Article pubs.acs.org/jced
Liquid−Liquid Equilibria for Ternary Mixtures of Methylphenyl Carbonate, Dimethyl Carbonate, Diphenyl Carbonate, Anisole, Methanol, Phenol, and Water at Several Temperatures So-Jin Park,* In-Chan Hwang, and Shang-Hong Shin Department of Chemical Engineering, Chungnam National University, 99 Daehak-ro, Yuseong-gu, Daejeon, 305-764, Republic of Korea ABSTRACT: The ternary liquid−liquid equilibria (LLE) at atmospheric pressure of the following systems have been studied at several temperatures in stirred, thermo-regulated cells: water + anisole + methyl phenyl carbonate (MPC) at 308.15 K, water + methanol + MPC at 308.15 K, water + dimethyl carbonate (DMC) + MPC at 308.15 K, water + phenol + MPC at 318.15 K, and water + diphenyl carbonate (DPC) + MPC at 358.15 K. The experimental ternary LLE data have been satisfactorily correlated with the well-known two activity coefficient models: the Non-Random TwoLiquid (NRTL) and UNIversal QUAsiChemical (UNIQUAC). In addition, the distribution coefficients and the selectivity values of MPC for anisole, methanol, DMC, phenol, and DPC were derived from the tie-line data.
1. INTRODUCTION Polycarbonate (PC) is a form of plastic that provides one of the highest impact resistances in a wide range of temperature and with extreme dimensional stability. These unique physical properties of polycarbonate enables to used it for a variety of applications, from bulletproof windows to compact disks. Traditionally, PC is produced using phosgene as an intermediate; however, this process has some drawbacks because it used phosgene, a highly toxic environmental pollutant, and the formation of undesired salts cannot be avoided. Therefore, it has been focused on the newly developed nonphosgene synthetic process for aromatic and aliphatic polycarbonates that using diphenyl carbonate (DPC) which has several usages as excellent solvent in pharmaceuticals, cosmetics, and synthetic resins industry. However, phosgenation of phenol is also the most prevalent route for the production of DPC. Oxidative carbonylation of phenol is one way to avoid toxic phosgene, and transesterification of dimethyl carbonate (DMC) with phenol is another way to synthesize DPC without phosgene.1 DPC reacts further with bisphenol A to form polycarbonate. In this nonphosgene synthetic process of polycarbonate, methyl phenyl carbonate (MPC), anisole, and methanol are also produced. Therefore, the phase behavior and physical properties of the reaction products for mutual separation are very important to optimize this synthetic process. Nevertheless, very few investigations of the phase equilibria and mixture properties for © 2014 American Chemical Society
the reaction products in the DPC synthetic process have been reported. This work is a continuation of the phase equilibrium measurements of MPC-containing systems.2,3 In the present work, using stirred, thermo-regulated cells at atmospheric pressure, we analytically determined the ternary liquid−liquid equilibrium (LLE) of the following systems: water + anisole + MPC at 308.15 K, water + methanol + MPC at 308.15 K, water + DMC + MPC at 308.15 K, water + phenol + MPC at 318.15 K, and water + DPC + MPC at 358.15 K. The experimental ternary LLE data were correlated with two activity coefficient models as programmed by DDB (Dortmund Data Bank): the NonRandom Two-Liquid (NRTL) and UNIversal QUAsiChemical (UNIQUAC) models.4 Additionally, to confirm the selectivity of MPC for organics, the distribution coefficient and selectivity of MPC for anisole, methanol, DMC, phenol, and DPC were determined.
2. EXPERIMENTAL SECTION 2.1. Materials. Analytical grade chemicals were used in this work. Water, anisole, and methanol with stated mass fraction purities higher than 0.999 were provided by J.T Baker Chemical Co. DMC, DPC, and phenol were supplied by Aldrich Ltd., and Received: August 28, 2013 Accepted: January 8, 2014 Published: January 13, 2014 323
dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
Journal of Chemical & Engineering Data
Article
Table 1. Specification and the UNIQUAC Parameters of Chemicals at 0.1 MPaa ρ/g·cm3 at 298.15 K
UNIQUACb
chemical
GC analysis (wt %)
water content (wt %)
this work
lit. value
r-value
q-value
MPC anisole methanol DMC phenol DPC water
> 99.1 > 99.9 > 99.9 > 99.9 > 99.9 > 99.8 > 99.9
< 0.01 < 0.01 < 0.01 < 0.01 < 0.01 < 0.01
1.14324 0.98942 0.78659 1.06326 1.05851e 1.11314c 0.99704
0.98930b 0.78660b 1.06328b 1.05830f 1.07400d 0.99704g
5.3437 4.1667 1.4311 3.0613 3.5517 7.6260 0.9200
4.2250 3.2080 1.4320 2.8160 2.6800 5.6340 1.4000
The uncertainty u of the water content is u(g) = 5·10−6 g·g−1. The uncertainty u of the density is u(ρ) = 1·10−5 g·cm−3, and the stability of the temperature was ± 0.01 K. bReference 4. cAt 358.15 K. dReference 5 at 393.15 K. eAt 313.15 K. fReference 6. gReference 7. a
Table 2. Experimental LLE Data, Distribution Coefficient (D), and Selectivity (S) for the Water + Anisole + MPC, Water + Methanol + MPC, and Water + DMC + MPC Systems at 308.15 K and 0.1 MPaa aqueous phase system water (1) + anisole (2) + MPC (3) at 308.15 K
water (1) + methanol (2) + MPC (3) at 308.15 K
water (1) + DMC (2) + MPC (3) at 308.15 K
a
organic phase
xI1
xI2
xII1
xII2
0.9995 0.9997 0.9998 0.9998 0.9998 0.9998 0.9998 0.9998 0.9998 0.9998 0.9995 0.9562 0.8525 0.8011 0.7150 0.6300 0.5374 0.4516 0.3545 0.9995 0.9983 0.9946 0.9905 0.9858 0.9819 0.9783 0.9733
0.0000 0.0002 0.0002 0.0002 0.0002 0.0002 0.0002 0.0002 0.0002 0.0002 0.0000 0.0437 0.1461 0.1895 0.2765 0.3567 0.4332 0.4979 0.5606 0.0000 0.0017 0.0054 0.0095 0.0142 0.0181 0.0217 0.0267
0.1210 0.1107 0.0995 0.0835 0.0758 0.0691 0.0625 0.0603 0.0551 0.0537 0.1210 0.1167 0.1149 0.1118 0.1125 0.1141 0.1263 0.1359 0.1590 0.1210 0.1052 0.1020 0.1063 0.1087 0.1234 0.1291 0.1533
0.0000 0.0635 0.1953 0.3604 0.4888 0.5796 0.6986 0.7639 0.8798 0.9456 0.0000 0.0297 0.1006 0.1341 0.2015 0.2623 0.3400 0.4175 0.4974 0.0000 0.0835 0.2555 0.4206 0.5888 0.6787 0.7653 0.8467
D
S
0.0026 0.0008 0.0005 0.0003 0.0003 0.0002 0.0002 0.0002 0.0002
3518.61 12029.50 26465.68 39533.87 51425.34 68582.76 77667.05 79749.77 80405.08
1.4735 1.4530 1.4124 1.3724 1.3600 1.2743 1.1926 1.1270
5.56 5.11 5.07 4.63 4.06 3.34 2.79 1.98
0.0200 0.0212 0.0226 0.0241 0.0266 0.0283 0.0315
475.65 460.13 412.18 375.96 298.91 267.55 201.33
The uncertainty u is u(x) = 1·10−3; the uncertainty u is u(T) = 0.02 K.
5·10−6 g·g−1 by manufacturer. A chemical sample description along with the literature values are given in Table 1.4−7 2.2. Apparatus and Procedures. An automatically calibrated Anton Paar DMA 5000 digital vibrating glass tube densitometer (Graz, Austria) was used to measure the density. The uncertainty of this densitometer is stated by the manufacturer to be better than 5·10−6 g·cm−3, and the temperature of the densitometer is stabilized within ± 0.01 K. We estimated that the experimental uncertainty and reproducibility of density was better than 1·10−5 g·cm−3. The details of the experimental technique have been described in our previous papers.8,9 The binodal curves were provided at various temperatures and atmospheric pressure by determining the end points of the tie lines using the self-designed LLE determination system. This
their stated purity was better than 0.995 mass fraction. The chemicals were used as received without any further purification after chromatography failed to show any significant impurities. In the meanwhile, MPC was provided from Samsung-Cheil Industry, Korea as a reaction mixture of MPC, DMC, and phenol. MPC was then purified from this mixture in a glass packed column at 50 kPa. The column length was 1 m, and the theoretical stage was estimated more than 20. After purification, the purity of the MPC was checked to be better than 0.994 mass fraction by gas chromatography. Pellet type molecular sieves (0.4 nm) were used for dehydration of the chemicals except water. After drying, the water content of the chemicals was less than 6· 10−5 g·g−1, determined by Karl Fischer titration (Metrohm 684 KF-Coulometer). The uncertainty of this titration is stated to be 324
dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
Journal of Chemical & Engineering Data
Article
Table 3. Experimental LLE Data, Distribution Coefficient (D), and Selectivity (S) for the Water + Phenol + MPC System at 318.15 K and the Water + DPC + MPC System at 358.15 K and 0.1 MPaa aqueous phase xI1
xI2
xII1
xII2
water (1) + phenol (2) + MPC (3) at 318.15 K
0.9994 0.9990 0.9980 0.9973 0.9942 0.9920 0.9899 0.9724 0.9563 0.9990 0.9995 0.9994 0.9995 0.9994 0.9997 0.9995 0.9995 0.9995 0.9999
0.0000 0.0002 0.0015 0.0024 0.0054 0.0078 0.0099 0.0265 0.0437 0.0000 0.0001 0.0001 0.0001 0.0001 0.0001 0.0001 0.0001 0.0001 0.0001
0.1341 0.1450 0.1834 0.2393 0.3301 0.4468 0.4737 0.5762 0.6791 0.2341 0.2031 0.1695 0.1495 0.1349 0.1319 0.1311 0.1299 0.1392 0.1347
0.0000 0.0510 0.1443 0.2302 0.3193 0.3829 0.3859 0.3752 0.3209 0.0000 0.0836 0.1995 0.3189 0.4292 0.5421 0.6429 0.7188 0.7888 0.8653
water (1) + DPC (2) + MPC (3) at 358.15 K
a
organic phase
system
D
S
0.0047 0.0102 0.0103 0.0169 0.0203 0.0255 0.0706 0.1362
1469.95 535.24 404.14 178.45 109.19 81.86 23.90 10.34
0.0012 0.0005 0.0003 0.0002 0.0002 0.0002 0.0001 0.0001 0.0001
4114.14 11762.85 21320.44 31797.07 41086.99 49014.38 55307.21 56638.33 64232.63
The uncertainty u is u(x) = 1·10−3; the uncertainty u is u(T) = 0.02 K.
system consists of a 70 cm3 glass equilibrium cell with a water jacket to maintain isothermal conditions, magnetic stirrer, and precision temperature measuring system. The temperature inside the equilibrium cell was kept constant by circulating thermally controlled water from water bath (Lauda MD 20 thermostat with a DLK 15 cooler) and monitored precisely with IBM PC and temperature measuring system (AΣA F250). About 50 mL of sample mixture was introduced into the equilibrium cell, and the temperature of the liquid sample in the cell was stabilized by thermostat as an accuracy of ± 0.02 K. The liquid sample was stirred vigorously in the equilibrium cell for about 3 h by using Corning PC-320 magnetic stirrer and then left for more than 8 h to settle down into two immiscible layers at the system temperature to reach phase equilibrium. When the equilibrium was arrived between the two liquid phases, sampling was carefully performed from top and bottom layers without any cross contamination. The equilibrated sample concentration was analyzed with an Agilent 6890N gas−liquid chromatography coupled to a personal computer. HP-FFAP (nitroterephthalic acid modified polyethylene glycol TPA, 25 m (length) × 0.20 mm (ID) × 0.30 μm (film)) capillary column as a stationary phase and a thermal conductivity detector (TCD) were used in this analysis. Before gas chromatographic analysis of the sample, the response factors of constituent components were carefully determined using self-made standards. The carrier gas was high purity helium, and the temperatures of the injector and detector were maintained at 503.15 K and 523.15 K, respectively. The column temperature was programmed initially set to 333.15 K for 4 min and then was increased at a rate of 50 °C·min−1. The final temperature was 503.15 K, which was maintained for 8 min. Each sample was analyzed five times and took a mean value as equilibrium concentration. In this analytical procedure, we estimated the uncertainty of the analyzed LLE mole fractions to be less than 1·10−3. The further details of experimental procedures have been described in our previous article.10
3. RESULTS AND DISCUSSION The experimental LLE data for the ternary systems water + anisole + MPC, water + methanol + MPC, and water + DMC + MPC at 308.15 K, and water + phenol + MPC at 318.15 K, and water + DPC + MPC at 358.15 K are listed in Tables 2 and 3. The organic chemicals showed very low solubility in the aqueous phase for all the considered systems except the system water + methanol + MPC, while the solubility of water in organic phase (MPC rich phase) was higher than 10 % in almost all of the concentration ranges. The NRTL and UNIQUAC models were employed to correlate the experimental LLE data for the ternary systems investigated, and these two models describe the equilibrium compositions with similar deviations. The nonrandomness parameter of the NRTL equation was set at a value of αij = 0.2. The molecular structure parameters of the pure component for UNIQUAC model were obtained from DDB and are given in Table 1. The interaction parameters of the NRTL and UNIQUAC equations were regressed by minimizing the following concentration-based objective function (OF) OF = min ∑ ∑ ∑ (xikα(exp) − xikα(cal))2 i
α
k
(1)
where xα(exp) and xα(cal) , respectively, are the experimental and ik ik calculated mole fractions of the component i in the phase α for kth tie-line. The comparison between the experimental and the calculated phase equilibrium concentration of each system was carried out through the root-mean-square deviation (RMSD %), given by RMSD % = 100
∑i ∑α ∑k (xikα(exp) − x jkα(cal))2 6N
(2)
where N is the number of tie lines. The binary interaction parameters for both models are given in Tables 4 and 5, together with the RMSD%. As shown in the tables, a very good correlation of the LLE experimental data with 325
dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
Journal of Chemical & Engineering Data
Article
Table 4. Optimized NRTL Interaction Parameters for the Water + Anisole + MPC, Water + Methanol + MPC, Water + DMC + MPC, Water + Phenol + MPC, and Water + DPC + MPC Systems at Several Temperatures NRTL parameters (K) system
i−j
(gij − gii)/R
(gji − gjj)/R
αij
RMSD (%)
water (1) + anisole (2) + MPC (3) at 308.15 K
1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3
1325.40 −321.87 1519.70 −355.77 619.83 2012.90 965.67 −817.40 1337.90 1634.90 −1444.60 1397.40 1474.30 −1058.80 1529.50
422.96 −693.99 189.36 351.48 −303.81 210.13 200.46 −644.86 212.00 −491.52 −408.13 174.15 205.07 −1091.80 16.94
0.20
0.28
water (1) + methanol (2) + MPC (3) at 308.15 K water (1) + DMC (2) + MPC (3) at 308.15 K water (1) + phenol (2) + MPC (3) at 318.15 K water (1) + DPC (2) + MPC (3) at 358.15 K
0.61
0.38
0.51
0.59
Figure 1. Binodal curves and tie lines for the ternary system water (1) + anisole (2) + MPC (3) at 308.15 K; ▼, experimental data; □, calculated data from the UNIQUAC model; ▼−▼, experimental tie line; □··□, tie line by the UNIQUAC model.
Table 5. Optimized UNIQUAC Interaction Parameters for the Water + Anisole + MPC, Water + Methanol + MPC, Water + DMC + MPC, Water + Phenol + MPC, and Water + DPC + MPC Systems at Several Temperatures UNIQUAC parameters (K) system water (1) + anisole (2) + MPC (3) at 308.15 K water (1) + methanol (2) + MPC (3) at 308.15 K water (1) + DMC (2) + MPC (3) at 308.15 K water (1) + phenol (2) + MPC (3) at 318.15 K water (1) + DPC (2) + MPC (3) at 358.15 K
i−j
(uij − uii)/R
(uji − ujj)/R
1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3 1−2 2−3 1−3
222.42 −62.15 169.78 −681.38 47.05 37.62 92.45 −198.33 17.37 236.55 −4.62 125.18 116.09 −43.33 151.17
388.09 −176.38 321.24 185.79 −263.34 467.93 376.16 16.95 471.76 −140.65 31.70 366.35 395.77 −261.34 241.38
RMSD (%) 0.20
0.68
0.54
0.75
0.20
Figure 2. Binodal curves and tie lines for the ternary system water (1) + methanol (2) + MPC (3) at 308.15 K; ▼, experimental data; □, calculated data from the NRTL model; ▼−▼, experimental tie line; □··□, tie line by the NRTL model.
the NRTL and UNIQUAC equations was obtained. The difference between the experimental data and the calculated data using the interaction parameters determined from experimental data was within the highest mean deviation of 0.75 % for all of the systems. The correlated model parameters are used also to draw LLE tie-lines. Figures 1 to 5 show the graphical comparisons between the experimental and the calculated ternary LLE concentrations and tie-lines. On the basis of the investigated ternary LLE phase diagram, there is no solutropic system. As shown in Figures 1, 3, 4, and 5, the ternary systems: water + anisole + MPC at 308.15 K, water + DMC + MPC at 308.15 K, water + phenol + MPC at 318.15 K, and water + DPC + MPC at 358.15 K had two immiscible binary systems. It is classified therefore as Treybal’s type II systems. In the meanwhile, the water + methanol + MPC system at 308.15 K in Figure 2 was Treybal’s type I system, since
it had only one miscible binary.11 The investigated tie lines in the figures showed that anisole, DMC, phenol, and DPC were much more soluble in MPC than in water. The distribution coefficient (D) and selectivity (S) are important parameters in assessing the feasibility of the solvent extraction. The D values of component 2: anisole, methanol, DMC, phenol, and DPC at equilibrium were determined with: D= 326
x 2I x 2II
(3) dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
Journal of Chemical & Engineering Data
Article
Figure 3. Binodal curves and tie lines for the ternary system water (1) + DMC (2) + MPC (3) at 308.15 K; ▼, experimental data; □, calculated data from the NRTL model; ▼−▼, experimental tie line; □·□, tie line by the NRTL model.
Figure 5. Binodal curves and tie lines for the ternary system water (1) + DPC (2) + MPC (3) at 358.15 K; ▼, experimental data; □, calculated data from the UNIQUAC model; ▼−▼, experimental tie line; □··□, tie line by the UNIQUAC model.
(water) in the aqueous phase and xII1 is the mole fraction of component 2 (anisole, methanol, DMC, phenol, or DPC) in the organic phase. The calculated D and S values for each system have been compiled in Tables 2 and 3. The D value of anisole, methanol, and DPC was decreased with increasing the compositions of component 2 and vice versa for DMC and phenol. The largest D value was found in the system water + methanol + MPC at 308.15 K. The S values were very large for the almost all of the systems considered except the water + methanol + MPC system.
4. CONCLUSIONS Liquid−liquid equilibrium (LLE) data were presented for the ternary systems: water + anisole +MPC, water + methanol + MPC, and water + DMC + MPC at 308.15 K, and water + phenol + MPC system at 318.15 K, and water + DPC + MPC system at 358.15 K at atmospheric pressure. Data were analytically obtained using thermostatted doubly jacketed glass cell at atmospheric pressure. The water + anisole + MPC, water + methanol + MPC, water + DMC + MPC, water + phenol + MPC, and water + DPC + MPC systems exhibited Type II phase behavior of LLE, whereas the water + methanol + MPC system showed Type I behavior. The NRTL and UNIQUAC models were used to correlate the experimental data. The calculated data using optimized binary interaction parameters of both models showed a very good correspondence with the experimental data. The average RMSD value between experimental and calculated equilibrium compositions were less than approximately 0.7 mol %. The largest D value was found in the system water + methanol + MPC at 308.15 K. In general, the S values were very large for the systems considered except the water + methanol + MPC system.
Figure 4. Binodal curves and tie lines for the ternary system water (1) + phenol (2) + MPC (3) at 318.15 K; ▼, experimental data; □, calculated data from the NRTL model; ▼−▼, experimental tie line; □··□, tie line by the NRTL model.
where the superscript I and II represent the aqueous and organic phases, respectively. If MPC is used to solvate organics, the extraction effectiveness of the organic chemicals (component 2) by MPC is given by the selectivity (S), as a measure of the ability of solvent to separate anisole, methanol, DMC, phenol, and DPC from water by the following equation. S=
■
x1Ix 2II x1IIx 2I
(4)
AUTHOR INFORMATION
Corresponding Author
*Tel.: +82-42-821-5684. Fax: +82-42-823-6414. E-mail: sjpark@ cnu.ac.kr (S.-J.P.).
where the subscript 1 is water and 2 means component 2. Therefore, xI1 represents the mole fraction of component 1 327
dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
Journal of Chemical & Engineering Data
Article
Funding
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (Grant No. 2012R1A1A2008315). Notes
The authors declare no competing financial interest.
■
REFERENCES
(1) Haubrock, J. The process of dimethyl carbonate to diphenyl carbonate: thermodynamics, reaction kinetics and conceptual process design. Ph.D. Thesis; University of Twente: The Netherlands, 2007. (2) Hwang, I. C.; Shin, S. H.; Jeong, I. Y.; Jeon, Y. H.; Park, S. J. Isobaric vapor-liquid equilibrium at 101.3 kPa and excess properties at 298.15 K for binary mixtures of methyl phenyl carbonate with methanol or dimethyl carbonate. Fluid Phase Equilib. 2013, 360, 260−264. (3) Hwang, I. C.; Park, S. J.; Han, K. J.; In, S. J. Liquid-liquid equilibria for the ternary systems of dimethylcarbonate + C1 - C4 alcohols + water at 298.15 K and atmospheric pressure. J. Ind. Eng. Chem. 2012, 18, 499− 503. (4) Dortmund Data Bank Software Package (DDBSP), version 2006 professional; Software and Separation Technology GmbH; http:// www.ddbst.de (accessed Feb 13, 2012). (5) Hendrik, M.; Oliver, H.; Florian, M. P. Structure and dynamics of liquid diphenyl carbonate investigated by molecular dynamics simulations. J. Phys. Chem. B 1999, 103, 10591−10598. (6) Klauck, M.; Grenner, A.; Taubert, K.; Martin, A.; Meinhardt, R.; Schmelzer, J. Vapor-Liquid Equilibria in Binary Systems of Phenol or Cresols + Water, + Toluene, and + Octane and Liquid-Liquid Equilibria in Binary Systems of Cresols + Water. Ind. Eng. Chem. Res. 2008, 47, 5119−5126. (7) Arce, A.; Marchiaro, A.; Rodríguez, O.; Soto, A. Densities, Refractive Indices, and Excess Molar Volumes of Water + Methanol + 2Methoxy-2-methylpropanea t 298.15 K. J. Chem. Eng. Data 1995, 40, 647−649. (8) Oh, J. H.; Park, S. J. Isothermal Vapor-Liquid Equilibria at 333.15 K and Excess Molar Volumes at 298.15 K of Ethyl tert-Butyl Ether (ETBE) + Alcoh-1-ol (C1-C4) Mixtures. J. Chem. Eng. Data 1998, 43, 1009− 1013. (9) Park, S. J.; Kim, H. H.; Han, K. J.; Won, D. B.; Lee, S. B.; Choi, M. J. Isothermal Vapor-Liquid Equilibria and Excess Molar Volumes for 2Methyl Pyrazine (2MP) Containing Binary Mixtures. Fluid Phase Equilib. 2001, 180, 361−373. (10) Hwang, I. C.; Park, S. J. Liquid−liquid equilibria of ternary mixtures of dimethyl carbonate, diphenyl carbonate, phenol and water at 358.15 K. Fluid Phase Equilib. 2011, 301, 18−21. (11) Novak, J. P.; Matous, J.; Pick, J. Liquid−Liquid Equilibria; Elsevier: New York, 1987.
328
dx.doi.org/10.1021/je400776b | J. Chem. Eng. Data 2014, 59, 323−328
