IUPAC-NIST Solubility Data Series. 90. Hydroxybenzoic Acid Derivatives in Binary and Ternary Systems
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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 hy- droxybenzoic 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, propylpa- raben, 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 a͒ Hydroxybenzoic Acid Salts in Binary Electronic mail: [email protected] © 2011 American Institute of Physics. Nonaqueous Systems...................... 6 0047-2689/2011/40„2…/023102/116/$47.00023102-1 J. Phys. Chem. Ref. Data, Vol. 40, No. 2, 2011 Downloaded 18 May 2011 to 132.163.193.247. Redistribution subject to AIP license or copyright; see http://jpcrd.aip.org/about/rights_and_permissions 023102-2 GOTO ET AL. 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 J. Phys. Chem. Ref. Data, Vol. 40, No. 2, 2011 Downloaded 18 May 2011 to 132.163.193.247. Redistribution subject to AIP license or copyright; see http://jpcrd.aip.org/about/rights_and_permissions IUPAC-NIST SOLUBILITY DATA SERIES. 90 023102-3 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................