乙腈+水+离子液体等压汽液平衡测定与计算
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摘要
采用改进的Ellis平衡蒸馏仪测定了乙腈+水+1-乙基-3-甲基咪唑磷酸二乙酯盐([EMIM][DEP])、乙腈+水+{1-乙基-3-甲基咪唑醋酸盐([EMIM][OAC])+[EMIM][DEP]}常压(101.3 kPa)等压汽液平衡(VLE)数据。实验结果表明,备选离子液体可促进水+乙腈混合物的分离并消除其共沸点。借助NRTL模型成功关联了含离子液体的三元和四元VLE实验数据,获得了乙腈-[EMIM][DEP]、水-[EMIM][DEP]和[EMIM][OAC]-[EMIM][DEP]二元交互作用参数。应用COSMO-SAC预测了实验VLE,结果令人满意。量化计算表明可与水形成强相互作用的离子液体更易促进乙腈与水的分离。
Acetonitrile is easy to form an azeotropic mixture with water and it is impossible to separate them through ordinary distillation technology. In this work, ionic liquids(ILs) are employed as entrainer to separate acetonitrile and water. The isobaric vapor liquid equilibria(VLE) of acetonitrile + water + 1-ethyl-3-methylimidazolium diethylphosphate([EMIM][DEP]), acetonitrile + water + {1-ethyl-3-methylimidazolium acetate([EMIM][OAC]) +[EMIM][DEP]} are determined at atmospheric pressure(101.3 kPa) in a glass equilibrium still with a vapor cycle,indicating that the selected ILs can well improve the separation of acetonitrile and water mixture, and further eliminate its azeotropy. The VLE data of ternary and quaternary mixtures containing ILs are well correlated with NRTL model, and the binary interaction parameters of acetonitrile-[EMIM][DEP], water-[EMIM][DEP] and[EMIM][OAC]-[EMIM][DEP] are obtained. The experimental VLE was predicted using COSMO-SAC and the results were satisfactory. The interactions among different molecules are analyzed through quantum calculations showing that the interactions between water and ILs are stronger than ones between water and acetonitrile so that the used ILs here can improve the separation of acetonitrile and water.
Acetonitrile is easy to form an azeotropic mixture with water and it is impossible to separate them through ordinary distillation technology. In this work, ionic liquids(ILs) are employed as entrainer to separate acetonitrile and water. The isobaric vapor liquid equilibria(VLE) of acetonitrile + water + 1-ethyl-3-methylimidazolium diethylphosphate([EMIM][DEP]), acetonitrile + water + {1-ethyl-3-methylimidazolium acetate([EMIM][OAC]) +[EMIM][DEP]} are determined at atmospheric pressure(101.3 kPa) in a glass equilibrium still with a vapor cycle,indicating that the selected ILs can well improve the separation of acetonitrile and water mixture, and further eliminate its azeotropy. The VLE data of ternary and quaternary mixtures containing ILs are well correlated with NRTL model, and the binary interaction parameters of acetonitrile-[EMIM][DEP], water-[EMIM][DEP] and[EMIM][OAC]-[EMIM][DEP] are obtained. The experimental VLE was predicted using COSMO-SAC and the results were satisfactory. The interactions among different molecules are analyzed through quantum calculations showing that the interactions between water and ILs are stronger than ones between water and acetonitrile so that the used ILs here can improve the separation of acetonitrile and water.
引文
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[21] Ma Y X, Xu X C, Wen G L, et al. Separation of azeotropes hexane+ethanol/1-propanol by ionic liquid extraction:liquidliquid phase equilibrium measurements and thermodynamic modeling[J]. J. Chem. Eng. Data, 2017, 62(12):4296-4300.
[22] Zhang Z G, Zhang D B, Li W X, et al. Separation of acetonitrile+ethanol mixture using imidazolium-based ionic liquids as entrainers[J]. Fluid Phase Equilib., 2018, 474:43-49.
[23] Navarro P, Larriba M, Garcia J, et al. Design of the recovery section of the extracted aromatics in the sparation of BTEX from naphtha feed to ethylene crackers using[4empy][Tf2N] and[emim][DCA] mixed ionic liquids as solvent[J]. Sep. Purif.Technol., 2017, 180:149-156.
[24] Pereiro A B, Rodriguez A. Phase equilibria of the azeotropic mixture hexane+ethyl acetate with ionic liquids at 298.15 K[J]. J.Chem. Thermodyn., 2008, 53(6):1360-1366.
[25] Kurzin A V, Evdokimov A N, Poltoratskiy G M, et al. Isothermal vapor-liquid equilibrium data for the systems 1, 4-dioxane+water+tetrabutylammonium nitrate and acetonitrile+water+tetrabutylammonium bromide[J]. J. Chem. Eng. Data, 2004, 49(2):208-211.
[26] Fang J, Liu J, Li C L, et al. Isobaric vapor-liquid equilibrium for the acetonitrile+water system containing different ionic liquids at atmospheric pressure[J]. J. Chem. Eng. Data, 2013, 58:1483-1489.
[27] Fang J, Zhao R, Wang H, et al. Salting-out effect of ionic liquids on isobaric vapor-liquid equilibrium of acetonitrile-water system[J]. Chin. J. Chem. Eng., 2015, 23(8):1369-1373.
[28] Kurzin A V, Evdokimov A N, Antipina V B, et al. Measurement and correlation of isothermal vapor-liquid equilibrium data for the system acetonitrile+water+tetrapropylammonium bromide[J]. J.Chem. Eng. Data, 2006, 51:1361-1363.
[29] Kurzin A V, Evdokimov A N, Antipina V B, et al. Vapor pressures for the acetonitrile+tetrabutylammonium bromide, water+tetrabutylammonium bromide, and acetonitrile+water+tetrabutylammonium bromide systems[J]. J. Chem. Eng. Data,2009, 54:1049-1051.
[30] Li T T, Yang Q, Ding H R, et al. Amino acid based ionic liquids as additives for separation of acetonitrile and water azeotropic mixture:COSMO-RS prediction and experimental verification[J].Ind. Eng. Chem. Res., 2015, 54:12143-12149.
[31] Li J L, Li T T, Peng C J, et al. Extractive distillation with ionic liquid entrainers for the separation of acetonitrile and water[J].Ind. Eng. Chem. Res., 2019, 58:5602-5612.
[32] Lu Q L, Li J L, Peng C J, et al. Experimental determination of vapor liquid equilibrium for methanol+methyl propionate+1-butyl-3-methylimidazo-lium bis(trifluoromethylsulfonyl)imide at atmospheric pressure[J]. J. Chem. Thermodyn., 2019, 132:289-294.
[33] Hiaki T, Kawai A. Vapor-liquid equilibria determination for a hydrofluoroether with several alcohols[J]. Fluid Phase Equilib.,1999, 158/159/160:979-989.
[34] Renon H, Prausnitz J M. Local compositions in thermodynamic excess functions for liquid mixtures[J]. AIChE J., 1968, 14:135-144.
[35] Klamt A, Eckert F. COSMO-RS:a novel and efficient method for the a priori prediction of thermophysical data of liquids[J]. Fluid Phase Equilib., 2000, 172:43-72.
[36] Hsieh C M, Sandler S I, Lin S T. Improvements of COSMO-SAC for vapor-liquid and liquid-liquid equilibrium predictions[J].Fluid Phase Equilib., 2010, 297:90-97.
[2] Rosen J, Hellenas K E. Analysis of acrylamide in cooked foods by liquid chromatography tandem mass spectrometry[J]. Analyst,2002, 127:880-882.
[3]贾自成,董满祥,童俊国,等.乙腈法抽提丁二烯装置的改扩建[J].石油炼制与化工, 1998, 29(9):36-39.Jia Z C, Dong M X, Tong J G, et al. Revamping and enlargement of a butadiene extraction unit with acetonitrile method[J].Petroleum Process. Petrochem., 1998, 29(9):36-39.
[4] Gmehling J, Menke J, Krafczyk J, et al. Azeotropic Data[M].Weinheim, Germany:VCH, 1994.
[5] Liang K, Li W S, Luo H T, et al. Energy-efficient extractive distillation process by combining preconcentration column and entrainer recovery column[J]. Ind. Eng. Chem. Res., 2014, 53:7121-7131.
[6] Acosta J, Arce A, Rodil E, et al. A thermodynamic study on binary and ternary mixtures of acetonitrile, water and butyl acetate[J].Fluid Phase Equilib., 2002, 203:83-98.
[7] Yu B Y, Huang R, Zhong X Y, et al. Energy-efficient extractiondistillation process for separating diluted acetonitrile-water mixture:rigorous design with experimental verification from ternary liquid-liquid equilibrium data[J]. Ind. Eng. Chem. Res.,2017, 56:15112-15121.
[8]许文友.乙腈-水-氟化钾及乙腈-水-碳酸钾液液相平衡数据的测定和关联[J].化工学报, 2001, 52(8):742-745.Xu W Y. Measurement and correlation of liquid-liquid equilibrium data for acetonitrile-water-potassium fluoride and acetonitrile-water-potassium carbonate systems[J]. Journal of Chemical Industry and Engineering(China), 2001, 52(8):742-745.
[9]崔现宝,李杨,冯天扬,等.加盐萃取精馏分离乙腈-水物系[J].石油化工, 2007, 36(12):1229-1233.Cui X B, Li Y, Feng T Y, et al. Separation of acetonitrile-water by saline extractive distillation[J]. Petrochem. Technol., 2007, 36(12):1229-1233.
[10] Wishart J F, Castner J E W. The physical chemistry of ionic liquids[J]. J. Phys. Chem. B, 2007, 111:201-208.
[11] Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis[J]. Chem. Rev., 1999, 99:2071-2083.
[12] Vogl T, Menne S, Kuhnel R S, et al. The beneficial effect of protic ionic liquids on the lithium environment in electrolytes for battery applications[J]. J. Mater. Chem. A, 2014, 2:8258-8265.
[13] Ye C F, Liu W M, Chen Y X, et al. Room-temperature ionic liquids:a novel versatile lubricant[J]. Chem. Commun., 2001,2244-2245.
[14] Seiler M, Jork C, Kavarnou A, et al. Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids[J]. AIChE J., 2004, 50(10):2439-2454.
[15] Lei Z G, Xi X M, Dai C N, et al. Extractive distillation with the mixture of ionic liquid and solid inorganic salt as entrainers[J].AIChE J., 2014, 60(8):2994-3004.
[16] Pereiro A B, Araujo J M M, Esperanca J M S S, et al. Ionic liquids in separations of azeotropic systems—a review[J]. J. Chem.Thermodyn., 2012, 46:2-28.
[17] Artemenko S, Haddad S, Mazur V. Azeotrope breaking potential of ionic liquids in separation processes[J]. J. Mol. Liq., 2017, 235:49-52.
[18] Boli E, Dimou E, Voutsas E. Separation of the isopropanol-water azeotropic mixture using ionic liquids[J]. Fluid Phase Equilib.,2018, 456:77-83.
[19] Li W X, Du Y, Li J P, et al. Isobaric vapor-liquid equilibrium for acetone+methanol system containing different ionic liquids at101.3 kPa[J]. Fluid Phase Equilib., 2018, 459:10-17.
[20] Wang P, Xu D M, Yan P S, et al. Separation of azeotrope(ethanol and ethyl methyl carbonate)by different imidazolium-based ionic liquids:ionic liquids interaction analysis and phase equilibrium measurements[J]. J. Mol. Liq., 2018, 261:89-95.
[21] Ma Y X, Xu X C, Wen G L, et al. Separation of azeotropes hexane+ethanol/1-propanol by ionic liquid extraction:liquidliquid phase equilibrium measurements and thermodynamic modeling[J]. J. Chem. Eng. Data, 2017, 62(12):4296-4300.
[22] Zhang Z G, Zhang D B, Li W X, et al. Separation of acetonitrile+ethanol mixture using imidazolium-based ionic liquids as entrainers[J]. Fluid Phase Equilib., 2018, 474:43-49.
[23] Navarro P, Larriba M, Garcia J, et al. Design of the recovery section of the extracted aromatics in the sparation of BTEX from naphtha feed to ethylene crackers using[4empy][Tf2N] and[emim][DCA] mixed ionic liquids as solvent[J]. Sep. Purif.Technol., 2017, 180:149-156.
[24] Pereiro A B, Rodriguez A. Phase equilibria of the azeotropic mixture hexane+ethyl acetate with ionic liquids at 298.15 K[J]. J.Chem. Thermodyn., 2008, 53(6):1360-1366.
[25] Kurzin A V, Evdokimov A N, Poltoratskiy G M, et al. Isothermal vapor-liquid equilibrium data for the systems 1, 4-dioxane+water+tetrabutylammonium nitrate and acetonitrile+water+tetrabutylammonium bromide[J]. J. Chem. Eng. Data, 2004, 49(2):208-211.
[26] Fang J, Liu J, Li C L, et al. Isobaric vapor-liquid equilibrium for the acetonitrile+water system containing different ionic liquids at atmospheric pressure[J]. J. Chem. Eng. Data, 2013, 58:1483-1489.
[27] Fang J, Zhao R, Wang H, et al. Salting-out effect of ionic liquids on isobaric vapor-liquid equilibrium of acetonitrile-water system[J]. Chin. J. Chem. Eng., 2015, 23(8):1369-1373.
[28] Kurzin A V, Evdokimov A N, Antipina V B, et al. Measurement and correlation of isothermal vapor-liquid equilibrium data for the system acetonitrile+water+tetrapropylammonium bromide[J]. J.Chem. Eng. Data, 2006, 51:1361-1363.
[29] Kurzin A V, Evdokimov A N, Antipina V B, et al. Vapor pressures for the acetonitrile+tetrabutylammonium bromide, water+tetrabutylammonium bromide, and acetonitrile+water+tetrabutylammonium bromide systems[J]. J. Chem. Eng. Data,2009, 54:1049-1051.
[30] Li T T, Yang Q, Ding H R, et al. Amino acid based ionic liquids as additives for separation of acetonitrile and water azeotropic mixture:COSMO-RS prediction and experimental verification[J].Ind. Eng. Chem. Res., 2015, 54:12143-12149.
[31] Li J L, Li T T, Peng C J, et al. Extractive distillation with ionic liquid entrainers for the separation of acetonitrile and water[J].Ind. Eng. Chem. Res., 2019, 58:5602-5612.
[32] Lu Q L, Li J L, Peng C J, et al. Experimental determination of vapor liquid equilibrium for methanol+methyl propionate+1-butyl-3-methylimidazo-lium bis(trifluoromethylsulfonyl)imide at atmospheric pressure[J]. J. Chem. Thermodyn., 2019, 132:289-294.
[33] Hiaki T, Kawai A. Vapor-liquid equilibria determination for a hydrofluoroether with several alcohols[J]. Fluid Phase Equilib.,1999, 158/159/160:979-989.
[34] Renon H, Prausnitz J M. Local compositions in thermodynamic excess functions for liquid mixtures[J]. AIChE J., 1968, 14:135-144.
[35] Klamt A, Eckert F. COSMO-RS:a novel and efficient method for the a priori prediction of thermophysical data of liquids[J]. Fluid Phase Equilib., 2000, 172:43-72.
[36] Hsieh C M, Sandler S I, Lin S T. Improvements of COSMO-SAC for vapor-liquid and liquid-liquid equilibrium predictions[J].Fluid Phase Equilib., 2010, 297:90-97.