Isobaric Vapor–Liquid Equilibrium for tert-Butyl Alcohol + Water + Propane-1,3-Diol + 1-Ethyl-3-Methylimidazolium Chloride at 101.3 kPa

Abstract

In this study, we used a mixture of organic liquid propane-1,3-diol and ionic liquid 1-ethyl-3-methylimidazolium chloride ([emim]Cl) as the entrainer to separate tert-butyl alcohol (TBA) + water. We measured the isobaric vapor–liquid equilibrium (VLE) for the quaternary system TBA + water + propane-1,3-diol + [emim]Cl at 101.3 kPa, and found the VLE data to be well correlated with the nonrandom two-liquid model. These results show that the mixed solvent of propane-1,3-diol + [emim]Cl can increase the relative volatility of TBA to water and break the azeotropic point. We found no notable synergetic effect between them, and observed that the liquid mixed solvent of propane-1,3-diol and [emim]Cl had lower viscosity than [emim]Cl, which makes it a promising entrainer for separating the TBA + water azeotrope in industrial applications.

Keywords

tert-Butyl alcohol / Water / Propane-1-3-diol / 1-Ethyl-3-methylimidazolium chloride / Vapor–liquid equilibrium

References

[1] Japar SM, Wallington TJ, Richert JFO, et al. The atmospheric chemistry of oxygenated fuel additives: t-butyl alcohol, dimethyl ether, and methyl t-butyl ether. Int J Chem Kinet, 1990, 22: 1257-1269.

[2] Han P, She J, Xü N, et al. Study on salting-out separation and industrialization of tertiary-butanol aqueous solution with potassium carbonate. Chem Ind Eng Prog, 2004, 23: 877-879 (in Chinese)

[3] Zhou J, Dong B, Li J, et al. Research progress of preparation of isobutylene by dehydrating tert-butanol. Appl Chem Ind, 2010, 39: 925-928 (in Chinese)

[4] Cheng N. Solvent handbook, 2007, Beijing, China: Chemical Industry Press (in Chinese)

[5] Lei Z, Chen B, Ding Z. Special distillation processes, 2005, Amsterdam, The Netherlands: Elsevier.

[6] Ren H, Zhou J, Li C, et al. Measurement and correlation of vapor-liquid equilibria for TBA-water-ethylene glycol ternary system. Chem Eng (China), 2017, 45: 35-38 (in Chinese)

[7] Han X, Armstrong DW. Ionic liquids in separations. Acc Chem Res, 2007, 40: 1079-1086.

[8] Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R. Solubility of carbohydrates in ionic liquids. Energy Fuels, 2010, 24: 737-745.

[9] Pereiro AB, Araújo JMM, Esperança JMSS, et al. Ionic liquids in separations of azeotropic systems—a review. J Chem Thermodyn, 2012, 46: 2-28.

[10] Lei Z, Li C, Chen B. Extractive distillation: a review. Sep Purif Rev, 2003, 32: 121-213.

[11] Lei Z, Dai C, Zhu J, et al. Extractive distillation with ionic liquids: a review. AlChE J, 2014, 60: 3312-3329.

[12] Orchillés AV, Miguel PJ, Vercher E, et al. Isobaric vapor–liquid and liquid–liquid equilibria for chloroform + ethanol + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa. J Chem Eng Data, 2008, 53: 2642-2648.

[13] Orchillés AV, Miguel PJ, González-Alfaro V, et al. 1-ethyl-3-methylimidazolium dicyanamide as a very efficient entrainer for the extractive distillation of the acetone + methanol system. J Chem Eng Data, 2012, 57: 394-399.

[14] Calvar N, González B, Gómez E, et al. Vapor-liquid equilibria for the ternary system ethanol + water + 1-ethyl-3-methylimidazolium ethylsulfate and the corresponding binary systems containing the ionic liquid at 101.3 kPa. J Chem Eng Data, 2008, 53: 820-825.

[15] Zhang Z, Zhang Q, Zhang Q, et al. Isobaric vapor-liquid equilibrium of tert-butyl alcohol + water + triethanolamine-based ionic liquid ternary systems at 101.3 kPa. J Chem Eng Data, 2015, 60: 2018-2027.

[16] Zhang Z, Zhang Q, Zhang T, et al. Effect of methylimidazolium-based ionic liquids on vapor–liquid equilibrium behavior of tert-butyl alcohol + water azeotropic mixture at 101.3 kPa. Chin J Chem Eng, 2016, 24: 365-372.

[17] Zhang Z, Xu H, Zhang Q, et al. Separation of methanol + dimethyl carbonate azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilib, 2017, 435: 98-103.

[18] Zhang Z, Zhang A, Wu K, et al. Separation of ethyl acetate and 2-propanol azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilib, 2016, 429: 331-338.

[19] Cai J, Cui X, Zhang Y, et al. Isobaric vapor-liquid equilibrium for methanol + methyl acetate + 1-octyl-3-methylimidazolium hexafluorophosphate at 101.3 kPa. J Chem Eng Data, 2011, 56: 2884-2888.

[20] Li R, Cui X, Zhang Y, et al. Vapor-liquid equilibrium and liquid-liquid equilibrium of ethyl acetate + ethanol + 1-ethyl-3-methylimidazolium acetate. J Chem Eng Data, 2012, 57: 911-917.

[21] Lin R, Cui X, Yu X, et al. Isobaric vapor-liquid equilibrium of acetic acid + N,N-dimethylacetamide + 1-butyl-3-methylimidazolium Bis[(trifluoromethyl)sulfonyl]-imide. Fluid Phase Equilib, 2016, 410: 1-8.

[22] Liu H, Cui X, Zhang Y, et al. Isobaric vapor-liquid equilibrium of ethanenitrile + water + 1,2-ethanediol + 1-ethyl-3-methylimidazolium chloride. Fluid Phase Equilib, 2014, 378: 13-20.

[23] Li Q, Zhang S, Ding B, et al. Isobaric vapor-liquid equilibrium for methanol + dimethyl carbonate + trifluoromethanesulfonate-based ionic liquids at 101.3 kPa. J Chem Eng Data, 2014, 59: 3488-3494.

[24] Zhu J, Li Q, Li M, et al. The isobaric vapor liquid equilibria of ethyl acetate + acetonitrile + bis(trifluoromethylsulfonyl)imide-based ionic liquids at 101.3 kPa. Fluid Phase Equilib, 2016, 425: 289-296.

[25] Li Q, Liu P, Cao L, et al. Vapor–liquid equilibrium for tetrahydrofuran + methanol + tetrafluoroborate-based ionic liquids at 101.3 kPa. Fluid Phase Equilib, 2013, 360: 439-444.

[26] Dai C, Dong Y, Han J, et al. Separation of benzene and thiophene with a mixture of N-methyl-2-pyrrolidinone (NMP) and ionic liquid as the entrainer. Fluid Phase Equilib, 2015, 388: 142-150.

[27] Dai C, Lei Z, Xi X, et al. Extractive distillation with a mixture of organic solvent and ionic liquid as entrainer. Ind Eng Chem Res, 2014, 53: 15786-15791.

[28] Han J, Lei Z, Dai C, et al. Vapor pressure measurements for binary mixtures containing ionic liquid and predictions by the conductor-like screening model for real solvents. J Chem Eng Data, 2016, 61: 1117-1124.

[29] Lei Z, Yu G, Su Y, et al. Vapor pressure measurements and predictions for the binary and ternary systems containing ionic liquid [EMIM][Tf₂ N]. J Mol Liq, 2017, 231: 272-280.

[30] Li Q, Zhang J, Lei Z, et al. Isobaric vapor–liquid equilibrium for (propan-2-ol + water + 1-butyl-3-methylimidazolium tetrafluoroborate). J Chem Eng Data, 2009, 54: 2785-2788.

[31] Liu X, Lei Z, Wang T, et al. Isobaric vapor-liquid equilibrium for the ethanol + water + 2-aminoethanol tetrafluoroborate system at 101.3 kPa. J Chem Eng Data, 2012, 57: 3532-3537.

[32] Li Q, Zhang J, Lei Z, et al. Isobaric vapor–liquid equilibrium for ethyl acetate + ethanol + 1-ethyl-3-methylimidazolium tetrafluoroborate. J Chem Eng Data, 2009, 54: 193-197.

[33] Zhang L, Qiao B, Ge Y, et al. Effect of ionic liquids on (vapor + liquid) equilibrium behavior of (water + 2-methyl-2-propanol). J Chem Thermodyn, 2009, 41: 138-143.

[34] Efimova A, Pfützner L, Schmidt P. Thermal stability and decomposition mechanism of 1-ethyl-3-methylimidazolium halides. Thermochim Acta, 2015, 604: 129-136.

[35] Knight JR, Doherty MF. Optimal design and synthesis of homogeneous azeotropic distillation sequences. Ind Eng Chem Res, 1989, 28: 564-572.

[36] Stephenson RM, Malanowski S. Handbook of the thermodynamics of organic compounds, 1987, New York, USA: Elsevier Science Publishing Co. Inc,

[37] Dykyj J, Svoboda J, Wilhoit RC, et al. Hall KR, et al. Organic compounds, C1 to C57. Part 1. Vapor pressure and antoine constants for oxygen containing organic compounds, 2000, Berlin, Germany: Springer.

[38] Renon H, Prausnitz JM. Local compositions in thermodynamic excess functions for liquid mixtures. AlChE J, 1968, 14: 135-144.