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.
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References
Japar SM, Wallington TJ, Richert JFO et al (1990) The atmospheric chemistry of oxygenated fuel additives: t-butyl alcohol, dimethyl ether, and methyl t-butyl ether. Int J Chem Kinet 22:1257–1269
Han P, She J, Xü N et al (2004) Study on salting-out separation and industrialization of tertiary-butanol aqueous solution with potassium carbonate. Chem Ind Eng Prog 23:877–879 (in Chinese)
Zhou J, Dong B, Li J et al (2010) Research progress of preparation of isobutylene by dehydrating tert-butanol. Appl Chem Ind 39:925–928 (in Chinese)
Cheng N (2007) Solvent handbook. Chemical Industry Press, Beijing, China (in Chinese)
Lei Z, Chen B, Ding Z (2005) Special distillation processes. Elsevier, Amsterdam, The Netherlands
Ren H, Zhou J, Li C et al (2017) Measurement and correlation of vapor-liquid equilibria for TBA-water-ethylene glycol ternary system. Chem Eng (China) 45:35–38 (in Chinese)
Han X, Armstrong DW (2007) Ionic liquids in separations. Acc Chem Res 40:1079–1086
Zakrzewska ME, Bogel-Łukasik E, Bogel-Łukasik R (2010) Solubility of carbohydrates in ionic liquids. Energy Fuels 24:737–745
Pereiro AB, Araújo JMM, Esperança JMSS et al (2012) Ionic liquids in separations of azeotropic systems—a review. J Chem Thermodyn 46:2–28
Lei Z, Li C, Chen B (2003) Extractive distillation: a review. Sep Purif Rev 32:121–213
Lei Z, Dai C, Zhu J et al (2014) Extractive distillation with ionic liquids: a review. AlChE J 60:3312–3329
Orchillés AV, Miguel PJ, Vercher E et al (2008) Isobaric vapor–liquid and liquid–liquid equilibria for chloroform + ethanol + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa. J Chem Eng Data 53:2642–2648
Orchillés AV, Miguel PJ, González-Alfaro V et al (2012) 1-ethyl-3-methylimidazolium dicyanamide as a very efficient entrainer for the extractive distillation of the acetone + methanol system. J Chem Eng Data 57:394–399
Calvar N, González B, Gómez E et al (2008) 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 53:820–825
Zhang Z, Zhang Q, Zhang Q et al (2015) Isobaric vapor-liquid equilibrium of tert-butyl alcohol + water + triethanolamine-based ionic liquid ternary systems at 101.3 kPa. J Chem Eng Data 60:2018–2027
Zhang Z, Zhang Q, Zhang T et al (2016) 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 24:365–372
Zhang Z, Xu H, Zhang Q et al (2017) Separation of methanol + dimethyl carbonate azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilib 435:98–103
Zhang Z, Zhang A, Wu K et al (2016) Separation of ethyl acetate and 2-propanol azeotropic mixture using ionic liquids as entrainers. Fluid Phase Equilib 429:331–338
Cai J, Cui X, Zhang Y et al (2011) Isobaric vapor-liquid equilibrium for methanol + methyl acetate + 1-octyl-3-methylimidazolium hexafluorophosphate at 101.3 kPa. J Chem Eng Data 56:2884–2888
Li R, Cui X, Zhang Y et al (2012) Vapor-liquid equilibrium and liquid-liquid equilibrium of ethyl acetate + ethanol + 1-ethyl-3-methylimidazolium acetate. J Chem Eng Data 57:911–917
Lin R, Cui X, Yu X et al (2016) Isobaric vapor-liquid equilibrium of acetic acid + N,N-dimethylacetamide + 1-butyl-3-methylimidazolium Bis[(trifluoromethyl)sulfonyl]-imide. Fluid Phase Equilib 410:1–8
Liu H, Cui X, Zhang Y et al (2014) Isobaric vapor-liquid equilibrium of ethanenitrile + water + 1,2-ethanediol + 1-ethyl-3-methylimidazolium chloride. Fluid Phase Equilib 378:13–20
Li Q, Zhang S, Ding B et al (2014) Isobaric vapor-liquid equilibrium for methanol + dimethyl carbonate + trifluoromethanesulfonate-based ionic liquids at 101.3 kPa. J Chem Eng Data 59:3488–3494
Zhu J, Li Q, Li M et al (2016) The isobaric vapor liquid equilibria of ethyl acetate + acetonitrile + bis(trifluoromethylsulfonyl)imide-based ionic liquids at 101.3 kPa. Fluid Phase Equilib 425:289–296
Li Q, Liu P, Cao L et al (2013) Vapor–liquid equilibrium for tetrahydrofuran + methanol + tetrafluoroborate-based ionic liquids at 101.3 kPa. Fluid Phase Equilib 360:439–444
Dai C, Dong Y, Han J et al (2015) Separation of benzene and thiophene with a mixture of N-methyl-2-pyrrolidinone (NMP) and ionic liquid as the entrainer. Fluid Phase Equilib 388:142–150
Dai C, Lei Z, Xi X et al (2014) Extractive distillation with a mixture of organic solvent and ionic liquid as entrainer. Ind Eng Chem Res 53:15786–15791
Han J, Lei Z, Dai C et al (2016) Vapor pressure measurements for binary mixtures containing ionic liquid and predictions by the conductor-like screening model for real solvents. J Chem Eng Data 61:1117–1124
Lei Z, Yu G, Su Y et al (2017) Vapor pressure measurements and predictions for the binary and ternary systems containing ionic liquid [EMIM][Tf2 N]. J Mol Liq 231:272–280
Li Q, Zhang J, Lei Z et al (2009) Isobaric vapor–liquid equilibrium for (propan-2-ol + water + 1-butyl-3-methylimidazolium tetrafluoroborate). J Chem Eng Data 54:2785–2788
Liu X, Lei Z, Wang T et al (2012) Isobaric vapor-liquid equilibrium for the ethanol + water + 2-aminoethanol tetrafluoroborate system at 101.3 kPa. J Chem Eng Data 57:3532–3537
Li Q, Zhang J, Lei Z et al (2009) Isobaric vapor–liquid equilibrium for ethyl acetate + ethanol + 1-ethyl-3-methylimidazolium tetrafluoroborate. J Chem Eng Data 54:193–197
Zhang L, Qiao B, Ge Y et al (2009) Effect of ionic liquids on (vapor + liquid) equilibrium behavior of (water + 2-methyl-2-propanol). J Chem Thermodyn 41:138–143
Efimova A, Pfützner L, Schmidt P (2015) Thermal stability and decomposition mechanism of 1-ethyl-3-methylimidazolium halides. Thermochim Acta 604:129–136
Knight JR, Doherty MF (1989) Optimal design and synthesis of homogeneous azeotropic distillation sequences. Ind Eng Chem Res 28:564–572
Stephenson RM, Malanowski S (1987) Handbook of the thermodynamics of organic compounds. Elsevier Science Publishing Co., Inc, New York, USA
Dykyj J, Svoboda J, Wilhoit RC et al (2000) Organic compounds, C1 to C57. Part 1. In: Hall KR (ed) Vapor pressure and antoine constants for oxygen containing organic compounds. Springer, Berlin, Germany
Renon H, Prausnitz JM (1968) Local compositions in thermodynamic excess functions for liquid mixtures. AlChE J 14:135–144
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This study was supported by the Innovation Fund of Tianjin University (No. 2010XJ-0022).
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Cui, X., Cheng, Q., Liu, H. et al. Isobaric Vapor–Liquid Equilibrium for tert-Butyl Alcohol + Water + Propane-1,3-Diol + 1-Ethyl-3-Methylimidazolium Chloride at 101.3 kPa. Trans. Tianjin Univ. 24, 424–433 (2018). https://doi.org/10.1007/s12209-018-0125-y
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DOI: https://doi.org/10.1007/s12209-018-0125-y