Article pubs.acs.org/jced
Isothermal Vapor−Liquid Equilibrium Data for the Methanol + Benzene + Tetraphenylphosphonium Chloride System Alexander V. Kurzin,*,† Andrey N. Evdokimov,† Victorija B. Antipina,† and Mariana A. Feofanova‡ †
Organic Chemistry Department, Institute of Technology, High School of Technology and Energetics, Saint-Petersburg State University of Industrial Technologies and Design (former Saint-Petersburg State Technological University of Plant Polymers); 4, Ivana Chernykh Street, Saint-Petersburg 198095, Russian Federation ‡ Inorganic and Analytical Chemistry Department, Faculty of Chemical Technology, Tver State University; 35, Sadovy Lane, Tver 170002, Russian Federation ABSTRACT: Isothermal vapor−liquid equilibrium data for the system methanol + benzene + tetraphenylphosphonium chloride at four salt molalities {(0.100, 0.200, 0.300, and 0.500) mol·kg−1} have been measured with the help of headspace gas chromatography at {(308.15 and 328.15) K}. Tetraphenylphosphonium chloride can be used as an entrainer for the separation of methanol + benzene mixture. The experimental data were correlated using the electrolyte NRTL model.
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INTRODUCTION The synthesis and design of industrial processes such as extractive distillation, extractive crystallization of salts, gas scrubbing, wastewater treatment, and others require an accurate description of the phase equilibrium behavior of electrolyte systems. Organic electrolytes (salts, hydroxides, alkoxides) are important and are usually used as intermediate chemicals, reaction catalysts, inhibitors to undesired reactions, supporting electrolytes, and surfactants. These salts are also used for separation processes to modify and improve distillation, evaporation, and pervaporation process performance as well as inorganic salts, alkali, and ionic liquids. The electrolyte systems containing salts with large organic ions (alkyl(aryl)borate, phosphate, sulfate, sulfonate, carboxylate anions; ternary sulfonium, quaternary phosphonium, ammonium, pyridinium, pyrrolidynium, imidazolium, imidazolinium, and other Nheterocyclic cations), betaines, cholines, lecithins, and ionic liquids continue to represent an important area of theoretical interest as well. The behavior of these systems has prompted investigations of the conductance, density, viscosity, vibrational spectroscopy, osmotic coefficient, and thermal diffusion of aqueous and mixed solvent solutions of these electrolytes in an effort to probe the influence of molecular structure on the properties of their solutions. Some years ago, there were a number of experimental studies of solutions consisting of phosphonium ionic liquids.1−8 The methanol−benzene mixture is widely encountered in the pharmaceutical industry. However, the existence of an azeotropic point of this binary mixture at atmospheric pressure makes it difficult to obtain high purity methanol from the mixtures by conventional distillation or rectification. The aims of this work are (1) to determine the effect of tetraphenylphosphonium chloride on the vapor−liquid equili© XXXX American Chemical Society
brium (VLE) of the methanol + benzene system at {(308.15 and 328.15) K} and different salt concentrations {(0.100, 0.200, 0.300, and 0.500) mol·kg−1} with the help of headspace gas chromatography, and (2) to achieve breaking an existing azeotrope in this system. No VLE data for the ternary system methanol + benzene + tetraphenylphosphonium chloride were found in the literature. This salt was not studied earlier in the azeotrope systems. There are many isothermal and isobaric VLE data for the binary methanol + benzene azeotropic system in the literature.9−12 The effects of some salts on the enthalpy of mixing of the methanol + benzene system were studied.13,14 Information about isothermal and isobaric VLE data for the ternary salt + methanol + benzene systems has also been published. The VLE of several inorganic and organic salts, LiCl, LiBr, LiI, NaCl, NaBr, NaI, KCl, CaCl 2 , ZnCl 2 , (CH3COO)2Mg, (CH3COO)2Cd, NaB(C6H5)4, and ionic liquids were studied in this ternary system.15−27 It was found that only 1-octyl-3-methylimidazolium tetrafluoroborate ionic liquid and LiI can be used as an entrainer for the separation of methanol and benzene.17,24−26 This work is a continuation of our investigation on phosphonium salts which are not room temperature ionic liquids to measurement and correlate VLE data in the ternary systems with mixed solvents.28 As we studied earlier, the triphenylbenzylphosphonium chloride can be used as an entrainer for the separation of methanol + toluene azeotrope mixture.28 Received: September 9, 2015 Accepted: February 4, 2016
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DOI: 10.1021/acs.jced.5b00770 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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The gas chromatograph was calibrated using the mixtures of methanol and benzene that were prepared gravimetrically by using an analytical balance with an uncertainty of ±0.1 mg. Because of negligible amounts in the vapor phase (small vapor volume, moderate pressure), it was reasonable to assume that the liquid phase composition is the same as the feed composition. To prepare the calibration samples for the vapor phase, various methanol and benzene mixtures were completely evaporated in a (1000 ± 0.1) cm3 vessel and injected. To obtain the calibration equation the required mass fractions and area fractions were correlated with a third-order polynomial by a least-squares method (mean deviation = 0.1%).
Several correlative and predictive models based on the local composition or group contribution concept have been proposed to calculate the VLE of systems formed by mixed solvents and electrolytes. The experimental data presented in this work were correlated using the electrolyte nonrandom twoliquid (NRTL) model of Mock et al.29 We earlier used this model for correlation of VLE data for the triphenylbenzylphosphonium chloride + methanol + toluene system.28
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EXPERIMENTAL SECTION Materials. Methanol (w ≥ 99.7%, Sigma-Aldrich) and benzene (w ≥ 99.6%, Sigma-Aldrich) were stored above the molecular sieves (3 Å) (Table 1). The purity of solvents was
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RESULTS AND DISCUSSION The vapor−liquid equilibria for the binary system of methanol + benzene were measured at {(308.15 and 328.15) K}. Our experimental data were in good agreement with those reported in the literature.9 The experimental results for the binary system
Table 1. Chemical Sample Table chemical name
a
source
initial mole fraction purity
methanol
SigmaAldrich
0.997
benzene
SigmaAldrich
0.996
TPPCb
SigmaAldrich
0.990
Gas−liquid chromatography. chloride.
purification method store above the molecular sieves store above the molecular sieves vacuum drying b
final mole fraction purity
analysis method
0.998
GCa
0.998
GCa
0.995
Volhard method (Cl−), melting point
Table 2. Experimental Vapor-Liquid Equilibrium Data for the System Methanol (1) + Benzene (2) + Tetraphenylphosphonium Chloride (3) without Vapor Pressure Measurement, Vapor Mole Fraction of Methanol (y1) as a Function of Liquid Mole Fraction of Methanol on a Salt-Free Basis (x1′) and Salt Molality m3 at Temperature T/ K = 308.15a
TPPC = tetraphenylphosphonium
x1′
y1
m3/(mol·kg−1) = 0.000 0.040 0.352 0.081 0.422 0.170 0.498 0.210 0.509 0.260 0.523 0.360 0.539 0.410 0.544 0.450 0.551 0.560 0.561 0.602 0.572 0.681 0.596 0.731 0.617 0.840 0.678 0.881 0.718 0.950 0.821 m3/(mol·kg−1) = 0.300 0.040 0.364 0.081 0.446 0.170 0.545 0.210 0.566 0.260 0.590 0.360 0.630 0.410 0.646 0.450 0.661 0.560 0.696 0.602 0.712 0.681 0.747 0.731 0.770 0.840 0.827 0.881 0.854 0.950 0.914
checked by gas chromatography. Tetraphenylphosphonium chloride [(C6H5)4P+]Cl− was obtained from Sigma-Aldrich (w ≥ 99.0%) and previously dried in a vacuum oven until a constant mass was reached (mp = 276−277 °C by Melting Point Meter M5000 (A.KRÜ SS Optronic GmbH), u(mp) = 0.4 °C) (Table 1). Procedure. Mixtures consisting of methanol, benzene, and tetraphenylphosphonium chloride were prepared gravimetrically with an analytical balance (Ohaus Explorer Pro Balance) with an uncertainty 0.1 mg. For each experiment, about 8 cm3 of sample was charged into the 30 cm3 heated sample vial. After the vial was closed by means of a special lid equipped with a washer, it was brought to the required temperature in a thermostatic cell. The mixture was continuously agitated for 6 h at the target temperature. The uncertainty of the measured temperature was 0.01 K. The combined standard uncertainties of the measured mole fraction in the vapor phase and mole fraction of solvents (on a salt-free basis) were 0.001. Analysis Method. Methanol and benzene mole fractions (on a salt-free basis) in the vapor (yi) phase were analyzed by the headspace gas chromatography method proposed by Takamatsu and Ohe.30 This method has been successfully used for isothermal studying of the ternary systems mixed solvent + electrolyte31,32 without vapor pressure measurement. For determination of the vapor phase composition, the vapor was automatically withdrawn using a PerkinElmer F45 GLC vapor analyzer and analyzed by a F22 gas chromatograph. The chromatographic column (3 m × 0.3 mm) was packed with Porapak-Q. The injector and chamber temperatures were 150 and 110 °C, respectively. The carrier gas was argon (purity = 99.9%) flowing at 0.5 cm3·s−1.
x1′
y1
m3/(mol·kg−1) = 0.100
x1′
y1
m3/(mol·kg−1) = 0.200
0.040 0.356 0.040 0.081 0.432 0.081 0.170 0.519 0.170 0.210 0.535 0.210 0.260 0.553 0.260 0.360 0.580 0.360 0.410 0.590 0.410 0.450 0.601 0.450 0.560 0.622 0.560 0.602 0.634 0.602 0.681 0.665 0.681 0.731 0.686 0.731 0.840 0.746 0.840 0.881 0.780 0.881 0.950 0.863 0.950 m3/(mol·kg−1) = 0.500 0.040 0.372 0.081 0.459 0.170 0.571 0.210 0.597 0.260 0.628 0.360 0.680 0.410 0.702 0.450 0.722 0.560 0.770 0.602 0.789 0.681 0.830 0.731 0.854 0.840 0.908 0.881 0.929 0.950 0.965
0.360 0.439 0.532 0.550 0.572 0.605 0.618 0.631 0.659 0.673 0.706 0.728 0.786 0.817 0.888
a
u(T) = 0.01 K, u(x) = u(y) = 0.001, and solvent is a methanol + benzene mixture. B
DOI: 10.1021/acs.jced.5b00770 J. Chem. Eng. Data XXXX, XXX, XXX−XXX
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Table 3. Experimental Vapor−Liquid Equilibrium Data for the System Methanol (1) + Benzene (2) + Tetraphenylphosphonium Chloride (3) without Vapor Pressure Measurement, Vapor Mole Fraction of Methanol (y1) as a Function of Liquid Mole Fraction of Methanol on a Salt-Free Basis (x1′), and Salt Molality m3 at Temperature T/ K = 328.15a x1′
y1 −1
m3/(mol·kg ) = 0.000 0.062 0.442 0.081 0.468 0.148 0.501 0.222 0.527 0.268 0.541 0.360 0.564 0.410 0.573 0.450 0.579 0.543 0.591 0.582 0.603 0.661 0.613 0.723 0.631 0.832 0.697 0.870 0.742 0.950 0.853 m3/(mol·kg−1) = 0.300 0.062 0.460 0.081 0.491 0.148 0.542 0.222 0.585 0.268 0.609 0.360 0.650 0.410 0.670 0.450 0.683 0.543 0.713 0.582 0.730 0.661 0.753 0.723 0.777 0.832 0.835 0.870 0.866 0.950 0.930
x1′
y1 −1
m3/(mol·kg ) = 0.100
x1′
y1 −1
m3/(mol·kg ) = 0.200
0.062 0.450 0.062 0.081 0.479 0.081 0.148 0.520 0.148 0.222 0.553 0.222 0.268 0.572 0.268 0.360 0.603 0.360 0.410 0.617 0.410 0.450 0.626 0.450 0.543 0.646 0.543 0.582 0.661 0.582 0.661 0.676 0.661 0.723 0.698 0.723 0.832 0.760 0.832 0.870 0.798 0.870 0.950 0.888 0.950 m3/(mol·kg−1) = 0.500 0.062 0.470 0.081 0.504 0.148 0.565 0.222 0.616 0.268 0.646 0.360 0.698 0.410 0.722 0.450 0.740 0.543 0.779 0.582 0.799 0.661 0.830 0.723 0.857 0.832 0.911 0.870 0.933 0.950 0.972
0.455 0.485 0.531 0.569 0.590 0.627 0.643 0.655 0.680 0.695 0.715 0.737 0.797 0.832 0.909
Figure 1. Vapor mole fraction (y1) of methanol in the methanol (1) + benzene (2) + tetraphenylphosphonium chloride (3) system at T = 308.15 K: ○, no salt (this work); ●, no salt (Scatchard et al.9); □, m3 = 0.100 mol·kg−1; ⧫, m3 = 0.200 mol·kg−1; ◊, m3 = 0.300 mol·kg−1; ×, m3 = 0.500 mol·kg−1. Liquid mole fraction of methanol (x1′) is on a salt-free basis. Solid line is line to identify the azeotropic behavior.
a
u(T) = 0.01 K, u(x) = u(y) = 0.001, and solvent is a methanol + benzene mixture.
of methanol + benzene are listed in Table 2 and Table 3 and compared to the literature in Figure 1 and Figure 2. Isothermal vapor−liquid equilibrium data for the ternary methanol + benzene + tetraphenylphosphonium chloride system are presented in Table 2, Table 3, Figure 1, and Figure 2. The addition of tetraphenylphosphonium chloride in the methanol + benzene system results in an increase of the methanol mole fraction in the vapor phase. The azeotrope of the methanol + benzene system disappears at salt concentration above 0.500 mol·kg−1. As shown in Table 4 tetraphenylphosphonium chloride is an effective agent for the elimination of azeotrope in the methanol + benzene system. Calculation of VLE for the Studied System. To describe the observed VLE behavior, the experimental data are correlated using the electrolyte NRTL model of Mock et al.29 The model parameters are specific for the solvent−solvent and solvent−salt pairs. For the system methanol + benzene + tetraphenylphosphonium chloride, six energy parameters (Δgij,
Figure 2. Vapor mole fraction (y1) of methanol in the methanol (1) + benzene (2) + tetraphenylphosphonium chloride (3) system at T = 328.15 K: ○, no salt (this work); ●, no salt (Scatchard et al.9); □, m3 = 0.100 mol·kg−1; ⧫, m3 = 0.200 mol·kg−1; ◊, m3 = 0.300 mol·kg−1; ×, m3 = 0.500 mol·kg−1. Liquid mole fraction of methanol (x1′) is on a salt-free basis. Solid line is line to identify the azeotropic behavior.
Δgji) and three nonrandomness factors (αij) are required. The binary model parameters, eqs 1 and 2, are expressed by29
τij =
Δgij RT
Gij = exp( −αijτij) C
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Liquid Chromatography at T = (313.15, 333.15, 353.15, and 373.15) K. J. Chem. Thermodyn. 2011, 43, 670−676. (7) Tumba, K.; Letcher, T.; Naidoo, P.; Ramjugernath, D. Activity Coefficients at Infinite Dilution of Organic Solutes in the Ionic Liquid Trihexyltetradecylphosphonium Hexafluorophosphate Using GasLiquid Chromatography at T = (313.15, 333.15, 353.15, and 363.15) K. J. Chem. Thermodyn. 2012, 49, 46−53. (8) Mutelet, F.; Alonso, D.; Stephens, T. W.; Acree, W. E., Jr; Baker, G. A. Infinite Dilution Activity Coefficients of Solutes Dissolved in Two Trihexyl(tetradecyl)phosphonium Ionic Liquids. J. Chem. Eng. Data 2014, 59, 1877−1885. (9) Scatchard, G.; Wood, S. E.; Mochel, J. M. Vapor-Liquid Equilibrium. VI. Benzene-Methanol Mixtures. J. Am. Chem. Soc. 1946, 68, 1957−1960. (10) Nagata, I. Vapor-Liquid Equilibrium Data for the Binary Systems Methanol-Benzene and Methyl Acetate-Methanol. J. Chem. Eng. Data 1969, 14, 418−420. (11) Toghiani, H.; Toghiani, R. K.; Viswanath, D. S. Vapor-Liquid Equilibria for the Methanol-Benzene and Methanol-Thiophene Systems. J. Chem. Eng. Data 1994, 39, 63−67. (12) Kurihara, K.; Hori, H.; Kojima, K. Vapor-Liquid Equilibrium Data for Acetone + Methanol + Benzene, Chloroform + Methanol + Benzene, and Constituent Binary Systems at 101.3 KPa. J. Chem. Eng. Data 1998, 43, 264−268. (13) Dharmendira Kumar, M.; Rajendran, M. Enthalpy of Mixing of Methanol + Benzene + Mercuric Chloride at 303.15 K. J. Chem. Eng. Data 1999, 44, 248−250. (14) Tamilarasan, R.; Anand Prabu, A.; Kap Jin, K.; Dharmendira Kumar, M. Effect of Dissolved Cadmium Chloride and Ammonium Chloride Salts on the Enthalpy of Mixing of the Methanol + Benzene System at 303.15 K. Chin. J. Chem. Eng. 2010, 18, 995−999. (15) Proszt, J.; Kollar, G. The Effect of Electrolyte on Azeotropic Systems. Magy. Kem. Foly. 1954, 60, 110−116. (16) Proszt, J.; Kollar, G. The Ebullioscopic Behavior of the Binary Liquid Mixtures. Acta Chim. Acad. Sci. Hung. 1955, 8, 171−189. (17) Proszt, J.; Kollar, G. Reducing of Boiling Point of the Salt Solutions in Mixed Systems. Roczn. Chem. 1958, 32, 611−621. (18) Rajamani, R.; Srinivasan, D. Salt Effect in Vapour-Liquid Equilibria. Indian Chem. Eng. 1977, 19, 36−39. (19) Natarajan, T. S.; Srinivasan, D. Vapor-Liquid Equilibrium Data for the Systems Acetone - Methanol and Methanol - Benzene in the Presence of Dissolved Salts. J. Chem. Eng. Data 1980, 25, 215−218. (20) Rath, P.; Suryanarayana, A.; Naik, S. C. Salt Effect in VapourLiquid Equilibria at Atmospheric Pressure. J. Inst. Eng. (India), Chem. Eng. Div. 1983, 64, 6−8. (21) Natarajan, T. S.; Srinivasan, D. Salt Effects in Vapour−Liquid Equilibria: Some Anomalies. In: Phase Equilibria and Fluid Properties in the Chemical Industry. Proceedings 2nd International Conference, Berlin (West), 17−21 March 1980, 225th Event of the EFCE. Dechema: Frankfurt, 1980. (22) Dharmendira Kumar, M.; Rajendran, M. Effect of Dissolved Salts on the Vapor-Liquid Equilibrium Relationships of Three Miscible Binary Systems at the Pressure of 101.3 kPa. J. Chem. Eng. Jpn. 1998, 31, 749−757. (23) Yang, M.; Leng, C.; Li, S.; Sun, R. Study of Activity Coefficients for Sodium Iodide in (Methanol + Benzene) System by (Vapour + Liquid) Equilibrium Measurements. J. Chem. Thermodyn. 2007, 39, 49−54. (24) Li, Q. S.; Zuhir, M.; Zhu, W.; Fu, Y. Q.; Li, L. Isobaric VaporLiquid Equilibrium Data for Methanol - Benzene - Ionic Liquid Ternary Systems. J. Beijing Univ. Chem. Technol., Nat. Sci. Ed. (Beijing Huagong Daxue Xuebao, Ziran Kexueban) 2011, 38, 12−16. (25) Li, Q. S.; Zuhir, M.; Zhu, W.; Fu, Y.; Li, L. Isobaric VaporLiquid Equilibrium for Methanol - Benzene - 1-Octyl-3-methylimidazolium Tetrafluoroborate Ternary System. Petrochem. Technol. (Shiyou Huagong) 2011, 40, 541−544. (26) Li, Q.; Zhu, W.; Fu, Y.; Zuhir, M.; Li, L.; Wang, B. Isobaric Vapor-Liquid Equilibrium for Methanol + Benzene + 1-Octyl-3-
Table 4. Efficiency of Electrolytes for Azeotrope Elimination in the Methanol (1) + Benzene (2) + Salt (3) System, Liquid Mole Fraction of Ionic Liquid x3, Salt Molality m3, Salt Molarity M3 salt
concentration of salt
LiI 1-octyl-3-methylimidazolium tetrafluoroborate (ionic liquid) tetraphenylphosphonium chloride
M3 = 2.64 mol·L−1 x3 = 0.3
17 24−26
ref
m3 = 0.5 mol ·kg−1
this work
Table 5. Energy Parameters (Δgij and Δgji) and Nonrandomness Factors αij for the Electrolyte NRTL Modela
a
i
j
αij
Δgji
Δgji
methanol methanol benzene
benzene saltb saltb
0.4837 0.2 0.3
2972.1 6844.3 33582.1
4754.1 −19354.5 −12697.3
Reference 29. bTetraphenylphosphonium chloride.
The NRTL energy parameters and nonrandomness factors are given in Table 5. Mean absolute deviation and standard deviation between experimental and calculated values of the vapor phase mole fractions are 0.008 and 0.007, respectively.
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CONCLUSION The VLE behavior of the system methanol + benzene + tetraphenylphosphonium chloride has been investigated at {(308.15 and 328.15) K} at four different salt concentrations {(0.100, 0.200, 0.300, and 0.500) mol·kg−1} with the help of headspace gas chromatography. This salt is effective in breaking the azeotrope. The electrolyte NRTL model was used for correlating the VLE behavior of the studied system. This model represented the experimental data with the required accuracy.
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. Notes
The authors declare no competing financial interest.
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REFERENCES
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