, A complete guide to the preparation and use of compila- and mole fraction are expressed as units. The measurement tions and evaluations for the IUPAC-NIST Solubility Data was carried out by the synthetic method and spectroscopy, as Series can be found in the articles9 jointly published by shown in Table 4. IUPAC and NIST. These procedures were applied to all the Data for the solubility of salicylic acid in heptane expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given data sources2–8,13–45 compiled here. in Sec. 1.3. The data points closely agree with Eq. ͑1͒ over Of particular interest for the present volume are the un- the whole range of temperatures, as shown in Fig. 1, but they ␥ ␸ common use of the symbols for mass concentration and deviated from Eq. ͑2͒. The equation parameters were derived for volume fraction. These symbols, defined in Ref. 9, are by multiple regression analysis using SPSS based on Eq. ͑1͒, often found in the pharmaceutical literature, particularly in with the following results: the older literature. Multiple correlation coefficient: 0.996 Sample size: 8 data points p-value ͑F test͒: 0.000 Constants: A=24560Ϯ5865, B=89.93Ϯ16.62, C= −602.3Ϯ114.3 White circles in Fig. 1 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 1 . ln x1 =24560 T+89.93 ln T−602.3 The observed data fit closely with the calculated values in the range of 298.2–422.7 K, with the multiple correlation coefficient of

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Auxiliary Information

Methods/Apparatus/Procedure: The solubility was determined synthetically. Weighed quantities of the acid and the solvent were enclosed in bulbs, which were then sealed and heated in a suitable bath. With the solvent, a correction was made at higher temperatures for the amount present as vapor in the bulb; for this purpose the vapor pressure of the saturated solution was assumed to be half that of the pure solvent at the same temperature. The thermometers had been compared with a standard instrument, and all readings were corrected. Source and Purity of Materials: The preparation and the purification of salicylic acid were described in ͓J. Walker and J.K Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of FIG. 1. Fitting curve of Eq. ͑1͒ and the observed data for salicylic acid in the purified acid was 159.0 °C. heptane. n-Heptane was a specimen from Pinus sabiniana, which had been purified by treatment with sulfuric and nitric acids, and distillation ͓T.E. Thorpe, J. Chem. Soc. 35,296͑1879͔͒. 0.996, as shown in Fig. 1. Therefore, the calculated value at Estimated Errors: each measured temperature is reasonably considered as a rec- Nothing specified. ommended value over the whole range of temperature. Table 5 shows the observed data in the range of 298.2–422.7 K and the recommended values calculated Components: Original Measurements: from Eq. ͑1͒ at each temperature. ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. acid͒;CH O ; ͓69-72-7͔ TABLE 5. Observed data and recommended values calculated according to 7 6 3 ͑2͒ n-Heptane ͑heptane͒;CH ; Eq. ͑1͒ for salicylic acid in heptane 7 16 ͓142-82-5͔ / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec Variables: Prepared by: t/ °C=25 A. Goto and H. Miyamoto 298.2 0.048 0.0497 365.4 1.52 1.14 385.6 3.95 4.25 Solubility of salicylic acid in n-heptane at 25 °C 397.9 7.651 9.99 407.5 15.5 19.9 Solubility 415.2 34.1 35.1 104x 103m /mol kg−1 418.7 52.3 45.5 1 1 422.7 76 61.5 4.8 3.3

Components: Original Measurements: Auxiliary Information ͑ ͒ 14 1 Benzoic acid, 2-hydroxy- N.V. Sidgwick and E.K. Methods/Apparatus/Procedure: ͑o-hydroxybenzoic acid, salicylic Ewbank, J. Chem. Soc. 1921, An amount of solid at least five times in excess of its solubility was acid͒;CH O ; ͓69-72-7͔ 979. 7 6 3 allowed to equilibrate with the solvent in a stoppered and sealed ͑2͒ n-Heptane ͑heptane͒;CH ; 7 16 volumetric flask, which was continuously shaken on a wrist-action shaker ͓142-82-5͔ in a thermostated bath for at least 24 h. An aliquot of the saturated Variables: Prepared by: solution was pipetted out and distilled accurately from 10 to 100 times in chloroform. The concentration of salicylic acid was determined by the UV t/ °C=92.2–149.5 A. Goto and H. Miyamoto spectrometric method. Source and Purity of Materials: Solubility of salicylic acid in n-heptane n-Heptane of reagent grade was purified by passing the solvent through a column of silica gel followed by distillation from sodium under reduced Temperature Solubility pressure. Salicylic acid was recrystallized from hot water. t/ °C w 100x ͑compiler͒ 1 1 Estimated Errors: 92.2 2.09 1.52 Nothing specified. 112.4 5.37 3.95 124.7 10.25 7.651 134.3 20.15 15.5 142.0 41.6 34.1 145.5 60.2 52.3 149.5 81.4 76.0

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White circles in Fig. 2 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 1 ln x1 =2292 T+11.58 ln T−75.60 . The observed data ﬁt closely with the calculated values in the range of 298.2–432.2 K, with the multiple correlation coefﬁcient of 1.000, as shown in Fig. 2. Therefore, the calculated value at each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Table 7 shows the observed data in the range of FIG. 2. Fitting curve of Eq. ͑1͒ and the observed data for salicylic acid in 298.2–432.2 K and the recommended values calculated ethanol. from Eq. ͑1͒ at each temperature.

2.1.2. Critical evaluation of the solubility of TABLE 7. Observed data and recommended values calculated according to hydroxybenzoic acids in alcohols Eq. ͑1͒ for salicylic acid in ethanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec 2.1.2.1. Salicylic acid 301.2 14.79 15.1 314.2 18.6 18.0 Components: Evaluators: 358.4 33.7 33.6 ͑1͒ Benzoic acid, 2-hydroxy- Ayako Goto, University of 398.4 59.0 60.2 ͑ o-hydroxybenzoic acid, salicylic Shizuoka, Shizuoka, Japan 432.2 100 98.5 ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Rensuke Goto, University of ͑2͒ Ethyl alcohol ͑ethanol͒; Shizuoka, Shizuoka, Japan ͓ ͔ C2H6O; 64-17-5 Hiroshi Fukuda, Kitasato University, Tokyo, Japan Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 14S.V. Sidgwick and E.K. ͑o-hydroxybenzoic acid, salicylic Embank, J. Chem. Soc. 1921, ͒ ͓ ͔ Critical Evaluation acid ;C7H6O3; 69-72-7 979. TABLE 6. Summary of experimental solubility data of salicylic acid in ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ ethanol C2H6O; 64-17-5

/ / −3 Variables: Prepared by: T K c1 mol dm 100w1 100x1 Analytical method Reference t/ °C=41.0–159.0 A. Goto and H. Miyamoto 293.2 2.041 Gravimetry 15 ͑ ͑ ͒ ͒ 301.2 14.79 Titration Ba OH 2 16 Solubility of salicylic acid in ethanol 303.8 2.76 Titration͑NaOH͒ 17 314.2 18.6 18.6a Synthetic method 14 Temperature Solubility 358.4 60.4 33.7a Synthetic method 14 398.4 81.2 59.0a Synthetic method 14 100x1 a / ͑ ͒ 432.2 100.0 100.0 Synthetic method 14 t °C 100w1 compiler a The mole-fraction solubilities were calculated based on w1. 159.0 100.0 100.0 The critical evaluation was carried out as described in 125.2 81.2 59.0 Sec. 2.1.1.1 for salicylic acid in n-heptane. 85.2 60.4 33.7 The number of publications: 4 41.0 40.6 18.6 The range of temperature: T/K=293.2–432.2 −3 The units: mass percent, mole fraction, and mol dm Auxiliary Information Analytical methods: gravimetry, synthetic method, and titration Methods/Apparatus/Procedure: Data for the solubility of salicylic acid in ethanol ex- The experimental details are given in the compilation of Ref. 14 for the pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given salicylic acid–n-heptane system in Sec. 2.1.1.1. ͑ ͒ Source and Purity of Materials: in Sec. 1.3 Table 6 . The data points closely agree with Eq. ͓ ͑ ͒ The preparation and purification methods were described in J. Walker and 1 over the whole range of temperatures, as shown in Fig. 2, J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of salicylic acid but they deviated from Eq. ͑2͒. Multiple regression analysis was 159.0 °C. according to Eq. ͑1͒ yielded the following results: Ethanol was distilled over calcium oxide, and the purity determined from Multiple correlation coefficient: 1.000 the density was 99.0%. Sample size: 5 data points Estimated Errors: p-value ͑F test͒: 0.001 Nothing specified. Constants: A=2292Ϯ839, B=11.58Ϯ2.35, C= −75.60Ϯ16.18

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Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. Methods/Apparatus/Procedure: ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 The solubility apparatus consisted of a 150 ml vessel equipped with a ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1935 . mechanical stirrer and a side tube which connected the vessel to a vacuum ͑2͒ Ethyl alcohol ͑ethanol͒; filtration system. During the measurements, the apparatus was immersed ͓ ͔ C2H6O; 64-17-5 in a water bath of constant temperature. A known mass of the compound to be studied was introduced into the solubility vessel. The mass varied Variables: Prepared by: between 2 and 10 g depending on the expected solubility of the t/ °C=28 A. Goto and H. Miyamoto compound. About 20 ml of solvent was added, the apparatus was closed tightly with rubber stoppers and immersed in a water bath so that only the upper part of the solubility vessel stayed above water. Stirring was The solubility of salicylic acid in ethanol at 28 °C was initiated and the compound allowed to dissolve during 30 min. The solution was vacuum filtered through a stinter and a known volume of reported as x1 =0.1479. filtered solution was transferred to a constant-mass evaporating dish. The Auxiliary Information solvent was carefully evaporated over a steam bath and the dish was placed in a drying oven. The temperature of the oven did not exceed Methods/Apparatus/Procedure: 100 °C. The dish was allowed to cool to room temperature in a desiccator Salicylic acid was saturated in 100 ml of ethanol in a series of flasks, and weighed. The solubility was calculated as grams per 100 ml of which were kept revolving on a wheel in an air thermostat at 28 °C for solution. 48 h. In order to avoid any error due to the absorption of the solute by the Source and Purity of Materials: filter paper, a fresh saturated solution was filtered through it before the Salicylic acid was obtained from Shuchardt, DAB6. solution used for the estimation of the acid was passed through. A suitable Ethanol: source and purity not given; relative density d=0.789 amount of the filtrate was titrated against barium hydroxide solution using ͑20 °C/4°C͒. phenolphthalein as an indicator. The stock solution of barium hydroxide Estimated Errors: was titrated against a standard solution of succinic acid. Nothing specified. According to the author, the values given are the mean Source and Purity of Materials: of three independent determinations. Salicylic acid was twice recrystallized. Ethanol was purified by distillation. Estimated Errors: Components: Original Measurements: Solubility: Three readings were taken in each case and the mean was 17 ͑1͒ Benzoic acid, 2-hydroxy- A.N. Paruta, B.J. Sciarrone, and taken. It was found by blank experiments ͑on solute-free solvent͒ that this ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, method gave reliable results, the precision being less than 0.5%. ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . Temperature: Nothing specified. ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ C2H6O; 64-17-5

Components: Original Measurements: Variables: Prepared by: / ͑1͒ Benzoic acid, 2-hydroxy- 15E. Bergroth, Farm. Aikak. 70, t °C=30.6 A. Goto, R. Goto, and H. ͑o-hydroxybenzoic acid, salicylic 91 ͑1961͒. Miyamoto ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑ ͒ ͑ ͒ 2 Ethyl alcohol ethanol ; Solubility of salicylic acid in ethanol at 30.6 °C ͓ ͔ C2H6O; 64-17-5 a Variables: Prepared by: Solubility t/ °C=20.0 P.Scharlin ␥ / −3 / −3 Dielectric constant 1 gdm c1 mol dm of solvent ͑compiler͒ ͑compiler͒

Solubility of salicylic acid in ethanol at 20 °C 20.7 381 2.76

a Solubility aIn the original paper, the solubility was given as milligrams per milliliter of ␥ / −3 / −3 solution. 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒

281.9 2.041

aIn the original paper, the solubility was given as grams per 100 ml of solution.

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Auxiliary Information

Methods/Apparatus/Procedure: The solubility of salicylic acid was determined in pure solvent using 15 ml screw-capped vials fitted with Teflon liners. The vials were attached to a rotating wheel in a water bath maintained at 30.6 °C. Equilibration time of 24 h was sufficient. Samples were withdrawn from the reaction vials using a pipet fitted with a glass wool filtering plug. The solubility of salicylic acid was determined by base titration using freshly prepared 0.1 mol dm−3 NaOH solution as titrant and phenolphthalein as an indicator. The dielectric constant of the ethanol were measured by a resonance method at 25 °C. Source and Purity of Materials: FIG. 3. Fitting curve of Eq. ͑1͒ and the observed data for salicylic acid in Ethanol was purified by the method described in A. Weissberger et al., 1-butanol. Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. Estimated Errors: Solubility: Nothing specified. the black line corresponds to calculated values according to Ϯ ͑ ͒ Ϯ ͑ Temperature: Precision of 0.2 °C solubility and 1.0 °C dielectric ͑ ͒ ͑ / ͒ constant͒. Eq. 1 ln x1 =6769 T+24.96 ln T−166.8 . The observed data fit closely with the calculated values in the range of 297.2–394.8 K, with the multiple correlation coefficient of Components: Evaluators: 0.998, as shown in Fig. 3. Therefore, the calculated value at ͑ ͒ 1 Benzoic acid, 2-hydroxy- Ayako Goto, University of each measured temperature is reasonably considered as a rec- ͑o-hydroxybenzoic acid, salicylic Shizuoka, Shizuoka, Japan ͒ ͓ ͔ ommended value over the whole range of temperature. acid ;C7H6O3; 69-72-7 Rensuke Goto, University of ͑2͒ 1-Butanol ͑butan-1-ol, butyl Shizuoka, Shizuoka, Japan Table 9 shows the observed data in the range of ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Hiroshi Fukuda, Kitasato 297.2–394.8 K and the recommended values calculated University, Tokyo, Japan from Eq. ͑1͒ at each temperature.

Critical Evaluation TABLE 9. Observed data and recommended values calculated according to TABLE 8. Summary of experimental solubility data of salicylic acid in Eq. ͑1͒ for salicylic acid in 1-butanol 1-butanol / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec / / −3 T K c1 mol dm 100w1 100x1 Analytical method Reference 297.2 14.75 15.5 a 297.2 24.36 14.75 Synthetic method 14 298.15 16.46 15.6 298.15 16.46 Spectroscopy 18 301.2 15.88 16.0 ͑ ͑ ͒ ͒ 301.2 15.88 Titration Ba OH 2 16 311.2 17.89 17.6 303.8 1.82 Titration͑NaOH͒ 17 358.8 33.9 34.3 a 311.2 28.88 17.89 Synthetic method 14 394.8 67.1 66.7 358.8 48.9 33.9a Synthetic method 14 394.8 79.2 67.1a Synthetic method 14 a Components: Original Measurements: The mole-fraction solubilities were calculated based on w1. 14 The critical evaluation was carried out as described in ͑1͒ Benzoic acid, 2-hydroxy- S.V. Sidgwick and E.K. ͑o-hydroxybenzoic acid, salicylic Embank, J. Chem. Soc. 1921, Sec. 2.1.1.1 for salicylic acid in n-heptane. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 979. The number of publications: 4 ͑2͒ 1-Butanol ͑butan-1-ol, butyl / ͒ ͓ ͔ The range of temperature: T K=297.2–394.8 alcohol ;C4H10O; 71-36-3 The units: mass percent, mole fraction, and mol dm−3 Variables: Prepared by: Analytical methods: synthetic method, spectroscopy, and t/ °C=24.0–121.6 A. Goto and H. Miyamoto titration Data for the solubility of salicylic acid in 1-butanol expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given Solubility of salicylic acid in 1-butanol ͑ ͒ in Sec. 1.3 Table 8 . The data points closely agree with Eq. Temperature Solubility ͑1͒ over the whole range of temperatures, as shown in Fig. 3, but they deviated from Eq. ͑2͒. Multiple regression analysis 100x1 / ͑ ͒ according to Eq. ͑1͒ yielded the following results: t °C 100w1 compiler Multiple correlation coefﬁcient: 0.998 121.6 79.2 67.1 Sample size: 6 data points 85.6 48.9 33.9 p-value ͑F test͒: 0.000 38.0 28.88 17.89 Constants: A=6769Ϯ1877, B=24.96Ϯ5.54, C= 24.0 24.36 14.75 −166.8Ϯ37.8 White circles in Fig. 3 represent the observed data and

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 14 for the The experimental details are given in the compilation of Ref. 17 for the salicylic acid–n-heptane system in Sec. 2.1.1.1. salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: The preparation and purification methods were described in ͓J. Walker and The solvents were purified by the method described in A. Weissberger et J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of salicylic acid al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 was 159.0 °C. and 5. 1-Butanol was repeatedly fractionated, and distilled within 0.1 °C. Estimated Errors: Estimated Errors: Solubility: Nothing specified. Nothing specified. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒.

Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. Components: Original Measurements: 18 ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͑1͒ Benzoic acid, 2-hydroxy- K.M. De Fina, T.L. Sharp, L.E. acid͒;CH O ; ͓69-72-7͔ ͑1935͒. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree, Jr., J. 7 6 3 ͒ ͓ ͔ ͑2͒ 1-Butanol ͑butan-1-ol, butyl acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 alcohol͒;CH O; ͓71-36-3͔ ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͑1999͒. 4 10 ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Variables: Prepared by: t/ °C=28 A. Goto and H. Miyamoto Variables: Prepared by: T/K=298.15 A. Goto and H. Miyamoto

The solubility of salicylic acid in 1-butanol at 28 °C was The solubility of salicylic acid in 1-butanol at 298.15 K x reported as 1 =0.1588. was reported as x1 =0.1646.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 16 for the Excess solute and solvent were placed in amber glass bottles and allowed salicylic acid–ethanol system in Sec. 2.1.2.1. to equilibrate in a constant-temperature water bath at 25.0 °C for at least Source and Purity of Materials: 3 days ͑often longer͒. Attainment of equilibrium was verified both by Salicylic acid was twice recrystallized. repetitive measurements after several additional days and by approaching 1-Butanol was purified by distillation. equilibrium from supersaturation. Aliquots of saturated salicylic acid Estimated Errors: solutions were transferred through a coarse filter into a tared volumetric Solubility: Three readings were taken in each case and the mean was flask to determine the amount of sample and diluted quantitatively with taken. It was found by blank experiments ͑on solute-free solvent͒ that this methanol for spectrophotometric analysis. Mole-fraction solubilities were ͑ / ͒ method gave reliable results, the precision being less than 0.5%. computed from mass mass solubility fraction using the molar masses Temperature: Nothing specified. of the solute and solvent. Source and Purity of Materials: Salicylic acid ͑Aldrich 99+%, ACS Reagent Grade͒ was dried in an oven for several hours at 80 °C and used without further purification. The Components: Original Measurements: purity of salicylic acid was 99.86Ϯ0.12 mass %, as determined by five 17 ͑1͒ Benzoic acid, 2-hydroxy- A.N. Paruta, B.J. Sciarrone, and volumetric titrations using a freshly standardized sodium hydroxide titrant ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, and phenolphthalein indicator. ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . 1-Butanol ͑Aldrich, HPLC, 99.8+%͒ was stored over molecular sieves ͑ ͒ ͑ 2 1-Butanol butan-1-ol, butyl before use. Gas chromatographic analysis showed solvent purities to be ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 99.7 mole % or better. Variables: Prepared by: Estimated Errors: t/ °C=30.6 A. Goto and H. Miyamoto Solubility: Nothing specified. Temperature: Precision of Ϯ0.1 °C.

Solubility of salicylic acid in 1-butanol at 30.6 °C

Solubilitya 2.1.2.2. 3-Hydroxybenzoic acid

␥ / −3 / −3 Dielectric constant 1 gdm c1 mol dm of solvent ͑compiler͒ ͑compiler͒ Components: Evaluators: ͑1͒ Benzoic acid, 3-hydroxy- Ayako Goto, University of 17.1 251 1.82 ͑m-hydroxybenzoic acid͒; Shizuoka, Shizuoka, Japan ͓ ͔ C7H6O3; 99-06-9 Rensuke Goto, University of aIn the original paper, the solubility was given as milligrams per milliliter of ͑2͒ Ethyl alcohol ͑ethanol͒ Shizuoka, Shizuoka, Japan ͓ ͔ solution. C7H6O; 64-17-5 Hiroshi Fukuda, Kitasato University, Tokyo, Japan

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TABLE 11. Observed data and recommended values calculated according to Eq. ͑1͒ for 3-hydroxybenzoic acid in ethanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

338.2 17.9 17.9 405.2 34.6 34.8 442.2 59.8 59.5 474.5 100 100

Components: Original Measurements: 14 FIG. 4. Fitting curve of Eq. ͑1͒ and the observed data for 3-hydroxybenzoic ͑1͒ Benzoic acid, 3-hydroxy- S.V. Sidgwick and E.K. acid in ethanol. ͑m-hydroxybenzoic acid͒; Embank, J. Chem. Soc. 1921, ͓ ͔ C7H6O3; 99-06-9 979. ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ Critical Evaluation C2H6O; 64-17-5 TABLE 10. Summary of experimental solubility data of 3-hydroxybenzoic acid in ethanol Variables: Prepared by: t/ °C=65.0–201.3 A. Goto and H. Miyamoto / / −3 T K c1 mol dm 100w1 100x1 Analytical method Reference Solubility of 3-hydroxybenzoic acid in ethanol 293.2 1.632 Gravimetry 14 338.2 39.6 17.9a Synthetic method 15 Temperature Solubility 405.2 61.3 34.6a Synthetic method 15 a 442.2 81.7 59.8 Synthetic method 15 100x1 a / ͑ ͒ 474.5 100.0 100.0 Synthetic method 15 t °C 100w1 compiler

a The mole-fraction solubilities were calculated based on w1. 201.3 100.0 100.0 The critical evaluation was carried out as described in 169.0 81.7 59.8 Sec. 2.1.1.1 for salicylic acid in n-heptane. 132.0 61.3 34.6 The number of publications: 2 65.0 39.6 17.9 The range of temperature: T/K=293.2–474.5 The units: mass percent, mole fraction, and mol dm−3 Auxiliary Information Analytical methods: synthetic method and gravimetry Methods/Apparatus/Procedure: Data for the solubility of 3-hydroxybenzoic acid in eth- The experimental details are given in the compilation of Ref. 14 for the anol expressed by mole fraction were fitted to Eqs. ͑1͒ and salicylic acid–n-heptane system in Sec. 2.1.1.1. ͑ ͒ ͑ ͒ Source and Purity of Materials: 2 given in Sec. 1.3 Table 10 . The data points closely ͓ ͑ ͒ The preparation and purification methods were described in J. Walker and agree with Eq. 1 over the whole range of temperatures, as J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of shown in Fig. 4, but they deviated from Eq. ͑2͒. Multiple 3-hydroxybenzoic acid was 201.5 °C. regression analysis according to Eq. ͑1͒ yielded the follow- Ethanol was distilled over calcium oxide, and the purity determined from ing results: the density was 99.0%. Estimated Errors: Multiple correlation coefficient: 1.000 Nothing specified. Sample size: 4 data points p-value ͑F test͒: 0.007 Constants: A=7204Ϯ281, B=23.16Ϯ0.71, C= Components: Original Measurements: −157.9Ϯ5.0 ͑1͒ Benzoic acid, 3-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑m-hydroxybenzoic acid͒; 91 ͑1961͒. White circles in Fig. 4 represent the observed data and ͓ ͔ C7H6O3; 99-06-9 the black line corresponds to calculated values according to ͑2͒ Ethyl alcohol ͑ethanol͒; ͑ ͒ ͑ / ͒ ͓ ͔ Eq. 1 ln x1 =7204 T+23.16 ln T−157.9 . The observed C2H6O; 64-17-5 data fit closely with the calculated values in the range of Variables: Prepared by: 338.2–474.5 K, with the multiple correlation coefficient of t/ °C=20.0 P.Scharlin 1.000, as shown in Fig. 4. Therefore, the calculated value at each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Table 11 shows the observed data in the range of 338.2–474.5 K and the recommended values calculated from Eq. ͑1͒ at each temperature.

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Solubility of 3-hydroxybenzoic acid in ethanol at 20.0 °C

Solubilitya

␥ / −3 / −3 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒

225.4 1.632

aIn the original paper, the solubility was given as grams per 100 ml of solution.

Auxiliary Information ͑ ͒ Methods/Apparatus/Procedure: FIG. 5. Fitting curve of Eq. 1 and the observed data for 4-hydroxybenzoic The experimental details are given in the compilation of Ref. 15 for the acid in ethanol. salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: 3-Hydroxybenzoic acid was obtained from Shuchardt, reinst. Multiple correlation coefficient: 0.999 Ethanol: source and purity not given; relative density Sample size: 5 data points d=0.789 ͑20 °C/4°C͒. p-value ͑F test͒: 0.003 Estimated Errors: Constants: A=4107Ϯ938, B=15.07Ϯ2.49, C= Nothing specified. According to the author, the values given are the mean of three independent determinations. −101.7Ϯ17.3 White circles in Fig. 5 represent the observed data and the black line corresponds to calculated values according to 2.1.2.3. 4-Hydroxybenzoic acid ͑ ͒ ͑ / ͒ Eq. 1 ln x1 =4107 T+15.07 ln T−101.7 . The observed data fit closely with the calculated values in the range of Components: Evaluators: 298.2–486.2 K, with the multiple correlation coefficient of ͑1͒ Benzoic acid, 4-hydroxy- Ayako Goto, University of ͑p-hydroxybenzoic acid͒; Shizuoka, Shizuoka, Japan 0.999, as shown in Fig. 5. Therefore, the calculated value at ͓ ͔ C7H6O3; 99-96-7 Rensuke Goto, University of each measured temperature is reasonably considered as a rec- ͑2͒ Ethyl alcohol ͑ethanol͒; Shizuoka, Shizuoka, Japan ͓ ͔ ommended value over the whole range of temperature. C2H6O; 64-17-5 Hiroshi Fukuda, Kitasato University, Tokyo, Japan Table 13 shows the observed data in the range of 298.2–486.2 K and the recommended values calculated Critical Evaluation from Eq. ͑1͒ at each temperature. TABLE 12. Summary of experimental solubility data of 4-hydroxybenzoic acid in ethanol TABLE 13. Observed data and recommended values calculated according to Eq. ͑1͒ for 4-hydroxybenzoic acid in ethanol / / −3 T K c1 mol dm 100w1 100x1 Analytical method Reference / ͑ ͒ ͑ ͒ 293.2 1.699 Gravimetry 15 T K 100x1 obs 100x1 rec 298.2 12.13 Spectroscopy 19 298.2 12.13 12.4 a 340.2 38.75 17.4 Synthetic method 14 340.2 17.4 16.5 a 409.7 60.9 34.2 Synthetic method 14 409.7 34.2 35.0 a 457.2 82.9 61.8 Synthetic method 14 457.2 61.8 64.6 a 486.2 100.0 100.0 Synthetic method 14 486.2 100 95.6 a The mole-fraction solubilities were calculated based on w1. The critical evaluation was carried out as described in Sec. 2.1.1.1 for salicylic acid in n-heptane. Components: Original Measurements: The number of publications: 3 ͑1͒ Benzoic acid, 4-hydroxy- 14S.V. Sidgwick and E.K. / ͑p-hydroxybenzoic acid͒; Embank, J. Chem. Soc. 1921, The range of temperature: T K=293.2–486.2 ͓ ͔ −3 C7H6O3; 99-96-7 979. The units: mass percent, mole fraction, and mol dm ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ Analytical methods: synthetic method, spectrophotom- C2H6O; 64-17-5 etry, and gravimetry Data for the solubility of 4-hydroxybenzoic acid in eth- Variables: Prepared by: / anol expressed by mole fraction were fitted to Eqs. ͑1͒ and t °C=67.0–213.0 A. Goto and H. Miyamoto ͑2͒ given in Sec. 1.3 ͑Table 12͒. The data points closely agree with Eq. ͑1͒ over the whole range of temperatures, as shown in Fig. 5, but they deviated from Eq. ͑2͒. Multiple regression analysis according to Eq. ͑1͒ yielded the following results:

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Solubility of 4-hydroxybenzoic acid in ethanol Components: Original Measurements: 19 Temperature Solubility ͑1͒ Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ 100x1 C7H6O3; 99-96-7 188 1984 . / ͑ ͒ ͑ ͒ ͑ ͒ t °C 100w1 compiler 2 Ethyl alcohol ethanol ; ͓ ͔ C2H6O; 64-17-5 67.0 38.75 17.4 136.5 60.9 34.2 Variables: Prepared by: 184.0 82.9 61.8 t/ °C=25 A. Goto and R. Goto 213.0 100.0 100.0 Solubility of 4-hydroxybenzoic acid in ethanol at 25 °C Auxiliary Information Molar volume of solvent Solubility Methods/Apparatus/Procedure: / 3 −1 The experimental details are given in the compilation of Ref. 14 for the v2 cm mol x1 salicylic acid–n-heptane system in Sec. 2.1.1.1. 58.7 0.1213 Source and Purity of Materials: The preparation and purification methods were described in ͓A. Beerbower, A. Martin, and P.L. Wu, J. Pharm. Sci. 73, 179 ͑1984͔͒. Auxiliary Information Melting point of 4-hydroxybenzoic acid was 213.0 °C. Ethanol was distilled over calcium oxide, and the purity determined from Methods/Apparatus/Procedure: the density was 99.0%. A suitable amount of solvent was introduced into screw-capped vials Estimated Errors: containing an excess amount of the solute. After being sealed with several turns of plastic tape, the vials were submerged in water at 25 °C and Nothing specified. shaken. After equilibrium had been attained, each vial was removed, wiped dry, and analyzed. The solutions were transferred to a syringe and filtered using a filter of pore size Ͻ1 ␮m. After suitable dilution, the Components: Original Measurements: solutions were assayed using a spectrophotometer. The solubility was ͑1͒ Benzoic acid, 4-hydroxy- 15E. Bergroth, Farm. Aikak. 70, determined at least six times for each solvent. ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. Source and Purity of Materials: ͓ ͔ C7H6O3; 99-96-7 4-Hydroxybenzoic acid was obtained from Matheson, Coleman, and Bell ͑2͒ Ethyl alcohol ͑ethanol͒; and the acid was recrystallized from aqueous alcohol and dried at 105 °C. ͓ ͔ C2H6O; 64-17-5 Melting point measured by a hot-stage method was 486.85 K. The solvent was spectrophotometric grade, ACS grade, or redistilled Variables: Prepared by: before use. t/ °C=20.0 P.Scharlin Estimated Errors: Nothing specified. Solubility of 4-hydroxybenzoic acid in ethanol at 20.0 °C

a Solubility Components: Evaluators: ͑ ͒ ␥ / −3 / −3 1 Benzoic acid, 4-hydroxy- Ayako Goto, University of 1 gdm c1 mol dm ͑ ͒ ͑ ͒ ͑ ͒ p-hydroxybenzoic acid ; Shizuoka, Shizuoka, Japan compiler compiler ͓ ͔ C7H6O3; 99-96-7 Rensuke Goto, University of ͑ ͒ ͑ 243.6 1.699 2 1-Butanol butan-1-ol, butyl Shizuoka, Shizuoka, Japan ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Hiroshi Fukuda, Kitasato University, Tokyo, Japan aIn the original paper, the solubility was given as grams per 100 ml of solution. Critical Evaluation Auxiliary Information TABLE 14. Summary of experimental solubility data of 4-hydroxybenzoic Methods/Apparatus/Procedure: acid in 1-butanol The experimental details are given in the compilation of Ref. 15 for the T/ w x salicylic acid–ethanol system in Sec. 2.1.2.1. K 100 1 100 1 Analytical method Reference Source and Purity of Materials: 298.2 11.54 Spectroscopy 19 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%. 305.7 19.50 11.50a Synthetic method 14 Ethanol source and purity not given; relative density d=0.789 335.2 25.08 15.23a Synthetic method 14 ͑20 °C/4°C͒. a 389.3 39.45 25.9 Synthetic method 14 Estimated Errors: a 440.2 62.4 47.1 Synthetic method 14 Nothing speciﬁed. According to the author, the values given are the mean a 467.2 85.5 76.0 Synthetic method 14 of three independent determinations. a The mole-fraction solubilities were calculated based on w1. The critical evaluation was carried out as described in Sec. 2.1.1.1 for salicylic acid in n-heptane. The number of publications: 2

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Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 14S.V. Sidgwick and E.K. ͑p-hydroxybenzoic acid͒; Embank, J. Chem. Soc. 1921, ͓ ͔ C7H6O3; 99-96-7 979. ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3

Variables: Prepared by: t/ °C=32.5–193.8 A. Goto and H. Miyamoto

Solubility of 4-hydroxybenzoic acid in 1-butanol FIG. 6. Fitting curve of Eq. ͑1͒ and the observed data for 4-hydroxybenzoic acid in 1-butanol. Temperature Solubility

100x1 / ͑ ͒ The range of temperature: T/K=298.2–467.2 t °C 100w1 compiler The units: mass percent and mole fraction 32.5 19.50 11.50 Analytical methods: synthetic method and spectropho- 62.0 25.08 15.23 116.1 39.45 25.91 tometry 167.0 62.4 47.1 Data for the solubility of 4-hydroxybenzoic acid in 193.8 85.5 76.0 1-butanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 14͒. The data points closely Auxiliary Information agree with Eq. ͑1͒ over the whole range of temperatures, as Methods/Apparatus/Procedure: shown in Fig. 6, but they deviated from Eq. ͑2͒. Multiple The experimental details are given in the compilation of Ref. 14 for the regression analysis according to Eq. ͑1͒ yielded the follow- salicylic acid–n-heptane system in Sec. 2.1.1.1. ing results: Source and Purity of Materials: The preparation and purification methods were described in ͓J. Walker and Multiple correlation coefficient: 0.999 J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of Sample size: 6 data points 4-hydroxybenzoic acid was 213.0 °C. p-value ͑F test͒: 0.000 1-Butanol was repeatedly fractionated, and distilled within 0.1 °C. Ϯ Ϯ Estimated Errors: Constants: A=4384 858, B=15.96 2.33, C= Nothing specified. −107.8Ϯ16.1 White circles in Fig. 6 represent the observed data and the black line corresponds to calculated values according to Components: Original Measurements: 19 ͑ ͒ ͑ / ͒ ͑1͒ Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. Eq. 1 ln x1 =4384 T+15.96 ln T−107.8 . The observed ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ data fit closely with the calculated values in the range of C7H6O3; 99-96-7 188 1984 . 298.2–467.2 K, with the multiple correlation coefficient of ͑2͒ 1-Butanol ͑butan-1-ol, butyl alcohol͒;CH O; ͓71-36-3͔ 0.999, as shown in Fig. 6. Therefore, the calculated value at 4 10 each measured temperature is reasonably considered as a rec- Variables: Prepared by: t/ °C=25 A. Goto and R. Goto ommended value over the whole range of temperature. Table 15 shows the observed data in the range of Solubility of 4-hydroxybenzoic acid in 1-butanol at 25 °C 298.2–467.2 K and the recommended values calculated from Eq. ͑1͒ at each temperature. Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1 TABLE 15. Observed data and recommended values calculated according to ͑ ͒ Eq. 1 for 4-hydroxybenzoic acid in 1-butanol 92.0 0.1154

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

298.2 11.54 11.4 305.7 11.5 11.9 335.2 15.23 14.6 389.3 25.91 25.9 440.2 47.1 50.1 467.2 76.0 72.9

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Auxiliary Information 2.1.3. Critical evaluation of the solubility of hydroxybenzoic acids in aromatic compounds Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the 2.1.3.1. Salicylic acid 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: Components: Evaluators: The details are given in the compilation of Ref. 19 for the ͑ ͒ 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 1 Benzoic acid, 2-hydroxy- Ayako Goto, University of ͑o-hydroxybenzoic acid, salicylic Shizuoka, Shizuoka, Japan Estimated Errors: ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Rensuke Goto, University of Nothing speciﬁed. ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 Shizuoka, Shizuoka, Japan Hiroshi Fukuda, Kitasato University, Tokyo, Japan

Critical Evaluation TABLE 16. Summary of experimental solubility data of salicylic acid in benzene

/ / −3 / −1 T K c1 mol dm m1 mol kg 100w1 100x1 Analytical method Reference a ͑ ͑ ͒ ͒ 284.9 0.0333 0.458 0.2606 Titration Ba OH 2 20 a ͑ ͑ ͒ ͒ 291.4 0.0419 0.576 0.3281 Titration Ba OH 2 20 298.2 0.057 68 Titration 21 ͑ ͑ ͒ ͒ 301.2 0.5541 Titration Ba OH 2 16 a ͑ ͑ ͒ ͒ 303.7 0.0717 0.981 0.562 Titration Ba OH 2 20 303.8 0.05 Titration ͑NaOH͒ 17 a ͑ ͑ ͒ ͒ 307.8 0.0913 1.245 0.717 Titration Ba OH 2 20 a ͑ ͑ ͒ ͒ 309.8 0.1035 1.410 0.814 Titration Ba OH 2 20 317.5 1.92 1.09a Synthetic method 14 a ͑ ͑ ͒ ͒ 322.6 0.1723 2.325 1.360 Titration Ba OH 2 20 a ͑ ͑ ͒ ͒ 337.4 0.319 4.215 2.540 Titration Ba OH 2 20 338.2 5.27 3.05a Synthetic method 14 371.7 20.8 12.9a Synthetic method 14 375.7 5.00 2.89a Fusion method 22 386.2 8.50 4.99a Fusion method 22 387.7 41.1 28.3a Synthetic method 14 400.2 18.95 11.68a Fusion method 22 404.7 64.5 50.4a Synthetic method 14 408.2 31.14 20.37a Fusion method 22 412.7 46.89 33.30a Fusion method 22 413.2 81.3 71.1a Synthetic method 14 418.2 70.0 56.89a Fusion method 22 421.7 84.97 76.17a Fusion method 22 428.2 100.0 100.0a Fusion method 22 432.2 100.0 100.0a Fusion method 14

a The mole-fraction solubilities were calculated based on w1. The critical evaluation was carried out as described in p-value ͑F test͒: 0.000 Sec. 2.1.1.1 for salicylic acid in n-heptane. The number of publications: 6 The range of temperature: T/K=284.9–432.2 The units: mass percent, mole fraction, molarity, and mol dm−3 Analytical methods: fusion method, synthetic method, and titration Data for the solubility of salicylic acid in benzene expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 16͒. The data points closely agree with Eq. ͑1͒ over the whole range of temperatures, as shown in Fig. 7, but they deviated from Eq. ͑2͒. Multiple regression analysis according to Eq. ͑1͒ yielded the following results:

Multiple correlation coefﬁcient: 0.972 FIG. 7. Fitting curve of Eq. ͑1͒ and the observed data for salicylic acid in Sample size: 23 data points benzene.

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Constants: A=8097Ϯ5739, B=36.83Ϯ16.31, C= Solubility of salicylic acid in benzene −242.3Ϯ112.1 Temperature Solubilitya White circles in Fig. 7 represent the observed data and / −1 the black line corresponds to calculated values according to 100w1 m1 mol kg t/ °C ͑compiler͒ ͑compiler͒ ͑ ͒ ͑ / ͒ Eq. 1 ln x1 =8097 T+36.83 ln T−242.3 . The observed data fit closely with the calculated values in the range of 11.7 0.460 0.0333 18.2 0.579 0.0419 284.9–432.2 K, with the multiple correlation coefficient of 30.5 0.991 0.0717 0.972, as shown in Fig. 7. Therefore, the calculated value at 34.6 1.261 0.0913 each measured temperature is reasonably considered as a rec- 36.6 1.430 0.1035 49.4 2.380 0.1723 ommended value over the whole range of temperature. 64.2 4.40 0.319 Table 17 shows the observed data in the range of 284.9–432.2 K and the recommended values calculated aIn the original paper, the solubility was given as grams per 100 g of sol- from Eq. ͑1͒ at each temperature. vent. Auxiliary Information TABLE 17. Observed data and recommended values calculated according to Eq. ͑1͒ for salicylic acid in benzene Methods/Apparatus/Procedure: Both undersaturation and supersaturation methods were used to obtain the / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec saturated solutions. The solutions were usually agitated by stirrers driven by a small turbine, but at the higher temperature, equilibrium was reached 284.9 0.2606 0.323 with only occasional agitation by hand. The salicylic acid solutions were 291.4 0.3281 0.394 titrated directly with barium hydroxide solution using Congo Red as an 301.2 0.5541 0.539 indicator, after previously diluting with water. The barium hydroxide 303.7 0.562 0.586 solution was standardized with pure succinic acid using phenolphthalein 307.8 0.717 0.673 as an indicator. In the case of benzene, the solvent was driven off by 309.8 0.814 0.721 evaporation under reduced pressure before the titration. 317.5 1.09 0.944 Source and Purity of Materials: 322.6 1.36 1.13 No information was given. 337.4 2.54 1.97 Estimated Errors: 338.2 3.05 2.03 Nothing specified. 371.7 12.9 7.60 375.7 2.89 8.94 386.2 4.99 13.7 Components: Original Measurements: 14 387.7 28.3 14.6 ͑1͒ Benzoic acid, 2-hydroxy- N.V. Sidgwick and E.K. ͑ 400.2 11.68 24.5 o-hydroxybenzoic acid, salicylic Ewbank, J. Chem. Soc. 1921, ͒ ͓ ͔ 404.7 50.4 29.5 acid ;C7H6O3; 69-72-7 979. ͑2͒ Benzene; C H ; ͓71-43-2͔ 408.2 20.37 34.1 6 6 412.7 33.3 41.1 Variables: Prepared by: 413.2 71.1 42.0 t/ °C=44.3–159.0 A. Goto and H. Miyamoto 418.2 56.89 51.8 421.7 76.17 59.9 428.2 100.0 78.6 Solubility of salicylic acid in benzene 432.2 100.0 92.9 Temperature Solubility

100x1 / ͑ ͒ Components: Original Measurements: t °C 100w1 compiler ͑1͒ Benzoic acid, 2-hydroxy- 20J. Walker and J.K. Wood, J. ͑o-hydroxybenzoic acid, salicylic Chem. Soc. Trans. 73, 618 44.3 1.92 1.09 ͒ ͓ ͔ ͑ ͒ 65.0 5.27 3.05 acid ;C7H6O3; 69-72-7 1898 . ͑ ͒ ͓ ͔ 98.5 20.8 12.9 2 Benzene; C6H6; 71-43-2 114.5 41.1 28.3 Variables: Prepared by: 131.5 64.5 50.4 / t °C=11.7–64.2 A. Goto and H. Miyamoto 140.0 81.3 71.1 159.0 100.0 100.0

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 14 for the The solubility was measured by rotating tubes of solvent and solute for at salicylic acid–n-heptane system in Sec. 2.1.1.1. least 8 h at 25 °C ͑preliminary experiments showed that saturation is Source and Purity of Materials: reached in 2 h͒. The solutions were concentrated, if necessary, and titrated The preparation and the purification of salicylic acid were described in ͓J. with standard alkali, bromothymol-blue-neutralred being used as mixed Walker and J.K Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of indicator. the purified acid was 159.0 °C. Source and Purity of Materials: Benzene was freed from thiophene by treatment with sulfuric acid, and The acid was either of AnalaR standard or was recrystallized before use. frozen out seven times. No information on the purity of the organic solvent was reported. Estimated Errors: Estimated Errors: Nothing specified. Nothing specified.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. ͑1͒ Benzoic acid, 2-hydroxy- 22I.L. Krupatkin, Zh. Obsh. ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͑o-hydroxybenzoic acid, salicylic Khim. 26,3240͑1956͓͒J. Gen. ͒ ͓ ͔ ͑ ͒ ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1935 . acid ;C7H6O3; 69-72-7 Chem. USSR Engl. Transl. 26, ͑ ͒ ͓ ͔ ͑ ͒ ͓ ͔ ͑ ͔͒ 2 Benzene; C6H6; 71-43-2 2 Benzene; C6H6; 71-43-2 3609 1956 .

Variables: Prepared by: Variables: Prepared by: t/ °C=28 A. Goto and H. Miyamoto t/ °C=102.5–155.0 H. Miyamoto and A. Goto

The solubility of salicylic acid in benzene at 28 °C was Solubility of salicylic acid in benzene 2 reported as 10 x1 =0.5441. Crystallization temperature Benzene Salicylic acid Auxiliary Information

100x2 100w1 100x1 Methods/Apparatus/Procedure: / ͑ ͒ ͑ ͒ ͑ ͒ t °C 100w2 compiler compiler compiler The experimental details are given in the compilation of Ref. 16 for the salicylic acid–ethanol system in Sec. 2.1.2.1. 102.5 95.00 97.11 5.00 2.89 Source and Purity of Materials: 113.0 91.50 95.01 8.50 4.99 Salicylic acid was twice recrystallized. 127.0 81.05 88.32 18.95 11.68 Benzene was puriﬁed by distillation at its known boiling point. 135.0 68.14 79.63 31.14 20.37 Estimated Errors: 139.5 53.11 66.70 46.89 33.30 Solubility: Three readings were taken in each case and the mean was 145.0 30.00 43.11 70.00 56.89 taken. It was found by blank experiments ͑on solute-free solvent͒ that this 148.5 15.03 23.83 84.97 76.17 method gave reliable results; the precision being less than 0.5%. 155.0 0.00 0.00 100.00 100.00 Temperature: Nothing speciﬁed.

Auxiliary Information

Components: Original Measurements: Methods/Apparatus/Procedure: 21 ͑1͒ Benzoic acid, 2-hydroxy- P. A. Ongley, J. Chem. Soc. The system salicylic acid–benzene was investigated by the fusion method. ͑ o-hydroxybenzoic acid, salicylic 1954, 3634. Source and Purity of Materials: ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 The melting point of C.P. grade salicylic acid used was 155 °C. ͑2͒ Benzene; C H ; ͓71-43-2͔ 6 6 The benzene fraction boiling in the range 90–120 °C was used. Variables: Prepared by: Estimated Errors: t/ °C=25 A. Goto and H. Miyamoto Nothing speciﬁed.

Solubility of salicylic acid in benzene at 25 °C Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and Solubility ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ c /mol dm−3 acid ;C7H6O3; 69-72-7 1349 1964 . 1 ͑ ͒ ͓ ͔ pS ͑compiler͒ 2 Benzene; C6H6; 71-43-2

1.239 0.057 68 Variables: Prepared by: t/ °C=30.6 A. Goto and H. Miyamoto pS: The negative logarithm of the concentration in the saturated solutions in mol/l.

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Solubility of salicylic acid in benzene at 30.6 °C Auxiliary Information

Solubilityb Estimated Errors: Solubility: Nothing speciﬁed. ␥ / −3 / −3 1 gdm c1 mol dm Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric a Dielectric constant ͑compiler͒ ͑compiler͒ constant͒. 2.2 7 0.05 aThe dielectric constant of the mixture at the maximum solubility of salicylic acid. bIn the original paper, the solubility was given as mg/ml of solution. 2.1.3.2. 3-Hydroxybenzoic acid

Auxiliary Information Components: Evaluators: Methods/Apparatus/Procedure: ͑1͒ Benzoic acid, 3-hydroxy- Ayako Goto, University of The experimental details are given in the compilation of Ref. 17 for the ͑m-hydroxybenzoic acid͒; Shizuoka, Shizuoka, Japan ͓ ͔ salicylic acid–ethanol system in Sec. 2.1.2.1. C7H6O3; 99-06-9 Rensuke Goto, University of ͑ ͒ ͓ ͔ Source and Purity of Materials: 2 Benzene; C6H6; 71-43-2 Shizuoka, Shizuoka, Japan The solvent was puriﬁed by the method described in A. Weissberger et al., Hiroshi Fukuda, Kitasato Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. University, Tokyo, Japan

Critical Evaluation TABLE 18. Summary of experimental solubility data of 3-hydroxybenzoic acid in benzene

/ / −3 / −1 T K c1 mol dm m1 mol kg 100w1 100x1 Analytical method Reference

298.2 0.000 633 9 Titration 21 ͑ ͑ ͒ ͒ 298.2 0.000 731 1.01 0.005 7 Titration Ba OH 2 20 303.2 0.005 04 Gravimetry 23 ͑ ͑ ͒ ͒ 307.3 0.001 02 0.007 97 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 319.2 0.001 69 0.013 2 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 331.2 0.003 15 0.024 6 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 337.2 0.004 29 0.033 5 Titration Ba OH 2 20 395.7 1.23 0.699a Synthetic method 14 414.2 2.95 1.69a Synthetic method 14 427.7 5.16 2.99a Synthetic method 14 435.2 10.54 6.24a Synthetic method 14 446.2 22.4 14.0a Synthetic method 14 455.7 41.6 28.7a Synthetic method 14 458.7 62.3 48.3a Synthetic method 14 465.7 83.3 73.8a Synthetic method 14 474.5 100.0 100.0a Synthetic method 14

a The mole-fraction solubilities were calculated based on w1. The critical evaluation was carried out as described in Constants: A=18788Ϯ2831, B=−71.40Ϯ7.60, C= Sec. 2.1.1.1 for salicylic acid in n-heptane. −479.6Ϯ52.7 The number of publications: 4 White circles in Fig. 8 represent the observed data and The range of temperature: T/K=298.2–474.5 the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ The units: mass percent, molarity, mole fraction, and Eq. 1 ln x1 =18788 T−71.40 ln T−479.6 . The observed mol dm−3 Analytical methods: synthetic method, titration, and 1 gravimetry -1

Data for the solubility of 3-hydroxybenzoic acid in ben- -3 zene expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ln -5 ͑2͒ given in Sec. 1.3 ͑Table 18͒. The data points closely x1 agree with Eq. ͑1͒ over the whole range of temperatures, as -7 shown in Fig. 8, but they deviated from Eq. ͑2͒. Multiple -9 ͑ ͒ regression analysis according to Eq. 1 yielded the follow- -11 0.002 0.0025 0.003 0.0035 ing results: (T/K)-1 Multiple correlation coefﬁcient: 0.998 Sample size: 15 data points FIG. 8. Fitting curve of Eq. ͑1͒ and the observed data for 3-hydroxybenzoic p-value ͑F test͒: 0.000 acid in benzene.

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data fit closely with the calculated values in the range of Auxiliary Information 298.2–474.5 K, with the multiple correlation coefficient of Methods/Apparatus/Procedure: 0.998, as shown in Fig. 8. Therefore, the calculated value at The experimental details are given in the compilation of Ref. 20 for the each measured temperature is reasonably considered as a rec- binary salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: ommended value over the whole range of temperature. No information was given. Table 19 shows the observed data in the range of Estimated Errors: 298.2–474.5 K and the recommended values calculated Nothing specified. from Eq. ͑1͒ at each temperature.

Components: Original Measurements: TABLE 19. Observed data and recommended values calculated according to ͑1͒ Benzoic acid, 3-hydroxy- 14N.V. Sidgwick and E.K. Eq. ͑1͒ for 3-hydroxybenzoic acid in benzene ͑m-hydroxybenzoic acid͒; Ewbank, J. Chem. Soc. 1921, ͓ ͔ / ͑ ͒ ͑ ͒ C7H6O3; 99-06-9 979. T K 100x1 obs 100x1 rec ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 298.2 0.0057 0.0059 Variables: Prepared by: 303.2 0.00504 0.0068 t/ °C=122.5–201.3 A. Goto and H. Miyamoto 307.3 0.00797 0.0078 319.2 0.0132 0.0120 331.2 0.0246 0.0198 Solubility of 3-hydroxybenzoic acid in benzene 337.2 0.0335 0.0260 395.7 0.699 0.630 Temperature Solubility 414.2 1.69 1.97 100x1 427.7 2.99 4.65 / ͑ ͒ t °C 100w1 compiler 435.2 6.24 7.55 446.2 14 15.5 122.5 1.23 0.699 455.7 28.7 28.9 141.0 2.95 1.69 458.7 48.3 35.3 154.5 5.16 2.99 465.7 73.8 56.3 162.0 10.54 6.24 474.5 100 101 173.0 22.4 14.0 182.5 41.6 28.7 185.5 62.3 48.3 Components: Original Measurements: 192.5 83.3 73.8 ͑1͒ Benzoic acid, 3-hydroxy- 20J. Walker and J.K. Wood, J. 201.3 100.0 100.0 ͑m-hydroxybenzoic acid͒; Chem. Soc. Trans. 73, 618 ͓ ͔ ͑ ͒ C7H6O3; 99-06-9 1898 . ͑ ͒ ͓ ͔ Auxiliary Information 2 Benzene; C6H6; 71-43-2 Methods/Apparatus/Procedure: Variables: Prepared by: The experimental details are given in the compilation of Ref. 14 for the t/ °C=25.0–64.0 A. Goto and H. Miyamoto salicylic acid–n-heptane system in Sec. 2.1.1.1. Source and Purity of Materials: Solubility of 3-hydroxybenzoic acid in benzene The details are given in the compilation of Ref. 14 for the binary salicylic acid–benzene system in Sec. 2.1.3.1. Temperature Solubility Estimated Errors: Nothing speciﬁed. a 3 / −1 100w1 10 m1 mol kg t/ °C ͑compiler͒ ͑compiler͒

25.0 0.0101 0.731 Components: Original Measurements: 34.1 0.0141 1.02 ͑1͒ Benzoic acid, 3-hydroxy- 21P.A. Ongley, J. Chem. Soc. 46.0 0.0234 1.69 ͑m-hydroxybenzoic acid͒; 1954, 3634. ͓ ͔ 58.0 0.0435 3.15 C7H6O3; 99-06-9 ͑ ͒ ͓ ͔ 64.0 0.0592 4.29 2 Benzene; C6H6; 71-43-2 Variables: Prepared by: a In the original paper, the solubility was given as grams per 100 g of sol- t/ °C=25 A. Goto and H. Miyamoto vent.

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Solubility of 3-hydroxybenzoic acid in benzene at 25 °C Solubility of 3-hydroxybenzoic acid in benzene at 30 °C

Solubility Solubility

103c /mol dm−3 a 1 100w1 pS ͑compiler͒ ͑ ͒ 100x1 compiler

3.198 0.6339 5.04ϫ10−3 8.99ϫ10−3

a pS: The negative logarithm of the concentration in the saturated solutions in In the original paper, the solubility was given as grams of acid per 100 g of moles per liter. saturated solution.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 21 for the Equilibrium was approached from the sides of both undersaturation and salicylic acid–benzene system in Sec. 2.1.3.1. supersaturation. Solvent and excess solute were mixed at about 25 °C in a ground-glass stoppered conical flask and left in a 30.00 °C water bath, Source and Purity of Materials: with periodic manual agitation, for several days. In a second flask, solvent The details are given in the compilation of Ref. 21 for the salicylic and excess solute were mixed and shaken thoroughly at 50 °C and then acid–benzene system in Sec. 2.1.3.1. left in the 30.00 °C water bath. A Soxhlet thimble equipped with a Estimated Errors: one-hole cork stopper and an inverted, U-shaped delivery tube extending Nothing specified. nearly to the bottom of the thimble, was half immersed in the saturated solution. Gentle suction was applied to transfer a part of the saturated solution, free of excess solute, to a second glass-stoppered flask suspended Components: Original Measurements: in the 30.00 °C bath. This second flask plus contents were weighed. ͑1͒ Benzoic acid, 3-hydroxy- 23C.K. Hancock, J.N. Pawloski, Successive portions of the contents were evaporated at room temperature ͑m-hydroxybenzoic acid͒; and J.P. Idoux, J. Org. Chem. 31, in a tared aluminum foil weighing dish under a bell jar through which a ͓ ͔ ͑ ͒ slow stream of dry air was passed. The second flask plus unused saturated C7H6O3; 99-06-9 3801 1966 . ͑ ͒ ͓ ͔ solution and the aluminum foil dish plus residue were weighed. 2 Benzene; C6H6; 71-43-2 Source and Purity of Materials:

Variables: Prepared by: Reagent-grade benzene was reﬂuxed over P2O5 for 24 h and then distilled. t/ °C=30 A. Goto and H. Miyamoto The 3-hydroxybenzoic acid was procured from commercial sources. After two or more recrystallizations from aqueous ethanol, the acid was dried

under vacuum over P2O5. The melting point was checked. Estimated Errors: Solubility ͑mole fraction units͒: The average deviation of the replicate values from the mean exceeded 3%. Temperature: Precision of Ϯ0.02 °C.

2.1.3.3. 4-Hydroxybenzoic acid

Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of ͑p-hydroxybenzoic acid͒; Shizuoka, Shizuoka, Japan ͓ ͔ C7H6O3; 99-96-7 Rensuke Goto, University of ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 Shizuoka, Shizuoka, Japan Hiroshi Fukuda, Kitasato University, Tokyo, Japan

Critical Evaluation TABLE 20. Summary of experimental solubility data of 4-hydroxybenzoic acid in benzene

/ / −3 / −1 T K c1 mol dm m1 mol kg 100w1 100x1 Analytical method Reference ͑ ͑ ͒ ͒ 284.2 0.000 143 0.001 97 0.001 12 Titration Ba OH 2 20 298.2 0.003 3 Spectroscopy 19 298.2 0.003 698 Titration 21 303.2 0.001 04 0.005 88 Gravimetry 23 ͑ ͑ ͒ ͒ 306.2 0.000 413 0.005 71 0.003 22 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 322.2 0.001 12 0.015 5 0.008 75 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 337.2 0.002 53 0.035 0 0.019 8 Titration Ba OH 2 20 ͑ ͑ ͒ ͒ 353.2 0.004 78 0.066 0 0.037 3 Titration Ba OH 2 20 405.4 1.04 0.59a Synthetic method 14 430.1 3.03 1.74a Synthetic method 14

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TABLE 20. Summary of experimental solubility data of 4-hydroxybenzoic acid in benzene—Continued

/ / −3 / −1 T K c1 mol dm m1 mol kg 100w1 100x1 Analytical method Reference

438.5 4.30 2.48a Synthetic method 14 451.2 10.3 6.10a Synthetic method 14 464.7 21.0 13.1a Synthetic method 14 468.9 40.6 27.9a Synthetic method 14 472 61.3 47.3a Synthetic method 14 479.2 83.0 73.4a Synthetic method 14 486.2 100.0 100.0a Synthetic method 14

a The mole-fraction solubilities were calculated based on w1. The critical evaluation was carried out as described in 284.2–486.2 K and the recommended values calculated Sec. 2.1.1.1 for salicylic acid in n-heptane. from Eq. ͑1͒ at each temperature. The number of publications: 5 The range of temperature: T/K=284.2–486.2 TABLE 21. Observed data and recommended values calculated according to The units: mass percent, mole fraction, molarity, and Eq. ͑1͒ for 4-hydroxybenzoic acid in benzene mol dm−3 T/K 100x ͑obs͒ 100x ͑rec͒ Analytical methods: synthetic method, titration, spec- 1 1 troscopy, and gravimetry 284.2 0.001 12 0.003 53 Data for the solubility of 4-hydroxybenzoic acid in ben- 298.2 0.003 3 0.004 58 zene expressed by mole fraction were fitted to Eqs. ͑1͒ and 303.2 0.005 88 0.005 19 ͑2͒ given in Sec. 1.3 ͑Table 20͒. The data points closely 306.2 0.003 22 0.005 63 322.2 0.008 75 0.009 41 agree with Eq. ͑1͒ over the whole range of temperatures, as 337.2 0.019 8 0.016 9 ͑ ͒ shown in Fig. 9, but they deviated from Eq. 2 . Multiple 353.2 0.037 3 0.034 5 regression analysis according to Eq. ͑1͒ yielded the follow- 405.4 0.59 0.547 ing results: 430.1 1.74 2.36 Multiple correlation coefficient: 0.986 438.5 2.48 3.93 Sample size: 16 data points 451.2 6.1 8.58 p-value ͑F test͒: 0.000 464.7 13.1 19.9 468.9 27.9 26.0 Constants: A=15140Ϯ3294, B=60.89Ϯ8.85, C= Ϯ 472 47.3 31.6 −408.1 61.4 479.2 73.4 49.8 White circles in Fig. 9 represent the observed data and 486.2 100 77.7 the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 1 ln x1 =15140 T+60.89 ln T−408.1 . The observed data fit closely with the calculated values in the range of Components: Original Measurements: 284.2–486.2 K, with the multiple correlation coefficient of ͑1͒ Benzoic acid, 4-hydroxy- 20J. Walker and J.K. Wood, J. ͑p-hydroxybenzoic acid͒; Chem. Soc. Trans. 73,618 0.986, as shown in Fig. 9. Therefore, the calculated value at ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 1898 . each measured temperature is reasonably considered as a rec- ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 ommended value over the whole range of temperature. Table 21 shows the observed data in the range of Variables: Prepared by: t/ °C=11.0–80.0 A. Goto and H. Miyamoto

Solubility of 4-hydroxybenzoic acid in benzene

Temperature Solubility

a 3 / −1 100w1 10 m1 mol kg t/ °C Original data ͑compiler͒ ͑compiler͒

11.0 0.001 97 0.001 97 0.143 33.0 0.005 71 0.005 71 0.413 49.0 0.015 5 0.015 5 1.12 64.0 0.035 0 0.035 0 2.53 80.0 0.066 0 0.066 0 4.78

aIn the original paper, the solubility was given as grams of solute per 100 g FIG. 9. Fitting curve of Eq. ͑1͒ and the observed data for 4-hydroxybenzoic of benzene. acid in benzene.

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Auxiliary Information Solubility of 4-hydroxybenzoic acid in benzene at 25 °C

Methods/Apparatus/Procedure: Solubility The experimental details are given in the compilation of Ref. 20 for the 3 / −3 binary salicylic acid–benzene system in Sec. 2.1.3.1. 10 c1 mol dm Source and Purity of Materials: pS ͑compiler͒ No information was given. 3.432 0.3698 Estimated Errors: Nothing speciﬁed. pS: The negative logarithm of the concentration in the saturated solutions in mol/l.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy- 14N.V. Sidgwick and E.K. Methods/Apparatus/Procedure: ͑p-hydroxybenzoic acid͒; Ewbank, J. Chem. Soc. 1921, ͓ ͔ The experimental details are given in the compilation of Ref. 21 for the C7H6O3; 99-96-7 979. ͑ ͒ ͓ ͔ salicylic acid–benzene system in Sec. 2.1.3.1. 2 Benzene; C6H6; 71-43-2 Source and Purity of Materials: Variables: Prepared by: The detail is given in the compilation of Ref. 21 for the salicylic acid– t/ °C=132.2–213.0 A. Goto and H. Miyamoto benzene system in Sec. 2.1.3.1. Estimated Errors: Nothing speciﬁed. Solubility of 4-hydroxybenzoic acid in benzene

Temperature Solubility Components: Original Measurements: 23 100x1 ͑1͒ Benzoic acid, 4-hydroxy- C.K. Hancock, J.N. Pawloski, / ͑ ͒ t °C 100w1 compiler ͑p-hydroxybenzoic acid͒; and J.P. Idoux, J. Org. Chem. 31, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 3801 1966 . 132.2 1.04 0.59 ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 156.9 3.03 1.74 165.3 4.30 2.48 Variables: Prepared by: 178.0 10.3 6.10 t/ °C=30 A. Goto and H. Miyamoto 191.5 21.0 13.1 195.7 40.6 27.9 Solubility of 4-hydroxybenzoic acid in benzene at 30 °C 198.8 61.3 47.3 206.0 83.0 73.4 Solubility 213.0 100.0 100.0 a 100x1 100w1

Auxiliary Information 5.88ϫ10−3 1.04ϫ10−2

Methods/Apparatus/Procedure: aIn the original paper, the solubility was given as grams of acid per 100 g of The experimental details are given in the compilation of Ref. 14 for the saturated solution. salicylic acid–n-heptane system in Sec. 2.1.1.1. Source and Purity of Materials: Auxiliary Information The preparation and the purification of 4-hydroxybenzoic acid were described in ͓J. Walker and J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Methods/Apparatus/Procedure: Melting point of the purified acid was 213.0 °C. The experimental details are given in the compilation of Ref. 23 for the Benzene was freed from thiophene by treatment with sulfuric acid, and 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. frozen out seven times. Source and Purity of Materials: Estimated Errors: The details are given in the compilation of Ref. 23 for the Nothing specified. 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. Estimated Errors: Solubility ͑mole fraction units͒: The average deviation of the replicate values from the mean did not exceed 3%. Components: Original Measurements: Temperature: Precision of Ϯ0.02 °C. ͑1͒ Benzoic acid, 4-hydroxy- 21P.A. Ongley, J. Chem. Soc. ͑p-hydroxybenzoic acid͒; 1954, 3634. ͓ ͔ C7H6O3; 99-96-7 ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. Variables: Prepared by: ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, t/ °C=25 A. Goto and H. Miyamoto ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of 4-hydroxybenzoic acid in benzene at 25 °C Solubility of salicylic acid in n-hexane at 25 °C

Molar volume Solubility of solvent Solubility 4 3 / −1 10 x1 10 m1 mol kg / 3 −1 v2 cm mol 100x1 4.8 3.4 89.4 0.33ϫ10−2

Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 13 for the The experimental details are given in the compilation of Ref. 19 for the salicylic acid–n-heptane system in Sec. 2.1.1.1. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: Source and Purity of Materials: n-Hexane ͑ACS͒ was of reagent grade and used without further The details are given in the compilation of Ref. 19 for the purification. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Salicylic acid was recrystallized from hot water. Estimated Errors: Estimated Errors: Nothing specified. Nothing specified.

2.1.4. Data for hydroxybenzoic acid–organic Components: Original Measurements: ͑ ͒ 13 compound systems 1 Benzoic acid, 2-hydroxy- H.-L. Fung and T. Higuchi, J. ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑ ͒ ͑ ͒ 2.1.4.1. Salicylic acid 2 n-Decane decane ;C10H22; ͓124-18-5͔

Components: Original Measurements: Variables: Prepared by: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. t/ °C=25 A. Goto and R. Goto ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͒ ͓ ͔ ͑ ͒ acid ;C6H6; 69-72-7 1935 . ͑ ͒ ͑ ͒ Solubility of salicylic acid in n-decane at 25 °C 2 n-Hexane hexane ;C6H14; ͓110-54-3͔ Solubility Variables: Prepared by: 104x 103m /mol kg−1 t/ °C=28 A. Goto and H. Miyamoto 1 1 6.2 3.2 The solubility of salicylic acid in n-hexane at 28 °C was 3 reported as 10 x1 =1.11. Auxiliary Information

Auxiliary Information Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 13 for the Methods/Apparatus/Procedure: salicylic acid–n-heptane system in Sec. 2.1.1.1. The experimental details are given in the compilation of Ref. 16 for the Source and Purity of Materials: salicylic acid–ethanol system in Sec. 2.1.2.1. Decane of reagent grade was purified by passing the solvent through a Source and Purity of Materials: column of silica gel followed by distillation from sodium under reduced Salicylic acid was twice recrystallized. pressure. n-Hexane was purified by distillation. Salicylic acid was recrystallized from hot water. Estimated Errors: Estimated Errors: Solubility: Three readings were taken in each case and the mean was Nothing specified. taken. It was found by blank experiments ͑on solute-free solvent͒ that this method gave reliable results; the precision being less than 0.5%. Temperature: Nothing specified. Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. Components: Original Measurements: acid͒;CH O ; ͓69-72-7͔ ͑ ͒ 13 7 6 3 1 Benzoic acid, 2-hydroxy- H.-L. Fung and T. Higuchi, J. ͑2͒ n-Dodecane ͑dodecane͒; ͑ ͑ ͒ o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 1971 . C H ; ͓112-40-3͔ ͒ ͓ ͔ 12 26 acid ;C7H6O3; 69-72-7 ͑ ͒ ͑ ͒ 2 n-Hexane hexane ;C6H14; Variables: Prepared by: ͓ ͔ 110-54-3 t/ °C=25 A. Goto and R. Goto Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of salicylic acid in n-dodecane at 25 °C Solubility of salicylic acid in isooctane at 25 °C

Solubility Solubility

4 3 / −1 4 3 / −1 10 x1 10 m1 mol kg 10 x1 10 m1 mol kg

6.4 2.8 3.8 2.3

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 13 for the The experimental details are given in the compilation of Ref. 13 for the salicylic acid–n-heptane system in Sec. 2.1.1.1. salicylic acid–n-heptane system in Sec. 2.1.1.1. Source and Purity of Materials: Source and Purity of Materials: Dodecane of reagent grade was passed through a column of silica gel. Isooctane of reagent grade was distilled over sodium. Salicylic acid was Salicylic acid was recrystallized from hot water. recrystallized from hot water. Estimated Errors: Estimated Errors: Nothing speciﬁed. Nothing speciﬁed.

Components: Original Measurements: Components: Original Measurements: 21 ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͑1͒ Benzoic acid, 2-hydroxy- P.A. Ongley, J. Chem. Soc. ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. ͑o-hydroxybenzoic acid, salicylic 1954, 3634. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 acid ;C7H6O3; 69-72-7 ͑ ͒ ͑2͒ n-Hexadecane ͑hexadecane͒; 2 Cyclohexane; C6H12; ͓ ͔ ͓ ͔ C16H34; 544-76-3 110-82-7

Variables: Prepared By: Variables: Prepared By: t/ °C=25 A. Goto and R. Goto t/ °C=25 A. Goto and H. Miyamoto

Solubility of salicylic acid in n-hexadecane at 25 °C Solubility of salicylic acid in cyclohexane at 25 °C

Solubility Solubility

4 3 / −1 3 / −3 10 x1 10 m1 mol kg 10 c1 mol dm pS ͑compiler͒ 10.4 3.0 2.192 6.427

Auxiliary Information pS: The negative logarithm of the concentration in the saturated solutions in mol/l. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 13 for the Auxiliary Information salicylic acid–n-heptane system in Sec. 2.1.1.1. Source and Purity of Materials: Methods/Apparatus/Procedure: n-Hexadecane of reagent grade was purified by passing the solvent The experimental details are given in the compilation of Ref. 21 for the through a column of silica gel followed by distillation from sodium under salicylic acid–benzene system in Sec. 2.1.3.1. reduced pressure. Source and Purity of Materials: Salicylic acid was recrystallized from hot water. The details are given in the compilation of Ref. 21 for the salicylic Estimated Errors: acid–benzene system in Sec. 2.1.3.1. Nothing specified. Estimated Errors: Nothing specified.

Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. Components: Original Measurements: ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. ͑ ͒ ͒ ͓ ͔ 2 2,2,4-Trimethylpentane acid ;C7H6O3; 69-72-7 ͑ ͒ ͓ ͔ ͑ ͒ isooctane ;C8H18; 540-84-1 2 Cyclohexane; C6H12; ͓110-82-7͔ Variables: Prepared By: t/ °C=25 A. Goto and R. Goto Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of salicylic acid in cyclohexane at 25 °C Auxiliary Information

Solubility Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 16 for the 4 3 / −1 10 x1 10 m1 mol kg salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: 4.3 4.0 Salicylic acid was twice recrystallized. Organic solvents were purified by distillation. Auxiliary Information Estimated Errors: Solubility: Three readings were taken in each case and the mean was Methods/Apparatus/Procedure: taken. It was found by blank experiments ͑on solute-free solvent͒ that this The experimental details are given in the compilation of Ref. 13 for the method gave reliable results; the precision being less than 0.5%. salicylic acid–n-heptane system in Sec. 2.1.1.1. Temperature: Nothing specified. Source and Purity of Materials: Cyclohexane of reagent grade was distilled over phosphorus pentaoxide. Salicylic acid was recrystallized from hot water. Components: Original Measurements: Estimated Errors: ͑1͒ Benzoic acid, 2-hydroxy- 21P.A. Ongley, J. Chem. Soc. Nothing specified. ͑o-hydroxybenzoic acid, salicylic 1954, 3634. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑2͒ Trichloromethane ͑ ͒ ͓ ͔ Components: Original Measurements: chloroform ; CHCl3; 67-66-3 ͑1͒ Benzoic acid, 2-hydroxy- 24W. Herz and W. Rathmann, Z. Variables: Prepared by: ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. ͒ ͓ ͔ t/ °C=25 A. Goto and H. Miyamoto acid ;C7H6O3; 69-72-7 ͑2͒ Trichloromethane ͑ ͒ ͓ ͔ chloroform ; CHCl3; 67-66-3 Solubility of salicylic acid in chloroform at 25 °C Variables: Prepared by: Solubility t/ °C=25 E. Königsberger and L.-C. Königsberger / −3 c1 mol dm pS ͑compiler͒

The solubility of salicylic acid in chloroform at 25 °C 0.680 0.2089 / −3 was reported as c1 mol dm =0.157. pS: The negative logarithm of the concentration in the saturated solutions in Auxiliary Information mol/l.

Methods/Apparatus/Procedure: Auxiliary Information Excess solid and solvents were shaken in a thermostat at 25 °C until saturation ͑time not speciﬁed͒. After the solid phase settled, a certain Methods/Apparatus/Procedure: volume of the clear liquid was pipetted, in which the acid concentration The experimental details are given in the compilation of Ref. 21 for the was determined by titration ͑details not given͒. salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: Source and Purity of Materials: Not stated. The details are given in the compilation of Ref. 21 for the salicylic Estimated Errors: acid–benzene system in Sec. 2.1.3.1. Not stated. Estimated Errors: Nothing speciﬁed.

Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. Components: Original Measurements: ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͒ ͓ ͔ ͑ ͒ ͑ ͑ ͒ acid ;C7H6O3; 69-72-7 1935 . o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 1971 . ͑ ͒ ͒ ͓ ͔ 2 Trichloromethane acid ;C7H6O3; 69-72-7 ͑ ͒ ͓ ͔ ͑ ͒ chloroform ; CHCl3; 67-66-3 2 Trichloromethane ͑ ͒ ͓ ͔ chloroform ; CHCl3; 67-66-3 Variables: Prepared by: t/ °C=28 A. Goto and H. Miyamoto Variables: Prepared by: t/ °C=30 A. Goto and R. Goto

The solubility of salicylic acid in chloroform at 28 °C 2 was reported as 10 x1 =2.679.

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Solubility of salicylic acid in chloroform at 30 °C Auxiliary Information

Solubility Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 16 for the a / −1 salicylic acid–ethanol system in Sec. 2.1.2.1. x1 m1 mol kg Source and Purity of Materials: −3 −1 1.3ϫ10 1.6ϫ10 Salicylic acid was twice recrystallized. Organic solvent was purified by distillation. aThe value was estimated by the author from A. Seidell, Solubilities of Estimated Errors: ͑ ͒ Organic Compounds, Vol. II, 3rd Ed. Van Nostrand, New York, 1941 . Solubility: Three readings were taken in each case and the mean was taken. It was found by blank experiments ͑on solute-free solvent͒ that this Auxiliary Information method gave reliable results; the precision being less than 0.5%. Methods/Apparatus/Procedure: Temperature: Nothing specified. The experimental details are given in the compilation of Ref. 13 for the salicylic acid–n-heptane system in Sec. 2.1.1.1. Source and Purity of Materials: Components: Original Measurements: Salicylic acid was recrystallized in hot water. ͑1͒ Benzoic acid, 2-hydroxy- 21P.A. Ongley, J. Chem. Soc. Chloroform was washed with distilled water five to six times, dried over ͑o-hydroxybenzoic acid, salicylic 1954, 3634. ͒ ͓ ͔ powdered calcium chloride overnight, filtered, and distilled over acid ;C7H6O3; 69-72-7 phosphorous pentoxide. ͑2͒ Methane, tetrachloro- Estimated Errors: ͑tetrachloromethane, carbon ͒ ͓ ͔ Not stated. tetrachloride ;CCl4; 56-23-5 Variables: Prepared by: t/ °C=25 A. Goto and H. Miyamoto Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 24W. Herz and W. Rathmann, Z. ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. Solubility of salicylic acid in carbon tetrachloride at 25 °C ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑2͒ Methane, tetrachloro- Solubility ͑tetrachloromethane, carbon ͒ ͓ ͔ / −3 tetrachloride ;CCl4; 56-23-5 c1 mol dm pS ͑compiler͒ Variables: Prepared by: t/ °C=25 E. Königsberger and L.-C. 1.644 0.02270 Königsberger pS: The negative logarithm of the concentration in the saturated solutions in mol/l. The solubility of salicylic acid in carbon tetrachloride at Auxiliary Information / −3 25 °C was reported as c1 mol dm =0.030. Methods/Apparatus/Procedure: Auxiliary Information The experimental details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. Methods/Apparatus/Procedure: Source and Purity of Materials: The experimental details are given in the compilation of Ref. 24 for the binary salicylic acid–chloroform system earlier in this section. The details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: Estimated Errors: Not stated. Nothing specified. Estimated Errors: Not stated.

Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1935 . ͑2͒ Methane, tetrachloro- ͑tetrachloromethane, carbon ͒ ͓ ͔ tetrachloride ;CCl4; 56-23-5

Variables: Prepared by: t/ °C=28 A. Goto and H. Miyamoto

The solubility of salicylic acid in carbon tetrachloride at

28 °C was reported as 100x1 =0.3803.

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 24W. Herz and W. Rathmann, Z. ͑1͒ Benzoic acid 2-hydroxy- 24W. Herz and W. Rathmann, Z. ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 acid ;C7H6O3; 69-72-7 ͑2͒ Ethane, 1,1,2,2-tetrachloro- ͑2͒ Ethene, trichloro- ͑1,1,2,2-tetrachloroethane, ͑1,1,2-trichloroethene, ͒ ͒ tetrachloroethane ;C2H2Cl4; trichloroethylene ;C2HCl3; ͓79-34-5͔ ͓79-01-6͔

Variables: Prepared by: Variables: Prepared by: t/ °C=25 E. Königsberger and L.-C. t/ °C=25 E. Königsberger and L.-C. Königsberger Königsberger

The solubility of salicylic acid in tetrachloroethane at The solubility of salicylic acid in trichloroethylene at / −3 / −3 25 °C was reported as c1 mol dm =0.151. 25 °C was reported as c1 mol dm =0.110.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 24 for the The experimental details are given in the compilation of Ref. 24 for the salicylic acid–chloroform system earlier in this section. salicylic acid–chloroform system earlier in this section. Source and Purity of Materials: Source and Purity of Materials: Not stated. Not stated. Estimated Errors: Estimated Errors: Not stated. Not stated.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 24W. Herz and W. Rathmann, Z. ͑1͒ Benzoic acid, 2-hydroxy- 25D.H. Wester and A. Bruins, ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. ͑o-hydroxybenzoic acid, salicylic Pharm. Weekblad. 51,1443 ͒ ͓ ͔ ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 acid ;C7H6O3; 69-72-7 1914 . ͑2͒ Ethane, pentachloro- ͑2͒ Ethene, trichloro- ͑1,1,1,2,2-pentachloroethane, ͑1,1,2-trichloroethene, ͒ ͒ pentachloroethane ;C2HCl5; trichloroethylene ;C2HCl3; ͓76-01-7͔ ͓79-01-6͔

Variables: Prepared by: Variables: Prepared by: t/ °C=25 E. Königsberger and L.-C. t/ °C=15 E. Königsberger and L.-C. Königsberger Königsberger

The solubility of salicylic acid in pentachloroethane at Solubility of salicylic acid in trichloroethylene at 15 °C / −3 25 °C was reported as c1 mol dm =0.077. Solubility

Auxiliary Information / −1 m1 mol kg ͑ ͒ 100w1 compiler Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 24 for the 0.757 0.0548 salicylic acid–chloroform system earlier in this section. Source and Purity of Materials: Auxiliary Information Not stated. Estimated Errors: Methods/Apparatus/Procedure: Not stated. A large excess of the solid substance was continuously shaken with the solvent in a water bath of 30 °C for 1 h. Then, the solution was brought to a cellar with a constant temperature of 15 °C and, after keeping it there under repeated shaking for at least 48 h, the quantity of the dissolved substance was determined ͑details not speciﬁed͒. The undissolved substance was used for a second solubility experiment, and then the remaining substance for a third one. The result of the ﬁrst experiment was discarded so that the value reported is the average of the other two determinations. Source and Purity of Materials: Not stated.

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Estimated Errors: Auxiliary Information Solubility: Nothing specified. Temperature: Uncertainty of Ϯ2K. Methods/Apparatus/Procedure: The solubility of salicylic acid in water was determined in PawlewskiЉs apparatus ͓B. Pawlewski, Ber. Dtsch. Chem. Ges. 32, 1040 ͑1899͔͒. The salicylic acid content was determined with standardized sodium hydroxide Components: Original Measurements: solution. The water and salicylic acid were placed in the test tube. The 24 ͑1͒ Benzoic acid 2-hydroxy- W. Herz and W. Rathmann, Z. tube was equipped with a condenser and a siphon glass tube, and ͑o-hydroxybenzoic acid, salicylic Elektrochem. 19, 887 ͑1913͒. connected with a weighing bottle equipped with a condenser. The ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 apparatus was placed into a large thermostated glass beaker to mix the ͑2͒ Ethene, tetrachloro- water and salicylic acid, and air was bubbled through the mixture. After ͑1,1,2,2-tetrachloroethene, equilibrium was established, the saturated solution in the tube was filtered ͒ tetrachloroethylene ;C2Cl4; into the weighing tube through the siphon tube equipped with a cotton ͓127-18-4͔ wool filter. The apparatus was removed from the large beaker, cooled and/or dried, and the bottle was weighed. Salicylic acid was determined Variables: Prepared by: gravimetrically after evaporation of the solvent. / t °C=25 E. Königsberger and L.-C. Source and Purity of Materials: Königsberger Salicylic acid was recrystallized before use. Estimated Errors: Ϯ The solubility of salicylic acid in tetrachloroethylene at Solubility: Precision of 1.5%. Temperature: Nothing specified. / −3 25 °C was reported as c1 mol dm =0.080.

Components: Original Measurements: The solubility of salicylic acid in methanol at 28 °C was ͑ ͒ 26 1 Benzoic acid, 2-hydroxy- E. Savorro, Atti accad. sci. reported as x =0.1252. ͑o-hydroxybenzoic acid, salicylic Torino 48, 948 ͑1914͓͒Chem. 1 ͒ ͓ ͔ ͑ ͔͒ acid ;C7H6O3; 69-72-7 Abs. 8, 340 1914 . Auxiliary Information ͑2͒ Methyl alcohol ͑methanol͒; ͓ ͔ CH4O; 67-56-1 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 16 for the Variables: Prepared by: salicylic acid–ethanol system in Sec. 2.1.2.1. t/ °C=15 A. Goto and H. Miyamoto Source and Purity of Materials: Salicylic acid was twice recrystallized. Solubility of salicylic acid in methanol at 15 °C Methanol was puriﬁed by distillation. Estimated Errors: Solubilitya Solubility: Three readings were taken in each case and the mean was taken. It was found by blank experiments ͑on solute-free solvent͒ that this / −1 100w1 m1 mol kg x1 method gave reliable results; the precision being less than 0.5%. Original data ͑compiler͒ ͑compiler͒ ͑compiler͒ Temperature: Nothing speciﬁed. 398.66 28.503 2.8863 0.0846

a In the original paper, the solubility was given as grams per 1000 g of Components: Original Measurements: methanol. ͑1͒ Benzoic acid, 2-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑o-hydroxybenzoic acid, salicylic 91 ͑1961͒. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑2͒ Methyl alcohol ͑methanol͒; ͓ ͔ CH4O; 67-56-1

Variables: Prepared by: t/ °C=20.0 P.Scharlin

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Solubility of salicylic acid in methanol at 20.0 °C Components: Original Measurements: 16 Solubilitya ͑1͒ Benzoic acid, 2-hydroxy- P.G. Desai and A.M. Patel, J. ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12,131 ␥ / −3 / −3 ͒ ͓ ͔ ͑ ͒ 1 gdm c1 mol dm acid ;C7H6O3; 69-72-7 1935 . ͑compiler͒ ͑compiler͒ ͑2͒ 1-Propanol ͑propan-1-ol, ͒ propyl alcohol ;C3H8O; 331.3 2.398 ͓71-23-8͔

aIn the original paper, the solubility was given as grams per 100 ml of Variables: Prepared by: solution. t/ °C=28 A. Goto and H. Miyamoto

Auxiliary Information The solubility of salicylic acid in 1-propanol at 28 °C Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 15 for the was reported as x1 =0.1438. salicylic acid–ethanol system in Sec. 2.1.2.1. Auxiliary Information Source and Purity of Materials: Salicylic acid was obtained from Shuchardt, DAB6. Methods/Apparatus/Procedure: Methanol: source and purity not given; relative density The experimental details are given in the compilation of Ref. 16 for the d=0.792 ͑20 °C/4°C͒. salicylic acid–ethanol system in Sec. 2.1.2.1. Estimated Errors: Source and Purity of Materials: Nothing specified. The value given was the mean of three independent Salicylic acid was twice recrystallized. determinations. 1-Propanol was purified by distillation. Estimated Errors: Solubility: Three readings were taken in each case and the mean was Components: Original Measurements: taken. It was found by blank experiments ͑on solute-free solvent͒ that this ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and method gave reliable results; the precision being less than 0.5%. ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, Temperature: Nothing specified. ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . ͑2͒ Methyl alcohol ͑methanol͒; CH O; ͓67-56-1͔ 4 Components: Original Measurements: ͑ ͒ 15 Variables: Prepared by: 1 Benzoic acid, 2-hydroxy- E. Bergroth, Farm. Aikak. 70, ͑ ͑ ͒ t/ °C=30.6 A. Goto and R. Goto o-hydroxybenzoic acid, salicylic 91 1961 . ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑2͒ 1-Propanol ͑propan-1-ol, ͒ Solubility of salicylic acid in methanol at 30.6 °C propyl alcohol ;C3H8O; ͓71-23-8͔ Solubilitya Variables: Prepared by: ␥ / −3 / −3 / Dielectric constant 1 gdm c1 mol dm t °C=20.0 P.Scharlin of solvent ͑compiler͒ ͑compiler͒

32.6 299 2.16 Solubility of salicylic acid in 1-propanol at 20.0 °C

aIn the original paper, the solubility was given as mg/ml of solution. Solubilitya

␥ / −3 / −3 Auxiliary Information 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the 222.5 1.611 salicylic acid–ethanol system in Sec. 2.1.2.1. aIn the original paper, the solubility was given as grams per 100 ml of The dielectric constant of the solvent was measured by a resonance method at 25 °C. solution. Source and Purity of Materials: Auxiliary Information Methanol was purified by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. Methods/Apparatus/Procedure: Estimated Errors: The experimental details are given in the compilation of Ref. 15 for the Solubility: Nothing specified. salicylic acid–ethanol system in Sec. 2.1.2.1. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric Source and Purity of Materials: constant͒. Salicylic acid was obtained from Shuchardt, DAB6. 1-Propanol: source and purity not given; relative density d=0.804 ͑20 °C/4°C͒. Estimated Errors: Nothing specified. The value given is the mean of three independent determinations.

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree, Jr., J. ͒ ͓ ͔ ͑ ͒ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 1349 1964 . acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 ͑2͒ 1-Propanol ͑propan-1-ol, ͑2͒ 1-Pentanol ͑pentan-1-ol, ͑1999͒. ͒ ͒ propyl alcohol ;C3H8O; pentyl alcohol ;C5H12O; ͓71-23-8͔ ͓71-41-0͔

Variables: Prepared by: Variables: Prepared by: t/ °C=30.6 A. Goto and R. Goto T/K=298.15 A. Goto and H. Miyamoto

Solubility of salicylic acid in 1-propanol at 30.6 °C The solubility of salicylic acid in 1-pentanol at 298.15 K

Solubilitya was reported as x1 =0.1611.

␥ / −3 / −3 Auxiliary Information Dielectric constant 1 gdm c1 mol dm of solvent ͑compiler͒ ͑compiler͒ Methods/Apparatus/Procedure: 20.1 287 2.08 The experimental details are given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. a In the original paper, the solubility was given as mg/ml of solution. Source and Purity of Materials: Salicylic acid was described in the compilation of Ref. 18 for the salicylic Auxiliary Information acid–1-butanol system in Sec. 2.1.2.1. ͑ ͒ Methods/Apparatus/Procedure: 1-Pentanol Aldrich, 99+% was stored over molecular sieves before use. The experimental details are given in the compilation of Ref. 17 for the Estimated Errors: salicylic acid–ethanol system in Sec. 2.1.2.1. Solubility: Nothing specified. Ϯ Source and Purity of Materials: Temperature: Precision of 0.1 °C. The solvent was purified by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. Estimated Errors: Components: Original Measurements: Solubility: Nothing specified. ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree, Jr., J. ͒ ͓ ͔ constant͒. acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͑1999͒. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

Components: Original Measurements: Variables: Prepared by: 18 ͑1͒ Benzoic acid, 2-hydroxy- K.M. De Fina, T.L. Sharp, L.E. T/K=298.15 A. Goto and H. Miyamoto ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 ͑2͒ 1-Propanol ͑propan-1-ol, ͑1999͒. The solubility of salicylic acid in 1-octanol at 298.15 K ͒ propyl alcohol ;C3H8O; ͓71-23-8͔ was reported as x1 =0.2143.

Variables: Prepared by: Auxiliary Information T/K=298.15 A. Goto and H. Miyamoto Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 18 for the The solubility of salicylic acid in 1-propanol at salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: 298.15 K was reported as x1 =0.1636. Salicylic acid was described in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. Auxiliary Information 1-Octanol ͑Aldrich, 99+%, anhydrous͒ was stored over molecular sieves Methods/Apparatus/Procedure: before use. The experimental details are given in the compilation of Ref. 18 for the Estimated Errors: salicylic acid–1-butanol system in Sec. 2.1.2.1. Solubility: Nothing speciﬁed. Source and Purity of Materials: Temperature: Precision of Ϯ0.1 °C. Salicylic acid was described in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. 1-Propanol ͑Aldrich, 99+%, anhydrous͒ was stored over molecular sieves before use. Estimated Errors: Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C.

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree, Jr., J. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree, Jr., J. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 ͑2͒ 2-Propanol ͑propan-2-ol, ͑1999͒. ͑2͒ 2-Methyl-1-propanol ͑1999͒. ͒ ͑ isopropyl alcohol ;C3H8O; 2-methylpropan-1-ol, isobutyl ͓ ͔ ͒ ͓ ͔ 67-63-0 alcohol ;C4H10O; 78-83-1

Variables: Prepared by: Variables: Prepared by: T/K=298.15 A. Goto and H. Miyamoto T/K=298.15 A. Goto and H. Miyamoto

The solubility of salicylic acid in 2-propanol at The solubility of salicylic acid in 2-methyl-1-propanol at

298.15 K was reported as x1 =0.1789. 298.15 K was reported as x1 =0.1430.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 18 for the The experimental details are given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: Salicylic acid was described in the compilation of Ref. 18 for the salicylic Salicylic acid was described in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. acid–1-butanol system in Sec. 2.1.2.1. 2-Propanol ͑Aldrich, 99+%, anhydrous͒ was stored over molecular sieves 2-Methyl-1-propanol ͑Aldrich, 99.5%, anhydrous͒ was stored over before use. molecular sieves before use. Estimated Errors: Estimated Errors: Solubility: Nothing speciﬁed. Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C. Temperature: Precision of Ϯ0.1 °C.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 ͑2͒ 2-Butanol ͑butan-2-ol, ͑1999͒. ͑2͒ 2-Methyl-2-propanol ͑1999͒. ͒ ͑ sec-butyl alcohol ;C4H10O; 2-methylpropan-2-ol, tert-butyl ͓ ͔ ͒ ͓ ͔ 78-92-2 alcohol ;C4H10O; 75-65-0

Variables: Prepared by: Variables: Prepared by: T/K=298.15 A. Goto and H. Miyamoto T/K=298.15 A. Goto and H. Miyamoto

The solubility of salicylic acid in 2-butanol at 298.15 K The solubility of salicylic acid in 2-methyl-2-propanol at

was reported as x1 =0.1869. 298.15 K was reported as x1 =0.2193.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 18 for the The experimental details are given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: Salicylic acid was described in the compilation of Ref. 18 for the salicylic Salicylic acid was described in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. acid–1-butanol system in Sec. 2.1.2.1. 2-Butanol ͑Aldrich, 99+ %, anhydrous͒ was stored over molecular sieves 2-Methyl-2-propanol ͑Arco Chemical Company, 99+%͒ was stored over before use. molecular sieves before use. Estimated Errors: Estimated Errors: Solubility: Nothing speciﬁed. Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C. Temperature: Precision of Ϯ0.1 °C.

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Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and Methods/Apparatus/Procedure: ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, The experimental details are given in the compilation of Ref. 17 for the ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . salicylic acid–ethanol system in Sec. 2.1.2.1. ͑ ͒ 2 Cyclohexanol; C6H12O; Source and Purity of Materials: ͓ ͔ 108-93-0 Benzyl alcohol was puriﬁed by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 Variables: Prepared by: and 5. t/ °C=30.6 A. Goto and R. Goto Estimated Errors: Solubility: Nothing speciﬁed. Solubility of salicylic acid in cyclohexanol at 30.6 °C Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒. Solubilitya

Dielectric constant ␥ /gdm−3 c /mol dm−3 1 1 Components: Original Measurements: of solvent ͑compiler͒ ͑compiler͒ ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and 15.0 217 1.57 ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . aIn the original paper, the solubility was given as mg/ml of solution. ͑2͒ Organic solvents: 1,2-Propanediol Auxiliary Information ͑propane-1,2-diol, propylene ͒ ͓ ͔ glycol ;C3H8O2; 57-55-6 Methods/Apparatus/Procedure: 1,2-Ethanediol ͑ethan-1,2-diol, ͒ The experimental details are given in the compilation of Ref. 17 for the ethylene glycol ;C2H6O2; salicylic acid–ethanol system in Sec. 2.1.2.1. ͓107-21-1͔ Source and Purity of Materials: 1,2,3-Propanetriol The solvent was puriﬁed by the method described in A. Weissberger et al., ͑propane-1,2,3-triol, glycerol͒; ͓ ͔ Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. C3H8O3; 56-81-5 Estimated Errors: Variables: Prepared by: Solubility: Nothing speciﬁed. t/ °C=30.6 A. Goto and R. Goto Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒. Solubility of salicylic acid in diols and triol at 30.6 °C

a Components: Original Measurements: Solubility ͑ ͒ 17 1 Benzoic acid, 2-hydroxy- A.N. Paruta, B.J. Sciarrone, and ␥ / −3 / −3 ͑ 1 gdm c1 mol dm o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͑ ͒ ͑ ͒ ͒ ͓ ͔ ͑ ͒ Solvent Dielectric constant of solvent compiler compiler acid ;C7H6O3; 69-72-7 1349 1964 . ͑ ͒ 2 Benzyl alcohol Propylene glycol 33.0 118 0.854 ͑ ͒ phenylmethanol ;C7H8O; Ethylene glycol 37.7 42 0.30 ͓100-51-6͔ Glycerol 42.5 15 0.11 Variables: Prepared by: aIn the original paper, the solubility was given as mg/ml of solution. t/ °C=30.6 A. Goto and R. Goto Auxiliary Information Solubility of salicylic acid in benzyl alcohol at 30.6 °C Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the Solubilitya salicylic acid–ethanol system in Sec. 2.1.2.1. ␥ / −3 / −3 1 gdm c1 mol dm Source and Purity of Materials: Dielectric constant of solvent ͑compiler͒ ͑compiler͒ The solvents were puriﬁed by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 13.0 203 1.47 and 5. Estimated Errors: aIn the original paper, the solubility was given as mg/ml of solution. Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒.

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Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 20J. Walker and J.K. Wood, J. Methods/Apparatus/Procedure: ͑o-hydroxybenzoic acid, salicylic Chem. Soc. Trans. 73, 618 Not stated. ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1898 . Source and Purity of Materials: ͑ ͒ 2 Ethane, 1,1Ј-oxybis- Not stated. ͑ ͒ ethoxyethane, diethyl ether ; Estimated Errors: C H O; ͓60-29-7͔ 4 10 Not stated. Variables: Prepared by: t/ °C=17 A. Goto and H. Miyamoto Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. Solubility of salicylic acid in diethyl ether at 17 °C ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͒ ͓ ͔ a acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 Solubility ͑2͒ Butane, 1,1Ј-oxybis- ͑1999͒. ͑ n ͒ ␥ /gdm−3 c /mol dm−3 2-butoxy ethanol, -butyl ether ; 1 1 H O; ͓142-96-1͔ Original data ͑compiler͒ ͑compiler͒ C8 18 Variables: Prepared by: 23.4 234 1.69 T/K=298.15 A. Goto and H. Miyamoto aIn the original paper, the solubility was given as grams of salicylic acid per 3 ␥ 100 cm of diethyl ether solution at 17 °C. The mass concentration, 1 / The solubility of salicylic acid in n-dibutyl ether at =m1 V, was calculated by the compiler, where m1 is the mass of component 1 and V is the total volume of solution. 298.15 K was reported as x1 =0.091 85.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the The experimental details are given in the compilation of Ref. 18 for the salicylic acid–benzene system in Sec. 2.1.2.1. salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: No information was given. The details are given in the compilation of Ref. 18 for the salicylic Estimated Errors: acid–1-butanol system in Sec. 2.1.2.1. ͑ ͒ Nothing speciﬁed. n-Dibutyl ether Aldrich, 99 % was stored over molecular sieves before use. Estimated Errors: Solubility: Nothing speciﬁed. Components: Original Measurements: Temperature: Precision of Ϯ0.1 °C. ͑1͒ Benzoic acid, 2-hydroxy- 13H.-L. Fung and T. Higuchi, J. ͑o-hydroxybenzoic acid, salicylic Pharm. Sci. 60, 1782 ͑1971͒. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 ͑2͒ Ethane, 1,1Ј-oxybis- Components: Original Measurements: ͑ethoxyethane, diethyl ether͒; ͑1͒ Benzoic acid, 2-hydroxy- 20J. Walker and J.K. Wood, J. ͓ ͔ ͑ C4H10O; 60-29-7 o-hydroxybenzoic acid, salicylic Chem. Soc. Trans. 73,618 ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1898 . Variables: Prepared by: ͑2͒ 2-Propanone ͑propan-2-one, / ͒ ͓ ͔ t °C=20 A. Goto and H. Miyamoto acetone ;C3H6O; 67-64-1

Variables: Prepared by: Solubility of salicylic acid in diethyl ether at 20 °C t/ °C=23 A. Goto and H. Miyamoto

Solubility Solubility of salicylic acid in acetone at 23 °C / −1 x1 m1 mol kg Solubilitya 2.5ϫ10−1a 2.4b ␥ /gdm−3 c /mol dm−3 a 1 1 The value was estimated by the author from A. Seidell, Solubilities of Original data ͑compiler͒ ͑compiler͒ Organic Compounds, 3rd Ed. ͑Van Nostrand, New York, 1941͒, Vol. II. bThe value was estimated by the author from The Merck Index, 8th ed. 31.3 313 2.27 ͑Merck, Rahway, NJ, 1968͒. aIn the original paper, the solubility was given as grams of salicylic acid per 3 ␥ / 100 cm of acetone solution at 23 °C. The mass concentration, 1 =m1 V,

was calculated by the compiler, where m1 is the mass of component 1 and V is the total volume of solution.

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 20 for the The experimental details are given in the compilation of Ref. 15 for the salicylic acid–benzene system in Sec. 2.1.3.1. salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: No information was given. Salicylic acid was obtained from Shuchardt, DAB6. Estimated Errors: Acetone: source and purity not given; relative density d=0.791 Nothing speciﬁed. ͑20 °C/4°C͒ Estimated Errors: Nothing speciﬁed. The value given is the mean of three independent Components: Original Measurements: determinations. ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12, 131 ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1935 . Components: Original Measurements: ͑2͒ 2-Propanone ͑propan-2-one, ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . Variables: Prepared by: ͑2͒ 2-Propanone ͑propan-2-one, t/ °C=28 A. Goto and H. Miyamoto ͒ ͓ ͔ acetone ;C3H6O; 67-64-1

Variables: Prepared by: The solubility of salicylic acid in acetone at 28 °C was t/ °C=30.6 A. Goto and R. Goto

reported as x1 =0.1906. Solubility of salicylic acid in acetone at 30.6 °C Auxiliary Information a Methods/Apparatus/Procedure: Solubility The experimental details are given in the compilation of Ref. 16 for the ␥ / −3 / −3 Dielectric constant 1 gdm c1 mol dm salicylic acid–ethanol system in Sec. 2.1.2.1. of solvent ͑compiler͒ ͑compiler͒ Source and Purity of Materials: Salicylic acid was twice recrystallized. 24.3 377 2.73 Acetone was purified by distillation at its known boiling point. a / Estimated Errors: In the original paper, the solubility was given as mg ml of solution. Solubility: Three readings were taken in each case and the mean was Auxiliary Information taken. It was found by blank experiments ͑on solute-free solvent͒ that this method gave reliable results; the precision being less than 0.5 %. Methods/Apparatus/Procedure: Temperature: Nothing specified. The experimental details are given in the compilation of Ref. 17 for the salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: Components: Original Measurements: The solvent was purified by the method described in A. Weissberger et al., ͑1͒ Benzoic acid, 2-hydroxy- 15E. Bergroth, Farm. Aikak. 70, Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. ͑o-hydroxybenzoic acid, salicylic 91 ͑1961͒. Estimated Errors: ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Solubility: Nothing specified. ͑2͒ 2-Propanone ͑propan-2-one, Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 constant͒. Variables: Prepared by: t/ °C=20 P.Scharlin Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. Solubility of salicylic acid in acetone at 20 °C ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 a Solubility ͑2͒ 2-Propanone ͑propan-2-one, ͑1999͒. acetone͒;CH O; ͓67-64-1͔ ␥ / −3 / −3 3 6 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ Variables: Prepared by: T/K=298.15 A. Goto and H. Miyamoto 294.4 2.131

a In the original paper, the solubility was given as grams per 100 ml of The solubility of salicylic acid in acetone at 298.15 K solution. was reported as x1 =0.1817.

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 18 for the The experimental details are given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: Salicylic acid is given in the compilation of Ref. 18 for the salicylic Salicylic acid is given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. acid–1-butanol system in Sec. 2.1.2.1. Acetone ͑Aldrich, HPLC, 99.9+%͒ was stored over molecular sieves 2-Butanone ͑Aldrich, HPLC, 99.5 %͒ was stored over molecular sieves before use. before use. Estimated Errors: Estimated Errors: Solubility: Nothing speciﬁed. Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C. Temperature: Precision of Ϯ0.1 °C.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑1͒ Benzoic acid, 2-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑o-hydroxybenzoic acid, salicylic 91 ͑1961͒. ͑o-hydroxybenzoic acid, salicylic 91 ͑1961͒. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 acid ;C7H6O3; 69-72-7 ͑2͒ 2-Butanone ͑butan-2-one, ͑2͒ 2-Pentanone ͑pentan-2-one, ͒ ͒ methyl ethyl ketone ;C4H8O; methyl propyl ketone ;C5H10O; ͓78-93-3͔ ͓107-87-9͔

Variables: Prepared by: Variables: Prepared by: t/ °C=20 P.Scharlin t/ °C=20 P.Scharlin

Solubility of salicylic acid in 2-butanone at 20 °C Solubility of salicylic acid in 2-pentanone at 20 °C

Solubilitya Solubilitya

␥ / −3 / −3 ␥ / −3 / −3 1 gdm c1 mol dm 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ ͑compiler͒ ͑compiler͒

235.6 1.706 209.2 1.515

aIn the original paper, the solubility was given as grams per 100 ml of aIn the original paper, the solubility was given as grams per 100 ml of solution. solution.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 15 for the The experimental details are given in the compilation of Ref. 15 for the salicylic acid–ethanol system in Sec. 2.1.2.1. salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: Source and Purity of Materials: Salicylic acid was obtained from Shuchardt, DAB6. Salicylic acid was obtained from Shuchardt, DAB6. 2-Butanone: source and purity not given; relative density d=0.805 2-Pentanone: source and purity not given; relative density ͑20 °C/4°C͒. d=0.812 ͑15 °C/15 °C͒. Estimated Errors: Estimated Errors: Nothing speciﬁed. The value given is the mean of three independent Nothing speciﬁed. The value given is the mean of three independent determinations. determinations.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. ͑1͒ Benzoic acid, 2-hydroxy- 18K. M. De Fina, T. L. Sharp, L. ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͑o-hydroxybenzoic acid, salicylic E. Roy, and W. E. Acree Jr., J. ͒ ͓ ͔ ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 ͑ ͒ ͑ ͒ ͑2͒ 2-Butanone ͑butan-2-one, ͑1999͒. 2 Cyclohexanone; C6H10O; 1999 . ͒ ͓ ͔ methyl ethyl ketone ;C4H8O; 108-94-1 ͓78-93-3͔ Variables: Prepared By: Variables: Prepared by: T/K=298.15 A. Goto and H. Miyamoto T/K=298.15 A. Goto and H. Miyamoto

The solubility of salicylic acid in cyclohexanone at The solubility of salicylic acid in 2-butanone at 298.15 K was reported as x1 =0.2301. 298.15 K was reported as x1 =0.1852.

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Auxiliary Information Components: Original Measurements: Methods/Apparatus/Procedure: ͑1͒ Benzoic acid, 2-hydroxy- 16P.G. Desai and A.M. Patel, J. The experimental details are given in the compilation of Ref. 18 for the ͑o-hydroxybenzoic acid, salicylic Indian Chem. Soc. 12,131 ͒ ͓ ͔ ͑ ͒ salicylic acid–1-butanol system in Sec. 2.1.2.1. acid ;C7H6O3; 69-72-7 1935 . Source and Purity of Materials: ͑2͒ Benzene derivatives: ͑ ͒ Salicylic acid is given in the compilation of Ref. 18 for the salicylic Benzene, methyl- toluene ; ͓ ͔ acid–1-butanol system in Sec. 2.1.2.1. C7H8; 108-88-3 Cyclohexanone ͑Aldrich, 99.8%͒ was stored over molecular sieves before Benzene, 1,3-dimethyl- ͑ ͒ use. 1,3-xylene, m-xylene ;C8H10; ͓108-38-3͔ Estimated Errors: Benzene, chloro- Solubility: Nothing speciﬁed. ͑chlorobenzene͒;CH Cl; Ϯ 6 5 Temperature: Precision of 0.1 °C. ͓108-90-7͔ Benzene, nitro- ͑nitrobenzene͒; ͓ ͔ C6H5NO2; 98-95-3 Components: Original Measurements: Variables: Prepared by: ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. / ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. t °C=28 A. Goto and H. Miyamoto ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 ͑2͒ Acetates: ͑1999͒. Solubility of salicylic acid in benzene derivatives at 28 °C Acetic acid, ethyl ester ͑ethyl ͒ ͓ ͔ acetate ;C4H8O2; 141-78-6 Solubility Acetic acid, butyl ester ͑butyl ͒ ͓ ͔ 2 acetate ;C6H12O2; 123-86-4 Solvent 10 x1

Variables: Prepared by: Toluene 0.6052 T/K=298.15 A. Goto and H. Miyamoto m-Xylene 0.6554 Chlorobenzene 0.7903 Nitrobenzene 2.509 Solubility of salicylic acid in acetates at 298.15 K

Solubility Auxiliary Information

Solvent x1 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 16 for the Ethyl acetate 0.1425 binary salicylic acid–ethanol system in Sec. 2.1.2.1. Butyl acetate 0.1363 Source and Purity of Materials: Salicylic acid was twice recrystallized. Auxiliary Information The organic solvents were purified by distillation. Estimated Errors: Methods/Apparatus/Procedure: Solubility: Three readings were taken in each case and the mean was The experimental details are given in the compilation of Ref. 18 for the taken. It was found by blank experiments ͑on solute-free solvent͒ that this salicylic acid–1-butanol system in Sec. 2.1.2.1. method gave reliable results; the precision being less than 0.5 %. Source and Purity of Materials: Temperature: Nothing specified. Salicylic acid is given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. ͑ ͒ ͑ Ethyl acetate Aldrich, HPLC, 99.9 % and butyl acetate Aldrich, HPLC, Components: Original Measurements: 99.7 %͒ were stored over molecular sieves before use. 27 ͑1͒ Benzoic acid, 2-hydroxy- C.R. Bailey, J. Chem. Soc. Estimated Errors: ͑o-hydroxybenzoic acid, salicylic Trans. 126, 1951 ͑1925͒. Solubility: Nothing specified. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Ϯ ͑ ͒ ͓ ͔ Temperature: Precision of 0.1 °C. 2 Phenol; C6H6O; 108-95-2

Variables: Prepared by: t/ °C=38.16–160.4 A. Goto and H. Miyamoto

Solubility of salicylic acid in phenol

Eutectic Duration of Temperature Solubility temperaturea eutectic haltb

100x1 / ͑ ͒ / t °C 100w1 compiler t °C min

40.80 0.0 0.0 — — 39.95 1.64 1.12 — — 39.12 3.17 2.18 38.10 18

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Solubility of salicylic acid in phenol Solubility of salicylic acid in 2-aminobenzoic acid

Eutectic Duration of Crystallization Temperature Solubility temperaturea eutectic haltb temperature Aminobenzoic acid Solubility of salicylic acid / 100x1 t °C 100w2 100x2 100w1 100x1 / ͑ ͒ / t °C 100w1 compiler t °C min 155.0 0.00 0.00 100.00 100.00 38.47 4.39 3.03 38.16 25 148.0 10.87 10.94 89.13 89.06 c 38.16 5.00 3.46 38.16 28.5 141.5 20.91 21.03 79.09 78.97 45.9 7.38 5.15 38.18 28 134.0 29.73 29.88 70.27 70.12 55.6 10.09 7.10 38.07 27.5 123.0 40.02 40.19 59.98 59.81 65.6 14.2 10.1 37.9 26 113.0 49.34 49.52 50.66 50.48 89.2 27.5 20.5 38.0 23 110.0a 53.00 53.18 47.00 46.82 113.5 46.0 36.7 — — 112.0 55.12 55.30 44.88 44.70 128.7 60.0 50.5 38.0 — 117.0 60.06 60.23 39.94 39.77 147.2 81.8 75.4 — — 122.0 65.15 65.31 34.85 34.69 157.0 94.9 92.7 — — 129.0 74.71 74.85 35.29 25.15 160.4 100.0 100.0 — — 136.0 85.13 85.22 14.87 14.78 145.0 100.00 100.00 0.00 0.00 aThe mixture of salicylic acid and phenol corresponds to a eutectic system and the temperature at which the solid phase begins to appear is called the aEutectic point eutectic temperature. b Auxiliary Information The eutectic halt ͑or arrest͒ means the time during which the solid phase appears at the eutectic temperature as the mixture is cooled. Methods/Apparatus/Procedure: c In this paper, the eutectic point was assumed to be 5.0 % salicylic acid and The experiment was performed by the fusion method. 38.16 °C by the eutectic halt. Source and Purity of Materials: Chemically pure grade salicylic acid with m.p. of 155 °C and chemically Auxiliary Information pure grade aminobenzoic acid with m.p. of 145 °C were used. Methods/Apparatus/Procedure: Estimated Errors: The synthetic method was used. At higher temperatures near the melting Nothing specified. point of salicylic acid, mixtures of phenol and salicylic acid were sealed in glass tubes, and the temperatures of appearance and disappearance of solid phase were noted. At lower temperature, the eutectic halt times ͑or Components: Original Measurements: ͒ arrests were measured. Salicylic acid was directly estimated with barium ͑1͒ Benzoic acid, 2-hydroxy- 18K.M. De Fina, T.L. Sharp, L.E. hydroxide; the indicator chosen was p-nitrophenol with titration to a color ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. match. ͒ ͓ ͔ acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44,1262 Source and Purity of Materials: ͑ ͒ ͑ ͒ 2 1,4-Dioxane; C4H8O2; 1999 . Commercial salicylic acid was recrystallized from water four times. The ͓123-91-1͔ physiologically pure salicylic acid was dissolved in a hot mixture of phenol and water, and the solution was slowly cooled. After the product Variables: Prepared by: was recrystallized twice, the m.p. of the purified product was 158.7 °C. T/K=298.15 A. Goto and H. Miyamoto When allowance was made for the exposed stem of the thermometer, the m.p. was reported as 160.4 °C. The phenol crystals were purchased from British Drug Houses and were The solubility of salicylic acid in 1,4-dioxane at distilled twice. The m.p. of the product was 40.8 °C. 298.15 K was reported as x1 =0.294. Estimated Errors: Nothing specified. Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 18 for the Components: Original Measurements: salicylic acid–1-butanol system in Sec. 2.1.2.1. ͑1͒ Benzoic acid, 2-hydroxy- 28I.L. Krupatkin, Sbornik Statei Source and Purity of Materials: ͑o-hydroxybenzoic acid, salicylic Obshchei po Khim., Akad. Nauk ͒ ͓ ͔ ͑ ͒ Salicylic acid is given in the compilation of Ref. 18 for the salicylic acid ;C7H6O3; 69-72-7 S.S.S.R. 2, 1221 1953 ͑2͒ Benzoic acid, 2-amino- acid–1-butanol system in Sec. 2.1.2.1. ͑ ͒ ͑2-aminobenzoic acid, anthranilic 1,4-Dioxane Aldrich, 99.8% anhydrous was stored over molecular sieves ͒ ͓ ͔ before use. acid ;C7H7NO2; 118-92-3 Estimated Errors: Variables: Prepared by: Solubility: Nothing speciﬁed. Composition and temperature H. Miyamoto and A. Goto Temperature: Precision of Ϯ0.1 °C.

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Solubility of salicylic acid in aminopyrine Components: Original Measurements: 18 ͑1͒ Benzoic acid, 2-hydroxy- K.M. De Fina, T.L. Sharp, L.E. Crystallization temperature Solubility ͑o-hydroxybenzoic acid, salicylic Roy, and W.E. Acree Jr., J. ͒ ͓ ͔ / acid ;C7H6O3; 69-72-7 Chem. Eng. Data 44, 1262 t °C 100w1 100x1 ͑2͒ Furan, tetrahydro- ͑oxolane, ͑1999͒. ͒ 97.0 37.4 50.0 tetrahydrofuran ;C4H8O; ͓109-99-9͔ 98.0 10.0 15.7 99.0 64.0 74.9 Variables: Prepared by: 103.0 65.0 75.7 / T K=298.15 A. Goto and H. Miyamoto 104.0 5.0 8.1 107.0 66.0 76.5 108.0 0.0 0.0 The solubility of salicylic acid in tetrahydrofuran at 116.0 38.0 50.6 298.15 K was reported as x1 =0.3642. 124.0 70.0 79.6 134.0 75.0 83.4 Auxiliary Information 142.0 80.0 87.0 Methods/Apparatus/Procedure: 152.0 90.0 93.8 The experimental details are given in the compilation of Ref. 18 for the 155.0 100.0 100.0 salicylic acid–1-butanol system in Sec. 2.1.2.1. Source and Purity of Materials: Auxiliary Information Salicylic acid is given in the compilation of Ref. 18 for the salicylic acid–1-butanol system in Sec. 2.1.2.1. Methods/Apparatus/Procedure: Tetrahydrofuran ͑Aldrich, 99.9% anhydrous͒ was stored over molecular The binary aminopyrine–salicylic acid system was studied by the fusion sieves before use. method. Estimated Errors: Source and Purity of Materials: Solubility: Nothing speciﬁed. Parmacopoeia aminopyrine with m.p. of 108 °C and c.p. salicylic acid Temperature: Precision of Ϯ0.1 °C. with m.p. of 155 °C were used. Estimated Errors: Nothing speciﬁed. Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 29I.L. Krupatkin, Zh. Obsh. ͑o-hydroxybenzoic acid, salicylic Khim. 26, 1050 ͑1956͓͒J. Gen. Components: Original Measurements: ͒ ͓ ͔ ͑ ͒ 17 acid ;C7H6O3; 69-72-7 Chem. USSR Engl. Transl. 26, ͑1͒ Benzoic acid, 2-hydroxy- A.N. Paruta, B.J. Sciarrone, and ͑2͒ Aminopyrine 1197 ͑1956͔͒. ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͑4-͑dimethylamino͒-1,5-dimethyl-2-phenylpyrazol-3-one͒; acid͒;CH O ; ͓69-72-7͔ 1349 ͑1964͒. ͓ ͔ 7 6 3 C13H17N3O; 58-15-1 ͑2͒ Ethanol, 2-ethoxy- ͑2-ethoxyethanol, ethyl Variables: Prepared by: ͒ ͓ ͔ cellosolve ;C4H10O2; 110-80-5 t/ °C=82.0–104.0 H. Miyamoto and A. Goto Variables: Prepared by: t/ °C=30.6 A. Goto and R. Goto Solubility of salicylic acid in aminopyrine

Crystallization temperature Solubility Solubility of salicylic acid in ethyl cellosolve at 30.6 °C

t/ °C 100w 100x 1 1 Solubilitya

82.0 51.5 64.0 ␥ / −3 / −3 Dielectric constant of 1 gdm c1 mol dm 83.0 52.0 64.5 solvent ͑compiler͒ ͑compiler͒ 84.0 50.0 62.6 87.0 18.0 26.9 14.5 425 3.08 88.0 20.0 29.5 a 90.0 45.0 57.8 In the original paper, the solubility was given as mg/ml of solution. 90.0 55.0 67.2 91.0 15.0 22.8 91.0 25.0 35.8 92.0 43.0 55.8 93.0 28.0 39.4 93.0 60.0 71.5 93.5 63.0 74.0 94.5 30.0 41.8 95.0 40.0 52.7 96.5 39.0 51.7 97.0 35.0 47.4

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Auxiliary Information Solubility of 3-hydroxybenzoic acid in cyclohexane at 25 °C.

Methods/Apparatus/Procedure: Solubility The experimental details are given in the compilation of Ref. 16 for the / −3 salicylic acid–ethanol system in Sec. 2.1.2.1. c1 mol dm ͑ ͒ Source and Purity of Materials: pS compiler et al. The solvent was purified by the method described in A. Weissberger , Ͼ6.000 Ͻ1.000ϫ10−6 Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5. Estimated Errors: pS: The negative logarithm of the concentration in the saturated solutions in Solubility: Nothing specified. mol/l. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒. Auxiliary Information Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: The details are given in the compilation of Ref. 21 for the salicylic 2.1.4.2. 3-Hydroxybenzoic acid acid–benzene system in Sec. 2.1.3.1. Estimated Errors: Nothing specified. Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 14N.V. Sidgwick and E.K. ͑m-hydroxybenzoic acid͒; Ewbank, J. Chem. Soc. 1921, ͓ ͔ Components: Original Measurements: C7H6O3; 99-06-9 979. ͑ ͒ ͓ ͔ ͑ ͒ 23 2 n-Heptane; C7H16; 142-82-5 1 Benzoic acid, 3-hydroxy- C.K. Hancock, J.N. Pawloski, ͑m-hydroxybenzoic acid͒; and J.P. Idoux, J. Org. Chem. 31, ͓ ͔ ͑ ͒ Variables: Prepared by: C7H6O3; 99-06-9 3801 1966 . / ͑ ͒ t °C=176.0 and 197.0 A. Goto and H. Miyamoto 2 Cyclohexane; C6H12; ͓110-82-7͔

Solubility of 3-hydroxybenzoic acid in n-heptane Variables: Prepared by: t/ °C=30 A. Goto and H. Miyamoto Temperature Solubility

100x1 Solubility of 3-hydroxybenzoic acid in cyclohexane at 30 °C / ͑ ͒ t °C 100w1 compiler Solubilitya 197.0͑liq.͒ 2.00 1.46

176.0 0.86 0.63 x1 100w1 197.0 Triple point ͑compiler͒ ͑compiler͒

9.73ϫ10−6 1.69ϫ10−3 Auxiliary Information aIn the original paper, the solubility was given as grams of acid per 100 g of Methods/Apparatus/Procedure: saturated solution. The experimental details are given in the compilation of Ref. 14 for the salicylic acid–n-heptane system in Sec. 2.1.1.1. Auxiliary Information Source and Purity of Materials: Methods/Apparatus/Procedure: The preparation and the purification of 3-hydroxybenzoic acid were The experimental details are given in the compilation of Ref. 23 for the ͓ ͑ ͔͒ described in J. Walker and J. K. Wood, J. Chem. Soc. 117,40 1920 . 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. Melting point of the purified acid was 201.5 °C. Source and Purity of Materials: n-Heptane was a specimen from Pinus sabiniana, which had been purified The details are given in the compilation of Ref. 23 for the by the method of Thorpe ͓T. E. Thorpe, J. Chem. Soc. 35, 296 ͑1879͔͒ by 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. treatment with sulfuric and nitric acids, and distillation. Estimated Errors: Estimated Errors: Solubility ͑mole fraction units͒: The average deviation of the replicate Nothing specified. values from the mean exceeds 3% only in the case of 5.5% for 3-hydroxybenzoic acid in cyclohexane. Temperature: Precision of Ϯ0.02 °C. Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 21P. A. Ongley, J. Chem. Soc. ͑m-hydroxybenzoic acid͒; 1954, 3634. Components: Original Measurements: ͓ ͔ C7H6O3; 99-06-9 ͑ ͒ 26 ͑ ͒ 1 Benzoic acid, 3-hydroxy- E. Savarro, Atti Accad. Sci. 2 Cyclohexane; C6H12; ͑ ͒ ͑ ͓͒ ͓ ͔ m-hydroxybenzoic acid ; Torino 48, 948 1914 Chem. 110-82-7 ͓ ͔ ͑ ͔͒ C7H6O3; 99-06-9 Abs. 8, 340 1914 . ͑ ͒ ͑ ͒ Variables: Prepared by: 2 Methyl alcohol methanol ; ͓ ͔ t/ °C=25 A. Goto and H. Miyamoto CH4O; 67-56-1

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Variables: Prepared by: t/ °C=15 A. Goto and H. Miyamoto Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑m-hydroxybenzoic acid͒; 91 ͑1961͒. ͓ ͔ Solubility of 3-hydroxybenzoic acid in methanol at 15 °C C7H6O3; 99-06-9 ͑2͒ 1-Propanol ͑propan-1-ol, a ͒ Solubility propyl alcohol ;C3H8O; ͓71-23-8͔ / −1 100w1 m1 mol kg Original data ͑compiler͒ ͑compiler͒ Variables: Prepared by: t/ °C=20.0 P.Scharlin 535.80 34.887 3.8792

aIn the original paper, the solubility was given as grams per 1000 g of Solubility of 3-hydroxybenzoic acid in 1-propanol at 20.0 °C methanol. Solubilitya Auxiliary Information ␥ / −3 / −3 1 gdm c1 mol dm Methods/Apparatus/Procedure: ͑compiler͒ ͑compiler͒ The experimental details are given in the compilation of Ref. 26 for the binary salicylic acid–methanol system in Sec. 2.1.2.1. 163.4 1.183 Source and Purity of Materials: a 3-Hydroxybenzoic acid was recrystallized. In the original paper, the solubility was given as grams per 100 ml of Estimated Errors: solution. Ϯ Solubility: Precision of 1.5%. Auxiliary Information Temperature: Nothing speciﬁed. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 15 for the Components: Original Measurements: salicylic acid–ethanol system in Sec. 2.1.2.1. ͑1͒ Benzoic acid, 3-hydroxy- 15E. Bergroth, Farm. Aikak. 70, Source and Purity of Materials: ͑m-hydroxybenzoic acid͒; 91 ͑1961͒. 3-Hydroxybenzoic acid was obtained from Shuchardt, reinst. ͓ ͔ C7H6O3; 99-06-9 The source and purity of 1-propanol was not given. Relative density ͑2͒ Methyl alcohol ͑methanol͒; source and purity not given; relative density d=0.804 ͑20 °C/4°C͒. ͓ ͔ CH4O; 67-56-1 Estimated Errors: Nothing speciﬁed. The values given are the mean of three independent Variables: Prepared by: determinations. t/ °C=20.0 P.Scharlin

Solubility of 3-hydroxybenzoic acid in methanol at 20.0 °C Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 14S.V. Sidgwick and E.K. Solubilitya ͑m-hydroxybenzoic acid͒; Embank, J. Chem. Soc. 1921, C H O ; ͓99-06-9͔ 979. ␥ /gdm−3 c /mol dm−3 7 6 3 1 1 ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͑ ͒ ͑ ͒ compiler compiler ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 278.6 2.017 Variables: Prepared by: t/ °C=36.5–180.3 A. Goto and H. Miyamoto aIn the original paper, the solubility was given as grams per 100 ml of solution. Solubility of 3-hydroxybenzoic acid in 1-butanol Auxiliary Information Temperature Solubility Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 15 for the 100x1 salicylic acid–ethanol system in Sec. 2.1.2.1. / ͑ ͒ t °C 100w1 compiler Source and Purity of Materials: 3-Hydroxybenzoic acid was obtained from Shuchardt, reinst. 180.3 84.7 74.8 The source and purity of methanol was not given; relative density d 151.2 59.2 43.8 =0.792 ͑20 °C/4°C͒. 115.0 40.8 27.0 Estimated Errors: 36.5 20.7 12.3 Nothing speciﬁed. The values given are the mean of three independent determinations.

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Auxiliary Information Solubility of 3-hydroxybenzoic acid in acetone at 23.0 °C

Methods/Apparatus/Procedure: Solubilitya The experimental details are given in the compilation of Ref. 14 for the ␥ / −3 / −3 salicylic acid–n-heptane system in Sec. 2.1.1.1. 1 gdm c1 mol dm Source and Purity of Materials: ͑compiler͒ ͑compiler͒ The preparation and puriﬁcation methods were described in ͓J. Walker and 260 1.88 J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. Melting point of 3-hydroxybenzoic acid was 201 °C. aThe solubility reported by the authors was expressed in grams per 100 cm3 1-Butanol was repeatedly fractionated, and distilled within 0.1 °C. of acetone solution at 23 °C and in grams per 100 cm3 of ether solution at Estimated Errors: 17 °C. The mass concentration, ␥ =m /V, was calculated by the compiler, Nothing speciﬁed. 1 1 where m1 is the mass of component 1 and V is the total volume of the solution.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 3-hydroxy- 20J. Walker and J.K. Wood, J. ͑m-hydroxybenzoic acid͒; Chem. Soc. Trans. 73, 618 Methods/Apparatus/Procedure: ͓ ͔ ͑ ͒ C7H6O3; 99-06-9 1898 . The experimental details are given in the compilation of Ref. 20 for the ͑2͒ Ethane, 1,1-oxybis- salicylic acid–benzene system in Sec. 2.1.3.1. ͑ethoxyethane, diethyl ether͒; Source and Purity of Materials: ͓ ͔ C4H10O; 60-29-7 No information was given. Estimated Errors: Variables: Prepared by: Nothing speciﬁed. t/ °C=17.0 A. Goto and H. Miyamoto

Solubility of 3-hydroxybenzoic acid in diethyl ether at 17.0 °C Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 15E. Bergroth, Farm. Aikak. 70, a Solubility ͑m-hydroxybenzoic acid͒; 91 ͑1961͒. ͓ ͔ ␥ / −3 / −3 C7H6O3; 99-06-9 1 gdm c1 mol dm ͑ ͒ ͑ ͑ ͒ ͑ ͒ 2 2-Propanone propan-2-one, compiler compiler ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 97.3 0.704 Variables: Prepared by: / aThe solubility reported by the authors was expressed in grams per 100 cm3 t °C=20.0 P.Scharlin of acetone solution at 23 °C and in grams per 100 cm3 of ether solution at ␥ / 17 °C. The mass concentration, 1 =m1 V, was calculated by the compiler, Solubility of 3-hydroxybenzoic acid in acetone at 20.0 °C

where m1 is the mass of component 1 and V is the total volume of solution. Solubilitya Auxiliary Information ␥ / −3 / −3 1 gdm c1 mol dm Methods/Apparatus/Procedure: ͑compiler͒ ͑compiler͒ The experimental details are given in the compilation of Ref. 20 for the salicylic acid–benzene system in Sec. 2.1.3.1. 207.2 1.500 Source and Purity of Materials: aIn the original paper, the solubility was given as grams per 100 ml of No information was given. solution. Estimated Errors: Nothing speciﬁed. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 15 for the ͑1͒ Benzoic acid, 3-hydroxy- 20J. Walker and J.K. Wood, J. salicylic acid–ethanol system in Sec. 2.1.2.1. ͑m-hydroxybenzoic acid͒; Chem. Soc. Trans. 73, 618 Source and Purity of Materials: ͓ ͔ ͑ ͒ C7H6O3; 99-06-9 1898 . 3-Hydroxybenzoic acid was obtained from Shuchardt, reinst. ͑2͒ 2-Propanone ͑propan-2-one, The source and purity of acetone were not given; relative density d=0.791 ͒ ͓ ͔ ͑ / ͒ acetone ;C3H6O; 67-64-1 20 °C 4°C. Estimated Errors: Variables: Prepared by: Nothing speciﬁed. According to the author, the values given are the mean / t °C=23.0 A. Goto and H. Miyamoto of three independent determinations.

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Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 15E. Bergroth, Farm. Aikak. 70, Methods/Apparatus/Procedure: ͑m-hydroxybenzoic acid͒; 91 ͑1961͒. The experimental details are given in the compilation of Ref. 14 for the ͓ ͔ C7H6O3; 99-06-9 salicylic acid–n-heptane system in Sec. 2.1.1.1. ͑2͒ Ketones: Source and Purity of Materials: ͑ 2-Butanone butan-2-one, methyl The preparation and the purification of 4-hydroxybenzoic acid were ͒ ͓ ͔ ethyl ketone ;C4H8O; 78-93-3 described in ͓J. Walker and J.K. Wood, J. Chem. Soc. 117,40͑1920͔͒. ͑ 2-Pentanone pentan-2-one, Melting point of the purified acid was 213.0 °C. ͒ methyl propyl ketone ;C5H10O; n-Heptane was a specimen from Pinus sabiniana, which had been purified ͓ ͔ 107-87-9 by treatment with sulfuric and nitric acids, and distillation. Variables: Prepared by: Estimated Errors: t/ °C=20.0 P.Scharlin Nothing specified.

Solubility of 3-hydroxybenzoic acid in ketones at 20.0 °C Components: Original Measurements: ͑ ͒ 21 Solubilitya 1 Benzoic acid, 4-hydroxy- P.A. Ongley, J. Chem. Soc. ͑p-hydroxybenzoic acid͒; 1954, 3634. ␥ / −3 / −3 ͓ ͔ 1 gdm c1 mol dm C7H6O3; 99-96-7 ͑ ͒ Solvent ͑compiler͒ ͑compiler͒ 2 Cyclohexane; C6H12; ͓110-82-7͔ 2-Butanone 156.9 1.136 2-Pentanone 126.3 0.914 Variables: Prepared by: t/ °C=25 A. Goto and H. Miyamoto aIn the original paper, the solubility was given as grams per 100 ml of solution. Solubility of 4-hydroxybenzoic acid in cyclohexane at 25 °C Auxiliary Information Solubility Methods/Apparatus/Procedure: 3 / −3 The experimental details are given in the compilation of Ref. 15 for the 10 c1 mol dm salicylic acid–ethanol system in Sec. 2.1.2.1. pS ͑compiler͒ Source and Purity of Materials: 3-Hydroxybenzoic acid was obtained from Shuchardt, reinst. 4.398 0.039 99 The source and purity of 2-butanone and 2-pentanone were not given. Relative density d of 2-butanone and 2-pentanone are 0.805 ͑20 °C/4°C͒ pS: The negative logarithm of the concentration in the saturated solution in and 0.812 ͑15 °C/15 °C͒, respectively. mol/l. Estimated Errors: Auxiliary Information Nothing speciﬁed. The values given are the mean of three independent determinations. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: 2.1.4.3. 4-Hydroxybenzoic acid The details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. The acid was either of AnarR Components: Original Measurements: standard or recrystallized before use. ͑1͒ Benzoic acid, 4-hydroxy- 14N.V. Sidgwick and E.K. No information of the purity of cyclohexane was reported. ͑p-hydroxybenzoic acid͒; Ewbank, J. Chem. Soc. 1921, Estimated Errors: ͓ ͔ C7H6O3; 99-96-7 979. Nothing speciﬁed. ͑ ͒ ͓ ͔ 2 n-Heptane; C7H16; 142-82-5

Variables: Prepared by: Components: Original Measurements: t/ °C=197.0 and 208.5 A. Goto and H. Miyamoto ͑1͒ Benzoic acid, 4-hydroxy- 23C.K. Hancock, J.N. Pawloski, ͑p-hydroxybenzoic acid͒; and J.P. Idoux, J. Org. Chem. 31, ͓ ͔ ͑ ͒ Solubility of 4-hydroxybenzoic acid in n-heptane C7H6O3; 99-96-7 3801 1966 . ͑ ͒ 2 Cyclohexane; C6H12; Temperature Solubility ͓110-82-7͔

100x1 Variables: Prepared by: / ͑ ͒ t °C 100w1 compiler t/ °C=30 A. Goto and H. Miyamoto

208.5͑liq.͒ 1.80 1.31 197.0 1.06 0.771 208.5 Triple point

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Solubility of 4-hydroxybenzoic acid in cyclohexane at 30 °C Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Solubilitya

5 10 x1 100w1 The solubility of 4-hydroxybenzoic acid in chloroform at ͑compiler͒ ͑compiler͒ 4 25 °C was reported as 10 x1 =1.5. ϫ −3 3.70 6.08 10 Auxiliary Information

a In the original paper, the solubility was given as grams of acid per 100 g of Methods/Apparatus/Procedure: saturated solution. The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Auxiliary Information Source and Purity of Materials: Methods/Apparatus/Procedure: The details are given in the compilation of Ref. 19 for the The experimental details are given in the compilation of Ref. 23 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. Estimated Errors: Source and Purity of Materials: Nothing speciﬁed. The details are given in the compilation of Ref. 23 for the 3-hydroxybenzoic acid–benzene system in Sec. 2.1.3.2. Estimated Errors: Components: Original Measurements: 21 Solubility ͑mole fraction units͒: The average deviation of the replicate ͑1͒ Benzoic acid, 4-hydroxy- P.A. Ongley, J. Chem. Soc. values from the mean did not exceed 3%. ͑p-hydroxybenzoic acid͒; 1954, 3634. ͓ ͔ Temperature: Precision of Ϯ0.02 °C. C7H6O3; 99-96-7 ͑2͒ Methane, tetrachloro- ͑tetrachloromethane, carbon ͒ ͓ ͔ tetrachloride ;CCl4; 56-23-5 Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 21P.A. Ongley, J. Chem. Soc. Variables: Prepared by: ͑p-hydroxybenzoic acid͒; 1954, 3634. t/ °C=25 A. Goto and H. Miyamoto ͓ ͔ C7H6O3; 99-96-7 ͑2͒ Trichloromethane ͑ ͒ ͓ ͔ Solubility of 4-hydroxybenzoic acid in carbon tetrachloride at 25 °C. chloroform ; CHCl3; 67-66-3

Variables: Prepared by: Solubility / t °C=25 A. Goto and H. Miyamoto 3 / −3 10 c1 mol dm pS ͑compiler͒ Solubility of 4-hydroxybenzoic acid in chloroform at 25 °C. 5.000 0.01000

Solubility pS: The negative logarithm of the concentration in the saturated solution in mol/l. 3 / −3 10 c1 mol dm pS ͑compiler͒ Auxiliary Information

2.991 1.021 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 21 for the pS: The negative logarithm of the concentration in the saturated solution in salicylic acid–benzene system in Sec. 2.1.3.1. mol/l. Source and Purity of Materials: Auxiliary Information The details are given in the compilation of Ref. 21 for the salicylic acid–benzene system in Sec. 2.1.3.1. Methods/Apparatus/Procedure: Estimated Errors: The experimental details are given in the compilation of Ref. 21 for the Nothing speciﬁed. salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: The details are given in the compilation of Ref. 21 for the salicylic Components: Original Measurements: acid–benzene system in Sec. 2.1.3.1. ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. Estimated Errors: ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ Nothing speciﬁed. C7H6O3; 99-96-7 188 1984 . ͑2͒ Ethane, 1,2-dichloro- ͑1,2-dichloroethane, ethylene dichloride͒;CH Cl ; ͓107-06-2͔ Components: Original Measurements: 2 4 2 ͑ ͒ 19 1 Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. Variables: Prepared by: ͑ ͒ p-hydroxybenzoic acid ; Beerbower, J. Pharm. Sci. 73, t/ °C=25 A. Goto and R. Goto ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . ͑2͒ Trichloromethane ͑ ͒ ͓ ͔ chloroform ; CHCl3; 67-66-3 The solubility of 4-hydroxybenzoic acid in ethylene 4 dichloride at 25 °C was reported as 10 x1 =1.1.

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: Source and Purity of Materials: The details are given in the compilation of Ref. 19 for the The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Estimated Errors: Nothing speciﬁed. Nothing speciﬁed.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑1͒ Benzoic acid, 4-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. ͓ ͔ ͓ ͔ C7H6O3; 99-96-7 C7H6O3; 99-96-7 ͑2͒ Methyl alcohol ͑methanol͒; ͑2͒ 1-Propanol ͑propan-1-ol, ͓ ͔ ͒ CH4O; 67-56-1 propyl alcohol ;C3H8O; ͓71-23-8͔ Variables: Prepared by: t/ °C=20.0 P.Scharlin Variables: Prepared by: t/ °C=20.0 P.Scharlin Solubility of 4-hydroxybenzoic acid in methanol at 20.0 °C Solubility of 4-hydroxybenzoic acid in 1-propanol at 20.0 °C Solubilitya Solubilitya ␥ / −3 / −3 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ ␥ / −3 / −3 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ 324.5 2.349 194.6 1.409 aIn the original paper, the solubility was given as grams per 100 ml of solution. aIn the original paper, the solubility was given as grams per 100 ml of Auxiliary Information solution.

Methods/Apparatus/Procedure: Auxiliary Information The experimental details are given in the compilation of Ref. 15 for the Methods/Apparatus/Procedure: salicylic acid–ethanol system in Sec. 2.1.2.1. The experimental details are given in the compilation of Ref. 15 for the Source and Purity of Materials: salicylic acid–ethanol system in Sec. 2.1.2.1. 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%. Source and Purity of Materials: The source and purity of methanol was not given; relative density d 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%. =0.792 ͑20 °C/4°C͒. The source and purity of 1-propanol was not given; relative density d Estimated Errors: =0.804 ͑20 °C/4°C͒. Nothing speciﬁed. The value given is the mean of three independent Estimated Errors: determinations. Nothing speciﬁed. The value given is the mean of three independent determinations.

Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. Components: Original Measurements: ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. C H O ; ͓99-96-7͔ 188 ͑1984͒. 7 6 3 ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͑2͒ Methyl alcohol ͑methanol͒; C H O ; ͓99-96-7͔ 188 ͑1984͒. CH O; ͓67-56-1͔ 7 6 3 4 ͑2͒ 1-Propanol ͑propan-1-ol, ͒ Variables: Prepared by: propyl alcohol ;C3H8O; ͓ ͔ t/ °C=25 A. Goto and H. Miyamoto 71-23-8

Solubility of 4-hydroxybenzoic acid in methanol at 25 °C

Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1

40.7 0.1142

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Variables: Prepared by: Solubility of 4-hydroxybenzoic acid in 1-hexanol at 25 °C t/ °C=25 A. Goto and R. Goto Molar volume of solvent Solubility

/ 3 −1 Solubility of 4-hydroxybenzoic acid in 1-propanol at 25 °C v2 cm mol x1

Molar volume of solvent Solubility 125.2 0.1121

/ 3 −1 v2 cm mol x1 Auxiliary Information 75.1 0.1084 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the Auxiliary Information 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: Methods/Apparatus/Procedure: The details are given in the compilation of Ref. 19 for the The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. salicylic acid–ethanol system in Sec. 2.1.2.1. Estimated Errors: Source and Purity of Materials: Nothing speciﬁed. The details are given in the compilation of Ref. 19 for the salicylic acid–ethanol system in Sec. 2.1.2.1. Estimated Errors: Nothing speciﬁed. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . Components: Original Measurements: ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . Variables: Prepared by: ͑2͒ 1-Pentanol ͑pentan-1-ol, t/ °C=25 A. Goto and R. Goto ͒ pentyl alcohol ;C5H12O; ͓71-41-0͔ Solubility of 4-hydroxybenzoic acid in 1-octanol at 25 °C Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1 Solubility of 4-hydroxybenzoic acid in 1-pentanol at 25 °C 158.4 0.1032 Molar volume of solvent Solubility

/ 3 −1 Auxiliary Information v2 cm mol x1

108.6 0.1145 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Auxiliary Information Source and Purity of Materials: The details are given in the compilation of Ref. 19 for the Methods/Apparatus/Procedure: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. The experimental details are given in the compilation of Ref. 19 for the Estimated Errors: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Nothing speciﬁed. Source and Purity of Materials: The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Components: Original Measurements: 19 Nothing speciﬁed. ͑1͒ Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . ͑2͒ 2-Propanol ͑propan-2-ol, Components: Original Measurements: isopropyl alcohol͒;CH O; 19 3 8 ͑1͒ Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. ͓67-63-0͔ ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . Variables: Prepared by: ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl t/ °C=25 A. Goto and R. Goto ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of 4-hydroxybenzoic acid in 2-propanol at 25 °C Solubility of 4-hydroxybenzoic acid in benzyl alcohol at 25 °C

Molar volume of solvent Solubility Molar volume of solvent Solubility

/ 3 −1 / 3 −1 v2 cm mol x1 v2 cm mol x1

76.9 0.1297 103.9 0.0784

Auxiliary Information Auxiliary Information

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . C7H6O3; 99-96-7 188 1984 . ͑2͒ 2-Methyl-1-propanol ͑2͒ Diols and triols: ͑2-methylpropan-1-ol, isobutyl 1,2-Ethanediol ͑ethane-1,2-diol, ͒ ͓ ͔ ͒ alcohol ;C4H10O; 78-83-1 ethylene glycol ;C2H6O; ͓107-21-1͔ Variables: Prepared by: 1,2-Propanediol t/ °C=25 A. Goto and R. Goto ͑propane-1,2-diol, propylene ͒ ͓ ͔ glycol ;C3H8O2; 57-55-6 1,2,3-Propanetriol Solubility of 4-hydroxybenzoic acid in 2-methyl-1-propanol at 25 °C ͑propane-1,2,3-triol, glycerol͒; ͓ ͔ C3H8O3; 56-81-5 Molar volume of solvent Solubility Variables: Prepared by: v /cm3 mol−1 x 2 1 t/ °C=25 A. Goto and R. Goto 92.4 0.0901 Solubility of 4-hydroxybenzoic acid in diols and triols at 25 °C Auxiliary Information Molar volume of Methods/Apparatus/Procedure: solvent Solubility The experimental details are given in the compilation of Ref. 19 for the Solvent v /cm3 mol−1 x 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 2 1 Source and Purity of Materials: Ethylene glycol 55.9 0.1132 The details are given in the compilation of Ref. 19 for the Propylene glycol 73.7 0.1308 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Glycerol 73.2 0.0301 Estimated Errors: Nothing speciﬁed. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 19 for the 19 ͑1͒ Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑ ͒ p-hydroxybenzoic acid ; A. Beerbower, J. Pharm. Sci. Source and Purity of Materials: ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 73,188 1984 . The details are given in the compilation of Ref. 19 for the ͑ ͒ 2 Benzyl alcohol 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑phenylmethanol͒; Estimated Errors: C H O; ͓100-51-6͔ 7 8 Nothing speciﬁed. Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 20J. Walker and J.K. Wood, J. ͑1͒ Benzoic acid, 4-hydroxy- 20J. Walker and J.K. Wood, J. ͑p-hydroxybenzoic acid͒; Chem. Soc. Trans. 73, 618 ͑p-hydroxybenzoic acid͒; Chem. Soc. Trans. 73,618 ͓ ͔ ͑ ͒ ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 1898 . C7H6O3; 99-96-7 1898 . ͑2͒ Ethane, 1,1Ј-oxybis- ͑2͒ 2-Propanone ͑propan-2-one, ͑ ͒ ͒ ͓ ͔ ethoxyethane, diethyl ether ; acetone ;C3H6O; 67-64-1 ͓ ͔ C4H10O; 60-29-7 Variables: Prepared by: Variables: Prepared by: t/ °C=23 A. Goto and H. Miyamoto t/ °C=17 A. Goto and H. Miyamoto Solubility of 4-hydroxybenzoic acid in acetone at 23 °C Solubility of 4-hydroxybenzoic acid in diethyl ether at 17 °C Solubilitya Solubilitya ␥ / −3 / −3 1 gdm c1 mol dm ␥ / −3 / −3 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ ͑compiler͒ ͑compiler͒ 227 1.64 94.3 0.683 aIn the original paper, the solubility was given as grams per 100 cm3 of the a In the original paper, the solubility was given as grams per 100 cm3 of acetone solution at 23 °C and in grams per 100 cm3 of the ether solution at 3 ␥ / acetone solution at 23 °C and in grams per 100 cm of ether solution at 17 °C. The mass concentration, 1 =m1 V, was calculated by the compiler, ␥ m /V 17 °C. The mass concentration, 1 = 1 , was calculated by the compiler, where m1 is the mass of component 1 and V is the total volume of the where m1 is the mass of component 1 and V is the total volume of the solution. solution. Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 20 for the The experimental details are given in the compilation of Ref. 20 for the binary salicylic acid–benzene system in Sec. 2.1.3.1. salicylic acid–benzene system in Sec. 2.1.3.1. Source and Purity of Materials: Source and Purity of Materials: No information was given. No information was given. Estimated Errors: Estimated Errors: Nothing speciﬁed. Nothing speciﬁed.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 15E. Bergroth, Farm. Aikak. 70, ͑ ͒ 19 1 Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. ͑ ͒ p-hydroxybenzoic acid ; Beerbower, J. Pharm. Sci. 73, C H O ; ͓99-96-7͔ ͓ ͔ ͑ ͒ 7 6 3 C7H6O3; 99-96-7 188 1984 . ͑2͒ 2-Propanone ͑propan-2-one, ͑2͒ Ethane, 1,1-oxybis- ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 ͑ethoxyethane, diethyl ether͒; ͓ ͔ C4H10O; 60-29-7 Variables: Prepared by: t/ °C=20 P.Scharlin Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Solubility of 4-hydroxybenzoic acid in acetone at 20 °C

Solubility of 4-hydroxybenzoic acid in diethyl ether at 25 °C a Solubility

␥ / −3 / −3 Molar volume of solvent Solubility 1 gdm c1 mol dm ͑compiler͒ ͑compiler͒ / 3 −1 2 v2 cm mol 10 x1 205.5 1.488 104.8 5.21 aIn the original paper, the solubility was given as grams per 100 ml of solution. Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the Methods/Apparatus/Procedure: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. The experimental details are given in the compilation of Ref. 15 for the Source and Purity of Materials: salicylic acid–ethanol system in Sec. 2.1.2.1. The details are given in the compilation of Ref. 19 for the Source and Purity of Materials: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%. Estimated Errors: Acetone: source and purity not given; relative density d=0.791 Nothing speciﬁed. ͑20 °C/4°C͒.

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Estimated Errors: 2-Butanone; source and purity not given; relative density d=0.805 Nothing speciﬁed. The value given is the mean of three independent ͑20 °C/4°C͒. determinations. Estimated Errors: Nothing speciﬁed. The value given is the mean of three independent determinations. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, Components: Original Measurements: ͓ ͔ ͑ ͒ 15 C7H6O3; 99-96-7 188 1984 . ͑1͒ Benzoic acid, 4-hydroxy- E. Bergroth, Farm. Aikak. 70, ͑2͒ 2-Propanone ͑propan-2-one, ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. ͒ ͓ ͔ ͓ ͔ acetone ;C3H6O; 67-64-1 C7H6O3; 99-96-7 ͑2͒ 2-Pentanone ͑pentan-2-one, Variables: Prepared by: ͒ methyl propyl ketone ;C5H10O; t/ °C=25 A. Goto and R. Goto ͓107-87-9͔

Variables: Prepared by: Solubility of 4-hydroxybenzoic acid in acetone at 25 °C t/ °C=20.0 P.Scharlin

Molar volume of solvent Solubility Solubility of 4-hydroxybenzoic acid in 2-pentanone at 20.0 °C / 3 −1 v2 cm mol x1 Solubilitya 74.0 0.1185 ␥ / −3 / −3 1 gdm c1 mol dm Auxiliary Information ͑compiler͒ ͑compiler͒

Methods/Apparatus/Procedure: 170.9 1.237

The experimental details are given in the compilation of Ref. 19 for the a 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. In the original paper, the solubility was given as grams per 100 ml of Source and Purity of Materials: solution. The details are given in the compilation of Ref. 19 for the Auxiliary Information 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Methods/Apparatus/Procedure: Nothing speciﬁed. The experimental details are given in the compilation of Ref. 15 for the salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: Components: Original Measurements: 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%. ͑1͒ Benzoic acid, 4-hydroxy- 15E. Bergroth, Farm. Aikak. 70, 2-Pentanone: source and purity not given; relative density ͑p-hydroxybenzoic acid͒; 91 ͑1961͒. d=0.812 ͑15 °C/15 °C͒. ͓ ͔ C7H6O3; 99-96-7 Estimated Errors: ͑2͒ 2-Butanone ͑butan-2-one, Nothing speciﬁed. The value given is the mean of three independent ͒ methyl ethyl ketone ;C4H8O; determinations. ͓78-93-3͔

Variables: Prepared by: t/ °C=20 P.Scharlin Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ Solubility of 4-hydroxybenzoic acid in 2-butanone at 20 °C C7H6O3; 99-96-7 188 1984 . ͑2͒ Carboxylic acids and their Solubilitya esters: Acetic acid; C H O ; ͓64-19-7͔ ␥ / −3 / −3 2 4 2 1 gdm c1 mol dm Propionic acid; C H O ; ͑ ͒ ͑ ͒ 3 6 2 compiler compiler ͓79-09-4͔ Ethyl acetate ͑ethyl acetate, 205.8 1.490 ͒ acetic acid, ethyl ester ;C4H8O2; ͓141-78-6͔ aIn the original paper, the solubility was given as grams per 100 ml of Butyl acetate ͑butyl acetate, solution. acetic acid, butyl ester͒; C H O ; ͓123-86-4͔ Auxiliary Information 6 12 2 Variables: Prepared by: Methods/Apparatus/Procedure: t/ °C=25 A. Goto and R. Goto The experimental details are given in the compilation of Ref. 15 for the salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: 4-Hydroxybenzoic acid was obtained from Shuchardt, purity of 99.5%.

J. Phys. Chem. Ref. Data, Vol. 40, No. 2, 2011

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Solubility of 4-hydroxybenzoic acid in acids and their esters at 25 °C Solubility of 4-hydroxybenzoic acid in toluene at 25 °C

Molar volume of Molar volume of solvent Solubility solvent Solubility / 3 −1 v2 cm mol 100x1 Solvent v /cm3 mol−1 102x 2 1 106.9 0.29ϫ10−2 Acetic acid 57.6 4.44 Propionic acid 75.0 3.47 Auxiliary Information Ethyl acetate 98.5 7.37 Butyl acetate 132.6 5.74 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Auxiliary Information Source and Purity of Materials: Methods/Apparatus/Procedure: The details are given in the compilation of Ref. 19 for the The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Source and Purity of Materials: Nothing specified. The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Components: Original Measurements: Nothing specified. ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . ͑2͒ Acetophenone Components: Original Measurements: ͑ ͑ ͒ 19 1-phenylethanone, methyl 1 Benzoic acid, 4-hydroxy- A. Martin, P.L. Wu, and A. ͒ ͑ ͒ phenyl ketone ;C8H8O; p-hydroxybenzoic acid ; Beerbower, J. Pharm. Sci. 73, ͓ ͔ ͓ ͔ ͑ ͒ 98-86-2 C7H6O3; 99-96-7 188 1984 . ͑ ͒ 2 Methane, 1,1Ј-sulfinyl-bis- Variables: Prepared by: ͑ methylsulfinylmethane, dimethyl t/ °C=25 A. Goto and R. Goto ͒ ͓ ͔ sulfoxide ;C2H6OS; 67-68-5

Variables: Prepared by: Solubility of 4-hydroxybenzoic acid in acetophenone at 25 °C t/ °C=25 A. Goto and R. Goto Molar volume of solvent Solubility

/ 3 −1 The solubility of 4-hydroxybenzoic acid in dimethyl sul- v2 cm mol x1

foxide at 25 °C was reported as x1 =0.3674. 117.4 0.0223 Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the Methods/Apparatus/Procedure: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. The experimental details are given in the compilation of Ref. 19 for the Source and Purity of Materials: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. The details are given in the compilation of Ref. 19 for the Source and Purity of Materials: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. The details are given in the compilation of Ref. 19 for the Estimated Errors: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Nothing speciﬁed. Estimated Errors: Nothing speciﬁed.

Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. Components: Original Measurements: ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, ͑ ͒ ͑ ͒ ͓ ͔ ͑ ͒ 2 Benzene, methyl- toluene ; C7H6O3; 99-96-7 188 1984 . ͓ ͔ ͑ ͒ ͓ ͔ C7H8; 108-88-3 2 Pyridine; C5H5N; 110-86-1

Variables: Prepared by: Variables: Prepared by: t/ °C=25 A. Goto and R. Goto t/ °C=25 A. Goto and R. Goto

The solubility of 4-hydroxybenzoic acid in pyridine at

25 °C was reported as x1 =0.1044.

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Auxiliary Information Solubility of salicylic acid in supercritical carbon dioxide at 373.2 K

Methods/Apparatus/Procedure: Pressurea Solubility The experimental details are given in the compilation of Ref. 19 for the 5 3 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 10 Pa 10 x1 Source and Purity of Materials: 207 2.07 The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 276 2.99 Estimated Errors: 345 3.53 Nothing speciﬁed. 414 6.99

aIn the original paper, the pressure was given as bar. 1 bar=105 Pa.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy- 19A. Martin, P.L. Wu, and A. ͑p-hydroxybenzoic acid͒; Beerbower, J. Pharm. Sci. 73, Methods/Apparatus/Procedure: ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 188 1984 . The solubility measurement was carried out in a flow system. For each ͑2͒ 1,4-Dioxane ͑dioxane͒; solubility test, about 30 g of oven-dried, powdered solid was charged ͓ ͔ C4H8O2; 123-91-1 between layers of glass wool to an extraction vessel, and connected to the system. The experimental setup for measuring solubilities in supercritical Variables: Prepared by: carbon dioxide was mainly made up as follows: gas cylinder, compressor, t/ °C=25 A. Goto and R. Goto surge tank, pressure gauge, extractor, heating tape, heated valve, U-tube, rotameter, and dry test meter ͑the experimental setup was shown in the ͒ Solubility of 4-hydroxybenzoic acid in dioxane at 25 °C paper . The glass wool served to keep the powder from compacting during passage of gas through the extractor. Carbon dioxide was supplied at about 87 bar pressure and 313 K to the suction side of a double-end Molar volume of solvent Solubility diaphragm compressor and was compressed to the measurement pressure. / 3 −1 2 The pressure was controlled by a back-pressure regulator which diverted v2 cm mol 10 x1 the bulk of the compressed gas from the surge tank back to the suction 85.7 8.44 side of the compressor, resulting in an almost pulse-free flow of gas to the extractor. The high-pressure gas passing downstream of the compressor was heated in a tube preheater to about 373 K and was passed through the Auxiliary Information extraction vessel, which was maintained at 373Ϯ2 K by a temperature Methods/Apparatus/Procedure: indicator/controller which measured the temperature via an iron-constantan thermocouple positioned in the bed of powder and which regulated power The experimental details are given in the compilation of Ref. 19 for the to a heater on the extractor. The solution ͑consisting of carbon dioxide 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. and dissolved solid͒ leaving the extraction vessel was passed through a Source and Purity of Materials: heated, flow-regulating, pressure let-down valve and expanded to ambient The details are given in the compilation of Ref. 19 for the pressure. The solid dissolved by the gas passing though the extraction 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. vessel precipitated during the pressure-reduction step and was separated Estimated Errors: from the gas in the U-tube collector whose exit junction was fitted with a Nothing specified. glass wool filter to prevent fine solids from passing through the tube; a second U-tube with a more tightly packed glass wool filter was positioned downstream of the first collector and served to trap any fine particles that might have passed through the first filter. The ambient gas leaving the collection system passed through a rotameter for flow rate measurement and through a dry test meter for flow volume integration. The flow rate of 2.1.5. Data for hydroxybenzoic acid–inorganic the carbon dioxide through the extractor was maintained at 3 SLPM ͑standard liters per minute͒; that flow rate was found to ensure that compound systems solubility equilibrium was achieved in the gas at the exit of the extractor. Gravimetric determinations of the amount of solid collected coupled with the integrated volume of gas passing through the system during a solubility test allowed concentration levels of the solute in the gas to be calculated. 2.1.5.1. Salicylic acid Source and Purity of Materials: Salicylic acid was purchased from Aldrich Chem. Co. and the purity of Components: Original Measurements: the acid was more than 99%. ͑1͒ Benzoic acid, 2-hydroxy- 30V.J. Krukonis and R.T. Kurnik, Carbon dioxide of grade 2.8 was purchased from Airco, Inc. ͑o-hydroxybenzoic acid, salicylic J. Chem. Eng. Data 30, 247 Estimated Errors: ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1985 . Solubility: Precision of 1%. ͑2͒ Carbon dioxide ͑supercritical Temperature: Precision of Ϯ2K. ͒ ͓ ͔ fluid ;CO2; 124-38-9 Pressure: Nothing specified.

Variables: Prepared by: Pressure: 207–414ϫ105 Pa H. Miyamoto and A. Goto T/K=373.2

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The first two equilibrium cells were 20 cm in length with an internal Components: Original Measurements: volume of 9.5 cm3, while the third cell consisted of a high-pressure reflex 31 ͑1͒ Benzoic acid, 2-hydroxy- G.S. Gurdial and N.R. Foster, Jerguson sight gauge. The sight gauge was considered important to ensure ͑o-hydroxybenzoic acid, salicylic Ind. Eng. Chem. Res. 30, 575 measurement of equilibrium solid solubility, since melting-point ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1991 . depression from interaction of high-pressure carbon dioxide with a solid ͑2͒ Carbon dioxide ͑supercritical has been observed ͓M.A. McHugh and T.J. Yogan, J. Chem. Eng. Data 29, ͒ ͓ ͔ fluid ;CO2; 124-38-9 112 ͑1984͒; H. Chang and D.G. Morrell, J. Chem. Eng. Data 30,74 ͑1985͔͒. The equilibrium cells were packed with the solute to be extracted Variables: Prepared by: with alternate layers of glass wool to prevent solid compaction. Glass 5 Pressure: 81.1–202ϫ10 Pa H. Miyamoto and A. Goto wool was also plugged at the outlet of each column to avoid blockage of t/ °C=35–55 the lines connecting the extraction tubes. A 5 ␮m filter was installed after the last extraction cell to prevent entrainment of the solid during the experiment. Solubility of salicylic acid in supercritical carbon dioxide The system was maintained at the desired temperature and pressure for approximately 30 min before continuous operation commenced. The Temperature, t/ °C equilibrium temperature and pressure of the system were measured at the 35 40 45 55 exit of the third equilibrium cell. The system pressure was measured with Pressurea a Druck digital pressure transducer and indicator. 5 4 10 Pa Solubility, 10 x1 After achievement of equilibrium, the back-pressure regulating valve was opened slightly and the inlet flow rate was adjusted to maintain a constant 81.1 0.34 0.11 0.07 — system pressure. Upon expansion to ambient conditions, the dissolved 86.1 0.75 0.18 — — solute precipitated out of the fluid phase. The precipitated solid was 91.2 1.23 0.66 0.17 — collected in a 2 ␮m filter, and the total flow of the gas was measured with 96.2 — 0.97 — — a wet test meter at ambient conditions after bubbling through a saturator. 101.3 1.64 1.36 0.83 0.34 To confirm that equilibrium solubility was being measured, measurements 3 111.4 1.86 1.63 1.27 0.73 were made at various flow rates ranging from 200 to 400 cm /min ͑STP͒. 121.6 2.08 1.92 1.72 1.3 Variation of the flow rate in this range was found to have no effect on the 131.7 2.21 2.23 2.27 2.28 observed solubilities, thereby confirming that equilibrium solubility was being measured. 141.8 — 2.53 2.59 2.68 The determination of equilibrium solubility was achieved by a gravimetric 152.0 2.41 2.76 3.05 3.34 method. At the end of each experiment, the mass of solid collected in the 162.1 — 3.02 3.25 4.01 filter was determined with a Mettler balance. The back-pressure regulating 172.2 2.62 3.15 3.59 4.81 valve and the transfer line were flushed with an organic solvent to recover 182.4 2.80 3.5 3.85 5.46 all the precipitate. 192.5 — 3.64 — 5.72 Source and Purity of Materials: 202.6 3.06 3.95 4.32 6.24 Salicylic acid was purchased from Unilab, and the purity was more than 99%. a 5 In the original paper, the pressure was given as bar. 1 bar=10 Pa. Liquid carbon dioxide was of food grade, and the minimum purity was 99.8%. All chemicals were used without further purification. Auxiliary Information Estimated Errors: Methods/Apparatus/Procedure: Temperature: Precision of Ϯ0.2 °C. Equilibrium solubility data were obtained by using a continuous flow Pressure: Precision within Ϯ0.5%.

apparatus. Experimental setup was as follows: CO2 cylinder, pressure gauge, shutoff valves, HPLC pump, temperature controller, surge tank, pressure transducer, equilibrium cell, Jerguson gauge, thermocouple, filter, regulating valve, collection tube, filter, saturator, wet test meter, and constant temperature bath ͑the experimental setup was shown in the paper͒. Liquid carbon dioxide was directed to a high-pressure liquid chromatography ͑HPLC͒ pump at ambient temperature after passing 2.1.5.2. 3-Hydroxybenzoic acid through a high-pressure 7 ␮m in-line filter. The HPLC pump was capable of delivering constant flow rates ranging from 0.1 to 9.9 ml/min at Components: Original Measurements: pressures up to 300 bar. ͑1͒ Benzoic acid, 3-hydroxy- 30V.J. Krukonis and R.T. Kurnik, After compression, the carbon dioxide was charged into a 300 cm3 sample ͑m-hydroxybenzoic acid͒; J. Chem. Eng. Data 30,247 cylinder that acted as a surge tank to dampen any pressure fluctuation. C H O ; ͓99-06-9͔ ͑1985͒. The high-pressure carbon dioxide then passed through a preheated coil, 7 6 3 ͑2͒ Carbon dioxide ͑supercritical enabling the solvent to reach the desired extraction temperature. After fluid͒;CO; ͓124-38-9͔ reaching thermal equilibrium within the constant-temperature bath 2 Ϯ controlled to within 0.5 °C, the solvent was introduced into a system of Variables: Prepared by: three high-pressure equilibrium cells connected in series. Pressure: 207–414ϫ105 Pa H. Miyamoto and A. Goto T/K=373.2

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Solubility of 3-hydroxybenzoic acid in supercritical carbon dioxide at Estimated Errors: 373.2 K Solubility: Precision of 1%. Temperature: Precision of Ϯ2K. a Pressure Solubility Pressure: Nothing speciﬁed.

5 5 10 Pa 10 x1 2.2. Paraben–organic compound systems 207 2.71 276 5.35 2.2.1. Critical evaluation of the solubility of 345 7.54 parabens in alcohols 414 11.2 2.2.1.1. Methylparaben aIn the original paper, the pressure was given as bar. 1 bar=105 Pa.

Auxiliary Information Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Methods/Apparatus/Procedure: methyl ester ͑methyl Shizuoka, Shizuoka, Japan The experimental details are given in the compilation of Ref. 30 for the 4-hydroxybenzoate, Rensuke Goto, University of ͒ salicylic acid–carbon dioxide system in Sec. 2.1.5.1. methylparaben ;C8H8O3; Shizuoka, Shizuoka, Japan ͓ ͔ Source and Purity of Materials: 99-76-3 Hiroshi Fukuda, Kitasato ͑2͒ Methyl alcohol ͑methanol͒; University, Tokyo, Japan 3-Hydroxybenzoic acid was purchased from Aldrich Chem. Co. and the CH O; ͓67-56-1͔ purity of the acid was 99%. 4 Carbon dioxide of grade 2.8 was purchased from Airco, Inc. Estimated Errors: Critical Evaluation Solubility: Precision of 1%. TABLE 22. Summary of experimental solubility data of methylparaben in Temperature: Precision of Ϯ2K. methanol Pressure: Nothing speciﬁed. / T K 100w1 100x1 Analytical method Reference

298.2 39.5 12.1 Spectroscopy, Gravimetry 32 2.1.5.3. 4-Hydroxybenzoic acid 298.2 39.5 12.1 Spectroscopy 33 298.2 12.54 Spectroscopy 19 303.2 43.3 13.9 Spectroscopy 33 Components: Original Measurements: 308.2 47.9 16.2 Spectroscopy 33 ͑1͒ Benzoic acid, 4-hydroxy- 30V.J. Krukonis and R.T. Kurnik, 313.2 50.8 17.8 Spectroscopy 33 ͑p-hydroxybenzoic acid͒; J. Chem. Eng. Data 30, 247 ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 1985 . The critical evaluation was carried out as described in ͑ ͒ ͑ 2 Carbon dioxide supercritical Sec. 2.1.1.1 for salicylic acid in n-heptane. fluid͒;CO; ͓124-38-9͔ 2 The number of publications: 3 Variables: Prepared by: The range of temperature: T/K=298.2–313.2 Pressure: 207–414ϫ105 Pa H. Miyamoto and A. Goto The units: mass percent and mole fraction / T K=373.2 Analytical methods: spectroscopy and gravimetry Data in Table 22 for the solubility of methylparaben in Solubility of 4-hydroxybenzoic acid in supercritical carbon dioxide at methanol expressed by mole fraction were fitted to Eqs. ͑1͒ 373.2 K and ͑2͒ given in Sec. 1.3. The data points nearly agree with ͑ ͒ Pressurea Solubility Eq. 2 over the whole range of temperatures, as shown in Fig. 10, but they deviated from Eq. ͑1͒. Multiple regression ͑ ͒ 105 Pa 105x analysis according to Eq. 2 yielded the following results: 1 Multiple correlation coefficient: 0.995 207 1.33 276 3.57 345 5.77 414 7.49 aIn the original paper, the pressure was given as bar. 1 bar=105 Pa.

Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 30 for the salicylic acid–carbon dioxide system in Sec. 2.1.5.1. Source and Purity of Materials: 4-Hydroxybenzoic acid was purchased from Aldrich Chem. Co. and the purity of the acid was more than 99%. ͑ ͒ Carbon dioxide of grade 2.8 was purchased from Airco, Inc. FIG. 10. Fitting curve of Eq. 2 and the observed data for methylparaben in methanol.

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Sample size: 6 data points Temperature: Precision of Ϯ0.1 °C. p-value ͑F test͒: 0.000 Constants: A=−2392Ϯ122, C=5.921Ϯ0.401 White circles in Fig. 10 represent the observed data and Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, the black line corresponds to calculated values according to ͑ ͑ ͒ ͑ / ͒ methyl ester methyl H. Petersen, Jr., and A. N. Eq. 2 ln x1 =−2392 T+5.921 . The observed data ﬁt 4-hydroxybenzoate, Paruta, J. Pharm. Sci. 66,42 ͒ ͑ ͒ closely with the calculated values in the range of methylparaben ;C8H8O3; 1977 . 298.2–313.2 K, with the multiple correlation coefﬁcient of ͓99-76-3͔ 0.995, as shown in Fig. 10. Therefore, the calculated value at ͑2͒ Methyl alcohol ͑methanol͒; ͓ ͔ each measured temperature is reasonably considered as a rec- CH4O; 67-56-1 ommended value over the whole range of temperature. Variables: Prepared by: Table 23 shows the observed data in the range of t/ °C=25–40 A. Goto and R. Goto 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature. Solubility of methylparaben in methanol

TABLE 23. Observed data and recommended values calculated according to Eq. ͑2͒ for methylparaben in methanol Temperature Solubility w a / ͑ ͒ ͑ ͒ 1 T K 100x1 obs 100x1 rec / ͑ ͒ t °C x1 compiler

298.2 12.1 12.3 25 0.121 0.395 303.2 13.9 14.0 30 0.139 0.433 308.2 16.2 15.9 35 0.162 0.479 313.2 17.8 18.0 40 0.178 0.508

aIn the original paper, the solubility was given as mg/g of solution. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Auxiliary Information methyl ester ͑methyl 216 ͑1969͒. Methods/Apparatus/Procedure: 4-hydroxybenzoate, methylparaben͒;CH O ; The solute and solvent were placed in 15 ml vials attached to a 8 8 3 ͓ ͓99-76-3͔ submerged rotating plastic disk A.N. Paruta, J. Pharm. Sci. 55, 1208 ͑ ͔͒ ͑2͒ Methyl alcohol ͑methanol͒; 1966 . After equilibration for 17 h at 25 °C, the sample of appropriate ͓ ͔ volume was withdrawn through a fine glass-wool plug fitted to a pipet CH4O; 67-56-1 with a short rubber tube. The sample solution was placed in a volumetric Variables: Prepared by: flask and diluted to the appropriate volume for analysis. The concentration t/ °C=25 A. Goto and R. Goto of solute in solutions was determined spectrophotometrically. A Beckman DK-2 spectrophotometer was used to determine the absorbance of the solutions. The solubility of each solute was determined at least eight times Solubility of methylparaben in methanol at 25 °C for each solvent and average values were taken. Source and Purity of Materials: Density Solubility Spectrograde methylparaben was purchased from Matheson Coleman and Bell Co. a 100w1 The source and the purity of methanol were not reported. ␳/ −3 ͑ ͒ gcm compiler x1 Estimated Errors: Solubility: Precision within 2.5%. 0.9166 39.5 0.121 Temperature: Precision of Ϯ0.1 °C. aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. ͑ Methods/Apparatus/Procedure: methyl ester methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. Screw-capped bottles with the ester in excess and solvent were rotated for methylparaben͒;CH O ; 24 h in a constant-temperature bath regulated at 25 °C. Samples were 8 8 3 ͓99-76-3͔ withdrawn through a pledget of glass wool into a pipet, which was wiped ͑2͒ Methyl alcohol ͑methanol͒; clean and allowed to drain into either a tared weighing bottle or a CH O; ͓67-56-1͔ volumetric flask. Solubilities were determined by either a 4 spectrophotometric or gravimetric procedure. Variables: Prepared by: Source and Purity of Materials: t/ °C=25 A. Goto and R. Goto Methanol ͑Fisher certified͒ was used. Methylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: Solubility: Nothing specified.

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Solubility of methylparaben in methanol at 25 °C

Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1

40.7 0.1254

Auxiliary Information

Methods/Apparatus/Procedure: FIG. 11. Fitting curve of Eq. ͑2͒ and the observed data for methylparaben in The experimental details are given in the compilation of Ref. 19 for the ethanol. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: ͑ ͒ Methylparaben Tenneco Chemical Inc. was used as obtained. Melting Eq. ͑2͒ ͑ln x =−1804/T+4.126͒. The observed data ﬁt point measured by a hot-stage method was 399.65 K. 1 The solvent was spectrophotometric grade, ACS grade, or redistilled closely with the calculated values in the range of before use. 298.2–313.2 K, with the multiple correlation coefﬁcient of Estimated Errors: 0.980, as shown in Fig. 11. Therefore, the calculated value at Solubility: The experimental variation was below 3%. each measured temperature is reasonably considered as a rec- Temperature: Precision of Ϯ0.2 °C. ommended value over the whole range of temperature. Table 25 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated Components: Evaluators: ͑ ͒ ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of from Eq. 2 at each temperature. methyl ester ͑methyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of TABLE 25. Observed data and recommended values calculated according to ͒ ͑ ͒ methylparaben ;C8H8O3 Shizuoka, Shizuoka, Japan Eq. 2 for methylparaben in ethanol ͓99-76-3͔ Hiroshi Fukuda, Kitasato / ͑ ͒ ͑ ͒ ͑2͒ Ethyl alcohol ͑ethanol͒; University, Tokyo, Japan T K 100x1 obs 100x1 rec ͓ ͔ C2H6O; 64-17-5 298.2 14.7 14.6 303.2 15.6 16.2 Critical Evaluation 308.2 17.4 17.8 TABLE 24. Summary of experimental solubility data of methylparaben in 313.2 20.1 19.5 ethanol

T/K100w 100x Analytical method Reference 1 1 Components: Original Measurements: 32 298.2 36.0 14.7 Spectroscopy, Gravimetry 32 ͑1͒ Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, 298.2 36.7 14.7 Spectroscopy 33 methyl ester ͑methyl 216 ͑1969͒. 298.2 14.95 Spectroscopy 19 4-hydroxybenzoate, methylparaben͒;CH O ; 303.2 37.9 15.6 Spectroscopy 33 8 8 3 ͓99-76-3͔ 308.2 41.0 17.4 Spectroscopy 33 ͑2͒ Ethyl alcohol ͑ethanol͒; 313.2 45.4 20.1 Spectroscopy 33 ͓ ͔ C2H6O; 64-17-5

The critical evaluation was carried out as described in Variables: Prepared by: Sec. 2.1.1.1 for salicylic acid in n-heptane. t/ °C=25 A. Goto and R. Goto The number of publications: 3 / The range of temperature: T K=298.2–313.2 Solubility of methylparaben in ethanol at 25 °C The units: mass percent and mole fraction Analytical methods: spectroscopy and gravimetry Density Solubility Data for the solubility of methylparaben in ethanol ex- ͑ ͒ ͑ ͒ a pressed by mole fraction were ﬁtted to Eqs. 1 and 2 given 100w1 ␳/ −3 ͑ ͒ in Sec. 1.3 ͑Table 24͒. The data points agree with Eq. ͑2͒ gcm compiler x1

over the whole range of temperatures, as shown in Fig. 11, 0.8970 36.0 0.147 but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following results: aIn the original paper, the solubility was given as milligrams of the ester per Multiple correlation coefﬁcient: 0.980 grams of solution. Sample size: 6 data points Auxiliary Information p-value ͑F test͒: 0.001 Constants: A=−1804Ϯ183, C=4.126Ϯ0.602 Methods/Apparatus/Procedure: White circles in Fig. 11 represent the observed data and The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. the black line corresponds to calculated values according to

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Source and Purity of Materials: Solubility of methylparaben in ethanol at 25 °C Absolute ethanol was obtained from U.S. Industrial Chem. Co. Methylparaben was obtained from Matheson, Coleman and Bell. Molar volume of solvent Solubility Estimated Errors: v /cm3 mol−1 x Solubility: Nothing speciﬁed. 2 1 Temperature: Precision of Ϯ0.1 °C. 58.7 0.1495

Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Methods/Apparatus/Procedure: methyl ester ͑methyl H. Petersen, Jr., and A.N. Paruta, The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͒ methylparaben ;C8H8O3; Source and Purity of Materials: ͓ ͔ 99-76-3 The details are given in the compilation of Ref. 19 for the ͑ ͒ ͑ ͒ 2 Ethyl alcohol ethanol ; 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͓ ͔ C2H6O; 64-17-5 Estimated Errors: Variables: Prepared by: Solubility: The experimental variation was below 3%. Ϯ t/ °C=25–40 A. Goto and R. Goto Temperature: Precision of 0.2 °C.

Solubility of methylparaben in ethanol Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Temperature Solubility methyl ester ͑methyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of w a 1 methylparaben͒;CH O ; Shizuoka, Shizuoka, Japan t/ °C x ͑compiler͒ 8 8 3 1 ͓99-76-3͔ Hiroshi Fukuda, Kitasato ͑ ͒ ͑ 25 0.147 0.367 2 1-Propanol propan-1-ol, University, Tokyo, Japan propyl alcohol͒;CH O; 30 0.156 0.379 3 8 ͓71-23-8͔ 35 0.174 0.410 40 0.201 0.454 Critical Evaluation a In the original paper, the solubility was given as mg/g of solution. TABLE 26. Summary of experimental solubility data of methylparaben in 1-propanol Auxiliary Information T/K 100w 100x Analytical method Reference Methods/Apparatus/Procedure: 1 1 The experimental details are given in the compilation of Ref. 33 for the 298.2 29.5 13.8 Spectroscopy, Gravimetry 32 methylparaben–methanol system in Sec. 2.2.1.1. 298.2 29.5 13.8 Spectroscopy 33 Source and Purity of Materials: 298.2 14.86 Spectroscopy 19 Spectrograde methylparaben was purchased from Matheson Coleman and 303.2 30.9 15.2 Spectroscopy 33 Bell Co. The melting point was within 1 °C of the literature value. 308.2 35.5 18.0 Spectroscopy 33 ͑ ͒ Ethanol J.T. Baker was of absolute reagent quality. The purity of the 313.2 38.3 19.9 Spectroscopy 33 alcohol was established by refractive-index and dielectric-constant measurements. The critical evaluation was carried out as described in Estimated Errors: Sec. 2.1.1.1 for salicylic acid in n-heptane. Solubility: Precision within 2.5%. The number of publications: 3 Ϯ Temperature: Precision of 0.1 °C. The range of temperature: T/K=298.2–313.2 The units: mass percent and mole fraction Analytical methods: spectroscopy and gravimetry Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. Data for the solubility of methylparaben in 1-propanol methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ 4-hydroxybenzoate, 188 ͑1984͒. given in Sec. 1.3 ͑Table 26͒. The data points nearly agree ͒ methylparaben ;C8H8O3; with Eq. ͑2͒ over the whole range of temperatures, as shown ͓ ͔ 99-76-3 in Fig. 12, but they deviated from Eq. ͑1͒. Multiple regres- ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ sion analysis according to Eq. ͑2͒ yielded the following re- C2H6O; 64-17-5 sults: Variables: Prepared by: Multiple correlation coefﬁcient: 0.975 t/ °C=25 A. Goto and R. Goto Sample size: 6 data points p-value ͑F test͒: 0.001 Constants: A=−2146Ϯ246, C=5.235Ϯ0.812 White circles in Fig. 12 represent the observed data and the black line corresponds to calculated values according to

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Auxiliary Information

FIG. 12. Fitting curve of Eq. ͑2͒ and the observed data for methylparaben in Components: Original Measurements: 1-propanol. ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, methyl ester ͑methyl H. Petersen, Jr., and A. N. ͑ ͒ ͑ / ͒ 4-hydroxybenzoate, Paruta, J. Pharm. Sci. 66,42 Eq. 2 ln x1 =−2146 T+5.235 . The observed data ﬁt ͒ ͑ ͒ methylparaben ;C8H8O3; 1977 . closely with the calculated values in the range of ͓99-76-3͔ 298.2–313.2 K, with the multiple correlation coefﬁcient of ͑2͒ 1-Propanol ͑propan-1-ol, ͒ propyl alcohol ;C3H8O; 0.975, as shown in Fig. 12. Therefore, the calculated value at ͓71-23-8͔ each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Variables: Prepared by: t/ °C=25–40 A. Goto and R. Goto Table 27 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated Solubility of methylparaben in 1-propanol from Eq. ͑2͒ at each temperature. Temperature Solubility TABLE 27. Observed data and recommended values calculated according to a Eq. ͑2͒ for methylparaben in 1-propanol w1 / ͑ ͒ t °C x1 compiler T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 25 0.138 0.295 298.2 13.8 14.0 30 0.152 0.309 303.2 15.2 15.8 35 0.180 0.355 308.2 18.0 17.7 40 0.199 0.383 313.2 19.9 19.8 aIn the original paper, the solubility was given as mg/g of solution.

Auxiliary Information Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Methods/Apparatus/Procedure: methyl ester ͑methyl 216 ͑1969͒. The experimental details are given in the compilation of Ref. 33 for the 4-hydroxybenzoate, methylparaben–methanol system in Sec. 2.2.1.1. ͒ methylparaben ;C8H8O3; Source and Purity of Materials: ͓99-76-3͔ Spectrograde methylparaben was purchased from Matheson Coleman and ͑2͒ 1-Propanol ͑propan-1-ol, Bell Co. Melting point was within 1 °C of literature values. ͒ propyl alcohol ;C3H8O; 1-Propanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the ͓71-23-8͔ alcohol was established by refractive-index and dielectric-constant measurements. Variables: Prepared by: Estimated Errors: t/ °C=25 A. Goto and R. Goto Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C. Solubility of methylparaben in 1-propanol at 25 °C

Density Solubility Components: Original Measurements: 19 a ͑1͒ Benzoic acid, 4-hydroxy-, A. Martin, P.L. Wu, and A. 100w1 ␳/ −3 ͑ ͒ methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, gcm compiler x1 4-hydroxybenzoate, 188 ͑1984͒. ͒ 0.8881 29.5 0.138 methylparaben ;C8H8O3; ͓99-76-3͔ aIn the original paper, the solubility was given as milligrams of the ester per ͑2͒ 1-Propanol ͑propan-1-ol, ͒ gram of solution. propyl alcohol ;C3H8O; ͓71-23-8͔

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Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

Solubility of methylparaben in 1-propanol at 25 °C

Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1

75.1 0.1486

Auxiliary Information

Methods/Apparatus/Procedure: FIG. 13. Fitting curve of Eq. ͑2͒ and the observed data for methylparaben in The experimental details are given in the compilation of Ref. 19 for the 1-butanol. 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: The details are given in the compilation of Ref. 19 for the White circles in Fig. 13 represent the observed data and 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. the black line corresponds to calculated values according to Estimated Errors: ͑ ͒ ͑ / ͒ Solubility: The experimental variation was below 3%. Eq. 2 ln x1 =−1590 T+3.405 . The observed data fit Temperature: Precision of Ϯ0.2 °C. closely with the calculated values in the range of 298.2–313.2 K, with the multiple correlation coefficient of 0.986, as shown in Fig. 13. Therefore, the calculated value at Components: Evaluators: each measured temperature is reasonably considered as a rec- ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of methyl ester ͑methyl Shizuoka, Shizuoka, Japan ommended value over the whole range of temperature. 4-hydroxybenzoate, Rensuke Goto, University of Table 29 shows the observed data in the range of ͒ methylparaben ;C8H8O3; Shizuoka, Shizuoka, Japan 298.2–313.2 K and the recommended values calculated ͓ ͔ 99-76-3 Hiroshi Fukuda, Kitasato from Eq. ͑2͒ at each temperature. ͑2͒ 1-Butanol ͑butan-1-ol, butyl University, Tokyo, Japan ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 TABLE 29. Observed data and recommended values calculated according to Eq. ͑2͒ for methylparaben in 1-butanol Critical Evaluation / ͑ ͒ ͑ ͒ TABLE 28. Summary of experimental solubility data of methylparaben in T K 100x1 obs 100x1 rec 1-butanol 298.2 14.6 14.6 / T K100w1 100x1 Analytical method Reference 303.2 15.4 15.9 308.2 17.2 17.3 298.2 26.2 14.6 Spectroscopy, Gravimetry 32 313.2 19.1 18.8 298.2 26.2 14.6 Spectroscopy 33 298.2 14.84 Spectroscopy 19 303.2 27.2 15.4 Spectroscopy 33 Components: Original Measurements: 308.2 29.8 17.2 Spectroscopy 33 ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, 313.2 32.6 19.1 Spectroscopy 33 methyl ester ͑methyl 216 ͑1969͒. 4-hydroxybenzoate, The critical evaluation was carried out as described in ͒ methylparaben ;C8H8O3; Sec. 2.1.1.1 for salicylic acid in n-heptane. ͓99-76-3͔ The number of publications: 3 ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ The range of temperature: T/K=298.2–313.2 alcohol ;C4H10O; 71-36-3 The units: mass percent and mole fraction Variables: Prepared by: Analytical methods: spectroscopy and gravimetry t/ °C=25 A. Goto and R. Goto Data for the solubility of methylparaben in 1-butanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ Solubility of methylparaben in 1-butanol at 25 °C given in Sec. 1.3 ͑Table 28͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown Density Solubility in Fig. 13, but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following re- a 100w1 ␳/ −3 ͑ ͒ sults: gcm compiler x1 Multiple correlation coefficient: 0.986 Sample size: 6 data points 0.8894 26.2 0.146 p-value ͑F test͒: 0.000 aIn the original paper, the solubility was given as milligrams of the ester per Constants: A=−1590Ϯ135, C=3.405Ϯ0.446 gram of solution.

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Auxiliary Information Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Solubility of methylparaben in 1-butanol at 25 °C Source and Purity of Materials: Molar volume of solvent Solubility The source of 1-butanol was not reported. Methyl 4-hydroxybenzoate was obtained from Matheson, Coleman, and / 3 −1 v2 cm mol x1 Bell. Estimated Errors: 92.0 0.1484 Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 19 for the 33 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑1͒ Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, methyl ester ͑methyl H. Petersen, Jr., and A.N. Paruta, Source and Purity of Materials: 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. The details are given in the compilation of Ref. 19 for the ͒ 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. methylparaben ;C8H8O3; ͓99-76-3͔ Estimated Errors: ͑2͒ 1-Butanol ͑butan-1-ol, butyl Solubility: The experimental variation was below 3%. ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Temperature: Precision of Ϯ0.2 °C.

Variables: Prepared by: t/ °C=25–40 A. Goto and R. Goto Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Solubility of methylparaben in 1-butanol methyl ester ͑methyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of ͒ Temperature Solubility methylparaben ;C8H8O3; Shizuoka, Shizuoka, Japan ͓99-76-3͔ Hiroshi Fukuda, Kitasato a ͑ ͒ ͑ w1 2 1-Hexanol hexan-1-ol, hexyl University, Tokyo, Japan / ͑ ͒ ͒ ͓ ͔ t °C x1 compiler alcohol ;C6H14O; 111-27-3

25 0.146 0.262 30 0.154 0.272 Critical Evaluation 35 0.172 0.298 TABLE 30. Summary of experimental solubility data of methylparaben in 1-hexanol 40 0.191 0.326 / aIn the original paper, the solubility was given as mg/g of solution. T K 100w1 100x1 Analytical method Reference

Auxiliary Information 298.2 20.5 15.5 Spectroscopy, Gravimetry 32 298.2 20.5 15.5 Spectroscopy 33 Methods/Apparatus/Procedure: 298.2 14.77 Spectroscopy 19 The experimental details are given in the compilation of Ref. 33 for the 303.2 21.2 16.6 Spectroscopy 33 methylparaben–methanol system in Sec. 2.2.1.1. 308.2 25.3 18.6 Spectroscopy 33 Source and Purity of Materials: 313.2 26.2 20.5 Spectroscopy 33 Spectrograde methylparaben was purchased from Matheson Coleman and Bell Co. Melting point was within 1 °C of literature values. The critical evaluation was carried out as described in 1-Butanol ͑TDY Mallinckrodt͒ was of analytical reagent quality. The Sec. 2.1.1.1 for salicylic acid in n-heptane. purity of the alcohol was established by refractive-index and The number of publications: 3 dielectric-constant measurements. The range of temperature: T/K=298.2–313.2 Estimated Errors: The units: mass percent and mole fraction Solubility: Precision within 2.5%. Analytical methods: spectroscopy and gravimetry Temperature: Precision of Ϯ0.1 °C. Data for the solubility of methylparaben in 1-hexanol expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 30͒. The data points closely agree Components: Original Measurements: ͑ ͒ ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. with Eq. 2 over the whole range of temperatures, as shown methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, in Fig. 14, but they deviated from Eq. ͑1͒. Multiple regres- 4-hydroxybenzoate, 188 ͑1984͒. sion analysis according to Eq. ͑2͒ yielded the following re- ͒ methylparaben ;C8H8O3; sults: ͓ ͔ 99-76-3 Multiple correlation coefﬁcient: 0.989 ͑2͒ 1-Butanol ͑butan-1-ol, butyl alcohol͒;CH O; ͓71-36-3͔ Sample size: 6 data points 4 10 p-value ͑F test͒: 0.000 Constants: A=−1836Ϯ139, C=4.272Ϯ0.459

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Auxiliary Information

FIG. 14. Fitting curve of Eq. ͑2͒ and the observed data for methylparaben in 1-hexanol. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, methyl ester ͑methyl H. Petersen, Jr., and A.N. Paruta, White circles in Fig. 14 represent the observed data and 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ the black line corresponds to calculated values according to methylparaben ;C8H8O3; ͑ ͒ ͑ / ͒ ͓99-76-3͔ Eq. 2 ln x1 =−1836 T+4.272 . The observed data ﬁt ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl closely with the calculated values in the range of ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 298.2–313.2 K, with the multiple correlation coefﬁcient of 0.989, as shown in Fig. 14. Therefore, the calculated value at Variables: Prepared by: / each measured temperature is reasonably considered as a rec- t °C=25–40 A. Goto and R. Goto ommended value over the whole range of temperature. Table 31 shows the observed data in the range of Solubility of methylparaben in 1-hexanol

298.2–313.2 K and the recommended values calculated Temperature Solubility from Eq. ͑2͒ at each temperature. a w1 t/ °C x ͑compiler͒ TABLE 31. Observed data and recommended values calculated according to 1 Eq. ͑2͒ for methylparaben in 1-hexanol 25 0.155 0.205 30 0.166 0.212 T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 35 0.186 0.253 298.2 15.5 15.2 40 0.205 0.262 303.2 16.6 16.8 a 308.2 18.6 18.6 In the original paper, the solubility was given as mg/g of solution. 313.2 20.5 20.4 Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 33 for the ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, methylparaben–methanol system in Sec. 2.2.1.1. methyl ester ͑methyl 216 ͑1969͒. Source and Purity of Materials: 4-hydroxybenzoate, Spectrograde methylparaben was purchased from Matheson Coleman and ͒ methylparaben ;C8H8O3; Bell Co. Melting points were within 1 °C of literature values. ͓99-76-3͔ The purity of 1-hexanol was 99 mol %. The purity of the alcohol was ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl established by refractive-index and dielectric-constant measurements. ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 Estimated Errors: Solubility: Precision within 2.5%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 A. Goto and R. Goto

Solubility of methylparaben in 1-hexanol at 25 °C Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. Density Solubility methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, ͑ ͒ 100w a 4-hydroxybenzoate, 188 1984 . 1 ͒ ␳/ −3 ͑ ͒ methylparaben ;C8H8O3; gcm compiler x1 ͓99-76-3͔ 0.8712 20.5 0.155 ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of methylparaben in 1-hexanol at 25 °C

Molar volume of solvent Solubility

/ 3 −1 v2 cm mol x1

125.2 0.1477

Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑ ͒ Source and Purity of Materials: FIG. 15. Fitting curve of Eq. 2 and the observed data for methylparaben in 1-decanol. The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: closely with the calculated values in the range of Solubility: The experimental variation was below 3%. Temperature: Precision of Ϯ0.2 °C. 298.2–313.2 K, with the multiple correlation coefﬁcient of 0.995, as shown in Fig. 15. Therefore, the calculated value at each measured temperature is reasonably considered as a rec- Components: Evaluators: ommended value over the whole range of temperature. ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Table 33 shows the observed data in the range of methyl ester ͑methyl Shizuoka, Shizuoka, Japan 298.2–313.2 K and the recommended values calculated 4-hydroxybenzoate, Rensuke Goto, University of ͑ ͒ ͒ from Eq. 2 at each temperature. methylparaben ;C8H8O3; Shizuoka, Shizuoka, Japan ͓99-76-3͔ Hiroshi Fukuda, Kitasato ͑2͒ 1-Decanol ͑decan-1-ol, decyl University, Tokyo, Japan TABLE 33. Observed data and recommended values calculated according to ͒ ͓ ͔ Eq. ͑2͒ for methylparaben in 1-decanol alcohol ;C10H22O; 112-30-1 / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec Critical Evaluation TABLE 32. Summary of experimental solubility data of methylparaben in 298.2 8.8 8.9 1-decanol 303.2 8.8 10.6 308.2 10.9 12.5 / T K100w1 100x1 Analytical method Reference 313.2 12.8 14.8

298.2 9.0 8.8 Spectroscopy, Gravimetry 32 298.2 8.8 8.8 Spectroscopy 33 Components: Original Measurements: 303.2 10.3 10.9 Spectroscopy 33 ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, 308.2 12.2 12.8 Spectroscopy 33 methyl ester ͑methyl 216 ͑1969͒. 313.2 13.9 14.4 Spectroscopy 33 4-hydroxybenzoate, ͒ methylparaben ;C8H8O3; The critical evaluation was carried out as described in ͓99-76-3͔ Sec. 2.1.1.1 for salicylic acid in n-heptane. ͑2͒ 1-Decanol ͑decan-1-ol, decyl ͒ ͓ ͔ The number of publications: 2 alcohol ;C10H22O; 112-30-1 / The range of temperature: T K=298.2–313.2 Variables: Prepared by: The units: mass percent and mole fraction t/ °C=25 A. Goto and R. Goto Analytical methods: spectroscopy and gravimetry Data for the solubility of methylparaben in 1-decanol Solubility of methylparaben in 1-decanol at 25 °C expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 32͒. The data points closely agree Density Solubility

with Eq. ͑2͒ over the whole range of temperatures, as shown a 100w1 ͑ ͒ ␳/ −3 ͑ ͒ in Fig. 15, but they deviated from Eq. 1 . Multiple regres- gcm compiler x1 sion analysis according to Eq. ͑2͒ yielded the following results: 0.8658 9.0 0.088 Multiple correlation coefﬁcient: 0.995 aIn the original paper, the solubility was given as milligrams of the ester per Sample size: 5 data points gram of solution. ͑ ͒ p-value F test : 0.000 Auxiliary Information Constants: A=−3136Ϯ189, C=8.100Ϯ0.622 White circles in Fig. 15 represent the observed data and Methods/Apparatus/Procedure: the black line corresponds to calculated values according to The experimental details are given in the compilation of Ref. 32 for the ͑ ͒ ͑ / ͒ methylparaben–methanol system in Sec. 2.2.1.1. Eq. 2 ln x1 =−3136 T+8.100 . The observed data ﬁt

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Source and Purity of Materials: The source of 1-decanol was not reported. Methylparaben was obtained from Matheson, Coleman and Bell. Estimated Errors: Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C.

Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, methyl ester ͑methyl H. Petersen, Jr., and A.N. Paruta, 66 ͑ ͒ 4-hydroxybenzoate, J. Pharm. Sci. ,42 1977 . FIG. 16. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in ͒ methylparaben ;C8H8O3; methanol. ͓99-76-3͔ ͑2͒ 1-Decanol ͑decan-1-ol, decyl ͒ ͓ ͔ alcohol ;C10H22O; 112-30-1 Critical Evaluation Variables: Prepared by: TABLE 34. Summary of experimental solubility data of ethylparaben in methanol t/ °C=25–40 A. Goto and R. Goto / T K 100w1 100x1 Analytical method Reference Solubility of methylparaben in 1-decanol 298.2 45.2 13.5 Spectroscopy, Gravimetry 32 Temperature Solubility 298.2 45.2 13.5 Spectroscopy 33 303.2 49.0 15.7 Spectroscopy 33 a w1 308.2 54.1 18.5 Spectroscopy 33 / ͑ ͒ t °C x1 compiler 313.2 57.0 20.8 Spectroscopy 33 25 0.088 0.088 30 0.109 0.103 The critical evaluation was carried out as described in 35 0.128 0.122 Sec. 2.1.1.1 for salicylic acid in n-heptane. 40 0.144 0.139 The number of publications: 2 / aIn the original paper, the solubility was given as mg/g of solution. The range of temperature: T K=298.2–313.2 The units: mass percent and mole fraction Auxiliary Information Analytical methods: spectroscopy and gravimetry Methods/Apparatus/Procedure: Data for the solubility of ethylparaben in methanol ex- The experimental details are given in the compilation of Ref. 33 for the pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given methylparaben–methanol system in Sec. 2.2.1.1. ͑ ͒ Source and Purity of Materials: in Sec. 1.3 Table 34 . The data points nearly agree with Eq. Spectrograde methylparaben was purchased from Matheson Coleman and ͑2͒ over the whole range of temperatures, as shown in Fig. Bell Co. Melting points were within 1 °C of literature values. 16, but they deviated from Eq. ͑1͒. Multiple regression The purity of 1-decanol was 99 mol %. The purity of the alcohol was ͑ ͒ established by refractive-index and dielectric-constant measurements. analysis according to Eq. 2 yielded the following results: Estimated Errors: Multiple correlation coefficient: 0.999 Solubility: Precision within 2.5%. Sample size: 5 data points Temperature: Precision of Ϯ0.1 °C. p-value ͑F test͒: 0.000 Constants: A=−2740Ϯ75, C=7.188Ϯ0.248 White circles in Fig. 16 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2740 T+7.188 . The observed data fit 2.2.1.2. Ethylparaben closely with the calculated values in the range of 298.2–313.2 K, with the multiple correlation coefficient of Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of 0.999, as shown in Fig. 16. Therefore, the calculated value at ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan each measured temperature is reasonably considered as a rec- 4-hydroxybenzoate, Rensuke Goto, University of ͒ ommended value over the whole range of temperature. ethylparaben ;C9H10O3; Shizuoka, Shizuoka, Japan ͓120-47-8͔ Hiroshi Fukuda, Kitasato Table 35 shows the observed data in the range of ͑2͒ Methyl alcohol ͑methanol͒; University, Tokyo, Japan 298.2–313.2 K and the recommended values calculated CH O; ͓67-56-1͔ 4 from Eq. ͑2͒ at each temperature.

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TABLE 35. Observed data and recommended values calculated according to Solubility of ethylparaben in methanol Eq. ͑2͒ for ethylparaben in methanol Temperature Solubility T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a w1 / ͑ ͒ 298.2 13.5 13.5 t °C x1 compiler 303.2 15.7 15.7 25 0.135 0.452 308.2 18.5 18.2 30 0.157 0.490 313.2 20.8 21.0 35 0.185 0.541 40 0.208 0.576

Components: Original Measurements: aIn the original paper, the solubility was given as mg/g of solution. ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ethyl ester ͑ethyl 216 ͑1969͒. Auxiliary Information 4-hydroxybenzoate, ͒ Methods/Apparatus/Procedure: ethylparaben ;C9H10O3; ͓120-47-8͔ The experimental details are given in the compilation of Ref. 33 for the ͑2͒ Methyl alcohol ͑methanol͒; methylparaben–methanol system in Sec. 2.2.1.1. ͓ ͔ Source and Purity of Materials: CH4O; 67-56-1 Spectrograde ethylparaben was purchased from Matheson Coleman and Variables: Prepared by: Bell Co. t/ °C=25 A. Goto and R. Goto The source and the purity of methanol were not reported. Estimated Errors: Solubility: Precision within 2.5%. Solubility of ethylparaben in methanol at 25 °C Temperature: Precision of Ϯ0.1 °C. Density Solubility

a 100w1 Components: Evaluators: ␳/ −3 ͑ ͒ gcm compiler x1 ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan 0.9256 45.2 0.135 4-hydroxybenzoate, Rensuke Goto, University of ethylparaben͒;CH O ; Shizuoka, Shizuoka, Japan a 9 10 3 In the original paper, the solubility was given as milligrams of the ester per ͓120-47-8͔ Hiroshi Fukuda, Kitasato gram of solution. ͑2͒ Ethyl alcohol ͑ethanol͒; University, Tokyo, Japan ͓ ͔ C2H6O; 64-17-5 Auxiliary Information

Methods/Apparatus/Procedure: Critical Evaluation The experimental details are given in the compilation of Ref. 32 for the TABLE 36. Summary of experimental solubility data of ethylparaben in methylparaben–methanol system in Sec. 2.2.1.1. ethanol Source and Purity of Materials: ͑ ͒ / Methanol Fisher certified was used. T K 100w1 100x1 Analytical method Reference Ethylparaben was obtained from Matheson, Coleman and Bell. Estimated Errors: 298.2 41.2 16.5 Spectroscopy, Gravimetry 32 Solubility: Nothing specified. 298.2 41.2 16.5 Spectroscopy 33 Temperature: Precision of Ϯ0.1 °C. 303.2 44.9 18.4 Spectroscopy 33 308.2 50.1 21.8 Spectroscopy 33 313.2 50.5 22.0 Spectroscopy 33 Components: Original Measurements: The critical evaluation was carried out as described in 33 ͑1͒ Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, Sec. 2.1.1.1 for salicylic acid in n-heptane. ethyl ester ͑ethyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. The number of publications: 2 ͒ T/ ethylparaben ;C9H10O3; The range of temperature: K=298.2–313.2 ͓120-47-8͔ The units: mass percent and mole fraction ͑2͒ Methyl alcohol ͑methanol͒; Analytical methods: spectroscopy and gravimetry ͓ ͔ CH4O; 67-56-1 Data for the solubility of ethylparaben in ethanol ex- Variables: Prepared by: pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given t/ °C=25–40 A. Goto and R. Goto in Sec. 1.3 ͑Table 36͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. 17, but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.971 Sample size: 5 data points p-value ͑F test͒: 0.006

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Auxiliary Information

FIG. 17. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in ethanol. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Constants: A=−1974Ϯ282, C=4.823Ϯ0.929 ethyl ester ͑ethyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. White circles in Fig. 17 represent the observed data and ͒ ethylparaben ;C9H10O3; the black line corresponds to calculated values according to ͓120-47-8͔ ͑ ͒ ͑ / ͒ ͑ ͒ ͑ ͒ Eq. 2 ln x1 =−1974 T+4.823 . The observed data ﬁt 2 Ethyl alcohol ethanol ; ͓ ͔ closely with the calculated values in the range of C2H6O; 64-17-5 298.2–313.2 K, with the multiple correlation coefﬁcient of Variables: Prepared by: 0.971, as shown in Fig. 17. Therefore, the calculated value at t/ °C=25–40 A. Goto and R. Goto each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Solubility of ethylparaben in ethanol Table 37 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated Temperature Solubility from Eq. ͑2͒ at each temperature. a w1 / ͑ ͒ t °C x1 compiler TABLE 37. Observed data and recommended values calculated according to Eq. ͑2͒ for ethylparaben in ethanol 25 0.165 0.412 30 0.184 0.449 / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec 35 0.218 0.501 40 0.220 0.505 298.2 16.5 16.6 303.2 18.4 18.5 aIn the original paper, the solubility was given as mg/g of solution. 308.2 21.8 20.6 Auxiliary Information 313.2 22.0 22.8 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 33 for the Components: Original Measurements: methylparaben–methanol system in Sec. 2.2.1.1. 32 ͑1͒ Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, Source and Purity of Materials: ͑ ͑ ͒ ethyl ester ethyl 216 1969 . Spectrograde ethylparaben was purchased from Matheson Coleman and 4-hydroxybenzoate, Bell Co. Melting point was within 1 °C of literature values. ethylparaben͒;CH O ; 9 10 3 Ethanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the ͓120-47-8͔ alcohol was established by refractive-index and dielectric-constant ͑2͒ Ethyl alcohol ͑ethanol͒; measurements. C H O; ͓64-17-5͔ 2 6 Estimated Errors: Variables: Prepared by: Solubility: Precision within 2.5%. t/ °C=25 A. Goto and R. Goto Temperature: Precision of Ϯ0.1 °C.

Solubility of ethylparaben in ethanol at 25 °C Components: Evaluators: ͑ ͒ Density Solubility 1 Benzoic acid, 4-hydroxy-, Ayako Goto, University of ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan a 100w1 4-hydroxybenzoate, Rensuke Goto, University of ␳/ −3 ͑ ͒ ͒ gcm compiler x1 ethylparaben ;C9H10O3; Shizuoka, Shizuoka, Japan ͓120-47-8͔ Hiroshi Fukuda, Kitasato 0.9098 41.2 0.165 ͑2͒ 1-Propanol ͑propan-1-ol, University, Tokyo, Japan propyl alcohol͒;CH O; a 3 8 In the original paper, the solubility was given as milligrams of the ester per ͓71-23-8͔ gram of solution.

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TABLE 39. Observed data and recommended values calculated according to Eq. ͑2͒ for ethylparaben in 1-propanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

298.2 17.6 17.4 303.2 18.8 19.2 308.2 21.6 21.1 313.2 22.9 23.1

FIG. 18. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in Components: Original Measurements: 1-propanol. ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, ethyl ester ͑ethyl J. Pharm. Sci. 53, 636 ͑1964͒. 4-hydroxybenzoate, Critical Evaluation ͒ ethylparaben ;C9H10O3; TABLE 38. Summary of experimental solubility data of ethylparaben in ͓120-47-8͔ 1-propanol ͑2͒ 1-Propanol ͑propan-1-ol, propyl alcohol͒;CH O; / 3 8 T K100w1 100x1 Analytical method Reference ͓71-23-8͔

298.2 36.3 17.1 Gravimetry, Spectroscopy 34 Variables: Prepared by: 298.2 36.2 17.6 Spectroscopy, Gravimetry 32 t/ °C=25 A. Goto and R. Goto 298.2 36.2 17.6 Spectroscopy 33 303.2 38.8 18.8 Spectroscopy 33 308.2 42.9 21.6 Spectroscopy 33 Solubility of ethylparaben in 1-propanol at 25 °C 313.2 44.7 22.9 Spectroscopy 33 Density Solubility

The critical evaluation was carried out as described in a w1 ␳/ −3 ͑ ͒ Sec. 2.1.1.1 for salicylic acid in n-heptane. gcm compiler x1

The number of publications: 3 0.9079 0.3626 0.171 The range of temperature: T/K=298.2–313.2 a The units: mass percent and mole fraction In the original paper, the solubility was given as grams of the ester per gram of saturated solution. Analytical methods: spectroscopy and gravimetry Data for the solubility of ethylparaben in 1-propanol ex- Auxiliary Information ͑ ͒ ͑ ͒ pressed by mole fraction were fitted to Eqs. 1 and 2 given Methods/Apparatus/Procedure: in Sec. 1.3 ͑Table 38͒. The data points nearly agree with Eq. A slight excess of the ester was added to approximately 40 ml of solvent ͑2͒ over the whole range of temperatures, as shown in Fig. in a screw-top bottle. A closure was made with aluminum foil, the top ͑ ͒ fixed tightly over the foil, and the whole sealed with several turns of 18, but they deviated from Eq. 1 . Multiple regression electrical tape. The bottles were shaken in a constant-temperature bath for analysis according to Eq. ͑2͒ yielded the following results: 24 h. The equilibrated solutions were removed and filtered. The analysis was carried out gravimetrically and spectrophotometrically. Multiple correlation coefficient: 0.989 Source and Purity of Materials: Sample size: 6 data points Fisher certified grade 1-propanol ͑b.p. 96.9–97.2 °C͒ was used without p-value ͑F test͒: 0.000 further purification. Constants: A=−1768Ϯ133, C=4.180Ϯ0.439 Estimated Errors: Solubility: Nothing specified. White circles in Fig. 18 represent the observed data and Temperature: Ϯ0.05 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−1768 T+4.180 . The observed data fit closely with the calculated values in the range of Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, 298.2–313.2 K, with the multiple correlation coefficient of ethyl ester ͑ethyl 216 ͑1969͒. 0.989, as shown in Fig. 18. Therefore, the calculated value at 4-hydroxybenzoate, ͒ each measured temperature is reasonably considered as a rec- ethylparaben ;C9H10O3; ͓120-47-8͔ ommended value over the whole range of temperature. ͑2͒ 1-Propanol ͑propan-1-ol, ͒ Table 39 shows the observed data in the range of propyl alcohol ;C3H8O; ͓71-23-8͔ 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature. Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of ethylparaben in 1-propanol at 25 °C

Density Solubility

a 100w1 ␳/ −3 ͑ ͒ gcm compiler x1

0.9081 36.2 0.176

aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

Auxiliary Information FIG. 19. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in Methods/Apparatus/Procedure: 1-butanol. The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Source and Purity of Materials: Components: Evaluators: 1-Propanol ͑Baker analyzed͒ was used. ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Ethylparaben was obtained from Matheson, Coleman, and Bell. ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan Estimated Errors: 4-hydroxybenzoate, Rensuke Goto, University of ͒ Solubility: Nothing specified. ethylparaben ;C9H10O3; Shizuoka, Shizuoka, Japan Temperature: Precision of Ϯ0.1 °C. ͓120-47-8͔ Hiroshi Fukuda, Kitasato ͑2͒ 1-Butanol ͑butan-1-ol, butyl University, Tokyo, Japan ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Critical Evaluation ethyl ester ͑ethyl H. Petersen, Jr., and A.N. Paruta, TABLE 40. Summary of experimental solubility data of ethylparaben in 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. 1-butanol ͒ ethylparaben ;C9H10O3; ͓ ͔ / 120-47-8 T K 100w1 100x1 Analytical method Reference ͑2͒ 1-Propanol ͑propan-1-ol, ͒ 298.2 34.0 18.7 Gravimetry, Spectroscopy 34 propyl alcohol ;C3H8O; ͓71-23-8͔ 298.2 34.0 17.8 Spectroscopy, Gravimetry 32 298.2 34.0 17.8 Spectroscopy 33 Variables: Prepared by: 303.2 33.5 18.3 Spectroscopy 33 / t °C=25–40 A. Goto and R. Goto 308.2 37.3 21.0 Spectroscopy 33 313.2 40.7 23.4 Spectroscopy 33 Solubility of ethylparaben in 1-propanol The critical evaluation was carried out as described in Temperature Solubility Sec. 2.1.1.1 for salicylic acid in n-heptane. The number of publications: 3 a w1 The range of temperature: T/K=298.2–313.2 / ͑ ͒ t °C x1 compiler The units: mass percent and mole fraction 25 0.176 0.362 Analytical methods: spectroscopy and gravimetry 30 0.188 0.388 Data for the solubility of ethylparaben in 1-butanol ex- 35 0.216 0.429 pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given 40 0.229 0.447 in Sec. 1.3 ͑Table 40͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. aIn the original paper, the solubility was given as mg/g of solution. 19, but they deviated from Eq. ͑1͒. Multiple regression Auxiliary Information analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.946 Methods/Apparatus/Procedure: Sample size: 6 data points The experimental details are given in the compilation of Ref. 33 for the ͑ ͒ methylparaben–methanol system in Sec. 2.2.1.1. p-value F test : 0.004 Source and Purity of Materials: Constants: A=−1537Ϯ263, C=3.431Ϯ0.867 Spectrograde ethylparaben was purchased from Matheson Coleman and White circles in Fig. 19 represent the observed data and Bell Co. Melting point was within 1 °C of literature value. the black line corresponds to calculated values according to 1-Propanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−1537 T+3.431 . The observed data fit alcohol was established by refractive-index and dielectric-constant closely with the calculated values in the range of measurements. Estimated Errors: 298.2–313.2 K, with the multiple correlation coefficient of Solubility: Precision within 2.5%. 0.946, as shown in Fig. 19. Therefore, the calculated value at Temperature: Precision of Ϯ0.1 °C. each measured temperature is reasonably considered as a recommended value over the whole range of temperature.

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Table 41 shows the observed data in the range of Solubility of ethylparaben in 1-butanol at 25 °C 298.2–313.2 K and the recommended values calculated Density Solubility from Eq. ͑2͒ at each temperature.

100w1 ␳/ −3 ͑ ͒ a TABLE 41. Observed data and recommended values calculated according to gcm compiler x1 Eq. ͑2͒ for ethylparaben in 1-butanol 0.9082 34.0 0.178

T/K 100x ͑obs͒ 100x ͑rec͒ a 1 1 In the original paper, the solubility was given as milligrams of the ester per 298.2 18.7 17.8 gram of solution. 303.2 18.3 19.4 Auxiliary Information 308.2 21.0 21.1 313.2 23.4 22.8 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, The source and the purity of 1-butanol were not reported. ethyl ester ͑ethyl J. Pharm. Sci. 53,636͑1964͒. Ethylparaben was obtained from Matheson, Coleman and Bell. 4-hydroxybenzoate, Estimated Errors: ͒ ethylparaben ;C9H10O3; Solubility: Nothing speciﬁed. ͓ ͔ 120-47-8 Temperature: Precision of Ϯ0.1 °C. ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3

Variables: Prepared by: Components: Original Measurements: t/ °C=25 A. Goto and R. Goto ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, ethyl ester ͑ethyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. Solubility of ethylparaben in 1-butanol at 25 °C ͒ ethylparaben ;C9H10O3; ͓120-47-8͔ Density Solubility ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ a alcohol ;C4H10O; 71-36-3 w1 ␳/gcm−3 ͑compiler͒ x 1 Variables: Prepared by: / 0.9071 0.3398 0.187 t °C=25–40 A. Goto and R. Goto

aIn the original paper, the solubility was given as grams of the ester per gram Solubility of ethylparaben in 1-butanol of saturated solution.

Auxiliary Information Temperature Solubility w a Methods/Apparatus/Procedure: 1 t/ °C x ͑compiler͒ The experimental details are given in the compilation of Ref. 34 for the 1 ethylparaben–1-propanol system in Sec. 2.2.1.2. 25 0.178 0.340 Source and Purity of Materials: 30 0.183 0.335 ͑ ͒ Fisher certified grade 1-butanol b.p. 116.6–117.8 °C was used without 35 0.210 0.373 further purification. 40 0.234 0.407 The ester ͑purified grade͒ was recrystallized from chloroform until a sharp melting point was reached. aIn the original paper, the solubility was given as mg/g of solution. Estimated Errors: Solubility: Nothing specified. Auxiliary Information Temperature: Ϯ0.05 °C. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 33 for the methylparaben–methanol system in Sec. 2.2.1.1. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Spectrograde ethylparaben was purchased from Matheson Coleman and ethyl ester ͑ethyl 216 ͑1969͒. Bell Co. Melting point was within 1 °C of literature value. 4-hydroxybenzoate, 1-Butanol ͑TDY Mallinckrodt͒ was of analytical reagent quality. The ethylparaben͒;CH O ; 9 10 3 purity of the alcohol was established by refractive-index and ͓120-47-8͔ dielectric-constant measurements. ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ Estimated Errors: alcohol ;C4H10O; 71-36-3 Solubility: Precision within 2.5%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 A. Goto and R. Goto

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Table 43 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

TABLE 43. Observed data and recommended values calculated according to Eq. ͑2͒ for ethylparaben in 1-hexanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

298.2 17.8 18.5 303.2 19.5 19.8 308.2 21.2 21.2 FIG. 20. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in 1-hexanol. 313.2 22.8 22.7

Components: Evaluators: Components: Original Measurements: ͑ ͒ 34 ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of 1 Benzoic acid, 4-hydroxy-, F.A. Restaino and A.N. Martin, ͑ ͑ ͒ ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan ethyl ester ethyl J. Pharm. Sci. 53, 636 1964 . 4-hydroxybenzoate, Rensuke Goto, University of 4-hydroxybenzoate, ͒ ethylparaben͒;CH O ; Shizuoka, Shizuoka, Japan ethylparaben ;C9H10O3; 9 10 3 ͓ ͔ ͓120-47-8͔ Hiroshi Fukuda, Kitasato 120-47-8 ͑ ͒ ͑ ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl University, Tokyo, Japan 2 1-Hexanol hexan-1-ol, hexyl ͒ ͓ ͔ ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 alcohol ;C6H14O; 111-27-3 Variables: Prepared by: Critical Evaluation t/ °C=25 A. Goto and R. Goto TABLE 42. Summary of experimental solubility data of ethylparaben in 1-hexanol Solubility of ethylparaben in 1-hexanol at 25 °C

T/K100w 100x Analytical method Reference 1 1 Density Solubility

298.2 26.0 17.8 Gravimetry, Spectroscopy 34 a w1 298.2 26.0 18.9 Spectroscopy, Gravimetry 32 ␳/ −3 ͑ ͒ gcm compiler x1 298.2 26.0 18.9 Spectroscopy 33 303.2 28.2 19.5 Spectroscopy 33 0.8888 0.2604 0.178 308.2 30.5 21.2 Spectroscopy 33 a 313.2 32.5 22.8 Spectroscopy 33 In the original paper, the solubility was given as grams of the ester per gram of saturated solution. The critical evaluation was carried out as described in Sec. 2.1.1.1 for salicylic acid in n-heptane. Auxiliary Information The number of publications: 3 Methods/Apparatus/Procedure: The range of temperature: T/K=298.2–313.2 The experimental details are given in the compilation of Ref. 34 for the The units: mass percent and mole fraction ethylparaben–1-propanol system in Sec. 2.2.1.2. Analytical methods: spectroscopy and gravimetry Source and Purity of Materials: Data for the solubility of ethylparaben in 1-hexanol ex- 1-Hexanol ͑b.p. 156.5–157.5 °C͒ obtained from Eastman Organic pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given Chemicals was redistilled. ͑ ͒ The ester ͑purified grade͒ was recrystallized from chloroform until a sharp in Sec. 1.3 Table 42 . The data points nearly agree with Eq. melting point was obtained. ͑ ͒ 2 over the whole range of temperatures, as shown in Fig. Estimated Errors: 20, but they deviated from Eq. ͑1͒. Multiple regression Solubility: Nothing specified. analysis according to Eq. ͑2͒ yielded the following results: Temperature: Ϯ0.05 °C. Multiple correlation coefficient: 0.966 Sample size: 6 data points p-value ͑F test͒: 0.002 Components: Original Measurements: Constants: A=−1278Ϯ172, C=2.595Ϯ0.566 ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ͑ ͑ ͒ White circles in Fig. 20 represent the observed data and ethyl ester ethyl 216 1969 . 4-hydroxybenzoate, the black line corresponds to calculated values according to ethylparaben͒;CH O ; ͑ ͒ ͑ / ͒ 9 10 3 Eq. 2 ln x1 =−1278 T+2.595 . The observed data fit ͓120-47-8͔ closely with the calculated values in the range of ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl ͒ ͓ ͔ 298.2–313.2 K, with the multiple correlation coefficient of alcohol ;C6H14O; 111-27-3 0.966, as shown in Fig. 20. Therefore, the calculated value at Variables: Prepared by: each measured temperature is reasonably considered as a rec- t/ °C=25 A. Goto and R. Goto ommended value over the whole range of temperature.

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Solubility of ethylparaben in 1-hexanol at 25 °C

Density Solubility

a 100w1 ␳/ −3 ͑ ͒ gcm compiler x1

0.8860 26.0 0.189

aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

Auxiliary Information FIG. 21. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in Methods/Apparatus/Procedure: 1-octanol. The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Source and Purity of Materials: Components: Evaluators: 1-Hexanol ͑Eastman-Kodak No. 50͒ was used. ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Ethylparaben was obtained from Matheson, Coleman, and Bell. ethyl ester ͑ethyl Shizuoka, Shizuoka, Japan Estimated Errors: 4-hydroxybenzoate, Rensuke Goto, University of Solubility: Nothing specified. ͒ ethylparaben ;C9H10O3; Shizuoka, Shizuoka, Japan Temperature: Precision of Ϯ0.1 °C. ͓120-47-8͔ Hiroshi Fukuda, Kitasato ͑2͒ 1-Octanol ͑octan-1-ol, octyl University, Tokyo, Japan ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Critical Evaluation ͑ ethyl ester ethyl H. Petersen, Jr., and A.N. Paruta, TABLE 44. Summary of experimental solubility data of ethylparaben in 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. 1-octanol ͒ ethylparaben ;C9H10O3; ͓120-47-8͔ / T K 100w1 100x1 Analytical method Reference ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 298.2 20.7 17.0 Gravimetry, Spectroscopy 34 298.2 20.7 15.6 Spectroscopy, Gravimetry 32 Variables: Prepared by: 298.2 20.7 15.6 Spectroscopy 33 t/ °C=25–40 A. Goto and R. Goto 303.2 22.2 18.3 Spectroscopy 33 303.2 15.0 Spectroscopy 35 Solubility of ethylparaben in 1-hexanol 308.2 24.6 20.4 Spectroscopy 33 313.2 27.1 22.6 Spectroscopy 33 Temperature Solubility The critical evaluation was carried out as described in a w1 Sec. 2.1.1.1 for salicylic acid in n-heptane. / ͑ ͒ t °C x1 compiler The number of publications: 4 25 0.189 0.260 The range of temperature: T/K=298.2–313.2 30 0.195 0.282 The units: mass percent and mole fraction 35 0.212 0.305 Analytical methods: spectroscopy and gravimetry 40 0.228 0.325 Data for the solubility of ethylparaben in 1-octanol ex- ͑ ͒ ͑ ͒ a pressed by mole fraction were fitted to Eqs. 1 and 2 given In the original paper, the solubility was given as mg/g of solution. in Sec. 1.3 ͑Table 44͒. The data points nearly agree with Eq. Auxiliary Information ͑2͒ over the whole range of temperatures, as shown in Fig. 21, but they deviated from Eq. ͑1͒. Multiple regression Methods/Apparatus/Procedure: analysis according to Eq. ͑2͒ yielded the following results: The experimental details are given in the compilation of Ref. 33 for the Multiple correlation coefficient: 0.977 methylparaben–methanol system in Sec. 2.2.1.1. ͑ Source and Purity of Materials: Sample size: 6 data points the datum from Ref. 35 of Spectrograde ethylparaben was purchased from Matheson Coleman and Table 44 was deleted because the multiple correlation coef- Bell Co. Melting point was within 1 °C of the literature value. ficient was shown to be 0.865͒ The purity of 1-hexanol was 99 mol %. The purity of the alcohol was p-value ͑F test͒: 0.001 established by refractive-index and dielectric-constant measurements. Constants: A=−2149Ϯ234, C=5.380Ϯ0.773 Estimated Errors: White circles in Fig. 21 represent the observed data and Solubility: Precision within 2.5%. the black line corresponds to calculated values according to Temperature: Precision of Ϯ0.1 °C. ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2149 T+5.380 . The observed data fit closely with the calculated values in the range of 298.2–313.2 K, with the multiple correlation coefficient of

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0.977, as shown in Fig. 21. Therefore, the calculated value at Variables: Prepared by: each measured temperature is reasonably considered as a rec- t/ °C=25 A. Goto and R. Goto ommended value over the whole range of temperature. Table 45 shows the observed data in the range of Solubility of ethylparaben in 1-octanol at 25 °C 298.2–313.2 K and the recommended values calculated a from Eq. ͑2͒ at each temperature. Density Solubility

100w1 ABLE ␳/ −3 ͑ ͒ T 45. Observed data and recommended values calculated according to gcm compiler x1 Eq. ͑2͒ for ethylparaben in 1-octanol 0.8791 20.7 0.156 / ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec aIn the original paper, the solubility was given as milligrams of the ester per 298.2 17.0 16.1 gram of solution. 303.2 18.3 18.1 308.2 20.4 20.3 Auxiliary Information 313.2 22.6 22.7 Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, 1-Octanol ͑Eastman-Kodak No. 50͒ was used. ethyl ester ͑ethyl J. Pharm. Sci. 53,636͑1964͒. Ethylparaben was obtained from Matheson, Coleman, and Bell. 4-hydroxybenzoate, ͒ Estimated Errors: ethylparaben ;C9H10O3; ͓120-47-8͔ Solubility: Nothing speciﬁed. ͑2͒ 1-Octanol ͑octan-1-ol, octyl Temperature: Precision of Ϯ0.1 °C. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

Variables: Prepared by: Components: Original Measurements: t/ °C=25 A. Goto and R. Goto ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, ethyl ester ͑ethyl H. Petersen, Jr., and A.N. Paruta, Solubility of ethylparaben in 1-octanol at 25 °C 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ ethylparaben ;C9H10O3; Density Solubility ͓120-47-8͔ a ͑2͒ 1-Octanol ͑octan-1-ol, octyl w1 ͒ ͓ ͔ ␳/ −3 ͑ ͒ alcohol ;C8H18O; 111-87-5 gcm compiler x1 Variables: Prepared by: 0.8780 0.2065 0.170 t/ °C=25–40 A. Goto and R. Goto aIn the original paper, the solubility was given as grams of the ester per gram of saturated solution. Solubility of ethylparaben in 1-octanol Auxiliary Information Temperature Solubilitya Methods/Apparatus/Procedure: w The experimental details are given in the compilation of Ref. 34 for the 1 t/ x ͑ ͒ ethylparaben–1-propanol system in Sec. 2.2.1.2. °C 1 compiler Source and Purity of Materials: 25 0.156 0.207 ͑ ͒ 1-Octanol b.p. 194–195 °C obtained from Eastman Organic Chemicals 30 0.183 0.222 was redistilled. 35 0.204 0.246 The ester ͑puriﬁed grade͒ was recrystallized from chloroform until a sharp 40 0.226 0.271 melting point was obtained. Estimated Errors: aIn the original paper, the solubility was given as mg/g of solution. Solubility: Nothing speciﬁed. Temperature: Ϯ0.05 °C.

Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ethyl ester ͑ethyl 216 ͑1969͒. 4-hydroxybenzoate, ͒ ethylparaben ;C9H10O3; ͓120-47-8͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

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Auxiliary Information -1

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 33 for the -1.5 methylparaben–methanol system in Sec. 2.2.1.1. lnx1 Source and Purity of Materials: -2 Spectrograde ethylparaben was purchased from Matheson Coleman and Bell Co. Melting point was within 1 °C of literature values. The purity of 1-octanol was 99 mol %. The purity of the alcohol was -2.5 established by refractive-index and dielectric-constant measurements. 0.0031 0.0032 0.0033 0.0034 Estimated Errors: (T/K)−1 Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C. FIG. 22. Fitting curve of Eq. ͑2͒ and the observed data for ethylparaben in 1-decanol.

Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 35S.H. Yalkowsky, S.C. Valvani, Critical Evaluation ethyl ester ͑ethyl and T.J. Roseman, J. Pharm. Sci. TABLE 46. Summary of experimental solubility data of ethylparaben in 4-hydroxybenzoate, 72,866͑1983͒. 1-decanol ͒ ethylparaben ;C9H10O3; ͓ ͔ / 120-47-8 T K 100w1 100x1 Analytical method Reference ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ 298.2 14.8 11.5 Spectroscopy, Gravimetry 32 alcohol ;C8H18O; 111-87-5 298.2 14.8 11.5 Spectroscopy 33 Variables: Prepared by: 303.2 18.2 17.5 Spectroscopy 33 t/ °C=30 A. Goto and R. Goto 308.2 20.0 19.2 Spectroscopy 33 313.2 22.3 21.5 Spectroscopy 33 Solubility of ethylparaben in 1-octanol at 30 °C The critical evaluation was carried out as described in Solubility Sec. 2.1.1.1 for salicylic acid in n-heptane. The number of publications: 2 x1 ͑ ͒ log10 x1 compiler The range of temperature: T/K=298.2–313.2

−0.83 0.15 The units: mass percent and mole fraction Analytical methods: spectroscopy and gravimetry Auxiliary Information Data for the solubility of ethylparaben in 1-decanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given Methods/Apparatus/Procedure: ͑ ͒ An excess amount of solute was allowed to equilibrate with water in a in Sec. 1.3 Table 46 . The data points nearly agree with Eq. sealed vial for 24 h at 30 °C. After equilibration, the samples were ͑2͒ over the whole range of temperatures, as shown in Fig. ␮ ␮ filtered through either a 0.22 m porous or a 1.2 m silver membrane 22, but they deviated from Eq. ͑1͒. Multiple regression filter which was preequilibrated at 30 °C. Analysis of the filtrate was performed using UV spectrophotometry. analysis according to Eq. ͑2͒ yielded the following results: Source and Purity of Materials: Multiple correlation coefficient: 0.952 Purest grade ethylparaben was obtained from commercial sources Sample size: 5 data points ͑Aldrich, Eastman, and Fluka͒, and was used as received. Reagent-grade octanol was obtained from Aldrich. p-value ͑F test͒: 0.013 Estimated Errors: Constants: A=−3993Ϯ741, C=11.28Ϯ2.44 Nothing specified. White circles in Fig. 22 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Components: Evaluators: Eq. 2 ln x1 =−3993 T+11.28 . The observed data fit ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of closely with the calculated values in the range of ͑ ethyl ester ethyl Shizuoka, Shizuoka, Japan 298.2–313.2 K, with the multiple correlation coefficient of 4-hydroxybenzoate, Rensuke Goto, University of ͒ ethylparaben ;C9H10O3; Shizuoka, Shizuoka, Japan 0.952, as shown in Fig. 22. Therefore, the calculated value at ͓120-47-8͔ Hiroshi Fukuda, Kitasato each measured temperature is reasonably considered as a rec- ͑2͒ 1-Decanol ͑decan-1-ol, decyl University, Tokyo, Japan ͒ ͓ ͔ ommended value over the whole range of temperature. alcohol ;C10H22O; 112-30-1 Table 47 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

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TABLE 47. Observed data and recommended values calculated according to Solubility of ethylparaben in 1-decanol Eq. ͑2͒ for ethylparaben in 1-decanol Temperature Solubility T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a w1 / ͑ ͒ 298.2 11.5 12.1 t °C x1 compiler 303.2 17.5 15.1 25 0.115 0.148 308.2 19.2 18.7 30 0.175 0.182 313.2 21.5 23.0 35 0.192 0.200 40 0.215 0.223

Components: Original Measurements: aIn the original paper, the solubility was given as mg/g of solution. ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ethyl ester ͑ethyl 216 ͑1969͒. Auxiliary Information 4-hydroxybenzoate, ͒ Methods/Apparatus/Procedure: ethylparaben ;C9H10O3; ͓120-47-8͔ The experimental details are given in the compilation of Ref. 33 for the ͑2͒ 1-Decanol ͑decan-1-ol, decyl methylparaben–methanol system in Sec. 2.2.1.1. ͒ ͓ ͔ Source and Purity of Materials: alcohol ;C10H22O; 112-30-1 Spectrograde ethylparaben was purchased from Matheson Coleman and Variables: Prepared by: Bell Co. Melting point was within 1 °C of the literature value. t/ °C=25 A. Goto and R. Goto The purity of 1-decanol was 99 mol %. The purity of the alcohol was established by refractive-index and dielectric-constant measurements. Estimated Errors: Solubility of ethylparaben in 1-decanol at 25 °C Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C. Density Solubilitya

100w1 ␳/gcm−3 ͑compiler͒ x 1 2.2.1.3. Propylparaben 0.8702 14.8 0.115 Components: Evaluators: aIn the original paper, the solubility was given as milligrams of the ester per ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of gram of solution. propyl ester ͑propyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of Auxiliary Information ͒ propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͓ ͔ Methods/Apparatus/Procedure: 94-13-3 Hiroshi Fukuda, Kitasato ͑2͒ Methyl alcohol ͑methanol͒; University, Tokyo, Japan The experimental details are given in the compilation of Ref. 32 for the CH O; ͓67-56-1͔ methylparaben–methanol system in Sec. 2.2.1.1. 4 Source and Purity of Materials: The source of 1-decanol was not reported. Critical Evaluation Ethylparaben was obtained from Matheson, Coleman, and Bell. TABLE 48. Summary of experimental solubility data of propylparaben in Estimated Errors: methanol Solubility: Nothing speciﬁed. / Temperature: Precision of Ϯ0.1 °C. T K 100w1 100x1 Analytical method Reference 298.2 54.0 17.2 Spectroscopy, Gravimetry 32 298.2 54.0 17.2 Spectroscopy 33 Components: Original Measurements: 303.2 59.5 20.7 Spectroscopy 33 ͑ ͒ 33 1 Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, 308.2 63.9 24.0 Spectroscopy 33 ͑ ethyl ester ethyl H. Petersen, Jr., and A.N. Paruta, 313.2 68.2 27.6 Spectroscopy 33 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ ethylparaben ;C9H10O3; The critical evaluation was carried out as described in ͓120-47-8͔ Sec. 2.1.1.1 for salicylic acid in n-heptane. ͑ ͒ ͑ 2 1-Decanol decan-1-ol, decyl The number of publications: 2 alcohol͒;C H O; ͓112-30-1͔ 10 22 The range of temperature: T/K=298.2–313.2 Variables: Prepared by: The units: mass percent and mole fraction t/ °C=25–40 A. Goto and R. Goto Analytical methods: spectroscopy and gravimetry Data for the solubility of propylparaben in methanol expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 48͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. 23, but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following results:

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Solubility of propylparaben in methanol at 25 °C

Density Solubility

a 100w1 ␳/ −3 ͑ ͒ gcm compiler x1

0.9318 54.0 0.172

aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

Auxiliary Information FIG. 23. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in methanol. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Multiple correlation coefficient: 0.999 Source and Purity of Materials: Methanol ͑Fisher certified͒ was used. Sample size: 5 data points Propylparaben was obtained from Matheson, Coleman, and Bell. p-value ͑F test͒: 0.000 Estimated Errors: Constants: A=−2962Ϯ84, C=8.179Ϯ0.275 Solubility: Nothing specified. Ϯ White circles in Fig. 23 represent the observed data and Temperature: Precision of 0.1 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2962 T+8.179 . The observed data fit Components: Original Measurements: closely with the calculated values in the range of ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, ͑ 298.2–313.2 K, with the multiple correlation coefficient of propyl ester propyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ 0.999, as shown in Fig. 23. Therefore, the calculated value at propylparaben ;C10H12O3; each measured temperature is reasonably considered as a rec- ͓94-13-3͔ ͑2͒ Methyl alcohol ͑methanol͒; ommended value over the whole range of temperature. ͓ ͔ CH4O; 67-56-1 Table 49 shows the observed data in the range of Variables: Prepared by: 298.2–313.2 K and the recommended values calculated t/ °C=25–40 A. Goto and R. Goto from Eq. ͑2͒ at each temperature.

Solubility of propylparaben in methanol TABLE 49. Observed data and recommended values calculated according to Eq. ͑2͒ for propylparaben in methanol Temperature Solubility

/ ͑ ͒ ͑ ͒ a T K 100x1 obs 100x1 rec w1 / ͑ ͒ t °C x1 compiler 298.2 17.2 17.3 303.2 20.7 20.4 25 0.172 0.540 308.2 24.0 23.9 30 0.207 0.595 313.2 27.6 27.8 35 0.240 0.639 40 0.276 0.682

a Components: Original Measurements: In the original paper, the solubility was given as mg/g of solution. ͑ ͒ 32 1 Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, Auxiliary Information propyl ester ͑propyl 216 ͑1969͒. 4-hydroxybenzoate, Methods/Apparatus/Procedure: ͒ propylparaben ;C10H12O3; The experimental details are given in the compilation of Ref. 33 for the ͓ ͔ 94-13-3 methylparaben–methanol system in Sec. 2.2.1.1. ͑2͒ Methyl alcohol ͑methanol͒; Source and Purity of Materials: CH O; ͓67-56-1͔ 4 Spectrograde propylparaben was purchased from Matheson Coleman and Variables: Prepared by: Bell Co. t/ °C=25 A. Goto and R. Goto The source and the purity of methanol were not reported. Estimated Errors: Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C.

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Table 51 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

TABLE 51. Observed data and recommended values calculated according to Eq. ͑2͒ for propylparaben in ethanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

298.2 19.7 19.8 303.2 22.8 23.2 308.2 29.6 27.1 ͑ ͒ FIG. 24. Fitting curve of Eq. 2 and the observed data for propylparaben in 313.2 29.8 31.4 ethanol.

Components: Original Measurements: Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of propyl ester ͑propyl 216 ͑1969͒. propyl ester ͑propyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, ͒ 4-hydroxybenzoate, Rensuke Goto, University of propylparaben ;C10H12O3; ͒ propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͓94-13-3͔ ͓94-13-3͔ Hiroshi Fukuda, Kitasato ͑2͒ Ethyl alcohol ͑ethanol͒; ͑ ͒ ͑ ͒ ͓ ͔ 2 Ethyl alcohol ethanol ; University, Tokyo, Japan C2H6O; 64-17-5 ͓ ͔ C2H6O; 64-17-5 Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Critical Evaluation TABLE 50. Summary of experimental solubility data of propylparaben in ethanol Solubility of propylparaben in ethanol at 25 °C

/ a T K100w1 100x1 Analytical method Reference Density Solubility

a 298.2 49.0 19.7 Spectroscopy, Gravimetry 32 100w1 ␳/ −3 ͑ ͒ 298.2 49.0 19.7 Spectroscopy 33 gcm compiler x1 303.2 53.5 22.8 Spectroscopy 33 0.9076 49.0 0.197 308.2 62.1 29.6 Spectroscopy 33 313.2 62.4 29.8 Spectroscopy 33 aIn the original paper, the solubility was given as milligrams of the ester per The critical evaluation was carried out as described in gram of solution. Sec. 2.1.1.1 for salicylic acid in n-heptane. Auxiliary Information The number of publications: 2 The range of temperature: T/K=298.2–313.2 Methods/Apparatus/Procedure: The units: mass percent and mole fraction The experimental details are given in the compilation of Ref. 32 for the Analytical methods: spectroscopy and gravimetry methylparaben–methanol system in Sec. 2.2.1.1. Data for the solubility of propylparaben in ethanol ex- Source and Purity of Materials: Absolute ethanol was obtained from U.S. Industrial Chemical Co. pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given ͑ ͒ Propylparaben was obtained from Matheson, Coleman, and Bell. in Sec. 1.3 Table 50 . The data points nearly agree with Eq. Estimated Errors: ͑ ͒ 2 over the whole range of temperatures, as shown in Fig. Solubility: Nothing specified. 24, but they deviated from Eq. ͑1͒. Multiple regression Temperature: Precision of Ϯ0.1 °C. analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.935 Sample size: 5 data points Components: Original Measurements: p-value ͑F test͒: 0.007 ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Constants: A=−2859Ϯ435, C=7.970Ϯ1.430 propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. White circles in Fig. 24 represent the observed data and ͒ propylparaben ;C10H12O3; the black line corresponds to calculated values according to ͓94-13-3͔ ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2859 T+7.970 . The observed data fit ͑2͒ Ethyl alcohol ͑ethanol͒; ͓ ͔ closely with the calculated values in the range of C2H6O; 64-17-5 298.2–313.2 K, with the multiple correlation coefficient of Variables: Prepared by: 0.935, as shown in Fig. 24. Therefore, the calculated value at t/ °C=25–40 A. Goto and R. Goto each measured temperature is reasonably considered as a recommended value over the whole range of temperature.

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Solubility of propylparaben in ethanol

Temperature Solubility

a w1 / ͑ ͒ t °C x1 compiler

25 0.197 0.490 30 0.228 0.535 35 0.296 0.621 40 0.298 0.624

a In the original paper, the solubility was given as mg/g of solution. FIG. 25. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in 1-propanol. Auxiliary Information

Methods/Apparatus/Procedure: in Fig. 25, but they deviated from Eq. ͑1͒. Multiple regres- The experimental details are given in the compilation of Ref. 33 for the methylparaben–methanol system in Sec. 2.2.1.1. sion analysis according to Eq. ͑2͒ yielded the following re- Source and Purity of Materials: sults: Spectrograde propylparaben was purchased from Matheson Coleman and Multiple correlation coefficient: 0.993 Bell Co. Melting point was within 1 °C of literature value. Ethanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the Sample size: 6 data points alcohol was established by refractive-index and dielectric-constant p-value ͑F test͒: 0.000 measurements. Constants: A=−2571Ϯ154, C=7.019Ϯ0.509 Estimated Errors: Solubility: Precision within 2.5%. White circles in Fig. 25 represent the observed data and Temperature: Precision of Ϯ0.1 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2571 T+7.019 . The observed data fit closely with the calculated values in the range of Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of 298.2–313.2 K, with the multiple correlation coefficient of propyl ester ͑propyl Shizuoka, Shizuoka, Japan 0.993, as shown in Fig. 25. Therefore, the calculated value at 4-hydroxybenzoate, Rensuke Goto, University of ͒ each measured temperature is reasonably considered as a rec- propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͓94-13-3͔ Hiroshi Fukuda, Kitasato ommended value over the whole range of temperature. ͑2͒ 1-Propanol ͑propan-1-ol, University, Tokyo, Japan Table 53 shows the observed data in the range of ͒ propyl alcohol ;C3H8O; ͓71-23-8͔ 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature. Critical Evaluation TABLE 53. Observed data and recommended values calculated according to TABLE 52. Summary of experimental solubility data of propylparaben in Eq. ͑2͒ for propylparaben in 1-propanol 1-propanol / ͑ ͒ ͑ ͒ / T K 100x1 obs 100x1 rec T K100w1 100x1 Analytical method Reference 298.2 20.5 20.2 298.2 43.6 20.5 Spectroscopy, Gravimetry 34 303.2 23.6 23.2 298.2 43.6 19.8 Spectroscopy, Gravimetry 32 308.2 27.3 26.7 298.2 43.6 19.8 Spectroscopy 33 313.2 29.8 30.5 303.2 47.8 23.6 Spectroscopy 33 308.2 52.7 27.3 Spectroscopy 33 313.2 55.7 29.8 Spectroscopy 33 Components: Original Measurements: The critical evaluation was carried out as described in ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, propyl ester ͑propyl J. Pharm. Sci. 53, 636 ͑1964͒. Sec. 2.1.1.1 for salicylic acid in n-heptane. 4-hydroxybenzoate, ͒ The number of publications: 3 propylparaben ;C10H12O3; The range of temperature: T/K=298.2–313.2 ͓94-13-3͔ ͑2͒ 1-Propanol ͑propan-1-ol, The units: mass percent and mole fraction ͒ propyl alcohol ;C3H8O; Analytical methods: spectroscopy and gravimetry ͓71-23-8͔

Data for the solubility of propylparaben in 1-propanol Variables: Prepared by: expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ t/ °C=25 A. Goto and R. Goto given in Sec. 1.3 ͑Table 52͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown

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Solubility of propylparaben in 1-propanol at 25 °C Components: Original Measurements: 33 Density Solubility ͑1͒ Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, a w1 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ␳/ −3 ͑ ͒ ͒ gcm compiler x1 propylparaben ;C10H12O3; ͓94-13-3͔ 0.9204 0.4363 0.205 ͑2͒ 1-Propanol ͑propan-1-ol, ͒ propyl alcohol ;C3H8O; aIn the original paper, the solubility was given as grams of the ester per gram ͓71-23-8͔ of saturated solution. Variables: Prepared by: Auxiliary Information t/ °C=25–40 A. Goto and R. Goto

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 34 for the Solubility of propylparaben in 1-propanol ethylparaben–1-propanol system in Sec. 2.2.1.2. Source and Purity of Materials: Temperature Solubility Fisher certified grade 1-propanol ͑b.p. 96.9–97.2 °C͒ was used without a w1 further purification. / ͑ ͒ t °C x1 compiler The ester ͑purified grade͒ was recrystallized from chloroform until a sharp melting point was obtained. 25 0.198 0.436 Estimated Errors: 30 0.236 0.478 Solubility: Nothing specified. 35 0.273 0.527 Temperature: Ϯ0.05 °C. 40 0.298 0.557

aIn the original paper, the solubility was given as mg/g of solution.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, propyl ester ͑propyl 216 ͑1969͒. Methods/Apparatus/Procedure: 4-hydroxybenzoate, The experimental details are given in the compilation of Ref. 33 for the ͒ propylparaben ;C10H12O3; methylparaben–methanol system in Sec. 2.2.1.1. ͓ ͔ 94-13-3 Source and Purity of Materials: ͑2͒ 1-Propanol ͑propan-1-ol, Spectrograde propylparaben was purchased from Matheson Coleman and propyl alcohol͒;CH O; 3 8 Bell Co. Melting point was within 1 °C of the literature value. ͓71-23-8͔ 1-Propanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the Variables: Prepared by: alcohol was established by refractive-index and dielectric-constant t/ °C=25 A. Goto and R. Goto measurements. Estimated Errors: Solubility: Precision within 2.5%. Solubility of propylparaben in 1-propanol at 25 °C Temperature: Precision of Ϯ0.1 °C.

Density Solubility a Components: Evaluators: 100w1 ␳/ −3 ͑ ͒ ͑ ͒ gcm compiler x1 1 Benzoic acid, 4-hydroxy-, Ayako Goto, University of propyl ester ͑propyl Shizuoka, Shizuoka, Japan 0.9112 43.6 0.198 4-hydroxybenzoate, Rensuke Goto, University of ͒ propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan a In the original paper, the solubility was given as milligrams of the ester per ͓94-13-3͔ Hiroshi Fukuda, Kitasato gram of solution. ͑2͒ 1-Butanol ͑butan-1-ol, butyl University, Tokyo, Japan ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Auxiliary Information

Methods/Apparatus/Procedure: Critical Evaluation The experimental details are given in the compilation of Ref. 32 for the TABLE 54. Summary of experimental solubility data of propylparaben in methylparaben–methanol system in Sec. 2.2.1.1. 1-butanol Source and Purity of Materials: ͑ ͒ / 1-Propanol Baker analyzed was used. T K 100w1 100x1 Analytical method Reference Propylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: 298.2 39.4 21.1 Spectroscopy, Gravimetry 34 Solubility: Nothing speciﬁed. 298.2 39.4 20.6 Spectroscopy, Gravimetry 32 Temperature: Precision of Ϯ0.1 °C. 298.2 39.4 20.6 Spectroscopy 33 303.2 44.1 24.5 Spectroscopy 33 308.2 48.4 27.8 Spectroscopy 33 313.2 52.8 31.6 Spectroscopy 33

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Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, propyl ester ͑propyl J. Pharm. Sci. 53, 636 ͑1964͒. 4-hydroxybenzoate, ͒ propylparaben ;C10H12O3; ͓94-13-3͔ ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

FIG. 26. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in 1-butanol. Solubility of propylparaben in 1-butanol at 25 °C

Density Solubility The critical evaluation was carried out as described in a w1 Sec. 2.1.1.1 for salicylic acid in n-heptane. ␳/ −3 ͑ ͒ gcm compiler x1 The number of publications: 3 The range of temperature: T/K=298.2–313.2 0.9146 0.3940 0.211

The units: mass percent and mole fraction aIn the original paper, the solubility was given as grams of the ester per gram Analytical methods: spectroscopy and gravimetry of saturated solution. Data for the solubility of propylparaben in 1-butanol ex- Auxiliary Information pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 54͒. The data points nearly agree with Eq. Methods/Apparatus/Procedure: ͑ ͒ The experimental details are given in the compilation of Ref. 34 for the 2 over the whole range of temperatures, as shown in Fig. ethylparaben–1-propanol system in Sec. 2.2.1.2. 26, but they deviated from Eq. ͑1͒. Multiple regression Source and Purity of Materials: analysis according to Eq. ͑2͒ yielded the following results: Fisher certified grade 1-butanol ͑b.p. 116.6–117.8 °C͒ was used without further purification. Multiple correlation coefficient: 0.998 The ester ͑purified grade͒ was recrystallized from chloroform until a sharp Sample size: 6 data points melting point was obtained. p-value ͑F test͒: 0.000 Estimated Errors: Solubility: Nothing specified. Constants: A=−2633Ϯ89, C=7.260Ϯ0.293 Temperature: Ϯ0.05 °C. White circles in Fig. 26 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Components: Original Measurements: Eq. 2 ln x1 =−2633 T+7.260 . The observed data fit ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, closely with the calculated values in the range of propyl ester ͑propyl 216 ͑1969͒. 298.2–313.2 K, with the multiple correlation coefficient of 4-hydroxybenzoate, ͒ 0.998, as shown in Fig. 26. Therefore, the calculated value at propylparaben ;C10H12O3; ͓94-13-3͔ each measured temperature is reasonably considered as a rec- ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ ommended value over the whole range of temperature. alcohol ;C4H10O; 71-36-3 Table 55 shows the observed data in the range of Variables: Prepared by: 298.2–313.2 K and the recommended values calculated t/ °C=25 A. Goto and R. Goto from Eq. ͑2͒ at each temperature. Solubility of propylparaben in 1-butanol at 25 °C TABLE 55. Observed data and recommended values calculated according to Eq. ͑2͒ for propylparaben in 1-butanol Density Solubility

100w a T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 1 ␳/ −3 ͑ ͒ gcm compiler x1 298.2 21.1 20.8 0.9066 39.4 0.206 303.2 24.5 24.1 308.2 27.8 27.8 aIn the original paper, the solubility was given as milligrams of the ester per 313.2 31.6 31.8 gram of solution.

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Auxiliary Information

FIG. 27. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in 1-hexanol. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, Critical Evaluation 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. TABLE 56. Summary of experimental solubility data of propylparaben in ͒ propylparaben ;C10H12O3; 1-hexanol ͓94-13-3͔ ͑2͒ 1-Butanol ͑butan-1-ol, butyl T/K 100w 100x Analytical method Reference ͒ ͓ ͔ 1 1 alcohol ;C4H10O; 71-36-3 298.2 32.7 21.6 Spectroscopy, Gravimetry 34 Variables: Prepared by: 298.2 32.6 21.0 Spectroscopy, Gravimetry 32 / t °C=25–40 A. Goto and R. Goto 298.2 32.6 21.0 Spectroscopy 33 303.2 36.2 25.6 Spectroscopy 33 Solubility of propylparaben in 1-butanol 308.2 41.2 28.5 Spectroscopy 33 313.2 43.4 30.3 Spectroscopy 33 Temperature Solubility The critical evaluation was carried out as described in a w1 / ͑ ͒ Sec. 2.1.1.1 for salicylic acid in n-heptane. t °C x1 compiler The number of publications: 3 25 0.206 0.394 The range of temperature: T/K=298.2−313.2 30 0.245 0.441 35 0.278 0.484 The units: mass percent and mole fraction 40 0.316 0.528 Analytical methods: spectroscopy and gravimetry Data for the solubility of propylparaben in 1-hexanol aIn the original paper, the solubility was given as mg/g of solution. expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ Auxiliary Information given in Sec. 1.3 ͑Table 56͒. The data points nearly agree ͑ ͒ Methods/Apparatus/Procedure: with Eq. 2 over the whole range of temperatures, as shown The experimental details are given in the compilation of Ref. 33 for the in Fig. 27, but they deviated from Eq. ͑1͒. Multiple regres- methylparaben–methanol system in Sec. 2.2.1.1. sion analysis according to Eq. ͑2͒ yielded the following re- Source and Purity of Materials: sults: Spectrograde propylparaben was purchased from Matheson Coleman and Bell Co. The melting point was within 1 °C of the literature value. Multiple correlation coefficient: 0.981 1-Butanol ͑TDY Mallinckrodt͒ was of analytical reagent quality. The Sample size: 6 data points purity of the alcohol was established by refractive-index and p-value ͑F test͒: 0.001 dielectric-constant measurements. Ϯ Ϯ Estimated Errors: Constants: A=−2355 232, C=6.360 0.765 Solubility: Precision within 2.5%. White circles in Fig. 27 represent the observed data and Temperature: Precision of Ϯ0.1 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2355 T+6.360 . The observed data fit closely with the calculated values in the range of Components: Evaluators: 298.2–313.2 K, with the multiple correlation coefficient of ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of propyl ester ͑propyl Shizuoka, Shizuoka, Japan 0.981, as shown in Fig. 27. Therefore, the calculated value at 4-hydroxybenzoate, Rensuke Goto, University of each measured temperature is reasonably considered as a rec- ͒ propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͓94-13-3͔ Hiroshi Fukuda, Kitasato ommended value over the whole range of temperature. ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl University, Tokyo, Japan Table 57 shows the observed data in the range of ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

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TABLE 57. Observed data and recommended values calculated according to Solubility of propylparaben in 1-hexanol at 25 °C Eq. ͑2͒ for propylparaben in 1-hexanol Density Solubility T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a 100w1 ␳/ −3 ͑ ͒ 298.2 21.6 21.5 gcm compiler x1 303.2 25.6 24.5 0.8981 32.6 0.210 308.2 28.5 27.7 313.2 30.3 31.3 aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, propyl ester ͑propyl J. Pharm. Sci. 53,636͑1964͒. Methods/Apparatus/Procedure: 4-hydroxybenzoate, The experimental details are given in the compilation of Ref. 32 for the ͒ methylparaben–methanol system in Sec. 2.2.1.1. propylparaben ;C10H12O3; ͓94-13-3͔ Source and Purity of Materials: ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl 1-Hexanol ͑Eastman-Kodak No. 50͒ was used. ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 Propylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: Variables: Prepared by: Solubility: Nothing speciﬁed. t/ °C=25 A. Goto and R. Goto Temperature: Precision of Ϯ0.1 °C.

Solubility of propylparaben in 1-hexanol at 25 °C Components: Original Measurements: Density Solubility ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, a propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, w 1 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ␳/gcm−3 ͑compiler͒ x 1 ͒ propylparaben ;C10H12O3; 0.8992 0.3265 0.216 ͓94-13-3͔ ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl ͒ ͓ ͔ aIn the original paper, the solubility was given as grams of the ester per gram alcohol ;C6H14O; 111-27-3 of saturated solution. Variables: Prepared by: t/ °C=25–40 A. Goto and R. Goto Auxiliary Information

Methods/Apparatus/Procedure: Solubility of propylparaben in 1-hexanol The experimental details are given in the compilation of Ref. 34 for the ethylparaben–1-propanol system in Sec. 2.2.1.2. Temperature Solubility Source and Purity of Materials: a 1-Hexanol ͑b.p. 156.5–157.5 °C͒ obtained from Eastman Organic w1 / ͑ ͒ Chemicals was redistilled. t °C x1 compiler The ester ͑puriﬁed grade͒ was recrystallized from chloroform until a sharp melting point was obtained. 25 0.210 0.326 Estimated Errors: 30 0.256 0.362 Solubility: Nothing speciﬁed. 35 0.285 0.412 Temperature: Ϯ0.05 °C. 40 0.303 0.434

aIn the original paper, the solubility was given as mg/g of solution.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, propyl ester ͑propyl 216 ͑1969͒. Methods/Apparatus/Procedure: 4-hydroxybenzoate, The experimental details are given in the compilation of Ref. 33 for the ͒ propylparaben ;C10H12O3; methylparaben–methanol system in Sec. 2.2.1.1. ͓94-13-3͔ Source and Purity of Materials: ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl Spectrograde propylparaben was purchased from Matheson Coleman and ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 Bell Co. The melting point was within 1 °C of the literature value. The purity of 1-hexanol was 99 mol %. The purity of the alcohol was Variables: Prepared by: established by refractive-index and dielectric-constant measurements. / t °C=25 A. Goto and R. Goto Estimated Errors: Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C.

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0.903, as shown in Fig. 28. Therefore, the calculated value at each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Table 59 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

TABLE 59. Observed data and recommended values calculated according to Eq. ͑2͒ for propylparaben in 1-octanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec FIG. 28. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in 1-octanol. 298.2 20.7 20.7 303.2 22.8 23.8 308.2 27.1 27.2 Components: Evaluators: 313.2 29.8 30.9 ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of propyl ester ͑propyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of Components: Original Measurements: ͒ 34 propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͑1͒ Benzoic acid, 4-hydroxy-, F.A. Restaino and A.N. Martin, ͓94-13-3͔ Hiroshi Fukuda, Kitasato propyl ester ͑propyl J. Pharm. Sci. 53, 636 ͑1964͒. ͑2͒ 1-Octanol ͑octan-1-ol, octyl University, Tokyo, Japan 4-hydroxybenzoate, ͒ ͓ ͔ ͒ alcohol ;C8H18O; 111-87-5 propylparaben ;C10H12O3; ͓94-13-3͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl Critical Evaluation ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 TABLE 58. Summary of experimental solubility data of propylparaben in 1-octanol Variables: Prepared By: t/ °C=25 A. Goto and R. Goto / / −3 T K c1 mol dm 100w1 100x1 Analytical method Reference

298.2 26.6 20.7 Spectroscopy, Gravimetry 34 Solubility of propylparaben in 1-octanol at 25 °C 298.2 26.6 20.0 Spectroscopy, Gravimetry 32 298.2 26.6 20.0 Spectroscopy 33 Density Solubility 298.2 2.39 Spectroscopy 36 ␳/gcm−3 w a x 303.2 29.0 22.8 Spectroscopy 33 1 1 303.2 28.0 Spectroscopy 35 0.8869 0.2655 0.207 308.2 33.9 27.1 Spectroscopy 33 a 313.2 37.0 29.8 Spectroscopy 33 In the original paper, the solubility was given as grams of the ester per gram of saturated solution. The critical evaluation was carried out as described in Sec. 2.1.1.1 for salicylic acid in n-heptane. Auxiliary Information The number of publications: 5 Methods/Apparatus/Procedure: / The range of temperature: T K=298.2–313.2 The experimental details are given in the compilation of Ref. 34 for the The units: molar concentration, mass percent, and mole ethylparaben–1-propanol system in Sec. 2.2.1.2. fraction Source and Purity of Materials: Analytical methods: spectroscopy and gravimetry 1-Octanol ͑b.p. 194–195 °C͒ obtained from Eastman Organic Chemicals Data for the solubility of propylparaben in 1-octanol ex- was redistilled. ͑ ͒ pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given The ester purified grade was recrystallized from chloroform until a sharp melting point was obtained. in Sec. 1.3 ͑Table 58͒. The data points nearly agree with Eq. ͑ ͒ Estimated Errors: 2 over the whole range of temperatures, as shown in Fig. Solubility: Nothing specified. ͑ ͒ 28, but they deviated from Eq. 1 . Multiple regression Temperature: Ϯ0.05 °C. analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.903 Sample size: 7 data points Components: Original Measurements: p-value ͑F test͒: 0.005 ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Constants: A=−2490Ϯ529, C=6.777Ϯ1.744 propyl ester ͑propyl 216 ͑1969͒. 4-hydroxybenzoate, White circles in Fig. 28 represent the observed data and ͒ propylparaben ;C10H12O3; the black line corresponds to calculated values according to ͓94-13-3͔ ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2490 T+6.777 . The observed data fit ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ closely with the calculated values in the range of alcohol ;C8H18O; 111-87-5 298.2–313.2 K, with the multiple correlation coefficient of

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Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 35S.H. Yalkowsky, S.C. Valvani, propyl ester ͑propyl and T.J. Roseman, J. Pharm. Sci. Solubility of propylparaben in 1-octanol at 25 °C 4-hydroxybenzoate, 72, 866 ͑1983͒. ͒ propylparaben ;C10H12O3; Density Solubility ͓94-13-3͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl w a 100 1 alcohol͒;CH O; ͓111-87-5͔ ␳/ −3 ͑ ͒ 8 18 gcm compiler x1 Variables: Prepared by: 0.8809 26.6 0.200 t/ °C=30 A. Goto and R. Goto aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Solubility of propylparaben in 1-octanol at 30 °C Auxiliary Information Solubility Methods/Apparatus/Procedure:

The experimental details are given in the compilation of Ref. 32 for the x1 ͑ ͒ methylparaben–methanol system in Sec. 2.2.1.1. log10 x1 compiler Source and Purity of Materials: 1-Octanol ͑Eastman-Kodak No. 50͒ was used. −0.55 0.28 Propylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: Auxiliary Information Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 35 for the ethylparaben–1-octanol system in Sec. 2.2.1.2. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Propylparaben of purest grade was obtained from commercial sources ͑ ͒ propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, Aldrich, Eastman, and Fluka and was used as received. 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. Reagent-grade octanol was obtained from Aldrich. ͒ propylparaben ;C10H12O3; Estimated Errors: ͓94-13-3͔ Nothing speciﬁed. ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

Variables: Prepared by: Components: Original Measurements: ͑ ͒ 36 t/ °C=25–40 A. Goto and R. Goto 1 Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. propyl ester ͑propyl Park, and G.J. Rimmer, 4-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ Solubility of propylparaben in 1-octanol propylparaben ;C10H12O3; 1991 . ͓94-13-3͔ Temperature Solubility ͑2͒ 1-Octanol ͑octan-1-ol, octyl alcohol͒;CH O; ͓111-87-5͔ a 8 18 w1 / ͑ ͒ t °C x1 compiler Variables: Prepared by: T/K=298 A. Goto and R. Goto 25 0.200 0.266 30 0.228 0.290 35 0.271 0.339 The solubility of propylparaben in 1-octanol at 298 K 40 0.298 0.370 / −3 was reported as c1 mol dm =2.16. aIn the original paper, the solubility was given as mg/g of solution. Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: A slight excess of the solute was introduced into 1-octanol, and after The experimental details are given in the compilation of Ref. 33 for the 2 days equilibration at 298.2 K, the solute concentrations were determined methylparaben–methanol system in Sec. 2.2.1.1. spectrophotometrically at 258 nm ͓A.E. Beezer, W.H. Hunter, and D. E. ͑ ͔͒ Source and Purity of Materials: Storey, J. Pharm. Pharmacol. 35, 350 1983 . Spectrograde propylparaben was purchased from Matheson Coleman and Source and Purity of Materials: Bell Co. The melting point was within 1 °C of the literature value. The propylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great ͒ Ͼ The purity of 1-octanol established by refractive-index and Britain and was used as received. The purity was speciﬁed as 99.5%. dielectric-constant measurements was 99 mol %. 1-Octanol was of Anala R grade. Estimated Errors: Estimated Errors: Solubility: Precision within 2.5%. Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C.

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298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

TABLE 61. Observed data and recommended values calculated according to Eq. ͑2͒ for propylparaben in 1-decanol

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec

298.2 17.1 17.6 303.2 22.5 21.1 308.2 26.4 25.3 FIG. 29. Fitting curve of Eq. ͑2͒ and the observed data for propylparaben in 1-decanol. 313.2 28.5 30.0

Components: Original Measurements: Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of propyl ester ͑propyl 216 ͑1969͒. propyl ester ͑propyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, 4-hydroxybenzoate, Rensuke Goto, University of ͒ ͒ propylparaben ;C10H12O3; propylparaben ;C10H12O3; Shizuoka, Shizuoka, Japan ͓ ͔ ͓ ͔ 94-13-3 94-13-3 Hiroshi Fukuda, Kitasato ͑ ͒ ͑ ͑ ͒ ͑ 2 1-Decanol decan-1-ol, decyl 2 1-Decanol decan-1-ol, decyl University, Tokyo, Japan ͒ ͓ ͔ ͒ ͓ ͔ alcohol ;C10H22O; 112-30-1 alcohol ;C10H22O; 112-30-1 Variables: Prepared by: Critical Evaluation t/ °C=25 A. Goto and R. Goto TABLE 60. Summary of experimental solubility data of propylparaben in 1-decanol Solubility of propylparaben in 1-decanol at 25 °C / T K100w1 100x1 Analytical method Reference Density Solubility

298.2 21.7 17.1 Spectroscopy, Gravimetry 32 a 100w1 298.2 21.7 17.1 Spectroscopy 33 ␳/ −3 ͑ ͒ gcm compiler x1 303.2 24.8 22.5 Spectroscopy 33 308.2 29.0 26.4 Spectroscopy 33 0.8732 21.7 0.171 313.2 31.2 28.5 Spectroscopy 33 aIn the original paper, the solubility was given as milligrams of the ester per The critical evaluation was carried out as described in gram of solution. Sec. 2.1.1.1 for salicylic acid in n-heptane. The number of publications: 2 Auxiliary Information The range of temperature: T/K=298.2–313.2 Methods/Apparatus/Procedure: The units: mass percent and mole fraction The experimental details are given in the compilation of Ref. 32 for the Analytical methods: spectroscopy and gravimetry methylparaben–methanol system in Sec. 2.2.1.1. Data for the solubility of propylparaben in 1-decanol ex- Source and Purity of Materials: pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given The source of 1-decanol was not reported. Propylparaben was obtained from Matheson, Coleman, and Bell. in Sec. 1.3 ͑Table 60͒. The data points nearly agree with Eq. ͑ ͒ Estimated Errors: 2 over the whole range of temperatures, as shown in Fig. Solubility: Nothing specified. ͑ ͒ 29, but they deviated from Eq. 1 . Multiple regression Temperature: Precision of Ϯ0.1 °C. analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.978 Sample size: 5 data points Components: Original Measurements: p-value ͑F test͒: 0.004 ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, Constants: A=−3330Ϯ414, C=9.427Ϯ1.362 propyl ester ͑propyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. White circles in Fig. 29 represent the observed data and ͒ propylparaben ;C10H12O3; the black line corresponds to calculated values according to ͓94-13-3͔ ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−3330 T+9.427 . The observed data fit ͑2͒ 1-Decanol ͑decan-1-ol, decyl ͒ ͓ ͔ closely with the calculated values in the range of alcohol ;C10H22O; 112-30-1 298.2–313.2 K, with the multiple correlation coefficient of Variables: Prepared by: 0.978, as shown in Fig. 29. Therefore, the calculated value at t/ °C=25–40 A. Goto and R. Goto each measured temperature is reasonably considered as a recommended value over the whole range of temperature. Table 61 shows the observed data in the range of

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Solubility of propylparaben in 1-decanol

Temperature Solubility

a w1 / ͑ ͒ t °C x1 compiler

25 0.171 0.217 30 0.225 0.248 35 0.264 0.290 40 0.285 0.312

a FIG. 30. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in In the original paper, the solubility was given as mg/g of solution. methanol. Auxiliary Information

Methods/Apparatus/Procedure: Multiple correlation coefficient: 0.986 The experimental details are given in the compilation of Ref. 33 for the Sample size: 5 data points methylparaben–methanol system in Sec. 2.2.1.1. p-value ͑F test͒: 0.002 Source and Purity of Materials: Constants: A=−2493Ϯ246, C=7.264Ϯ0.808 Spectrograde propylparaben was purchased from Matheson Coleman and White circles in Fig. 30 represent the observed data and Bell Co. The melting point was within 1°C of the literature value. The purity of 1-decanol was 99 mol %. The purity of the alcohol was the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ established by refractive-index and dielectric-constant measurements. Eq. 2 ln x1 =−2493 T+7.264 . The observed data fit Estimated Errors: closely with the calculated values in the range of Solubility: Precision within 2.5%. 298.2–313.2 K, with the multiple correlation coefficient of Temperature: Precision of Ϯ0.1 °C. 0.986, as shown in Fig. 30. Therefore, the calculated value at each measured temperature is reasonably considered as a recommended value over the whole range of temperature. 2.2.1.4. Butylparaben Table 63 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature. Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of butyl ester ͑butyl Shizuoka, Shizuoka, Japan TABLE 63. Observed data and recommended values calculated according to ͑ ͒ 4-hydroxybenzoate, Rensuke Goto, University of Eq. 2 for butylparaben in methanol butylparaben͒;C H O ; Shizuoka, Shizuoka, Japan 11 14 3 / ͑ ͒ ͑ ͒ ͓94-26-8͔ Hiroshi Fukuda, Kitasato T K 100x1 obs 100x1 rec ͑2͒ Methyl alcohol ͑methanol͒; University, Tokyo, Japan 298.2 33.6 33.4 CH O; ͓67-56-1͔ 4 303.2 36.9 38.3 308.2 45.7 43.8 Critical Evaluation 313.2 49.1 49.8 TABLE 62. Summary of experimental solubility data of butylparaben in methanol Components: Original Measurements: T/K100w 100x Analytical method Reference 32 1 1 ͑1͒ Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, ͑ ͑ ͒ 298.2 75.5 33.6 Spectroscopy, Gravimetry 32 1-butyl ester butyl 216 1969 . 4-hydroxybenzoate, 298.2 75.5 33.6 Spectroscopy 33 butylparaben͒;C H O ; 303.2 77.9 36.9 Spectroscopy 33 11 14 3 ͓94-26-8͔ 308.2 83.4 45.7 Spectroscopy 33 ͑2͒ Methyl alcohol ͑methanol͒; 313.2 85.4 49.1 Spectroscopy 33 ͓ ͔ CH4O; 67-56-1

Data for the solubility of butylparaben in methanol ex- a 100w1 pressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given ␳/ −3 ͑ ͒ gcm compiler x1 in Sec. 1.3 ͑Table 62͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. 0.9896 75.5 0.336 ͑ ͒ a 30, but they deviated from Eq. 1 . Multiple regression In the original paper, the solubility was given as milligrams of the ester per analysis according to Eq. ͑2͒ yielded the following results: gram of solution.

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Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Source and Purity of Materials: Methanol ͑Fisher certified͒ was used. Butylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: Solubility: Nothing specified. Temperature: Precision of Ϯ0.1 °C. FIG. 31. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in ethanol. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, Critical Evaluation 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. TABLE 64. Summary of experimental solubility data of butylparaben in ͒ ethanol butylparaben ;C11H14O3; ͓94-26-8͔ / ͑2͒ Methyl alcohol ͑methanol͒; T K 100w1 100x1 Analytical method Reference CH O; ͓67-56-1͔ 4 298.2 70.3 36.0 Spectroscopy, Gravimetry 32 Variables: Prepared by: 298.2 70.3 36.0 Spectroscopy 33 t/ °C=25–40 A. Goto and R. Goto 303.2 73.4 39.5 Spectroscopy 33 308.2 76.6 43.7 Spectroscopy 33 313.2 80.7 50.0 Spectroscopy 33 Solubility of butylparaben in methanol The critical evaluation was carried out as described in Temperature Solubility Sec. 2.1.1.1 for salicylic acid in n-heptane. a w1 / ͑ ͒ The number of publications: 2 t °C x1 compiler The range of temperature: T/K=298.2–313.2 25 0.336 0.755 The units: mass percent and mole fraction 30 0.369 0.779 35 0.457 0.834 Analytical methods: spectroscopy and gravimetry 40 0.491 0.854 Data for the solubility of butylparaben in ethanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given aIn the original paper, the solubility was given as mg/g of solution. in Sec. 1.3 ͑Table 64͒. The data points nearly agree with Eq. Auxiliary Information ͑2͒ over the whole range of temperatures, as shown in Fig. Methods/Apparatus/Procedure: 31, but they deviated from Eq. ͑1͒. Multiple regression The experimental details are given in the compilation of Ref. 33 for the analysis according to Eq. ͑2͒ yielded the following results: methylparaben–methanol system in Sec. 2.2.1.1. Multiple correlation coefficient: 0.996 Source and Purity of Materials: Spectrograde butylparaben was purchased from Matheson Coleman and Sample size: 5 data points Bell Co. The melting point was within 1 °C of the literature value. p-value ͑F test͒: 0.000 The source and the purity of methanol were not reported. Constants: A=−1991Ϯ109, C=5.649Ϯ0.359 Estimated Errors: Solubility: Precision within 2.5%. White circles in Fig. 31 represent the observed data and Temperature: Precision of Ϯ0.1 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−1991 T+5.649 . The observed data fit closely with the calculated values in the range of Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of 298.2–313.2 K, with the multiple correlation coefficient of butyl ester ͑butyl Shizuoka, Shizuoka, Japan 0.996, as shown in Fig. 31. Therefore, the calculated value at 4-hydroxybenzoate, Rensuke Goto, University of each measured temperature is reasonably considered as a rec- ͒ butylparaben ;C11H14O3; Shizuoka, Shizuoka, Japan ͓94-26-8͔ Hiroshi Fukuda, Kitasato ommended value over the whole range of temperature. ͑2͒ Ethyl alcohol ͑ethanol͒; University, Tokyo, Japan Table 65 shows the observed data in the range of C H O; ͓64-17-5͔ 2 6 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

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TABLE 65. Observed data and recommended values calculated according to Solubility of butylparaben in ethanol Eq. ͑2͒ for butylparaben in ethanol Temperature Solubility T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a w1 / ͑ ͒ 298.2 36.0 35.8 t °C x1 compiler 303.2 39.5 39.9 25 0.360 0.703 308.2 43.7 44.4 30 0.395 0.734 313.2 50.0 49.2 35 0.437 0.766 40 0.500 0.807

Components: Original Measurements: aIn the original paper, the solubility was given as mg/g of solution. ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, 1-butyl ester ͑butyl 216 ͑1969͒. Auxiliary Information 4-hydroxybenzoate, ͒ Methods/Apparatus/Procedure: butylparaben ;C11H14O3; ͓94-26-8͔ The experimental details are given in the compilation of Ref. 33 for the ͑2͒ Ethyl alcohol ͑ethanol͒; methylparaben–methanol system in Sec. 2.2.1.1. ͓ ͔ Source and Purity of Materials: C2H6O; 64-17-5 Spectrograde butylparaben was purchased from Matheson Coleman and Variables: Prepared by: Bell Co. The melting point was within 1 °C of the literature value. t/ °C=25 A. Goto and R. Goto Ethanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the alcohol was established by refractive-index and dielectric-constant measurements. Solubility of butylparaben in ethanol at 25 °C Estimated Errors: Solubility: Precision within 2.5%. Density Solubilitya Temperature: Precision of 1 °C.

100w1 ␳/ −3 ͑ ͒ gcm compiler x1 Components: Evaluators: 0.9730 70.3 0.360 ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of butyl ester ͑butyl Shizuoka, Shizuoka, Japan a In the original paper, the solubility was given as milligrams of the ester per 4-hydroxybenzoate, Rensuke Goto, University of ͒ gram of solution. butylparaben ;C11H14O3; Shizuoka, Shizuoka, Japan ͓94-26-8͔ Hiroshi Fukuda, Kitasato Auxiliary Information ͑2͒ 1-Propanol ͑propan-1-ol, University, Tokyo, Japan ͒ propyl alcohol ;C11H14O3; Methods/Apparatus/Procedure: ͓71-23-8͔ The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Source and Purity of Materials: Critical Evaluation Absolute ethanol was obtained from U.S. Industrial Chemical Co. TABLE 66. Summary of experimental solubility data of butylparaben in Butylparaben was obtained from Matheson, Coleman, and Bell. 1-propanol Estimated Errors: T/ w x Solubility: Nothing speciﬁed. K 100 1 100 1 Analytical method Reference Ϯ Temperature: Precision of 0.1 °C. 298.2 64.7 36.1 Spectroscopy, Gravimetry 34 298.2 64.7 35.5 Spectroscopy, Gravimetry 32 298.2 64.7 35.5 Spectroscopy 33 Components: Original Measurements: 303.2 68.2 40.2 Spectroscopy 33 33 ͑1͒ Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, 308.2 72.9 45.8 Spectroscopy 33 butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, 313.2 76.3 50.2 Spectroscopy 33 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ butylparaben ;C11H14O3; The critical evaluation was carried out as described in ͓94-26-8͔ Sec. 2.1.1.1 for salicylic acid in n-heptane. ͑ ͒ ͑ ͒ 2 Ethyl alcohol ethanol ; The number of publications: 3 C H O; ͓64-17-5͔ 2 6 The range of temperature: T/K=298.2–313.2 Variables: Prepared by: The units: mass percent and mole fraction t/ °C=25–40 A. Goto and R. Goto Analytical methods: spectroscopy and gravimetry Data for the solubility of butylparaben in 1-propanol expressed by mole fraction were ﬁtted to Eqs. ͑1͒ and ͑2͒ given in Sec. 1.3 ͑Table 66͒. The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. 32, but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following results:

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Solubility of butylparaben in 1-propanol at 25 °C

Density Solubility

a w1 ␳/ −3 ͑ ͒ gcm compiler x1

0.9724 0.6466 0.361

aIn the original paper, the solubility was given as grams of the ester per gram of solution.

Auxiliary Information

Methods/Apparatus/Procedure: FIG. 32. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in The experimental details are given in the compilation of Ref. 34 for the 1-propanol. ethylparaben–1-propanol system in Sec. 2.2.1.2. Source and Purity of Materials: ͑ ͒ Multiple correlation coefficient: 0.998 Fisher certified grade 1-propanol b.p. 96.9−97.2 °C was used without further purification. Sample size: 6 data points The ester ͑purified grade͒ was recrystallized from chloroform until a sharp p-value ͑F test͒: 0.000 melting point was obtained. Constants: A=−2166Ϯ67, C=6.243Ϯ0.221 Estimated Errors: Solubility: Nothing specified. White circles in Fig. 32 represent the observed data and Temperature: Ϯ0.05 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2166 T+6.234 . The observed data fit closely with the calculated values in the range of Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, 298.2–313.2 K, with the multiple correlation coefficient of 1-butyl ester ͑butyl 216 ͑1969͒. 0.998, as shown in Fig. 32. Therefore, the calculated value at 4-hydroxybenzoate, ͒ each measured temperature is reasonably considered as a rec- butylparaben ;C11H14O3; ͓94-26-8͔ ommended value over the whole range of temperature. ͑2͒ 1-Propanol ͑propan-1-ol, ͒ Table 67 shows the observed data in the range of propyl alcohol ;C3H8O; ͓71-23-8͔ 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature. Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

TABLE 67. Observed data and recommended values calculated according to Eq. ͑2͒ for butylparaben in 1-propanol Solubility of butylparaben in 1-propanol at 25 °C

/ ͑ ͒ ͑ ͒ T K 100x1 obs 100x1 rec Density Solubility

298.2 36.1 35.7 a 100w1 303.2 40.2 40.3 ␳/ −3 ͑ ͒ gcm compiler x1 308.2 45.8 45.2 313.2 50.2 50.6 0.9719 64.7 0.355

aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Components: Original Measurements: ͑ ͒ 34 1 Benzoic acid, 4-hydroxy-, F.A. Restaino and A.N. Martin, Auxiliary Information butyl ester ͑butyl J. Pharm. Sci. 53,636͑1964͒. 4-hydroxybenzoate, Methods/Apparatus/Procedure: ͒ butylparaben ;C11H14O3; The experimental details are given in the compilation of Ref. 32 for the ͓ ͔ 94-26-8 methylparaben–methanol system in Sec. 2.2.1.1. ͑ ͒ ͑ 2 1-Propanol propan-1-ol, Source and Purity of Materials: propyl alcohol͒;CH O; 3 8 1-Propanol ͑Baker analyzed͒ was used. ͓71-23-8͔ Butylparaben was obtained from Matheson, Coleman, and Bell. Variables: Prepared by: Estimated Errors: t/ °C=25 A. Goto and R. Goto Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.1 °C.

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Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ butylparaben ;C11H14O3; ͓94-26-8͔ ͑2͒ 1-Propanol ͑propan-1-ol, ͒ propyl alcohol ;C3H8O; ͓71-23-8͔

Variables: Prepared by: FIG. 33. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in t/ °C=25–40 A. Goto and R. Goto 1-butanol.

Solubility of butylparaben in 1-propanol The critical evaluation was carried out as described in Sec. 2.1.1.1 for salicylic acid in n-heptane. Temperature Solubility The number of publications: 3 a The range of temperature: T/K=298.2–313.2 w1 / ͑ ͒ t °C x1 compiler The units: mass percent and mole fraction Analytical methods: spectroscopy and gravimetry 25 0.355 0.647 Data for the solubility of butylparaben in 1-butanol ex- 30 0.402 0.682 pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given 35 0.458 0.729 ͑ ͒ 40 0.502 0.763 in Sec. 1.3 Table 68 . The data points nearly agree with Eq. ͑2͒ over the whole range of temperatures, as shown in Fig. aIn the original paper, the solubility was given as mg/g of solution 33, but they deviated from Eq. ͑1͒. Multiple regression analysis according to Eq. ͑2͒ yielded the following results: Auxiliary Information Multiple correlation coefficient: 0.989 Methods/Apparatus/Procedure: Sample size: 6 data points The experimental details are given in the compilation of Ref. 33 for the p-value ͑F test͒: 0.000 methylparaben–methanol system in Sec. 2.2.1.1. Constants: A=−1911Ϯ146, C=5.392Ϯ0.481 Source and Purity of Materials: White circles in Fig. 33 represent the observed data and Spectrograde butylparaben was purchased from Matheson Coleman and the black line corresponds to calculated values according to Bell Co. The melting point was within 1 °C of the literature value. ͑ ͒ ͑ x /T ͒ 1-Propanol ͑J.T. Baker͒ was of absolute reagent quality. The purity of the Eq. 2 ln 1 =−1911 +5.392 . The observed data fit alcohol was established by refractive-index and dielectric-constant closely with the calculated values in the range of measurements. 298.2–313.2 K, with the multiple correlation coefficient of Estimated Errors: 0.989, as shown in Fig. 33. Therefore, the calculated value at Solubility: Precision within 2.5%. each measured temperature is reasonably considered as a rec- Temperature: Precision of Ϯ0.1 °C. ommended value over the whole range of temperature. Table 69 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated Components: Evaluators: from Eq. ͑2͒ at each temperature. ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of butyl ester ͑n-butyl Shizuoka, Shizuoka, Japan TABLE 69. Observed data and recommended values calculated according to 4-hydroxybenzoate, Rensuke Goto, University of ͑ ͒ ͒ Eq. 2 for butylparaben in 1-butanol butylparaben ;C11H14O3; Shizuoka, Shizuoka, Japan ͓94-26-8͔ Hiroshi Fukuda, Kitasato / ͑ ͒ ͑ ͒ ͑2͒ 1-Butanol ͑butan-1-ol, butyl University, Tokyo, Japan T K 100x1 obs 100x1 rec alcohol͒;CH O; ͓71-36-3͔ 4 10 298.2 36.5 36.1 303.2 38.8 40.2 Critical Evaluation 308.2 43.9 44.5 TABLE 68. Summary of experimental solubility data of butylparaben in 313.2 50.1 49.1 1-butanol

/ T K100w1 100x1 Analytical method Reference Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, 298.2 60.1 36.5 Spectroscopy, Gravimetry 34 butyl ester ͑butyl J. Pharm. Sci. 53, 636 ͑1964͒. 298.2 60.1 36.4 Spectroscopy, Gravimetry 32 4-hydroxybenzoate, ͒ 298.2 60.1 36.4 Spectroscopy 33 butylparaben ;C11H14O3; 303.2 62.5 38.8 Spectroscopy 33 ͓94-26-8͔ 308.2 67.2 43.9 Spectroscopy 33 ͑2͒ 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ 313.2 72.5 50.1 Spectroscopy 33 alcohol ;C4H10O; 71-36-3

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Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, Solubility of butylparaben in 1-butanol at 25 °C 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ butylparaben ;C11H14O3; Density Solubility ͓94-26-8͔ ͑2͒ 1-Butanol ͑butan-1-ol, butyl w a ͒ ͓ ͔ 1 alcohol ;C4H10O; 71-36-3 ␳/ −3 ͑ ͒ gcm compiler x1 Variables: Prepared by: 0.9592 0.6005 0.365 t/ °C=25–40 A. Goto and R. Goto

aIn the original paper, the solubility was given as grams of the ester per gram of solution. Solubility of butylparaben in 1-butanol

Auxiliary Information Temperature Solubility

a Methods/Apparatus/Procedure: w1 / ͑ ͒ The experimental details are given in the compilation of Ref. 34 for the t °C x1 compiler ethylparaben–1-propanol system in Sec. 2.2.1.2. 25 0.364 0.601 Source and Purity of Materials: 30 0.388 0.625 Fisher certified grade 1-butanol ͑b.p. 116.6–117.8 °C͒ was used without further purification. 35 0.439 0.672 The ester ͑purified grade͒ was recrystallized from chloroform until a sharp 40 0.501 0.725 melting point was obtained. aIn the original paper, the solubility was given as mg/g of solution. Estimated Errors: Solubility: Nothing specified. Auxiliary Information Temperature: Ϯ0.05 °C. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 33 for the Components: Original Measurements: methylparaben–methanol system in Sec. 2.2.1.1. ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Source and Purity of Materials: 1-butyl ester ͑butyl 216 ͑1969͒. Spectrograde butylparaben was purchased from Matheson Coleman and 4-hydroxybenzoate, Bell Co. The melting point was within 1 °C of the literature value. ͒ 1-Butanol ͑Mallinckrodt͒ was of analytical reagent quality. The purity of butylparaben ;C11H14O3; ͓94-26-8͔ the alcohol was established by refractive-index and dielectric-constant ͑2͒ 1-Butanol ͑butan-1-ol, butyl measurements. ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 Estimated Errors: Solubility: Precision within 2.5%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 A. Goto and R. Goto

Solubility of butylparaben in 1-butanol at 25 °C Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of Density Solubility butyl ester ͑n-butyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of 100w a ͒ 1 butylparaben ;C11H14O3; Shizuoka, Shizuoka, Japan ␳/ −3 ͑ ͒ gcm compiler x1 ͓94-26-8͔ Hiroshi Fukuda, Kitasato ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl University, Tokyo, Japan 0.9612 60.1 0.364 ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Critical Evaluation TABLE 70. Summary of experimental solubility data of butylparaben in Auxiliary Information 1-hexanol Methods/Apparatus/Procedure: / The experimental details are given in the compilation of Ref. 32 for the T K 100w1 100x1 Analytical method Reference methylparaben–methanol system in Sec. 2.2.1.1. 298.2 52.9 37.1 Spectroscopy, Gravimetry 34 Source and Purity of Materials: 298.2 52.6 36.9 Spectroscopy, Gravimetry 32 The source of 1-butanol was not reported. 298.2 52.6 36.9 Spectroscopy 33 Butylparaben was obtained from Matheson, Coleman, and Bell. 303.2 55.2 39.5 Spectroscopy 33 Estimated Errors: 308.2 60.3 44.4 Spectroscopy 33 Solubility: Nothing speciﬁed. 313.2 66.1 50.7 Spectroscopy 33 Temperature: Precision of Ϯ0.1 °C.

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-0.6 Components: Original Measurements: -0.7 ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, butyl ester ͑butyl J. Pharm. Sci. 53, 636 ͑1964͒. lnx1 -0.8 4-hydroxybenzoate, ͒ butylparaben ;C11H14O3; -0.9 ͓94-26-8͔ ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl -1 ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3

-1.1 Variables: Prepared by: 0.0031 0.0032( /K)−1 0.0033 0.0034 T t/ °C=25 A. Goto and R. Goto

FIG. 34. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in 1-hexanol. Solubility of butylparaben in 1-hexanol at 25 °C

Density Solubilitya The critical evaluation was carried out as described in a Sec. 2.1.1.1 for salicylic acid in n-heptane. w1 x1 The number of publications: 3 ␳/gcm−3 ͑compiler͒ ͑compiler͒ The range of temperature: T/K=298.2–313.2 0.9467 0.5292 0.371 The units: mass percent and mole fraction a Analytical methods: spectroscopy and gravimetry In the original paper, the solubility was given as grams of the ester per gram of solution. Data for the solubility of butylparaben in 1-hexanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given Auxiliary Information in Sec. 1.3 ͑Table 70͒. The data points nearly agree with Eq. Methods/Apparatus/Procedure: ͑2͒ over the whole range of temperatures, as shown in Fig. The experimental details are given in the compilation of Ref. 34 for the ethylparaben–1-propanol system in Sec. 2.2.1.2. 34, but they deviated from Eq. ͑1͒. Multiple regression Source and Purity of Materials: analysis according to Eq. ͑2͒ yielded the following results: 1-Hexanol ͑b.p. 156.5–157.5 °C͒ obtained from Eastman Organic Multiple correlation coefficient: 0.990 Chemicals was redistilled. ͑ ͒ Sample size: 6 data points The butylparaben purified grade was recrystallized from chloroform until a sharp melting point was obtained. p-value ͑F test͒: 0.000 Estimated Errors: Constants: A=−1892Ϯ137, C=5.341Ϯ0.454 Solubility: Nothing specified. Ϯ White circles in Fig. 34 represent the observed data and Temperature: 0.05 °C. the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−1892 T+5.341 . The observed data fit Components: Original Measurements: closely with the calculated values in the range of ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ͑ ͑ ͒ 298.2–313.2 K, with the multiple correlation coefficient of 1-butyl ester butyl 216 1969 . 4-hydroxybenzoate, ͒ 0.990, as shown in Fig. 34. Therefore, the calculated value at butylparaben ;C11H14O3; each measured temperature is reasonably considered as a rec- ͓94-26-8͔ ͑2͒ 1-Hexanol ͑hexan-1-ol, hexyl ommended value over the whole range of temperature. ͒ ͓ ͔ alcohol ;C6H14O; 111-27-3 Table 71 shows the observed data in the range of Variables: Prepared by: 298.2–313.2 K and the recommended values calculated t/ °C=25 A. Goto and R. Goto from Eq. ͑2͒ at each temperature.

Solubility of butylparaben in 1-hexanol at 25 °C TABLE 71. Observed data and recommended values calculated according to Eq. ͑2͒ for butylparaben in 1-hexanol Density Solubility

T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a w1 x1 298.2 37.1 36.7 ␳/gcm−3 ͑compiler͒ ͑compiler͒ 303.2 39.5 40.7 308.2 44.4 45.0 0.9413 52.6 0.369 313.2 50.7 49.7 aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

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Auxiliary Information

aIn the original paper, the solubility was given as mg/g of solution. Analytical methods: spectroscopy and gravimetry Data for the solubility of butylparaben in 1-octanol ex- Auxiliary Information pressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given Methods/Apparatus/Procedure: in Sec. 1.3 ͑Table 72͒. The data points nearly agree with Eq. The experimental details are given in the compilation of Ref. 33 for the ͑2͒ over the whole range of temperatures, as shown in Fig. methylparaben–methanol system in Sec. 2.2.1.1. 35, but they deviated from Eq. ͑1͒. Multiple regression Source and Purity of Materials: ͑ ͒ Spectrograde butylparaben was purchased from Matheson Coleman and analysis according to Eq. 2 yielded the following results: Bell Co. The melting point was within 1 °C of the literature value. Multiple correlation coefficient: 0.910 The purity of 1-hexanol established by refractive-index and Sample size: 7 data points dielectric-constant measurements was 99 mol %. p-value ͑F test͒: 0.004 Estimated Errors: Ϯ Ϯ Solubility: Precision within 2.5%. Constants: A=−2349 478, C=6.774 1.577 Temperature: Precision of Ϯ0.1 °C. White circles in Fig. 35 represent the observed data and the black line corresponds to calculated values according to ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−2349 T+6.774 . The observed data fit Components: Evaluators: closely with the calculated values in the range of ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of butyl ester ͑n-butyl Shizuoka, Shizuoka, Japan 298.2–313.2 K, with the multiple correlation coefficient of 4-hydroxybenzoate, Rensuke Goto, University of 0.910, as shown in Fig. 35. Therefore, the calculated value at ͒ butylparaben ;C11H14O3; Shizuoka, Shizuoka, Japan each measured temperature is reasonably considered as a rec- ͓94-26-8͔ Hiroshi Fukuda, Kitasato ͑2͒ 1-Octanol ͑octan-1-ol, octyl University, Tokyo, Japan ommended value over the whole range of temperature. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Table 73 shows the observed data in the range of 298.2–313.2 K and the recommended values calculated from Eq. ͑2͒ at each temperature.

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TABLE 73. Observed data and recommended values calculated according to Solubility of butylparaben in 1-octanol at 25 °C Eq. ͑2͒ for butylparaben in 1-octanol Density Solubility T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 a 100w1 ␳/ −3 ͑ ͒ 298.2 36.0 33.2 gcm compiler x1 303.2 37.9 37.8 0.9346 45.7 0.331 308.2 44.0 42.8 313.2 49.7 48.4 aIn the original paper, the solubility was given as milligrams of the ester per gram of solution.

Components: Original Measurements: Auxiliary Information ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, butyl ester ͑butyl J. Pharm. Sci. 53,636͑1964͒. Methods/Apparatus/Procedure: 4-hydroxybenzoate, The experimental details are given in the compilation of Ref. 32 for the ͒ butylparaben ;C11H14O3; methylparaben–methanol system in Sec. 2.2.1.1. ͓94-26-8͔ Source and Purity of Materials: ͑2͒ 1-Octanol ͑octan-1-ol, octyl 1-Octanol ͑Eastman-Kodak No. 50͒ was used. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Butylparaben was obtained from Matheson, Coleman, and Bell. Estimated Errors: Variables: Prepared by: Solubility: Nothing speciﬁed. t/ °C=25 A. Goto and R. Goto Temperature: Precision of Ϯ0.1 °C.

Solubility of butylparaben in 1-octanol at 25 °C Components: Original Measurements: Density Solubility ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, ␳/gcm−3 w a x 1 1 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ 0.9291 0.4565 0.360 butylparaben ;C11H14O3; ͓94-26-8͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl aIn the original paper, the solubility was given as grams of the ester per gram alcohol͒;CH O; ͓111-87-5͔ of solution. 8 18 Variables: Prepared by: Auxiliary Information t/ °C=25–40 A. Goto and R. Goto Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 34 for the Solubility of butylparaben in 1-octanol ethylparaben–1-propanol system in Sec. 2.2.1.2. Source and Purity of Materials: Temperature Solubility 1-Octanol ͑b.p. 194–195 °C͒ obtained from Eastman Organic Chemicals a was redistilled. w1 / ͑ ͒ The butylparaben ͑puriﬁed grade͒ was recrystallized from chloroform until t °C x1 compiler a sharp melting point was obtained. 25 0.331 0.457 Estimated Errors: 30 0.379 0.476 Solubility: Nothing speciﬁed. 35 0.440 0.539 Temperature: Ϯ0.05 °C. 40 0.497 0.595

aIn the original paper, the solubility was given as mg/g of solution. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, Auxiliary Information 1-butyl ester ͑butyl 216 ͑1969͒. 4-hydroxybenzoate, Methods/Apparatus/Procedure: ͒ The experimental details are given in the compilation of Ref. 33 for the butylparaben ;C11H14O3; ͓94-26-8͔ methylparaben–methanol system in Sec. 2.2.1.1. ͑2͒ 1-Octanol ͑octan-1-ol, octyl Source and Purity of Materials: ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Spectrograde butylparaben was purchased from Matheson Coleman and Bell Co. The melting point was within 1 °C of the literature value. Variables: Prepared by: The purity of 1-octanol established by refractive-index and t/ °C=25 A. Goto and R. Goto dielectric-constant measurements was 99 mol %. Estimated Errors: Solubility: Precision within 2.5%. Temperature: Precision of Ϯ0.1 °C.

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Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 35S.H. Yalkowsky, S.C. Valvani, butyl ester ͑butyl and T.J. Roseman, J. Pharm. Sci. 4-hydroxybenzoate, 72,866͑1983͒. ͒ butylparaben ;C11H14O3; ͓94-26-8͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

Variables: Prepared by: t/ °C=30 A. Goto and R. Goto

Solubility of butylparaben in 1-octanol at 30 °C FIG. 36. Fitting curve of Eq. ͑2͒ and the observed data for butylparaben in 1-decanol. Solubility

x1 ͑ ͒ log10 x1 compiler Components: Evaluators: ͑1͒ Benzoic acid, 4-hydroxy-, Ayako Goto, University of −0.48 0.33 butyl ester ͑butyl Shizuoka, Shizuoka, Japan 4-hydroxybenzoate, Rensuke Goto, University of butylparaben͒;C H O ; Shizuoka, Shizuoka, Japan Auxiliary Information 11 14 3 ͓94-26-8͔ Hiroshi Fukuda, Kitasato ͑ ͒ ͑ Methods/Apparatus/Procedure: 2 1-Decanol decan-1-ol, decyl University, Tokyo, Japan alcohol͒;C H O; ͓112-30-1͔ The experimental details are given in the compilation of Ref. 35 for the 10 22 ethylparaben–1-octanol system in Sec. 2.2.1.2. Source and Purity of Materials: Critical Evaluation Reagent-grade octanol was obtained from Aldrich. TABLE 74. Summary of experimental solubility data of butylparaben in Butylparaben of purest grade was obtained from commercial sources 1-decanol ͑Aldrich, Eastman, and Fluka͒ and was used as received. / Estimated Errors: T K 100w1 100x1 Analytical method Reference Nothing specified. 298.2 39.2 29.3 Spectroscopy, Gravimetry 32 298.2 39.2 29.3 Spectroscopy 33 303.2 42.1 37.1 Spectroscopy 33 Components: Original Measurements: 308.2 47.7 42.7 Spectroscopy 33 ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. 313.2 54.2 49.1 Spectroscopy 33 butyl ester ͑butyl Park, and G.J. Rimmer, 4-hydroxybenzoate, Thermochim. Acta 178,59 The critical evaluation was carried out as described in ͒ ͑ ͒ butylparaben ;C11H14O3; 1991 . Sec. 2.1.1.1 for salicylic acid in n-heptane. ͓94-26-8͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl The number of publications: 2 ͒ ͓ ͔ / alcohol ;C8H18O; 111-87-5 The range of temperature: T K=298.2–313.2. The units: mass percent and mole fraction Variables: Prepared by: Analytical methods: spectroscopy and gravimetry / T K=298.2 A. Goto and R. Goto Data for the solubility of butylparaben in 1-decanol expressed by mole fraction were fitted to Eqs. ͑1͒ and ͑2͒ given The solubility of butylparaben in 1-octanol at 298.2 K in Sec. 1.3 ͑Table 74͒. The data points nearly agree with Eq. / −3 ͑2͒ over the whole range of temperatures, as shown in Fig. was reported as c1 mol dm =2.39. 36, but they deviated from Eq. ͑1͒. Multiple regression Auxiliary Information analysis according to Eq. ͑2͒ yielded the following results: Multiple correlation coefficient: 0.994 Methods/Apparatus/Procedure: The experimental detail is given in the compilation of Ref. 36 for the Sample size: 5 data points propylparaben–1-octanol system in Sec. 2.2.1.3. p-value ͑F test͒: 0.001 Source and Purity of Materials: Constants: A=−3246Ϯ212, C=9.672Ϯ0.698 The butylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great White circles in Fig. 36 represent the observed data and Britain͒ and was used as received. The purity was specified as Ͼ99.5%. the black line corresponds to calculated values according to 1-Octanol was of Anala R grade. ͑ ͒ ͑ / ͒ Eq. 2 ln x1 =−3246 T+9.672 . The observed data fit Estimated Errors: closely with the calculated values in the range of Nothing specified. 298.2–313.2 K, with the multiple correlation coefficient of 0.994, as shown in Fig. 36. Therefore, the calculated value at each measured temperature is reasonably considered as a recommended value over the whole range of temperature.

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Table 75 shows the observed data in the range of Solubility of butylparaben in 1-decanol 298.2–313.2 K and the recommended values calculated Temperature Solubilitya from Eq. ͑2͒ at each temperature. w1 / ͑ ͒ t °C x1 compiler TABLE 75. Observed data and recommended values calculated according to ͑ ͒ Eq. 2 for butylparaben in 1-decanol 25 0.293 0.392 30 0.371 0.421 T/K 100x ͑obs͒ 100x ͑rec͒ 1 1 35 0.427 0.477 298.2 29.3 29.7 40 0.491 0.542 303.2 37.1 35.6 aIn the original paper, the solubility was given as mg/g of solution. 308.2 42.7 42.3 313.2 49.1 50.1 Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 33 for the Components: Original Measurements: methylparaben–methanol system in Sec. 2.2.1.1. ͑ ͒ 32 1 Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, Source and Purity of Materials: 1-butyl ester ͑butyl 216 ͑1969͒. Spectrograde butylparaben was purchased from Matheson Coleman and 4-hydroxybenzoate, Bell Co. The melting point was within 1 °C of the literature value. butylparaben͒;C H O ; 11 14 3 The purity of 1-decanol was 99 mol %. The purity of the alcohol was ͓94-26-8͔ established by refractive-index and dielectric-constant measurements. ͑2͒ 1-Decanol ͑decan-1-ol, decyl ͒ ͓ ͔ Estimated Errors: alcohol ;C10H22O; 112-30-1 Solubility: Precision within 2.5%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 A. Goto and R. Goto

Solubility of butylparaben in 1-decanol at 25 °C 2.2.2. Data for paraben–organic compound systems Density Solubility 2.2.2.1. Methylparaben ␳/ −3 a gcm 100w1 x1

0.9313 39.2 0.293 Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. aIn the original paper, the solubility was given as milligrams of the ester per methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, ͑ ͒ gram of solution. 4-hydroxybenzoate, 188 1984 . ͒ methylparaben ;C8H8O3; Auxiliary Information ͓99-76-3͔ ͑2͒ Hydrocarbons ͑alkanes͒: ͑ ͒ Methods/Apparatus/Procedure: n-Pentane pentane ;C5H12; The experimental details are given in the compilation of Ref. 32 for the ͓109-66-0͔ ͑ ͒ methylparaben–methanol system in Sec. 2.2.1.1. n-Hexane hexane ;C6H14; ͓ ͔ Source and Purity of Materials: 110-54-3 ͑ ͒ The source of 1-decanol was not reported. n-Heptane heptane ;C7H16; ͓142-82-5͔ Butylparaben was obtained from Matheson, Coleman, and Bell. n-Nonane ͑nonane͒;CH ; Estimated Errors: 9 20 ͓111-84-2͔ Solubility: Nothing speciﬁed. n-Decane ͑decane͒;C H ; Ϯ 10 22 Temperature: Precision of 0.1 °C. ͓124-18-5͔

Variables: Prepared by: / Components: Original Measurements: t °C=25 A. Goto and R. Goto ͑1͒ Benzoic acid, 4-hydroxy-, 33K.S. Alexander, J.W. Mauger, butyl ester ͑n-butyl H. Petersen, Jr., and A.N. Paruta, Solubility of methylparaben in hydrocarbons at 25 °C 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. ͒ butylparaben ;C11H14O3; Molar volume of solvent Solubility ͓94-26-8͔ / 3 −1 4 ͑2͒ 1-Decanol ͑decan-1-ol, decyl Solvent v2 cm mol 10 x1 ͒ ͓ ͔ alcohol ;C10H22O; 112-30-1 n-Pentane 116.1 0.63 Variables: Prepared by: n-Hexane 131.6 0.77 t/ °C=25–40 A. Goto and R. Goto n-Heptane 147.5 0.83 n-Nonane 179.7 1.06 n-Decane 195.9 1.21

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Auxiliary Information Solubility of methylparaben in 1-pentanol at 25 °C

Methods/Apparatus/Procedure: Density Solubility The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 100w a Source and Purity of Materials: 1 ␳/gcm−3 ͑compiler͒ x The detail is given in the compilation of Ref. 19 for the methylparaben– 1 ethanol system in Sec. 2.2.1.1. 0.8819 24.6 0.149 Estimated Errors: Solubility: Errors were below 3%. aIn the original paper, the solubility was given as milligrams of the ester per Temperature: Precision of Ϯ0.2 °C. gram of solution.

Auxiliary Information

Components: Original Measurements: Methods/Apparatus/Procedure: ͑ ͒ 36 1 Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. The experimental details are given in the compilation of Ref. 32 for the ͑ methyl ester methyl Park, and G.J. Rimmer, methylparaben–methanol system in Sec. 2.2.1.1. 4-hydroxybenzoate, Thermochim. Acta 178,59 Source and Purity of Materials: methylparaben͒;CH O ; ͑1991͒. 8 8 3 1-Pentanol ͑Eastman-Kodak No. 50͒ was used. ͓99-76-3͔ ͑ ͒ ͑ ͒ Methylparaben was obtained from Matheson, Coleman, and Bell. 2 n-Hexane hexane ;C6H14; ͓110-54-3͔ Estimated Errors: Solubility: Nothing speciﬁed. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto

Solubility of methylparaben in n-hexane Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. ͑ Temperature Solubility methyl ester methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. / 3 / −3 ͒ T K10c1 mol dm methylparaben ;C8H8O3; ͓99-76-3͔ 288.2 1.09 ͑2͒ 1-Pentanol ͑pentan-1-ol, ͒ 293.2 2.50 pentyl alcohol ;C5H12O; 298.2 2.21 ͓71-41-0͔

Variables: Prepared by: Auxiliary Information t/ °C=25 A. Goto and R. Goto

Methods/Apparatus/Procedure: The experimental detail is given in the compilation of Ref. 36 for the Solubility of methylparaben in 1-pentanol at 25 °C propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: Molar volume of solvent Solubility The methylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great /cm3 mol−1 x Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. v2 1 n-Hexane was of Anala R grade. 108.6 0.1528 Estimated Errors: Nothing speciﬁed. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 19 for the 32 ͑1͒ Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑ ͑ ͒ methyl ester methyl 216 1969 . Source and Purity of Materials: 4-hydroxybenzoate, The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic ͒ methylparaben ;C8H8O3; acid–ethanol system in Sec. 2.1.2.3. ͓99-76-3͔ Estimated Errors: ͑2͒ 1-Pentanol ͑pentan-1-ol, Solubility: Errors were below 3%. pentyl alcohol͒;CH O; 5 12 Ϯ ͓71-41-0͔ Temperature: Precision of 0.2 °C.

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Methylparaben was obtained from Matheson, Coleman, and Bell. Components: Original Measurements: Estimated Errors: ͑ ͒ 19 1 Benzoic acid, 4-hydroxy-, A. Martin, P.L. Wu, and A. Solubility: Nothing speciﬁed. ͑ 73 methyl ester methyl Beerbower, J. Pharm. Sci. , Temperature: Precision of Ϯ0.1 °C. 4-hydroxybenzoate, 188 ͑1984͒. ͒ methylparaben ;C8H8O3; ͓99-76-3͔ ͑2͒ 1-Heptanol ͑heptan-1-ol, Components: Original Measurements: ͒ ͑ ͒ 33 heptyl alcohol ;C7H16O; 1 Benzoic acid, 4-hydroxy-, K.S. Alexander, J.W. Mauger, ͓111-70-6͔ methyl ester ͑methyl H. Petersen, Jr., and A.N. Paruta, 4-hydroxybenzoate, J. Pharm. Sci. 66,42͑1977͒. Variables: Prepared by: ͒ methylparaben ;C8H8O3; t/ °C=25 A. Goto and R. Goto ͓99-76-3͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl alcohol͒;CH O; ͓111-87-5͔ Solubility of methylparaben in 1-heptanol at 25 °C 8 18 Variables: Prepared by: Molar volume of solvent Solubility t/ °C=25–40 A. Goto and R. Goto / 3 −1 v2 cm mol x1 Solubility of methylparaben in 1-octanol 141.9 0.1483 Temperature Solubility Auxiliary Information a w1 / ͑ ͒ Methods/Apparatus/Procedure: t °C x1 compiler The experimental details are given in the compilation of Ref. 19 for the 25 0.111 0.147 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Source and Purity of Materials: 30 0.151 0.172 35 0.166 0.188 The details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 40 0.172 0.195 Estimated Errors: aIn the original paper, the solubility was given as mg/g of solution. Solubility: The experimental variation was below 3%. Ϯ Temperature: Precision of 0.2 °C. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 33 for the ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, methylparaben–methanol system in Sec. 2.2.1.1. methyl ester ͑methyl 216 ͑1969͒. Source and Purity of Materials: 4-hydroxybenzoate, Spectrograde methylparaben was purchased from Matheson Coleman and ͒ methylparaben ;C8H8O3; Bell Co. Melting point was within 1 °C of literature values. ͓99-76-3͔ 1-Octanol was 99 mol %. The purity of the alcohol was established by ͑2͒ 1-Octanol ͑octan-1-ol, octyl refractive-index and dielectric-constant measurements. ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Estimated Errors: Solubility: Precision within 2.5%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 A. Goto and R. Goto

Solubility of methylparaben in 1-octanol at 25 °C Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 35S.H. Yalkowsky, S.C. Valvani, Density Solubility methyl ester ͑methyl and T.J. Roseman, J. Pharm. Sci. 4-hydroxybenzoate, 72, 866 ͑1983͒. a ͒ 100w1 methylparaben ;C8H8O3; ␳/ −3 ͑ ͒ ͓ ͔ gcm compiler x1 99-76-3 ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ 0.8712 14.7 0.111 alcohol ;C8H8O3; 111-87-5 a In the original paper, the solubility was given as milligrams of the ester per Variables: Prepared by: gram of solution. t/ °C=30 A. Goto and R. Goto Auxiliary Information

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Solubility of methylparaben in 1-octanol at 30 °C Components: Original Measurements: 36 Solubility ͑1͒ Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. methyl ester ͑methyl Park, and G.J. Rimmer, x1 4-hydroxybenzoate, Thermochim. Acta 178,59 ͑ ͒ ͒ ͑ ͒ log10 x1 compiler methylparaben ;C8H8O3; 1991 . ͓99-76-3͔ −0.96 0.11 ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5

Auxiliary Information Variables: Prepared by: / Methods/Apparatus/Procedure: T K=298.2 A. Goto and R. Goto The experimental details are given in the compilation of Ref. 35 for the ethylparaben–1-octanol system in Sec. 2.2.1.2. The solubility of methylparaben in 1-octanol at 298.2 K Source and Purity of Materials: / −3 Methylparaben of purest grade was obtained from commercial sources was reported as c1 mol dm =0.71. ͑Aldrich, Eastman, and Fluka͒ and was used as received. Auxiliary Information 1-Octanol was of reagent grade. Estimated Errors: Methods/Apparatus/Procedure: Nothing specified. The experimental details are given in the compilation of Ref. 36 for the propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: Components: Original Measurements: The methylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. Britain͒ and was used as received. The purity was specified as Ͼ99.5%. methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, 1-Octanol was of Anala R grade. 4-hydroxybenzoate, 188 ͑1984͒. Estimated Errors: ͒ methylparaben ;C8H8O3; Nothing specified. ͓99-76-3͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Components: Original Measurements: Variables: Prepared by: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. t/ °C=25 A. Goto and R. Goto methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. ͒ methylparaben ;C8H18O; Solubility of methylparaben in 1-octanol at 25 °C ͓99-76-3͔ ͑2͒ Diols and triols: Molar volume of solvent Solubility 1,2-Ethandiol ͑ethane-1,2-diol, ethylene glycol͒;CH O ; / 3 −1 2 6 2 v2 cm mol x1 ͓107-21-1͔ 1,2-Propandiol ͑propane-1,2-diol, 158.4 0.1381 ͒ propylene glycol ;C3H8O2; ͓57-55-6͔ Auxiliary Information 1,3-Propanediol ͑propane-1,3-diol, trimethylene ͒ ͓ ͔ Methods/Apparatus/Procedure: glycol ;C3H8O2; 504-63-2 The experimental details are given in the compilation of Ref. 19 for the 1,4-Butanediol ͑butane-1,4-diol, ͒ 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. tetramethylene glycol ;C4H10O2; Source and Purity of Materials: ͓110-63-4͔ The details are given in the compilation of Ref. 19 for the 1,2,3-Propanetriol ͑ ͒ 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. propane-1,2,3-triol, glycerol ; ͓ ͔ Estimated Errors: C3H8O3; 56-81-5 Solubility: The experimental variation was below 3%. Variables: Prepared by: Ϯ Temperature: Precision of 0.2 °C. t/ °C=25 A. Goto and R. Goto

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Solubility of methylparaben in diols and triols at 25 °C Source and Purity of Materials: The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic Molar volume of acid–ethanol system in Sec. 2.1.2.3. solvent Solubility Estimated Errors: Solubility: The experimental variation was below 3%. Solvent v /cm3 mol−1 x 2 1 Temperature: Precision of Ϯ0.2 °C Ethylene glycol 55.9 0.0480 Propylene glycol 73.7 0.0941 Trimethylene glycol 72.5 0.0766 Components: Original Measurements: 1,4-Butanediol 88.6 0.1202 ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. Glycerol 73.2 0.0064 methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. ͒ methylparaben ;C8H8O3; Auxiliary Information ͓99-76-3͔ ͑2͒ Carboxylic acids: Methods/Apparatus/Procedure: ͓ ͔ Acetic acid; C2H4O2; 64-19-7 The experimental details are given in the compilation of Ref. 19 for the Propionic acid ͑propanoic acid͒; 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͓ ͔ C3H6O2; 79-09-4 Source and Purity of Materials: The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic Variables: Prepared by: acid–ethanol system in Sec. 2.1.2.3. t/ °C=25 A. Goto and R. Goto Estimated Errors: Solubility: The experimental variation was below 3%. Solubility of methylparaben in carboxylic acids at 25 °C Temperature: Precision of Ϯ0.2 °C. Molar volume of solvent Solubility Components: Original Measurements: / 3 −1 ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. Solvent v2 cm mol x1 methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, Acetic acid 57.6 0.0532 4-hydroxybenzoate, 188 ͑1984͒. ͒ Propionic acid 75.0 0.0386 methylparaben ;C8H8O3; ͓99-76-3͔ ͑ ͒ 2 Ethers: Auxiliary Information Ethane, 1,1Ј-oxybis- ͑ethoxyethane, diethyl ether͒; Methods/Apparatus/Procedure: ͓ ͔ C4H10O; 60-29-7 The experimental details are given in the compilation of Ref. 19 for the Propane, 1,1Ј-oxybis- 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. ͑ 1-propoxypropane, dipropyl Source and Purity of Materials: ͒ ͓ ͔ ether ;C6H14O; 111-43-3 The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic Ј Butane, 1,1 -oxybis- acid–ethanol system in Sec. 2.1.2.3. ͑2-butoxyethanol, dibutyl ether͒; Estimated Errors: C H O; ͓142-96-1͔ 8 18 Solubility: Errors were below 3%. Variables: Prepared by: Temperature: Precision of Ϯ0.2 °C. t/ °C=25. A. Goto and R. Goto

Components: Original Measurements: Solubility of methylparaben in ethers at 25 °C ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, Molar volume of 4-hydroxybenzoate, 188 ͑1984͒. solvent Solubility ͒ methylparaben ;C8H8O3; / 3 −1 ͓99-76-3͔ Solvent v2 cm mol x1 ͑2͒ Acetates: Diethyl ether 104.8 0.0840 Acetic acid, ethyl ester ͑ethyl ͒ ͓ ͔ Dipropyl ether 139.4 0.0314 acetate ;C4H8O; 141-78-6 Dibutyl ether 170.4 0.0268 Acetic acid, propyl ester ͑propyl ͒ ͓ ͔ acetate ;C5H10O2; 109-60-4 Acetic acid, butyl ester ͑butyl ͒ ͓ ͔ Auxiliary Information acetate ;C6H12O2; 123-86-4 Acetic acid, hexyl ester ͑hexyl Methods/Apparatus/Procedure: ͒ ͓ ͔ acetate ;C8H16O2; 142-92-7 The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Solubility of methylparaben in acetates at 25 °C Components: Original Measurements: 19 Molar volume of ͑1͒ Benzoic acid, 4-hydroxy-, A. Martin, P.L. Wu, and A. solvent Solubility methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. / 3 −1 ͒ Solvent v2 cm mol x1 methylparaben ;C8H8O3; ͓99-76-3͔ Ethyl acetate 98.5 0.1270 ͑2͒ Amides: ͓ ͔ Propyl acetate 115.7 0.1366 Formamide; CH3NO; 75-12-7 Butyl acetate 132.6 0.1326 Formamide, N-methyl- Hexyl acetate 164.5 0.1164 ͑N-methylformamide, ͒ methylformamide ;C2H5NO; ͓123-39-7͔ Auxiliary Information Formamide, N,N-dimethyl- ͑N,N-dimethylformamide, Methods/Apparatus/Procedure: ͒ dimethylformamide ;C3H7NO; The experimental details are given in the compilation of Ref. 19 for the ͓68-12-2͔ 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Formamide, N,N-diethyl- Source and Purity of Materials: ͑N,N-diethylformamide, ͒ The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic diethylformamide ;C5H11NO; acid–ethanol system in Sec. 2.1.2.3. ͓617-84-5͔ Estimated Errors: Acetamide, N,N-dimethyl- Solubility: The experimental variation was below 3%. ͑N,N-dimethylacetamide, ͒ Temperature: Precision of Ϯ0.2 °C. dimethylacetamide ;C4H9NO; ͓127-19-5͔ Acetamide, N,N-diethyl- ͑N,N-diethylacetamide, Components: Original Measurements: diethylacetamide͒;CH NO; 19 6 13 ͑1͒ Benzoic acid, 4-hydroxy-, A. Martin, P.L. Wu, and A. ͓685-91-6͔ methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, 4-hydroxybenzoate, 188 ͑1984͒. Variables: Prepared by: ͒ methylparaben ;C8H8O3; t/ °C=25 A. Goto and R. Goto ͓99-76-3͔ ͑2͒ Methane, 1,1Ј-sulﬁnylbis- ͑methylsulﬁnylmethane, dimethyl Solubility of methylparaben in amides at 25 °C ͒ ͓ ͔ sulfoxide ;C2H6OS; 67-68-5 Molar volume of Variables: Prepared by: solvent Solubility t/ °C=25 A. Goto and R. Goto / 3 −1 Solvent v2 cm mol x1

The solubility of methylparaben in dimethyl sulfoxide at Formamide 39.9 0.0765 N-Methylformamide 59.1 0.2981 25 °C was reported as x1 =0.5839. N,N-Dimethylformamide 77.4 0.4605 N,N-Diethylformamide 112.0 0.4907 Auxiliary Information N,N-Dimethylacetamide 93.0 0.5418 Methods/Apparatus/Procedure: N,N-Diethylacetamide 126.6 0.5299 The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Auxiliary Information Source and Purity of Materials: The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic Methods/Apparatus/Procedure: acid–ethanol system in Sec. 2.1.2.3. The experimental details are given in the compilation of Ref. 19 for the Estimated Errors: 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Solubility: The experimental variation was below 3%. Source and Purity of Materials: Temperature: Precision of Ϯ0.2 °C. The detail is given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Solubility: The experimental variation was below 3%. Temperature: Precision of Ϯ0.2 °C.

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 19A. Martin, P.L. Wu, and A. ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. methyl ester ͑methyl Beerbower, J. Pharm. Sci. 73, propyl ester ͑propyl Park, and G.J. Rimmer, 4-hydroxybenzoate, 188 ͑1984͒. 4-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͒ ͑ ͒ methylparaben ;C8H8O3; propylparaben ;C10H12O3; 1991 . ͓99-76-3͔ ͓94-13-3͔ ͑ ͒ ͓ ͔ ͑ ͒ ͑ ͒ 2 Pyridine; C5H5N; 110-86-1 2 n-Hexane hexane ;C6H14; ͓110-54-3͔ Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Variables: Prepared by: T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto The solubility of methylparaben in pyridine at 25 °C Solubility of propylparaben in n-hexane was reported as x1 =0.3243.

Auxiliary Information Temperature Solubility

/ 3 / −3 Methods/Apparatus/Procedure: T K10c1 mol dm The experimental details are given in the compilation of Ref. 19 for the 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. 288.2 0.667 Source and Purity of Materials: 293.2 0.867 The details are given in the compilation of Ref. 19 for the 298.2 1.28 4-hydroxybenzoic acid–ethanol system in Sec. 2.1.2.3. Estimated Errors: Auxiliary Information Solubility: The experimental variation was below 3%. Temperature: Precision of Ϯ0.2 °C. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: The propylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great 2.2.2.2. Ethyl-, propyl-, and butylparaben Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. n-Hexane was of Anala R grade. Components: Original Measurements: Estimated Errors: ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. Nothing speciﬁed. ethyl ester ͑ethyl Park, and G.J. Rimmer, 4-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ ethylparaben ;C9H10O3; 1991 Components: Original Measurements: ͓120-47-8͔ ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. ͑2͒ n-Hexane ͑hexane͒;CH ; 6 14 butyl ester; ͑n-butyl Park, and G.J. Rimmer, ͓110-54-3͔ 4-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ Variables: Prepared by: butylparaben ;C11H14O3; 1991 . ͓ ͔ / 94-26-8 T K=288.2, 293.2, and 298.2 A. Goto and R. Goto ͑ ͒ ͑ ͒ 2 n-Hexane hexane ;C6H14; ͓110-54-3͔ Solubility of ethylparaben in n-hexane Variables: Prepared by: Temperature Solubility T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto

/ 4 / −3 T K10c1 mol dm Solubility of butylparaben in n-hexane 288.2 2.56 293.2 4.38 Temperature Solubility 298.2 5.33 / 3 / −3 T K10c1 mol dm

Auxiliary Information 288.2 1.39 293.2 2.23 Methods/Apparatus/Procedure: 298.2 2.54 The experimental details are given in the compilation of Ref. 36 for the propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: The ethylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. n-Hexane was of Anala R grade. Estimated Errors: Nothing speciﬁed.

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Auxiliary Information Solubility of ethylparaben in 1-pentanol at 25 °C

Methods/Apparatus/Procedure: Density Solubility The experimental details are given in the compilation of Ref. 36 for the a propylparaben–1-octanol system in Sec. 2.2.1.3. 100w1 ␳/ −3 ͑ ͒ Source and Purity of Materials: gcm compiler x1 The butylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great 0.8911 29.9 0.185 Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. n-Hexane was of Anala R grade. aIn the original paper, the solubility was given as milligrams of the ester per Estimated Errors: gram of solution. Nothing speciﬁed. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 32 for the ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, methylparaben–methanol system in Sec. 2.2.1.1. ethyl ester ͑ethyl J. Pharm. Sci. 53,636͑1964͒. 4-hydroxybenzoate, Source and Purity of Materials: ͒ 1-Pentanol ͑Eastman-Kodak No. 50͒ was used. ethylparaben ;C9H10O3; ͓120-47-8͔ Ethylparaben was obtained from Matheson, Coleman, and Bell. ͑2͒ 1-Pentanol ͑pentan-1-ol, Estimated Errors: ͒ pentyl alcohol ;C5H12O; Solubility: Nothing speciﬁed. ͓71-41-0͔ Temperature: Precision of Ϯ0.1 °C.

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 34F.A. Restaino and A.N. Martin, Solubility of ethylparaben in 1-pentanol at 25 °C propyl ester ͑propyl J. Pharm. Sci. 53, 636 ͑1964͒. 4-hydroxybenzoate, ͒ Density Solubility propylparaben ;C10H12O3; ͓94-13-3͔ ␳/ −3 a gcm w1 x1 ͑2͒ 1-Pentanol ͑pentan-1-ol, pentyl alcohol͒;CH O; 0.8961 0.2987 0.184 5 12 ͓71-41-0͔ a In the original paper, the solubility was given as grams of the ester per gram Variables: Prepared by: of saturated solution. t/ °C=25 A. Goto and R. Goto Auxiliary Information Solubility of propylparaben in 1-pentanol at 25 °C Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 34 for the Density Solubilitya ethylparaben–1-propanol system in Sec. 2.2.1.2. ␳/ −3 a Source and Purity of Materials: gcm w1 x1 The source and the purity of 1-pentanol were not reported. 0.9059 0.3623 0.217 The ester ͑puriﬁed grade͒ was recrystallized from chloroform until a sharp melting point was obtained. aIn the original paper, the solubility was given as grams of the ester per gram Estimated Errors: of saturated solution. Solubility: Nothing speciﬁed. Temperature: Ϯ0.05 °C. Auxiliary Information

Methods/Apparatus/Procedure: Components: Original Measurements: The experimental details are given in the compilation of Ref. 34 for the ethylparaben–1-propanol system in Sec. 2.2.1.2. ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, ethyl ester ͑ethyl 216 ͑1969͒. Source and Purity of Materials: 4-hydroxybenzoate, The source and the purity of 1-pentanol were not reported. ͒ ͑ ͒ ethylparaben ;C9H10O3; The propylparaben puriﬁed grade was recrystallized from chloroform ͓120-47-8͔ until a sharp melting point was obtained. ͑2͒ 1-Pentanol ͑pentan-1-ol, Estimated Errors: ͒ pentyl alcohol ;C5H12O; Solubility: Nothing speciﬁed. ͓71-41-0͔ Temperature: Ϯ0.05 °C.

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto

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Source and Purity of Materials: Components: Original Measurements: The source and the purity of 1-pentanol were not reported. ͑ ͒ 32 1 Benzoic acid, 4-hydroxy-, A.N. Paruta, J. Pharm. Sci. 58, The butylparaben ͑puriﬁed grade͒ was recrystallized from chloroform until ͑ ͑ ͒ propyl ester propyl 216 1969 . a sharp melting point was obtained. 4-hydroxybenzoate, Estimated Errors: propylparaben͒;C H O ; 10 12 3 Solubility: Nothing speciﬁed. ͓94-13-3͔ Temperature: Ϯ0.05 °C. ͑2͒ 1-Pentanol ͑pentan-1-ol, ͒ pentyl alcohol ;C5H12O; ͓71-41-0͔ Components: Original Measurements: Variables: Prepared by: ͑1͒ Benzoic acid, 4-hydroxy-, 32A.N. Paruta, J. Pharm. Sci. 58, / t °C=25 A. Goto and R. Goto 1-butyl ester ͑butyl 216 ͑1969͒. 4-hydroxybenzoate, ͒ Solubility of propylparaben in 1-pentanol at 25 °C butylparaben ;C11H14O3; ͓94-26-8͔ a ͑2͒ 1-Pentanol ͑pentan-1-ol, Density Solubility ͒ pentyl alcohol ;C5H12O; ␳/ −3 ͑ ͒ ͓71-41-0͔ gcm 100w1 compiler x1

0.8994 36.2 0.212 Variables: Prepared by: t/ °C=25 A. Goto and R. Goto aIn the original paper, the solubility was given as milligrams of the ester per gram of solution. Solubility of butylparaben in 1-pentanol at 25 °C Auxiliary Information Density Solubility Methods/Apparatus/Procedure: ␳/ −3 w a x The experimental details are given in the compilation of Ref. 32 for the gcm 100 1 1 methylparaben–methanol system in Sec. 2.2.1.1. 0.9547 55.8 0.363 Source and Purity of Materials: 1-Pentanol ͑Eastman-Kodak No. 50͒ was used. aIn the original paper, the solubility was given as milligrams of the ester per Propylparaben was obtained from Matheson, Coleman, and Bell. gram of solution. Estimated Errors: Solubility: Nothing speciﬁed. Auxiliary Information Temperature: Precision of Ϯ0.1 °C. Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 32 for the methylparaben–methanol system in Sec. 2.2.1.1. Components: Original Measurements: Source and Purity of Materials: ͑ ͒ 34 1 Benzoic acid, 4-hydroxy-, F.A. Restaino and A.N. Martin, 1-Pentanol ͑Eastman-Kodak No. 50͒ was used. butyl ester ͑butyl J. Pharm. Sci. 53,636͑1964͒. Butylparaben was obtained from Matheson, Coleman, and Bell. 4-hydroxybenzoate, ͒ Estimated Errors: butylparaben ;C11H14O3; ͓94-26-8͔ Solubility: Nothing speciﬁed. ͑2͒ 1-Pentanol ͑pentan-1-ol, Temperature: Precision of Ϯ0.1 °C. ͒ pentyl alcohol ;C5H12O; ͓71-41-0͔

Variables: Prepared by: t/ °C=25 A. Goto and R. Goto 2.2.2.3. Hexyl-, heptyl-, octyl-, and decylparaben Solubility of butylparaben in 1-pentanol at 25 °C

Density Solubilitya Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. ␳/ −3 a gcm w1 x1 hexyl ester ͑hexyl Park, and G.J. Rimmer, p-hydroxybenzoate, Thermochim. Acta 178,59 0.9527 0.5579 0.364 ͒ ͑ ͒ hexylparaben ;C13H18O3; 1991 . ͓ ͔ a 1083-27-8 In the original paper, the solubility was given as grams of the ester per gram ͑ ͒ ͑ ͒ 2 n-Hexane hexane ;C6H14; of solution. ͓110-54-3͔

Auxiliary Information Variables: Prepared by: T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 34 for the ethylparaben–1-propanol system in Sec. 2.2.1.2.

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Solubility of hexylparaben in n-hexane Components: Original Measurements: 36 Temperature Solubility ͑1͒ Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. octyl ester ͑octyl Park, and G.J. Rimmer, / 2 / −3 T K10c1 mol dm p-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ octylparaben ;C15H22O3; 1991 . 288.2 1.90 ͓1219-38-1͔ ͑ ͒ ͑ ͒ 293.2 3.00 2 n-Hexane hexane ;C6H14; 298.2 3.90 ͓110-54-3͔

Variables: Prepared by: Auxiliary Information T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the Solubility of octylparaben in n-hexane propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: Temperature Solubility The hexylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great / 2 / −3 Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. T K10c1 mol dm n-Hexane was of Anala R grade. 288.2 0.678 Estimated Errors: 293.2 1.10 Nothing speciﬁed. 298.2 1.80

Auxiliary Information Components: Original Measurements: ͑ ͒ 36 1 Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. Methods/Apparatus/Procedure: ͑ heptyl ester heptyl Park, and G.J. Rimmer, The experimental details are given in the compilation of Ref. 36 for the p 178 -hydroxybenzoate, Thermochim. Acta ,59 propylparaben–1-octanol system in Sec. 2.2.1.3. heptylparaben͒;C H O ; ͑1991͒. 14 20 3 Source and Purity of Materials: ͓1085-12-7͔ ͑ ͑2͒ n-Hexane ͑hexane͒;CH ; The octylparaben was the gift of Apin Chemicals Ltd. Abingdon, Great 6 14 ͒ Ͼ ͓110-54-3͔ Britain and was used as received. The purity was speciﬁed as 99.5%. n-Hexane was of Anala R grade. Variables: Prepared by: Estimated Errors: T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto Nothing speciﬁed.

Solubility of heptylparaben in n-hexane Components: Original Measurements: 36 Temperature Solubility ͑1͒ Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. decyl ester ͑decyl Park, and G.J. Rimmer, / 2 / −3 T K10c1 mol dm p-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ decylparaben ;C17H26O3; 1991 . 288.2 1.0 ͓99-76-3͔ ͑ ͒ ͑ ͒ 293.2 2.80 2 n-Hexane hexane ;C6H14; 298.2 3.20 ͓110-54-3͔

Variables: Prepared by: Auxiliary Information T/K=288.2, 293.2, and 298.2 A. Goto and R. Goto

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the Solubility of decylparaben in n-hexane propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: Temperature Solubility The heptylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great / 3 / −3 Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. T K10c1 mol dm n-Hexane was of Anala R grade. 288.2 3.08 Estimated Errors: 293.2 4.57 Nothing speciﬁed. 298.2 7.16

Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the propylparaben–1-octanol system in Sec. 2.2.1.3.

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Source and Purity of Materials: The decylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great Components: Original Measurements: 36 Britain͒ and was used as received. The purity speciﬁed as Ͼ99.5%. ͑1͒ Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. ͑ n-Hexane was of Anala R grade. octyl ester octyl Park, and G.J. Rimmer, p 178 Estimated Errors: -hydroxybenzoate, Thermochim. Acta ,59 octylparaben͒;C H O ; ͑1991͒. Nothing speciﬁed. 15 22 3 ͓1219-38-1͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ alcohol ;C8H18O; 111-87-5 Components: Original Measurements: ͑ ͒ 36 1 Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. Variables: Prepared by: hexyl ester ͑hexyl Park, and G.J. Rimmer, T/K=298 A. Goto and R. Goto p-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ hexylparaben ;C13H18O3; 1991 . ͓ ͔ 1083-27-8 The solubility of octylparaben in 1-octanol at 298 K was ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ / −3 alcohol ;C8H18O; 111-87-5 reported as c1 mol dm =3.67.

Variables: Prepared by: Auxiliary Information T/K=298 A. Goto and R. Goto Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the The solubility of hexylparaben in 1-octanol at 298 K propylparaben–1-octanol system in Sec. 2.2.1.3. was reported as c /mol dm−3=6.39. Source and Purity of Materials: 1 The octylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great ͒ Ͼ Auxiliary Information Britain and was used as received. The purity was specified as 99.5%. 1-Octanol was of Anala R grade. Methods/Apparatus/Procedure: Estimated Errors: The experimental details are given in the compilation of Ref. 36 for the Nothing specified. propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: ͑ The hexylparaben was the gift of Apin Chemicals Ltd. Abingdon, Great Components: Original Measurements: Britain͒ and was used as received. The purity was specified as Ͼ99.5%. ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. 1-Octanol was of Anala R grade. decyl ester ͑decyl Park, and G.J. Rimmer, Estimated Errors: p-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ Nothing specified. decylparaben ;C17H26O3; 1991 . ͓2664-60-0͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ Components: Original Measurements: alcohol ;C8H18O; 111-87-5 ͑ ͒ 36 1 Benzoic acid, 4-hydroxy-, A.E. Beezer, S. Forster, W.-B. Variables: Prepared by: heptyl ester ͑heptyl Park, and G.J. Rimmer, T/K=298 A. Goto and R. Goto 4-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ heptylparaben ;C14H20O3; 1991 . ͓ ͔ 1085-12-7 The solubility of decylparaben in 1-octanol at 298 K was ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ / −3 alcohol ;C8H18O; 111-87-5 reported as c1 mol dm =1.96.

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2.2.2.4. Methylpropyl-, pentyl-, and benzylparaben Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. Components: Original Measurements: phenylmethyl ester ͑benzyl Park, and G.J. Rimmer, ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. p-hydroxybenzoate, Thermochim. Acta 178,59 ͒ ͑ ͒ 2-methylpropyl ester ͑isobutyl Park, and G.J. Rimmer, benzylparaben ;C14H12O3; 1991 . p-hydroxybenzoate, Thermochim. Acta 178,59 ͓94-18-8͔ ͒ ͑ ͒ ͑ ͒ ͑ isobutylparaben ;C11H14O3; 1991 . 2 1-Octanol octan-1-ol, octyl ͒ ͓ ͔ ͓4247-02-3͔ alcohol ;C8H18O; 111-87-5 ͑2͒ 1-Octanol ͑octan-1-ol, octyl ͒ ͓ ͔ Variables: Prepared by: alcohol ;C8H18O; 111-87-5 T/K=298 A. Goto and R. Goto Variables: Prepared by: T/K=298 A. Goto and R. Goto The solubility of benzylparaben in 1-octanol at 298 K was reported as c /mol dm−3=9.76. The solubility of isobutylparaben in 1-octanol at 298 K 1 / −3 Auxiliary Information was reported as c1 mol dm =2.81.

Auxiliary Information Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the Methods/Apparatus/Procedure: propylparaben–1-octanol system in Sec. 2.2.1.3. The experimental details are given in the compilation of Ref. 36 for the Source and Purity of Materials: propylparaben–1-octanol system in Sec. 2.2.1.3. The benzylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great Source and Purity of Materials: Britain͒ and was used as received. The purity specified as Ͼ99.5%. The isobutylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, 1-Octanol was of Anala R grade. Great Britain͒ and was used as received. The purity was specified as Estimated Errors: Ͼ99.5%. Nothing specified. 1-Octanol was of Anala R grade. Estimated Errors: Nothing specified.

Components: Original Measurements: 2.3. Hydroxybenzoic acid salt–organic ͑1͒ Benzoic acid, 4-hydroxy-, 36A.E. Beezer, S. Forster, W.-B. pentyl ester ͑pentyl Park, and G.J. Rimmer, compound systems p-hydroxybenzoate, Thermochim. Acta 178,59 2.3.1. 2-Hydroxybenzoic acid salt Na ͒ ͑ ͒ „ … pentylparaben ;C12H16O3; 1991 . ͓6521-29-5͔ ͑2͒ 1-Octanol ͑octan-1-ol, octyl Components: Original Measurements: ͒ ͓ ͔ 37 alcohol ;C8H18O; 111-87-5 ͑1͒ Benzoic acid, 2-hydroxy-, H. Henstock, J. Chem. Soc. monosodium salt ͑sodium 1934, 1340. Variables: Prepared by: ͒ ͓ ͔ salicylate ;C7H5NaO3; 54-21-7 T/K=298 A. Goto and R. Goto ͑2͒ Methyl alcohol ͑methanol͒; ͓ ͔ CH4O; 67-56-1 The solubility of pentylparaben in 1-octanol at 298 K Variables: Prepared by: / ͑ was reported as c /mol dm−3=3.96. t °C=15 and 67.2 boiling point H. Miyamoto and A. Goto 1 of solution͒ Auxiliary Information Solubility of sodium salicylate in methanol Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 36 for the Temperature Solubility propylparaben–1-octanol system in Sec. 2.2.1.3. Source and Purity of Materials: b / −1 w1 m1 mol kg The pentylparaben was the gift of Apin Chemicals Ltd. ͑Abingdon, Great t/ °C Original dataa ͑compiler͒ ͑compiler͒ Britain͒ and was used as received. The purity was speciﬁed as Ͼ99.5%. 1-Octanol was of Anala R grade. 15 26.28 0.2081 1.641 Estimated Errors: 67.2 ͑boiling point͒ 34.73 0.2578 2.169 Nothing speciﬁed. aIn the original paper, the solubility was given as grams of salt per 100 g of solvent. b /⌺ w1 =m1 mi, where w1 is the mass fraction of sodium salicylate. m1 and ⌺ mi are mass of sodium salicylate and mass of solution, respectively.

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Auxiliary Information Source and Purity of Materials: Ethanol and methanol were refluxed over silver oxide, distilled and Methods/Apparatus/Procedure: dehydrated with magnesium. The water content of methanol ranged from The apparatus used for the measurements at 15 °C was similar to that 0% to 0.03%, while that of ethanol varied from 0.01% to 0.07%. ͓ described in J.N. Bronsted and A. Petersen, J. Am. Chem. Soc. 43, 2265 The silver salt of the acid was precipitated from solutions of the ͑ ͔͒ 1921 . It was immersed in a thermostat. At boiling temperature, the corresponding sodium salt with a slight excess of silver nitrate. The solutions were made in a wide flask under reflux. To determine the precipitates were washed and recrystallized from hot water. The product quantities of solutes, portions of the saturated solutions were weighed at was washed with water, then with ethanol, and air dried. ͓ 15 °C in a graduated pipette of the type used by F.D. Chattaway and Estimated Errors: W.J. Lambert, J. Chem. Soc. 107,1766͑1915͔͒; a filter thimble was Nothing specified. introduced into the solution to separated undissolved salt. The contents being discharged into a weighing bottle, the pipette was washed with the boiling solvent, and the residue was weighed after evaporation of solvent; thus the weights of solute and solvent were both obtained. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 2-hydroxy-, 39N.A. Izmailov and V.S. Sodium salicylate was recrystallized twice from boiling methanol. silver salt ͑silver salicylate͒; Chernyi, Zh. Fiz. Khim. 34,319 ͑ ͒ ͑ ͓͒ Methanol was purified by first removing acetone by Minuses’ method, C7H5O3Ag Merck , 1960 Russ. J. Phys. Chem. ͑ ͒ ͑ ͒ ͑ ͒ ͑ ͔͒ aldehyde was abstracted by treatment with iodine, and distillation with 2 OH C6H4CO2Ag Aldrich , Engl. Transl. 34,149 1960 . ͑ ͒ ͓ ͔ concentrated sulfuric acid removed basic substance as well as most of the C7H6O3Ag CA ; 35959-19-4 ͑ ͒ water. Acid substances were removed by distillation from caustic potash, 2 Alcohols: ͑ ͒ and the alcohol was distilled over metallic sodium; b.p. 66 °C at Methyl alcohol methanol ; ͓ ͔ 758 mmHg. CH4O; 67-56-1 ͑ ͒ Estimated Errors: Ethyl alcohol ethanol ;C2H6O; ͓ ͔ Ϯ 64-17-5 Solubility: Precision of 1%. ͑ Ϯ 1-Butanol butan-1-ol, butyl Temperature: Precision of 0.1 °C. ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 1-Butanol, 3-methyl- ͑3-methylbutan-1-ol, isoamyl 2.3.2. 2-Hydroxybenzoic acid salt Ag ͒ ͓ ͔ „ … alcohol ;C5H12O; 123-51-3 1-Hexanol ͑hexan-1-ol, hexyl alcohol͒;CH O; ͓111-27-3͔ Components: Original Measurements: 6 14 1-Heptanol ͑n-heptan-1-ol, heptyl ͑1͒ Benzoic acid, 2-hydroxy-, 38I.M. Kolthoff, J.J. Lingane, and alcohol͒;CH O; ͓111-70-6͔ silver salt ͑silver salicylate͒; W.D. Larson, J. Am. Chem. Soc. 7 16 ͓ ͔ ͑ ͒ C7H5O3Ag; 35959-19-4 60, 2512 1938 . Variables: Prepared by: ͑ ͒ 2 Alcohols: t/ °C=25 H. Miyamoto Methyl alcohol ͑methanol͒; ͓ ͔ CH4O; 67-56-1 ͑ ͒ Ethyl alcohol ethanol ;C2H6O; Solubility of silver salicylate in alcohols at 25 °C ͓64-17-5͔ Solubility Variables: Prepared by: / 4 / −1 t °C=25 H. Miyamoto Solvent 10 m1 mol kg

Methanol 6.54 Solubility of silver salicylate in alcohols at 25 °C Ethanol 5.15 1-Butanol 1.11 Solubility Isoamyl alcohol 1.09 4 / −3 Solvent 10 c1 mol dm n-Hexyl alcohol 1.91 n-Heptyl alcohol 1.64 Methanol 5.69 Ethanol 3.10 Auxiliary Information

Auxiliary Information Methods/Apparatus/Procedure: The solubility determination of the silver salt used the radioactive isotope Methods/Apparatus/Procedure: 110Ag. The silver salt with solvent was placed in a tube, sealed and placed Saturated solution of the silver salt was prepared in conductance cells in an air thermostat. Equilibrium was reached in 16–18 h. The solution through which a stream of previously dried nitrogen, saturated with the removed from the tube was centrifuged. The samples were withdrawn by vapor of the solvent, was led to provide stirring. When the conductance a micropipette and run on to a disk of ﬁlter paper, dried, and sealed in had become constant, samples of the saturated aqueous solutions were tracing cloth or Cellophane. The prepared specimens were found on a withdrawn and analyzed for silver by the potentiometric method. The cylindrical counter and their radioactivity was measured. The methods of solubilities in ethanol and methanol were determined by the conductance preparing saturated solutions, sampling, and the radioactive measurement ͓ method. The conductance cells were of the type used by I.M. Kolthoff are described in ͓N.A. Izmailov and V.S. Chernyi, Zh. Fiz. Khim. 34,127 ͑ ͔͒ and A. Willman, J. Am. Chem. Soc. 56,1008 1934 . Their cell constants ͑1960͒; Russ. J. Phys. Chem. ͑Engl. Transl.͒ 34,59͑1960͔͒.The were determined in the usual way. The conductance of methanol at 25 °C concentration of silver salicylate was analyzed for silver content. varied from 2.9 to 5.0 and the range in the corresponding values for ethanol was from 0.4 to 1.2ϫ10−4 Scm−1. The conductance of the pure alcohol was subtracted from the observed conductivities where necessary.

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Source and Purity of Materials: Solubility of ammonium salicylate in acetone at 15 °C The silver salt of salicylic acid was prepared from silver nitrate labeled with radioactive 110Ag and the sodium or potassium salts of the acid. Solubility The solvents were carefully purified. w b m /mol kg−1 Estimated Errors: 1 1 Original dataa ͑compiler͒ ͑compiler͒ Solubility: Relative accuracy was 1%–3% at a confidence limit of 0.95. Temperature: Precision of Ϯ0.5 °C. 69.65 0.4105 4.489 aThe solubility was originally reported as grams of ammonium salicylate per 100 g of solvent. Components: Original Measurements: b /⌺ w1 =m1 mi, where w1 is the mass fraction of sodium salicylate. m1 and ͑1͒ Benzoic acid, 2-hydroxy-, 39N.A. Izmailov and V.S. ⌺ mi are the mass of sodium salicylate and mass of solution, respectively. silver salt ͑silver salicylate͒; Chernyi, Zh. Fiz. Khim. 34, 319 ͑ ͒ ͑ ͓͒ C7H5OAg Merck , 1960 Russ. J. Phys. Chem. Auxiliary Information ͑ ͒ ͑ ͒ ͑ ͒ ͑ ͔͒ 2 OH C6H4CO2Ag Aldrich , Engl. Transl. 34, 149 1960 . ͑ ͒ ͓ ͔ C7H6O3Ag CA ; 35959-19-4 Methods/Apparatus/Procedure: ͑2͒ Ketones: The experimental details are given in the compilation of Ref. 37 for the 2-Propanone ͑propan-2-one, binary sodium salicylate–methanol system in Sec. 2.3.1. ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 Source and Purity of Materials: 2-Butanone ͑butan-2-one, methyl Ammonium salicylate was recrystallized from boiling methanol. ͒ ͓ ͔ ethyl ketone ;C4H8O; 78-93-3 Acetone was purified by way of its sodium iodide compound, dried over ͑ 4-Heptanone heptan-4-one, calcium chloride and redistilled; b.p. 56.2 °C at 759 mmHg. ͒ dipropyl ketone ;C7H14O; Estimated Errors: ͓123-19-3͔ Solubility: Accuracy of 1%. Variables: Prepared by: Temperature: Precision of Ϯ0.1 °C. t/ °C=25 H. Miyamoto

Solubility of silver salicylate in ketones at 25 °C 2.3.4. 4-Hydroxybenzoic acid salt „Ag…

Solubility Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 39N.A. Izmailov and V.S. Solvent 104m /mol kg−1 1 monosilver salt ͑silver Chernyi, Zh. Fiz. Khim. 34,319 ͒ ͑ ͓͒ Acetone 1.35 4-hydroxybenzoate ;C7H5O3Ag; 1960 Russ. J. Phys. Chem. ͓͔ ͑ ͒ ͑ ͔͒ 2-Butanone 0.996 Engl. Transl. 34,149 1960 . ͑2͒ Alcohols: Dipropyl ketone 0.431 Methyl alcohol ͑methanol͒; ͓ ͔ CH4O; 67-56-1 ͑ ͒ Auxiliary Information Ethyl alcohol ethanol ;C2H6O; ͓64-17-5͔ Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 39 for the Variables: Prepared by: binary silver salicylate–methanol system earlier in this section. t/ °C=25 H. Miyamoto and A. Goto Source and Purity of Materials: The silver salt of salicylic acid was prepared from silver nitrate labeled Solubility of silver 4-hydroxybenzoate in alcohols at 25 °C with radioactive 110Ag and the sodium or potassium salts of the acid. The solvents were carefully puriﬁed. Solubility Estimated Errors: 3 / −1 Solubility: Relative accuracy is 1%–3% at a conﬁdence limit of 0.95. Solvent 10 m1 mol kg Temperature: Precision of Ϯ0.5 °C. Methanol 1.51 Ethanol 0.371

Auxiliary Information

2.3.3. 2-Hydroxybenzoic acid salt „NH4… Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 39 for the binary silver salicylate–methanol system in Sec. 2.3.2. Components: Original Measurements: Source and Purity of Materials: ͑1͒ Benzoic acid, 2-hydroxy-, 37H. Henstock, J. Chem. Soc. The silver salt of 4-hydroxybenzoic acid was prepared from silver nitrate monoammonium salt ͑ammonium 1934, 1340. labeled with radioactive 110Ag and the sodium or potassium salts of the salicylate͒;CH NO ; ͓528-94-9͔ 7 9 3 acid. ͑2͒ 2-Propanone ͑propan-2-one, ͒ ͓ ͔ The solvents were carefully puriﬁed. acetone ;C3H6O; 67-64-1 Estimated Errors: Variables: Prepared by: Solubility: Relative accuracy is 1%–3% at a conﬁdence limit of 0.95. t/ °C=15 H. Miyamoto Temperature: Precision of Ϯ0.5 °C.

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3. Hydroxybenzoic Acids and Parabens in Components: Original Measurements: Ternary Nonaqueous Systems ͑1͒ Benzoic acid, 2-hydroxy- 40J.W. Marden and M.V. Dover, ͑o-hydroxybenzoic acid, salicylic J. Am. Chem. Soc. 39,1͑1917͒. ͒ ͓ ͔ 3.1. Hydroxybenzoic acid and paraben–organic acid ;C7H6O3; 69-72-7 compound 1 –organic compound 2 systems ͑2͒ 2-Propanone ͑propan-2-one, „ … „ … ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 3.1.1. Salicylic acid ͑ ͒ ͓ ͔ 3 Benzene; C6H6; 71-43-2

Variables: Prepared by: Components: Original Measurements: Concentration of acetone H. Miyamoto and A. Goto ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and t/ °C=25 ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . ͑ ͒ ͓ ͔ 2 Benzene; C6H6; 71-43-2 Solubility of salicylic acid in acetone–benzene mixtures at 25 °C ͑3͒ Second component of organic solvent: Concentration of acetone Solubilitya Methyl alcohol ͑methanol͒; ͓ ͔ / −1 CH4O; 67-56-1 100x2 Original 100w1 m1 mol kg ͑ ͒ ͑ ͒ ͑ ͒ ͑ ͒ Ethyl alcohol ethanol ;C2H6O; 100w2 compiler data compiler compiler ͓64-17-5͔ 1-Propanol ͑propan-1-ol, propyl 100 100.0 55.5 35.7 4.02 ͒ ͓ ͔ alcohol ;C3H8O; 71-23-8 90 92.3 51.1 33.8 3.70 2-Propanone ͑propan-2-one, 80 84.3 46.4 31.7 3.36 ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 70 75.8 ͑42.3͒ 29.7 3.06 Ethanol, 2-ethoxy- 60 64.7 36.7 26.8 2.66 ͑ 2-ethoxyethanol, ethyl 50 57.4 ͑31.0͒ 23.7 2.24 ͒ ͓ ͔ cellosolve ;C4H10O2; 110-80-5 40 47.3 25.3 20.2 1.83 ͑ ͒ Variables: Prepared by: 30 36.6 20.0 16.7 1.45 t/ °C=30.6 H. Miyamoto and A. Goto 20 25.2 15.0 13.0 1.08 10 13.0 7.1 6.6 0.51 0 0.0 0.92 0.91 0.067 Solubility of salicylic acid in benzene–alcohol mixtures at 30.6 °C aIn the original paper, the solubility was given as grams per 100 g of the b Solubility mixed solvent. The values enclosed in parentheses were taken from the ␥ / −3 / −3 curve by the authors. Dielectric 1 gdm c1 mol dm Solvent system constanta ͑compiler͒ ͑compiler͒ Auxiliary Information Benzene 2.2 7 0.05 Methods/Apparatus/Procedure: Benzene–methanol 16.0 390 2.82 The solvents, with a large excess of solid salicylic acid, were shaken in a Benzene–ethanol 15.8 430 3.11 thermostat for 8–12 h at 25 °C. The solutions were forced out of the Benzene–1-propanol 15.3 315 2.28 bottles through glass wool filters into a weighing pipet, from which the Benzene–ethyl cellosolve 14.5 425 3.08 solutions were weighed directly into small glass evaporating dishes and Benzene–2-propanone ͑acetone͒ 15.6 510 2.69 dried on a steam bath and in sulfuric acid desiccators. Source and Purity of Materials: a The dielectric constant of the solvent mixtures at the maximum solubility of Salicylic acid was completely volatilized on heating, leaving no weighable salicylic acid. residue. The melting point of the purified acid was 126 °C. bIn the original paper, the solubility was given as mg/ml of solution. Estimated Errors: Nothing specified. Auxiliary Information

Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the Components: Original Measurements: salicylic acid–ethanol system in Sec. 2.1.2.1. ͑1͒ Benzoic acid, 2-hydroxy- 40J.W. Marden and M.V. Dover, Source and Purity of Materials: ͑o-hydroxybenzoic acid, salicylic J. Am. Chem. Soc. 39,1͑1917͒. ͒ ͓ ͔ The solvents were puriﬁed by the method described in A. Weissberger et acid ;C7H6O3; 69-72-7 al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 ͑2͒ Acetic acid, ethyl ester ͑ethyl ͒ ͓ ͔ and 5. acetate ;C4H8O2; 141-78-6 ͑ ͒ ͓ ͔ Estimated Errors: 3 Benzene; C6H6; 71-43-2 Solubility: Nothing speciﬁed. Variables: Prepared by: Ϯ ͑ ͒ Ϯ ͑ Temperature: Precision of 0.2 °C solubility and 1.0 °C dielectric Concentration of ethyl acetate H. Miyamoto and A. Goto ͒ constant . t/ °C=25

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Solubility of salicylic acid in ethyl acetate–benzene mixtures at 25 °C Auxiliary Information

Concentration of ethyl Methods/Apparatus/Procedure: acetate Solubilitya The solubility of salicylic acid was determined according to the method of Herz and Lorenz ͓W. Herz and L. Lorenz, Kolloid Z. 47,331͑1929͔͒. / −1 100x2 Original 100w1 m1 mol kg Concentrations of saturated solutions were determined by a titrimetric ͑ ͒ ͑ ͒ ͑ ͒ 100w2 compiler data compiler compiler method. Source and Purity of Materials: 100 100.0 38.0 27.5 2.75 “Best commercial quality” of salicylic acid was puriﬁed by 90 88.9 24.2 19.5 1.75 recrystallization. 80 78.0 22.7 18.5 1.64 Estimated Errors: 70 67.4 ͑19.5͒ 16.3 1.41 Not stated. 60 57.1 16.6 14.2 1.20 50 47.0 ͑14.5͒ 12.7 1.05 40 37.1 12.8 11.3 0.927 Components: Original Measurements: 30 27.5 ͑9.6͒ 8.8 0.695 ͑1͒ Benzoic acid, 2-hydroxy- 42I.L. Krupatkin, Zh. Obsh. 20 18.1 6.2 5.8 0.449 ͑o-hydroxybenzoic acid, salicylic Khim. 25,2189͑1955͓͒J. Gen. 10 9.0 3.42 3.3 0.248 ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 Chem. USSR Engl. Transl. 25, 0 0.0 0.92 0.91 0.067 ͑2͒ 2151 ͑1955͔͒.

a 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one In the original paper, the solubility was given as grams per 100 g of the ͑1,5-dimethyl-2-phenylpyrazol-3-one, ͒ mixed solvent. The values enclosed in parentheses were taken from the antipyrine ;C11H12N2O; curve by the authors. ͓60-80-0͔ ͑3͒ Gasoline Auxiliary Information Variables: Prepared by: Methods/Apparatus/Procedure: t/ °C=76.0–178.0 H. Miyamoto and A. Goto The experimental details are given in the compilation of Ref. 40 for the Composition ternary salicylic acid–acetone–benzene system earlier in this section. Source and Purity of Materials: Solubility of salicylic acid in antipyrine–gasoline mixtures Salicylic acid was completely volatilized on heating, leaving no weighable residue. Composition of saturated solutions Estimated Errors: Demixing Nothing speciﬁed. Salicylic acid Antipyrine Gasoline temperature

100w1 100w2 Section number ͑compiler͒ ͑compiler͒ 100w t/ °C Components: Original Measurements: 3 ͑ ͒ 41 1 Benzoic acid 2-hydroxy- W. Herz and M. Levi, Kolloid 1 13.95 79.05 7.00 86.0 ͑ ͑ ͒ o-hydroxybenzoic acid, salicylic Z. 50,21 1930 . Salicylic acid 15% 13.37 75.40 10.90 117.0 acid͒;CH O ; ͓69-72-7͔ 7 6 3 Antipyrine 85% 13.20 74.80 12.00 128.0 ͑2͒ Methane, tetrachloro- 12.02 68.09 19.90 164.0 ͑tetrachloromethane, carbon ͒ ͓ ͔ 2.10 11.90 86.00 162.0 tetrachloride ;CCl4; 56-23-5 ͑ ͒ ͓ ͔ 1.50 8.50 90.00 149.0 3 Benzene; C6H6; 71-43-2 0.75 4.25 95.00 114.0 Variables: Prepared by: 0.45 2.55 97.00 96.0 Concentration of benzene E. Königsberger and L.-C. 2 27.75 64.75 7.50 84.0 / t °C=25 Königsberger Salicylic acid 30% 27.00 63.00 10.00 111.0 Antipyrine 70% 25.50 59.50 15.00 145.0 Solubility of salicylic acid in benzene–tetrachloromethane mixtures at 24.60 57.40 18.00 161.0 25 °C 3.60 8.40 88.00 159.0 2.40 5.60 9.20 134.0 Concentration of benzene Solubility 1.50 3.50 9.60 120.0 0.90 2.10 9.70 99.0 ␸ / −3 2 c1 mmol dm 3 40.21 53.30 6.50 76.0 Salicylic acid 43% 100 50.0 39.17 51.93 8.90 100.0 Antipyrine 57% 80 47.3 38.70 51.30 10.00 111.0 60 44.9 36.55 48.45 15.00 139.0 40 42.2 34.40 45.60 20.00 160.0 20 37.1 4.30 5.70 90.00 159.0 0 29.7 2.15 2.85 95.00 125.0 1.29 1.71 97.00 94.0

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Solubility of salicylic acid in antipyrine–gasoline mixtures Source and Purity of Materials: Pharmaceutical antipyrine and chemically pure grade salicylic acid were Composition of saturated solutions used. Demixing A gasoline fraction boiling in the 120–140 °C range was used. Salicylic acid Antipyrine Gasoline temperature Estimated Errors: Nothing speciﬁed. 100w1 100w2 ͑ ͒ ͑ ͒ / Section number compiler compiler 100w3 t °C

4 46.25 46.25 7.50 84.0 Components: Original Measurements: Salicylic acid 50% 45.00 45.00 10.00 102.0 ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and Antipyrine 50% 43.40 43.40 13.20 138.0 ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ 40.50 40.50 19.00 163.0 acid ;C7H6O3; 69-72-7 1349 1964 . 5.00 5.00 90.00 155.0 ͑2͒ Acetic acid, ethyl ester ͑ethyl ͒ ͓ ͔ 2.50 2.50 95.00 117.0 acetate ;C4H8O2; 141-78-6 ͑ ͒ 2.00 2.00 96.00 114.0 3 Second component of organic 1.50 1.50 97.00 98.0 solvent: Methyl alcohol ͑methanol͒; 5 55.20 36.80 8.00 85.0 CH O; ͓67-56-1͔ Salicylic acid 60% 54.00 36.00 10.00 100.0 4 Ethyl alcohol ͑ethanol͒;CH O; Antipyrine 40% 2 6 53.22 35.48 11.30 110.0 ͓64-17-5͔ 51.00 34.00 15.00 135.0 1-Propanol ͑propan-1-ol, propyl ͒ ͓ ͔ 48.00 32.00 20.00 160.0 alcohol ;C3H8O; 71-23-8 6.00 4.00 90.00 156.0 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ 3.00 2.00 95.00 121.0 alcohol ;C4H10O; 71-36-3 1.80 1.20 97.00 96.0 Ethanol, 2-ethoxy- ͑ 6 60.90 26.10 13.00 95.0 2-ethoxyethanol, ethyl ͒ ͓ ͔ Salicylic acid 70% 59.50 25.50 15.00 120.0 cellosolve ;C4H10O2; 110-80-5 2-Propanone ͑propan-2-one, Antipyrine 30% 56.00 24.00 20.00 145.0 acetone͒;CH O; ͓67-64-1͔ 53.90 23.10 23.00 154.0 3 6 1,2-Propanediol 51.10 21.90 27.00 162.0 ͑propane-1,2-diol, propylene 14.00 6.00 80.00 178.0 ͒ ͓ ͔ glycol ;C3H8O2; 57-55-6 7.00 3.00 90.00 154.0 3.50 1.50 95.00 120.0 Variables: Prepared by: 2.10 0.90 97.00 98.0 t/ °C=30.6 H. Miyamoto and A. Goto 7 63.20 15.8 21.00 99.0 Salicylic acid 80% 62.40 15.6 22.00 109.0 Solubility of salicylic acid in ethyl acetate–alcohol mixtures at 30.6 °C Antipyrine 20% 60.00 15.0 25.00 122.0 56.00 14.0 30.00 130.0 Solubilityb 52.00 13.0 35.00 149.0 ␥ / −3 / −3 41.12 10.28 48.60 151.5 Dielectric 1 gdm c1 mol dm Solvent system constanta ͑compiler͒ ͑compiler͒ 36.00 9.00 55.00 154.0 28.00 7.30 65.00 163.0 Ethyl acetate 6.0 23 0.17 20.00 5.00 75.00 163.0 Ethyl acetate–methanol 16.0 335 2.43 16.00 4.00 80.00 152.0 Ethyl acetate–ethanol 15.7 390 2.82 12.00 3.00 85.00 139.0 Ethyl acetate–1-propanol ͑n-propanol͒ 15.3 355 2.57 8.00 2.00 90.00 123.0 Ethyl acetate–1-butanol ͑n-butanol͒ 14.0 330 2.39 4.80 1.20 94.00 109.0 Ethyl acetate–ethanol, 14.5 425 3.08 8 49.50 5.00 45.00 95.0 2-ethoxy- ͑ethyl cellosolve͒ Salicylic acid 90% 45.00 5.00 50.00 110.0 Ethyl acetate–2-propanone ͑acetone͒ 16.1 415 3.00 Antipyrine 10% 36.00 4.00 60.00 123.0 Ethyl acetate–1,2-propanediol 16.2 160 1.16 27.00 3.00 70.00 128.0 ͑propylene glycol͒ 18.00 2.00 80.00 132.0 aThe dielectric constant of the binary mixtures at the maximum solubility of 13.50 1.50 85.00 125.0 salicylic acid. 9.00 1.00 90.00 103.0 bIn the original paper, the solubility was given as mg/ml of solution.

Auxiliary Information Auxiliary Information Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the The experiment was performed by the polythermic method in sealed glass salicylic acid–ethanol system in Sec. 2.1.2.1. ampoules. The three-component system was studied by polythermic Source and Purity of Materials sections through their prisms taken from the edge for gasoline to the plane for the binary system antipyrine–salicylic acid. The solvents were puriﬁed by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5.

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Estimated Errors: Estimated Errors: Solubility: Nothing speciﬁed. Solubility: Nothing speciﬁed. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric constant͒. constant͒.

Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and ͑1͒ Benzoic acid, 2-hydroxy- 17A.N. Paruta, B.J. Sciarrone, and ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͑o-hydroxybenzoic acid, salicylic N.G. Lordi, J. Pharm. Sci. 53, ͒ ͓ ͔ ͑ ͒ ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 1349 1964 . acid ;C7H6O3; 69-72-7 1349 1964 . ͑ ͒ ͑ ͒ 2 Chloroform; CHCl3; 2 1,4-Dioxane; C4H8O2; ͓67-66-3͔ ͓123-91-1͔ ͑3͒ Second component of organic ͑3͒ Second component of organic solvent: solvent: Methyl alcohol ͑methanol͒; Methyl alcohol ͑methanol͒; ͓ ͔ ͓ ͔ CH4O; 67-56-1 CH4O; 67-56-1 ͑ ͒ ͑ ͒ Ethyl alcohol ethanol ;C2H6O; Ethyl alcohol ethanol ;C2H6O; ͓64-17-5͔ ͓64-17-5͔ 1-Propanol ͑propan-1-ol, propyl 1-Propanol ͑propan-1-ol, propyl ͒ ͓ ͔ ͒ ͓ ͔ alcohol ;C3H8O; 71-23-8 alcohol ;C3H8O; 71-23-8 1-Butanol ͑butan-1-ol, butyl 1-Butanol ͑butan-1-ol, butyl ͒ ͓ ͔ ͒ ͓ ͔ alcohol ;C4H10O; 71-36-3 alcohol ;C4H10O; 71-36-3 Ethanol, 2-ethoxy- Ethanol, 2-ethoxy- ͑2-ethoxyethanol, ethyl ͑2-ethoxyethanol, ethyl ͒ ͓ ͔ ͒ ͓ ͔ cellosolve ;C4H10O2; 110-80-5 cellosolve ;C4H10O2; 110-80-5 2-Propanone ͑propan-2-one, 2-Propanone ͑propan-2-one, ͒ ͓ ͔ ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 acetone ;C3H6O; 67-64-1 1,2-Propanediol 1,2-Ethanediol ͑ethane-1,2-diol, ͑ ͒ propane-1,2-diol, propylene ethylene glycol ;C2H6O2; ͒ ͓ ͔ ͓ ͔ glycol ;C3H8O2; 57-55-6 107-21-1 1,2-Propanediol Variables: Prepared by: ͑propane-1,2-diol, propylene / ͒ ͓ ͔ t °C=30.6 H. Miyamoto and A. Goto glycol ;C3H8O2; 57-55-6

Variables: Prepared by: Solubility of salicylic acid in chloroform–alcohol mixtures at 30.6 °C t/ °C=30.6 H. Miyamoto and A. Goto

Solubilityb Solubility of salicylic acid in dioxane–alcohols mixtures at 30.6 °C ␥ / −3 / −3 Dielectric 1 gdm c1 mol dm a ͑ ͒ ͑ ͒ b Solvent system constant compiler compiler Solubility

Chloroform 4.8 2 0.014 ␥ / −3 / −3 Dielectric 1 gdm c1 mol dm Chloroform–methanol 16.0 348 2.52 Solvent system constanta ͑compiler͒ ͑compiler͒ Chloroform–ethanol 15.7 595 4.31 Chloroform–1-propanol 15.3 315 2.28 1,4-Dioxane 2.2 40 0.29 Chloroform–1-butanol 14.0 425 2.04 1,4-Dioxane–methanol 16.3 440 3.19 Chloroform–ethyl cellosolve 14.5 425 3.08 1,4-Dioxane–ethanol 15.0 495 3.58 Chloroform–acetone 16.1 445 3.22 1,4-Dioxane–propanol 14.8 305 2.21 Chloroform–propylene glycol 15.2 292 2.11 1,4-Dioxane–1-butanol 14.5 268 1.94 1,4-Dioxane–ethyl cellosolve 14.5 425 3.08 aThe dielectric constant of the binary mixtures at the maximum solubility of 1,4-Dioxane–acetone 15.6 475 3.44 salicylic acid. 1,4-Dioxane–ethylene glycol 17.5 89 0.64 bIn the original paper, the solubility was given as mg/ml of solution. 1,4-Dioxane–propylene glycol 15.1 290 2.10

Auxiliary Information aThe dielectric constant of the solvent mixtures at the maximum solubility of salicylic acid. Methods/Apparatus/Procedure: b In the original paper, the solubility was given as mg/ml of solution. The experimental details are given in the compilation of Ref. 17 for the salicylic acid–ethanol system in Sec. 2.1.2.1. Source and Purity of Materials: The solvents were puriﬁed by the method described in A. Weissberger et al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 and 5.

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 17 for the Solvent mixtures were prepared by mixing exactly measured volumes of salicylic acid–ethanol system in Sec. 2.1.2.1. absolute ethanol and cyclohexane. A suitable amount of solvent was Source and Purity of Materials: introduced into a stoppered test tube containing an excess amount of The solvents were purified by the method described in A. Weissberger et solute, and was kept at least 24 h in a constant-temperature bath with al., Organic Solvents, 2nd ed. ͑Interscience, New York, 1955͒, Chaps. 4 adequate shaking. Samples were taken with a small diameter tube having and 5. a piece of sintered glass in its end to avoid contamination with the solid. Estimated Errors: Pipettes and filter devices were previously heated in an oven to reach the same temperature as that of the experiment. The ester concentration was Solubility: Nothing specified. determined spectrophotometrically. Temperature: Precision of Ϯ0.2 °C ͑solubility͒ and Ϯ1.0 °C ͑dielectric Source and Purity of Materials: constant͒. Methylparaben was obtained from Aldrich and purified by recrystallization, m.p. 398.4 K ͓R.H. Manzo, A.A. Ahumada, and E. Luna, J. Pharm. Sci. 73, 1094 ͑1984͒; R.H. Manzo, A.A. Ahumada, and E. Luna, J. Pharm. Sci. 73, 1869 ͑1984͔͒. Ethanol was analytical grade obtained from Merck. Cyclohexane ͑analytical grade͒ was obtained from Mallinckrodt. 3.1.2. Methylparaben Estimated Errors: Nothing specified. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy-, 43R.H. Manzo and A.A. methyl ester ͑methyl Ahumada, J. Pharm. Sci. 79, 3.1.3. Propylparaben 4-hydroxybenzoate, 1109 ͑1990͒. ͒ methylparaben ;C8H8O3; Components: Original Measurements: ͓ ͔ 99-76-3 ͑1͒ Benzoic acid, 4-hydroxy-, 43R.H. Manzo and A.A. ͑ ͒ ͑ ͒ 2 Ethyl alcohol ethanol ; propyl ester ͑propyl Ahumada, J. Pharm. Sci. 79, ͓ ͔ C2H6O; 64-17-5 p-hydroxybenzoate, 1109 ͑1990͒. ͑ ͒ 3 Cyclohexane; C6H12; propylparaben͒;C H O ; ͓ ͔ 10 12 3 110-82-7 ͓94-13-3͔ ͑ ͒ ͑ ͒ Variables: Prepared by: 2 Ethyl alcohol ethanol ; C H O; ͓64-17-5͔ Concentration of cyclohexane A. Goto and R. Goto 2 6 ͑3͒ Cyclohexane; C H ; t/ °C=15–50 6 12 ͓110-82-7͔

Solubility of methylparaben in ethanol–cyclohexane mixtures Variables: Prepared by: Concentration of cyclohexane A. Goto and R. Goto / Concentration t °C=15–50 Temperature of cyclohexane Solubility Solubility of propylparaben in ethanol–cyclohexane mixtures / ␸ 3 t °C 100 3 10 x3

15 100 0.0441 Concentration of Temperature cyclohexane Solubility 96 6.85 92 15.9 / ␸ 3 t °C 100 3 10 x1 83 32.4 25 100 0.0726 15 100 0.0944 96 8.33 96 17.0 92 19.4 92 38.1 85 42.9 83 68.3 40 100 0.247 25 100 0.224 96 13.3 96 23.8 92 30.8 92 46.8 85 62.6 85 91.3 50 100 0.425 40 100 0.682 96 18.0 96 43.4 92 41.2 92 92.9 85 75.0 85 155 50 100 1.59 96 64.8 92 171 85 249

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Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 43 for the The solubilities were determined using a continuous flow apparatus ͓G.S. methylparaben–ethanol–cyclohexane system in Sec. 3.1.2. Gurdial and N.R. Foster, Ind. Eng. Chem. Res. 30, 575 ͑1991͔͒.The Source and Purity of Materials: high-pressure liquid chromatography pump was replaced with a Propylparaben was obtained from Aldrich and purified by recrystallization, high-pressure syringe pump to facilitate preparation of the CO2-cosolvent m.p. 369.2 K ͓R.H. Manzo, A.A. Ahumada, and E. Luna, J. Pharm. Sci. mixtures. 73, 1094 ͑1984͒; R.H. Manzo, A.A. Ahumada, and E. Luna, J. Pharm. Sci. The binary mixtures of CO2 with methanol were prepared directly by 73, 1869 ͑1984͔͒. loading a high-pressure syringe pump with a known volume of the organic Ethanol was analytical grade obtained from Merck. solvent and then adding the liquid CO2 at about 50 bar. The total volume Ϯ 3 Cyclohexane ͑analytical grade͒ was obtained from Mallinckrodt. of the syringe pump was 260 5cm. The pump was calibrated with N2 Estimated Errors: gas at various pressures. To facilitate the flow of liquid CO2 from the cylinder to the syringe pump, a cooling jacket was installed around the Nothing specified. barrel of the syringe. Cooling water at approximately 274 K was recirculating through the jacket with a magnetic pump during the preparation stage. The temperature of the recirculating water was determined with a thermometer located at the exit of the cooling jacket. 3.2. Hydroxybenzoic acid–organic The pressure in the syringe pump was adjusted to yield the desired value compound–inorganic compound systems of CO2 density. After the solvent mixture was prepared, the contents were heated to approximately 313 K by recirculating warm water in the 3.2.1. Salicylic acid cooling/heating jacket for duration of 10 min. The contents were cooled to about 280 K for approximately 10 min. The heating and cooling sequence was repeated several times, after which the contents were allowed to Components: Original Measurements: further mix and equilibrate for 6 h at ambient temperature. ͑1͒ Benzoic acid, 2-hydroxy- 44G.S. Gurdial, S.J. A given mixture of CO –cosolvent was prepared, the equilibrium cells ͑o-hydroxybenzoic acid, salicylic Macnaughton, D.L. Tomasko, 2 were charged with the binary mixture and the system temperature was acid͒;CH O ; ͓69-72-7͔ and N.R. Foster, Ind. Eng. Chem. 7 6 3 raised to the desired value. Extraction of the solid was initially performed ͑2͒ Carbon dioxide ͑supercritical Res. 32, 1488 ͑1993͒. at the desired pressure until the entire content of the syringe pump was fluid͒;CO; ͓124-38-9͔ 2 used. Solubilities were determined at temperatures and pressures above the ͑3͒ Methyl alcohol ͑methanol͒; mixture critical point to ensure operation in the supercritical region. The CH O; ͓67-56-1͔ 4 minimum extraction temperature and pressure used were 318 K and Variables: Prepared by: 90 bar, respectively. The solubility measurements in these ternary systems ͓ T/K=318.2, 323.2, and 328.2 H. Miyamoto and A. Goto were determined using the same procedure G. S. Gurdial and N. R. ͑ ͔͒ Pressure: 91–201ϫ105 Pa Foster, Ind. Eng. Chem. Res. 30,575 1991 . The procedure involved flushing the regulating valve with an organic solvent and measuring the Solubility of salicylic acid in supercritical carbon dioxide–methanol amount of solute deposited in a Petri dish after drying its contents. The ͑3.5 mol %͒ mixture amount of solute collected in the 2 mm filter used as a collection device was determined gravimetrically. In order to remove traces of cosolvent, a b the in-line filter was placed in an oven at a temperature of 318 K for Temperature Pressure Density Solubility approximately 1 h. / 5 ␳/ −3 3 T K10Pa gdm 10 x1 The solubility was determined from the total mass of the solute collected and the total volume of gas measured with a wet test meter at ambient 318.2 96 432.3 1.25 conditions. Each reported data point represents an average of three trials. 101 514.1 1.62 Source and Purity of Materials: 111 611.5 2.49 Carbon dioxide was purchased from Liquid Air, and the purity was 121 663.4 2.97 99.8%. 131 697.9 3.28 Methanol was from GDH, and the purity was 99.8%. 141 724.0 3.51 Salicylic acid was from Ajax Chemicals, and the purity of the acid was 161 762.6 3.93 99.0%. 181 791.4 4.26 These materials were used without further purification. 201 814.5 4.48 Estimated Errors:

323.2 101 397.3 1.21 Solubility: Precision less than 5% CO2. 111 514.4 2.11 Pressure: Uncertainty within Ϯ2%. 121 592.5 2.68 Temperature: Nothing speciﬁed. 141 676.6 3.59 161 725.1 4.07 201 786.3 4.76 328.2 101 333.3 1.12 111 425.5 1.66 121 513.9 2.52 141 623.9 3.64 161 684.7 4.28 201 756.8 5.12 aIn the original paper, the pressure was given as “bar.” 1 bar=105 Pa. b3.5 mol % cosolvent concentration on a solute-free basis.

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Components: Original Measurements: Components: Original Measurements: ͑1͒ Benzoic acid, 2-hydroxy- 44G.S. Gurdial, S.J. ͑1͒ Benzoic acid, 2-hydroxy- 45Z. Liu, D. Li, G. Yang, and B. ͑o-hydroxybenzoic acid, salicylic Macnaughton, D.L. Tomasko, ͑o-hydroxybenzoic acid, salicylic Han, J. Supercrit. Fluids 18, 111 ͒ ͓ ͔ ͒ ͓ ͔ ͑ ͒ acid ;C7H6O3; 69-72-7 and N.R. Foster, Ind. Eng. Chem. acid ;C7H6O3; 69-72-7 2000 . ͑2͒ Carbon dioxide ͑supercritical Res. 32, 1488 ͑1993͒. ͑2͒ Carbon dioxide ͑supercritical ͒ ͓ ͔ ͒ ͓ ͔ ﬂuid ;CO2; 124-38-9 ﬂuid ;CO2; 124-38-9 ͑3͒ 2-Propanone ͑propan-2-one, ͑3͒ Acetic acid, ethyl ester ͑ethyl ͒ ͓ ͔ ͒ ͓ ͔ acetone ;C3H6O; 67-64-1 acetate ;C4H8O2; 141-78-6

Variables: Prepared by: Variables: Prepared by: / T K=318.2, 323.2, and 328.2 H. Miyamoto and A. Goto Concentration of CO2 H. Miyamoto and A. Goto Pressure: 86–201ϫ105 Pa T/K=308.15 and 318.15 p/MPa=2.22–8.02

Solubility of salicylic acid in supercritical carbon dioxide–acetone ͑3.5 mol %͒ mixture Solubility of salicylic acid in supercritical carbon dioxide–ethyl acetate mixtures Temperature Pressurea Density Solubilityb Concentration Molar volume of T/K105 Pa ␳/gdm−3 103x 1 Temperature Pressure of CO2 Solubility the liquid solution 318.2 86 302.4 0.68 / ͑ / ͒ T K MPa x2 x1 Vm ml mol 91 352.2 0.80 101 514.1 1.25 308.15 2.22 0.3502 0.091 8 79.9 111 611.5 1.48 3.01 0.4548 0.070 7 73.5 121 663.4 1.72 3.54 0.5231 0.049 6 70.3 141 724.0 1.85 4.02 0.5992 0.038 5 67.4 161 762.6 1.94 4.35 0.6381 0.032 3 65.8 201 814.5 2.10 4.63 0.6750 0.025 2 64.5 323.2 91 293.2 0.72 4.90 0.7265 0.019 8 63.6 96 340.2 0.83 5.40 0.7895 0.011 8 62.5 101 397.3 1.09 5.93 0.8581 0.006 27 59.0 111 514.4 1.46 6.32 0.8939 0.003 84 58.8 121 592.5 1.70 6.68 0.9140 0.001 19 61.2 141 676.6 2.02 318.15 2.51 0.3498 0.099 8 81.1 161 725.1 2.13 3.07 0.4177 0.086 1 77.6 201 786.3 2.33 3.41 0.4549 0.072 6 74.9 328.2 101 333.3 0.93 4.16 0.5366 0.058 3 69.4 111 425.5 1.22 4.79 0.6087 0.038 2 66.1 121 513.9 1.54 5.32 0.6646 0.029 6 68.1 141 623.9 2.10 5.56 0.6825 0.024 2 65.9 161 684.7 2.33 201 756.8 2.52 Auxiliary Information

a In the original paper, the pressure was given as “bar.” 1 bar=105 Pa. Methods/Apparatus/Procedure: b 3.5 mol % cosolvent concentration on a solute-free basis. The apparatus for determining the solubility of a solute in a liquid solvent expanded with high-pressure gas or supercritical fluid was used. It is Auxiliary Information mainly composed of a gas cylinder, a high-pressure syringe pump, a solenoid-operated circulating pump, a liquid sample bomb, a view cell, a Methods/Apparatus/Procedure pressure gauge, a constant-temperature bath, and valves and fitting of The experimental details are given in the compilation of Ref. 44 for the different kinds. All metallic parts in direct contact with the chemicals ͑ ͒ salicylic acid–carbon dioxide supercritical –methanol system earlier in were made of stainless steel ͑the experimental setup was shown in the this section. paper͒. The volume of the view cell in which the liquid solution was Source and Purity of Materials: allowed to contact with antisolvent carbon dioxide was about 200 ml. The Carbon dioxide was purchased from Liquid Air, and the purity was solenoid-operated pump was used to circulate the vapor phase in order to 99.8%. equilibrate the system quickly. The system pressure was monitored Acetone was from BDH, and the purity was 99.5%. through the pressure gauge, which was composed of a transducer and an Salicylic acid was from Ajax Chemicals and the purity of the acid was indicator. 99.0%. These materials were used without further purification. Estimated Errors: Solubility: Precision less than 5%. Ϯ ͑ ͒ CO2 pressure: Uncertainty within 2% relative . Temperature: Nothing specified.

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The ethyl acetate solution saturated with a solute at ambient temperature Variables: Prepared by: was sucked into the view cell by evacuating the system. After thermal T/K=318.2, 323.2, and 328.2 H. Miyamoto and A. Goto equilibrium was reached, carbon dioxide was charged into the system until Pressure: 91–201ϫ105 Pa the desired pressure was reached. The solenoid-operated pump was started to circulate the vapor phase through valve V4 and the bottom of the view cell. All experiments were conducted with V-L-S three phases. After the Solubility of 3-hydroxybenzoic acid in supercritical carbon dioxide– pressure and the vapor-liquid interface had been unchanged for 2 h, the methanol ͑3.5 mol %͒ mixture solid-liquid-vapor equilibrium was considered reached. The a b solenoid-operated pump was stopped and the system was maintained at Temperature Pressure Density Solubility static conditions to allow the solid to deposit until the solution became / 5 ␳/ −3 5 completely clear. Then valves V3 and V7 were opened. The liquid T K10Pa gdm 10 x1 solution in the view cell began to flow into the sample bomb to replace 318.2 91 352.2 1.59 the vapor in it, which resulted from hydraulic pressure. When the 101 514.1 2.63 vapor-liquid interface in the view cell was the same as that in the V3, V5, V6, V8, V7 loop, it remained unchanged with time. At this time, the 111 611.5 3.07 liquid sample bomb was full of liquid solution. Valves ͑V5–V8͒ were 121 663.4 3.26 closed and the sample bomb was removed for composition analysis. 141 724.0 3.49 The mass of the sample in the sample bomb was determined by a balance. 161 762.6 3.76 The sample bomb was connected to an analysis system. The experimental 201 814.5 3.99 setup consisted of a pressure gauge, liquid sample bomb, flush vessel, and 323.2 101 397.3 2.04 constant-temperature bath ͑the experimental setup was shown in the 111 514.4 2.81 ͒ paper . Then the apparatus was put into ice water. After evacuating the 121 592.5 3.22 system, the solution in the sample bomb was flushed into the vessel and 141 676.6 3.59 vapor-liquid equilibrium was reached at low pressure ͑Ͻ0.5 MPa͒. The 161 725.1 3.98 amount of carbon dioxide in the vapor phase was calculated from the 201 786.3 4.19 Huang equation of state on the basis of the pressure, temperature, volume of the system, and the saturated vapor pressure of ethyl acetate. The 328.2 101 333.3 1.78 amount of carbon dioxide in the liquid phase was relatively small and was 111 425.5 2.65 estimated from a solubility versus pressure curve in the pressure range 121 513.9 3.18 from 0 to 0.5 MPa at the analysis temperature, which was determined 141 623.9 3.86 experimentally in this study. The solute in the analysis system was washed into a beaker using ethyl acetate and dried and its mass was determined aIn the original paper, the pressure was given as “bar.” 1 bar=105 Pa. gravimetrically. The amount of the ethyl acetate in the sample was known b3.5 mol % cosolvent concentration on a solute-free basis. from the total mass of the sample, the mass of carbon dioxide, and the mass of the solute. Thus, the moles of the three components were Auxiliary Information calculated. From the volume of the sample bomb and the total moles of the three components, the molar volumes of the mixture were easily Methods/Apparatus/Procedure: obtained. The experimental details are given in the compilation of Ref. 44 for the Source and Purity of Materials: salicylic acid–carbon dioxide ͑supercritical͒–methanol system in Sec. Carbon dioxide with a purity of 99.95% was supplied by Haunxin Gas 3.2.1. Company. Source and Purity of Materials: Beijing Chemical Reagent Plant supplied ethyl acetate with a purity of Carbon dioxide was purchased from Liquid Air, and the purity was 99.9%. 99.8%. Salicylic acid with purity of 99.9% was purchased from Beijing Chemical Methanol was from BDH, and the purity was 99.8%. Reagent Plant, and was not purified further. 3-Hydroxybenzoic acid was from BDH and the purity of the acid was Estimated Errors: 99.0%. The accuracy of the pressure gauge was Ϯ0.025 MPa in the pressure These materials were used without further purification. range 0–20 MPa. Estimated Errors: The accuracy of the temperature was within Ϯ0.1 K. Solubility: Precision less than 5%. Ϯ The accuracy of the method for the amount of carbon dioxide was better CO2 pressure: Uncertainty within 2%. than Ϯ0.5%. Temperature: Nothing specified. The accuracy of the solute mass was Ϯ0.2%.

Components: Original Measurements: ͑1͒ Benzoic acid, 3-hydroxy- 44G.S. Gurdial, S.J. 3.2.2. 3-Hydroxybenzoic acid ͑m-hydroxybenzoic acid͒; Macnaughton, D.L. Tomasko, ͓ ͔ C7H6O3; 99-06-9 and N.R. Foster, Ind. Eng. Chem. ͑2͒ Carbon dioxide ͑supercritical Res. 32, 1488 ͑1993͒. Components: Original Measurements: ͒ ͓ ͔ ﬂuid ;CO2; 124-38-9 ͑1͒ Benzoic acid, 3-hydroxy- 44G.S. Gurdial, S.J. ͑3͒ 2-Propanone ͑propan-2-one, ͑ ͒ ͒ ͓ ͔ m-hydroxybenzoic acid ; Macnaughton, D.L. Tomasko, acetone ;C3H6O; 67-64-1 ͓ ͔ C7H6O3; 99-06-9 and N.R. Foster, Ind. Eng. Chem. ͑2͒ Carbon dioxide ͑supercritical Res. 32, 1488 ͑1993͒. Variables: Prepared by: ͒ ͓ ͔ / ﬂuid ;CO2; 124-38-9 T K=318.2, 323.2, and 328.2 H. Miyamoto and A. Goto ͑3͒ Methyl alcohol ͑methanol͒; Pressure: 86–201ϫ105 Pa ͓ ͔ CH4O; 67-56-1

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Solubility of 3-hydroxybenzoic acid in supercritical carbon dioxide– Solubility of 4-hydroxybenzoic acid in supercritical carbon dioxide–ethyl acetone ͑3.5 mol %͒ mixture acetate mixtures

Temperature Pressurea Density Solubilityb Concentration Molar volume of

Temperature Pressure of CO2 Solubility the liquid solution / 5 ␳/ −3 5 T K10Pa gdm 10 x1 / ͑ / ͒ T K MPa x2 x1 Vm ml mol 318.2 91 352.2 1.50 101 514.1 2.56 308.15 2.33 0.3871 0.024 9 78.7 111 611.5 3.26 2.57 0.4323 0.021 6 73.6 121 663.4 3.73 2.97 0.4724 0.018 0 73.9 141 724.0 4.28 3.05 0.5090 0.015 5 71.8 161 762.6 4.49 4.08 0.6394 0.010 6 64.7 181 791.4 4.58 4.59 0.6957 0.006 67 63.7 201 814.5 4.83 5.17 0.7862 0.002 92 59.0 323.2 96 340.2 1.67 5.80 0.8374 0.001 69 58.7 106 459.0 2.47 6.66 0.9063 0.000 30 57.0 111 514.4 2.85 6.78 0.9397 0.000 17 56.2 121 592.5 3.36 6.96 0.9528 0.000 070 56.0 141 676.6 4.37 318.15 2.58 0.3544 0.032 5 80.7 161 725.1 4.72 3.74 0.5055 0.018 2 72.5 201 786.3 5.16 5.05 0.6377 0.012 8 67.4 328.2 101 333.3 1.77 5.21 0.6753 0.009 46 59.1 111 425.5 2.40 5.94 0.7423 0.005 64 60.0 121 513.9 3.14 6.72 0.8251 0.003 51 63.4 131 578.4 3.95 7.58 0.9037 0.000 55 62.2 141 623.9 4.45 7.91 0.9175 0.000 21 62.0 8.00 0.9404 0.000 082 60.6 aIn the original paper, the pressure was given as “bar.” 1 bar=105 Pa. 8.18 0.9546 0.000 013 59.0 b3.5 mol % cosolvent concentration on a solute-free basis.

Auxiliary Information Auxiliary Information

Methods/Apparatus/Procedure: Methods/Apparatus/Procedure: The experimental details are given in the compilation of Ref. 44 for the The apparatus and procedure for determining the solubility of salicylic acid–carbon dioxide–methanol system in Sec. 3.2.1. 4-hydroxybenzoic acid in supercritical carbon dioxide with ethyl acetate Source and Purity of Materials: were identical with that used for the solubility determination of salicylic Carbon dioxide was purchased from Liquid Air, and the purity was acid in supercritical carbon dioxide with ethyl acetate; see the compilation 99.8%. of Ref. 45 in Sec. 3.2.1. Acetone was from BDH, and the purity was 99.5%. Source and Purity of Materials: 3-Hydroxybenzoic acid was from BDH and the purity of the acid was Carbon dioxide with a purity of 99.95% was supplied by Haunxin Gas 99.0%. Company. These materials were used without further purification. Beijing Chemical Reagent Plant supplied ethyl acetate with a purity of Estimated Errors: 99.9%. Solubility: Precision less than 5%. 4-Hydroxybenzoic acid with purity of 99.9% was purchased from Beijing Ϯ CO2 pressure: Uncertainty within 2%. Chemical Reagent Plant, and was not purified further. Temperature: Nothing specified. Estimated Errors: The accuracy of the pressure gauge was Ϯ0.025 MPa in the pressure range 0–20 MPa. The accuracy of the temperature was within Ϯ0.1 K. 3.2.3. 4-Hydroxybenzoic acid The accuracy of the method for the amount of carbon dioxide was better than Ϯ0.5%. The accuracy of the solute mass was Ϯ0.2%. Components: Original Measurements: ͑1͒ Benzoic acid, 4-hydroxy- 45Z. Liu, D. Li, G. Yang, and B. ͑p-hydroxybenzoic acid͒; Han, J. Supercrit. Fluids 18, 111 4. References ͓ ͔ ͑ ͒ C7H6O3; 99-96-7 2000 . ͑2͒ Carbon dioxide ͑supercritical 1 A. Goto, H. Miyamoto, M. Salomon, R. Goto, H. Fukuda, E. Königs- ͒ ͓ ͔ fluid ;CO2; 124-38-9 berger, and L.-C. Königsberger, J. Phys. Chem. Ref. Data 40, 013101 ͑3͒ Acetic acid, ethyl ester ͑ethyl ͑2011͒. ͒ ͓ ͔ 2 ͑ ͒ acetate ;C4H8O2; 141-78-6 A. Goto, F. Endo, and K. Ito, Chem. Pharm. Bull. Tokyo 25,1165 ͑1977͒. Variables: Prepared by: 3 A. Goto and F. Endo, J. Colloid Interface Sci. 66,26͑1978͒. 4 Concentration of CO H. Miyamoto and A. Goto A. Goto and F. Endo, J. Colloid Interface Sci. 68, 163 ͑1979͒. 2 5 T/K=308.15 and 318.15 A. Goto, R. Sakura, and F. Endo, Chem. Pharm. Bull. ͑Tokyo͒ 28,14 ͑ ͒ p/MPa=2.33–8.18 1980 . 6 A. Goto, M. Takemoto, and F. Endo, J. Phys. Chem. 84, 2268 ͑1980͒.

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