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Liquid-Liquid Equilibrium Data in Aqueous Solutions of Propionic and Butyric Acids with 1-Heptanol at T=(298.15, 308.15, and 318.15) K

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Liquid-Liquid Equilibrium Data in Aqueous Solutions of Propionic and Butyric Acids with 1-Heptanol at T=(298.15, 308.15, and 318.15) K Korean J. Chem. Eng., 33(4), 1408-1415 (2016) pISSN: 0256-1115 DOI: 10.1007/s11814-015-0278-5 eISSN: 1975-7220 INVITED REVIEW PAPER Liquid-liquid equilibrium data in aqueous solutions of propionic and butyric acids with 1-heptanol at T=(298.15, 308.15, and 318.15) K Ali Ghanadzadeh Gilani*,†, Hossein Ghanadzadeh Gilani**, Seyedeh Laleh Seyed Saadat*, Elham Nasiri-Touli*, and Mahrokh Peer*** *Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran **Department of Chemical Engineering, University of Guilan, Rasht, Iran ***Department of Chemistry, University Campus 2, University of Guilan, Rasht, Iran (Received 24 August 2015 • accepted 11 December 2015) Abstract−Liquid-liquid phase equilibrium (LLE) data were determined for the (water+propionic or butyric acid+1- heptanol) ternary systems at T=(298.15, 308.15, and 318.15) K and p=101.3 kPa. For both systems, a type-1 LLE phase diagram was obtained. The quality of the experimental LLE data was determined through the Othmer-Tobias and Ban- croft equations. The experimental tie-lines were fitted using the UNIQUAC and NRTL correlation models. For the studied systems, a comparison was made between the experimental and correlated distribution coefficients and separa- tion factors. The LSER model of Katritzky was applied to obtain the contributions of intermolecular interactions in these systems. Keywords: Liquid-liquid Equilibrium, Carboxylic Acid, UNIQUAC Model, NRTL Model, LSER Model INTRODUCTION bution coefficients (D) and separation factors (S) were determined from the tie-line data. The quality of the experimental data was tested Carboxylic acids are scientifically and industrially important by the Othmer-Tobias [27] and Bancroft [28] equations. The experi- group of organic compounds produced by chemical synthetic or mental tie lines were fitted by using the NRTL [29] and the UNI- fermentation methods [1-4]. Due to their wide industrial applica- QUAC models [30]. The values for the interaction parameters were tions, extraction of carboxylic acids from aqueous solutions is an obtained and the calculated compositions compared with the exper- important problem [5-7]. Thus, accurate equilibrium data for the imental ones. In this work, the Katritzky LSER model [31] was ap- ternary systems consisting of water, carboxylic acid, and various plied to correlate distribution coefficients and separation factors. solvents are always necessary for the understanding and interpre- tation of phase behavior. EXPERIMENTAL In this study, two carboxylic acids, propionic acid (PA) and butyric acid (BA), were used. They have just one carbon difference in their The supplier, purity, and their selected properties of materials carbon chain length. These organic acids are produced mainly by used in this study are given in Table 1. Purchased materials were biochemical methods and their efficient separation from water is used as received. Deionized and redistilled water with an electrical − an important issue [8-10]. Up to now, various investigations have conductivity less than 5 μS·cm 1 at T=298.15 K was used. been carried out on the extraction and liquid-liquid equilibrium Refractive indices and densities of the pure liquids were measured (LLE) measurements of PA and BA from water, and several research- at 298.15 K with a CETI Abbe Refractometer (accuracy; ±0.0002) ers have examined the extractability of these acids by various organic and a Kyoto electronic DA210 density meter (accuracy; ±0.05 kg· − solvents with different chemical properties [11-17]. Heavy alcohols m 3), respectively. The sample weighing involved an HR 200 AND [18-21], hydrocarbons [22,23], and esters [24-26] were mainly used electronic analytical balance (accuracy; ±0.0001 g). Karl-Fisher as extractants in the LLE measurements. However, further studies titration was carried out using a Metrohm 870 KF Titrino plus Karl- in this area are still important and required for various industrial Fisher titrator. The temperature of the liquids was measured with a goals. In this study, ternary LLE data of (water-propionic acid-1- Lutron TM-917 precision digital thermometer (accuracy; ±0.01 K). heptanol) and (water-butyric acid-1-heptanol) systems were ob- The detailed experimental procedure and measurements are tained at T=(298.15, 308.15, 318.2) K, where no such data are avail- described in our previous publication [21]. The procedure used to able in the literature. obtain the LLE data essentially consisted of solubility and tie line At each temperature, the phase compositions and tie-line data data. The solubility curves were determined by the cloud point were measured and ternary phase diagrams were plotted. Distri- titration method. To obtain the solubility data of the aqueous-rich and organic-rich sides of the curves, the feed homogeneous mix- †To whom correspondence should be addressed. tures of either (water-acid) or (solvent-acid) were titrated against E-mail: [email protected] solvent or water. The consistency of the cloud point method depends Copyright by The Korean Institute of Chemical Engineers. on the accuracy of the micropipette (±0.005 ml) and restriction of 1408 Liquid-liquid equilibrium data in aqueous solutions of propionic and butyric acids with 1-heptanol at T=(298.15, 308.15, and 318.15) K 1409 Table 1. Source, purity, refractive index (nD), density (ρ), and the UNIQUAC structural parameters (r and q) of the pure components at T= 298.15 K (the literature data are included [19,36-38])a ρ −3 nD /(kg·m ) Component Source Purity r q Exp. Lit. Exp. Lit. Propionic acid Chemlab >0.99 2.88 2.61 1.3807 1.3809 [37] 987.92 988.20 [37] Butyric acid Merck >0.99 3.55 3.15 1.3977 1.3975 [19] 952.68 952.80 [19] 1-Heptanol Merck ≥0.99 5.47 4.67 1.4240 1.4249 [38] 821.41 822.46 [38] Water -- Deionized & bidistilled 0.92 1.40 1.3324 1.3325 [39] 997.01 997.05 [39] a ρ −3 Standard uncertainties u are u(nD)=0.0002, u( )=0.05 kgm , u(T)=0.01 K, and u(p)=0.4 kPa the visual examination. The standard uncertainty [32] in the mass fraction of the solubility data was estimated to be better than ±0.0009. Tie-line measurements for the ternary systems were made at T=(298.15, 308.15, and 318.15) K. The prepared ternary mixtures by mass were placed in the extraction cell (250 ml glass cell) and were vigorously agitated by a magnetic stirrer for 4 h, and then left to settle for 4 h for phase separation. Preliminary tests showed that these times are adequate to achieve phase equilibrium. The tie lines were analyzed by acidimetric titration, the Karl- Fisher technique, and refractive index measurements. The mass fractions of the acid in the both phases (w21 and w23) were mea- sured by acidimetric titration using phenolphthalein as an indica- tor. The water content of the organic and aqueous phases (w11 and w13) was measured by the Karl-Fisher and refractive index mea- surement methods, respectively. Thus, knowing the two mass frac- tions in each phase, the mass of the third component (w31 or w33) Σ was evaluated using the equation of {w1+w2+w3= wi=1}. The stan- dard curves at three different temperatures are shown in Fig. 1(a)- (b). The best-fit straight lines (trend lines) for refractive index (nD) vs. w11 at various temperatures are presented in Supplementary data Table S1. The estimated standard uncertainty [32] of the measured compositions is better than ±0.002. RESULTS AND DISCUSSION 1. Solubility and Tie Line Data Experimental solubility curve data determined for the (water- PA-1-heptanol) and (water-BA-1-heptanol) ternary systems at T= (298.15, 308.15, and 318.15) K and p=101.3 kPa. Supplementary data Table S2 contains the measured solubility data for the studied systems at each temperature. For verification of the applied method, the mutual binary solubilities between water-1-heptanol obtained in this work were compared with the literature data [33], which indicates that the method used in this work is appropriate. To show the small effect of temperature on the solubility curves and bipha- sic region, the corresponding diagrams at three different tempera- tures were plotted and compared in Supplementary data Fig. S1. As a result, the immiscibility region for the system containing BA is larger than that of the other. Fig. 1. Refractive index standard curves for (a) [water+propionic The experimental tie lines for the systems studied here were acid+1-heptanol], (b) [water+butyric acid+1-heptanol] in aque- determined at the same range of temperatures. Typical phase dia- ○ T ous phase (w11) at various temperatures; ( ) =298.15 K, grams for the ternary systems at T=298.15 K are plotted and shown (□) T=308.15 K, (△) T=318.15 K. in Fig. 2(a)-(b). The tie line data for the studied ternary systems at Korean J. Chem. Eng.(Vol. 33, No. 4) 1410 A. Ghanadzadeh Gilani et al. Table 2. Experimental tie-line data in mass fraction for [water (1)+ carboxylic acid (2)+1-heptanol (3)] at T=(298.15, 308.15, and 318.15) K and p=101.3 kPaa Aqueous phase mass fraction Organic phase mass fraction w1 (water) w2 (PA) w1 (water) w2 (PA) Water (1)+propionic acid (2)+1-heptanol (3) T=298.15 K 0.931 0.066 0.090 0.171 0.911 0.086 0.095 0.209 0.895 0.101 0.105 0.255 0.870 0.126 0.121 0.299 0.828 0.167 0.148 0.349 0.784 0.209 0.210 0.401 T=308.15 K 0.928 0.068 0.092 0.175 0.908 0.087 0.100 0.213 0.888 0.107 0.108 0.243 0.873 0.122 0.115 0.280 0.837 0.156 0.137 0.314 0.792 0.201 0.192 0.370 T=318.15 K 0.920 0.075 0.097 0.169 0.907 0.088 0.105 0.199 0.881 0.112 0.111 0.239 0.857 0.136 0.123 0.278 0.849 0.145 0.139 0.303 0.797 0.195 0.194 0.361 Water (1)+butyric acid (2)+1-heptanol (3) T=298.15 K 0.974 0.022 0.077 0.190 0.958 0.039 0.096 0.291 0.945 0.052 0.109 0.381 Fig.
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