Abstract
An experimental study on the isobaric vapor–liquid equilibria for the ternary system of acetone + methanol + 1-methyl-3-octylimidazolium thiocyanate ([Omim][SCN]) as well as the two acetone + ionic liquid (IL) and methanol + IL binary systems was performed at 100 kPa using a recirculating still (VLE 602 Fischer apparatus). A low IL mole fraction of 0.027 was found to be sufficient break the azeotrope due to the high and specific interactions with acetone and methanol. The nonrandom two-liquid model was used to represent the experimental data. The results are compared with those in the literature for the same mixed solvent system using other ILs.
Similar content being viewed by others
References
Keskin, S., Kayrak-Talay, D., Akman, U., Hortaçsu, Ö.: A review of ionic liquids towards supercritical fluid applications. J. Supercrit. Fluid 43, 150–180 (2007)
Orchillés, A.V., Miguel, P.J., González-Alfaro, V., Vercher, E., Martínez-Andreu, A.: 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 (2012)
Orchillés, A.V., Miguel, P.J., Vercher, E., Martínez-Andreu, A.: Ionic liquids as entrainers in extractive distillation: isobaric vapor–liquid equilibria for acetone + methanol + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. J. Chem. Eng. Data 52, 141–147 (2007)
Pereiro, A., Araújo, J., Esperança, J., Marrucho, I., Rebelo, L.: Ionic liquids in separations of azeotropic systems—a review. J. Chem. Thermodyn. 46, 2–28 (2012)
Roughton, B.C., Christian, B., White, J., Camarda, K.V., Gani, R.: Simultaneous design of ionic liquid entrainers and energy efficient azeotropic separation processes. Comput. Chem. Eng. 42, 248–262 (2012)
Werner, S., Haumann, M., Wasserscheid, P.: Ionic liquids in chemical engineering. Annu. Rev. Chem. Biomol. Eng. 1, 203–230 (2010)
Orchillés, A.V., Miguel, P.J., Vercher, E., Martínez-Andreu, A.: 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 (2008)
Seiler, M., Jork, C., Kavarnou, A., Arlt, W., Hirsch, R.: Separation of azeotropic mixtures using hyperbranched polymers or ionic liquids. AIChE J. 50, 2439–2454 (2004)
Matsuda, H., Liebert, V., Tochigi, K., Gmehling, J.: Influence of sulfate-based anion ionic liquids on the separation factor of the binary azeotropic system acetone + methanol. Fluid Phase Equilib. 340, 27–30 (2013)
Berg, L., Yeh, A.-I.: Separation of methanol from acetone by extractive distillation. US Patent 4501645 (1985)
Li, W., Xu, N., Xu, H., Zhang, A., Zhang, Z.V., Zhang, T.: Isobaric vapor–liquid equilibrium for ternary mixtures of acetone + methanol + ionic liquids at 101.3 kPa. Fluid Phase Equilib. 442, 20–27 (2017)
Orchillés, A.V., Miguel, P.J., Llopis, F.J., Vercher, E., Martínez-Andreu, A.: Influence of some ionic liquids containing the trifluoromethanesulfonate anion on the vapor–liquid equilibria of the acetone + methanol system. J. Chem. Eng. Data 56, 4430–4435 (2011)
Li, W., Sun, D., Zhang, T., Dai, S., Pan, F., Zhang, Z.: Separation of acetone and methanol azeotropic system using ionic liquid as entrainer. Fluid Phase Equilib. 383, 182–187 (2014)
Li, W., Sun, D., Zhang, T., Huang, Y., Zhang, L., Zhang, Z.: Phase equilibrium study of binary and ternary mixtures of ionic liquids + acetone + methanol. J. Chem. Eng. Data 59, 3975–3981 (2014)
Zhang, Z., Zhang, Q., Zhang, Q.Q., Zhang, T., Li, W.: 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 (2015)
Ruiz, E., Ferro, V.R., Palomar, J., Ortega, J., Rodriguez, J.J.: Interactions of ionic liquids and acetone: thermodynamic properties, quantum-chemical calculations, and NMR analysis. J. Phys. Chem. B 117, 7388–7398 (2013)
Chen, X., Yang, B., Abdeltawab, A.A., Al-Deyab, S.S., Yu, G., Yong, X.: Isobaric vapor–liquid equilibrium for acetone + methanol + phosphate ionic liquids. J. Chem. Eng. Data 60, 612–620 (2015)
Bates, E.D., Mayton, R.D., Ntai, I., Davis, J.H.: CO2 capture by a task-specific ionic liquid. J. Am. Chem. Soc. 124, 926–927 (2002)
Seiler, M., Jork, C., Schneider, W., Arlt, W.: Ionic liquids and hyperbranched polymers-promising new classes of selective entrainers for extractive distillation. In: Proceedings of the International Conference on Distillation and Absorption, 2002. GVC-VDI, Düsseldorf (2002)
Li, Q.S., Zhang, J.G., Lei, Z.G., Zhu, J.Q., Zhu, J.J., Huang, X.Q.: Selection of ionic liquids as entrainers for the separation of ethyl acetate and ethanol. Ind. Eng. Chem. Res. 48, 9006–9012 (2009)
Arlt, W., Seiler, M., Jork, C., Schneider, T.: Ionic liquids as selective additive for the separation of close-boiling or azeotropic mixtures. WO2002/074718 A2, 2002-09-26
Cao, Y., Mu, T.: Comprehensive investigation on the thermal stability of 66 ionic liquids by thermogravimetric analysis. Ind. Eng. Chem. Res. 53, 8651–8664 (2014)
Navarro, P., Larriba, M., Rojo, E., García, J., Rodríguez, F.: Thermal properties of cyano-based ionic liquids. J. Chem. Eng. Data 58, 2187–2193 (2013)
Siedlecka, E.M., Czerwicka, M., Stolte, S., Stepnowski, P.: Stability of ionic liquids in application conditions. Curr. Org. Chem. 15, 1974–1991 (2011)
Larriba, M., Navarro, P., García, J., Rodríguez, F.: Selective extraction of toluene from n-heptane using [emim][SCN] and [bmim][SCN] ionic liquids as solvents. J. Chem. Thermodyn. 79, 266–271 (2014)
Hansmeier, A.R., Ruiz, M.M., Meindersma, G.W., de Haan, A.B.: Liquid–liquid equilibria for the three ternary systems (3-methyl-n-butylpyridinium dicyanamide + toluene + heptane), (1-butyl-3-methylimidazolium dicyanamide + toluene + heptane) and (1-butyl-3-methylimidazolium thiocyanate + toluene + heptane) at T = (313.15 and 348.15) K and p = 0.1 MPa. J. Chem. Eng. Data 55, 708–713 (2010)
Navarro, P., Larriba, M., García, J., Rodríguez, F.: Design of the hydrocarbon recovery section from the extract stream of the aromatic separation from reformer and pyrolysis gasolines using a binary mixture of [4empy][Tf2N] + [emim][DCA] ionic liquids. Energy Fuel 31, 1035–1043 (2017)
Mokhtarani, B., Valialahi, L., Heidar, K.T., Mortaheb, H.R., Sharifi, A., Mirzaei, M.: Experimental study on (vapor + liquid) equilibria of ternary systems of hydrocarbons/ionic liquid using headspace gas chromatography. J. Chem. Thermodyn. 51, 77–81 (2012)
Heidari, M.R., Mokhtarani, B., Seghatoleslami, N., Sharifi, A., Mirzaei, M.: Liquid–liquid extraction of aromatics from their mixtures with alkanes using 1-methyl 3-octylimidazolium thiocyanate ionic liquid. J. Chem. Thermodyn. 54, 310–315 (2012)
Huang, H.Y., Wang, H.M., Hou, R.S., Cheng, H.T., Chen, L.C.: Hypervalent iodine(III) sulfonate mediated synthesis of α-thiocynanatoketones in a task-specific ionic liquid [bmim]SCN. J. Chin. Chem. Soc. 55, 1204–1207 (2008)
Huddleston, J.G., Visser, A.E., Reichert, W.M., Willauer, H.D., Broker, G.A., Rogers, R.D.: Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 3, 156–164 (2001)
Ambrose, D., Sprake, C.H.S., Townsend, R.: Thermodynamic properties of organic oxygen compounds, XXXIII. The vapour pressure of acetone. J. Chem. Thermodyn. 6, 693–700 (1974)
Osada, O., Sato, M., Uematsu, M.: Thermodynamic properties of {xCH3OH + (1 − x) H2O} with x = (1.0000 and 0.4993) in the temperature range from 320 K to 420 K at pressures up to 200 MPa. J. Chem. Thermodyn. 31, 451–463 (1999)
Leu, A.-D., Robinson, D.B., Chung, S.Y.-K., Chen, C.-J.: The equilibrium phase properties of the propane–methanol and n-butane–methanol binary systems. Can. J. Chem. Eng. 70, 330–334 (1992)
Muthu, O., Munjal, S., Smith, B.D.: Total-pressure vapor–liquid equilibrium data for binary systems of acetone with isopropylbenzene and isopropenylbenzene. J. Chem. Eng. Data 28, 192–196 (1983)
Maher, P.J., Smith, B.D.: Vapor–liquid equilibrium data for binary systems of chlorobenzene with acetone, acetonitrile, ethyl acetate, ethylbenzene, methanol, and 1-pentene. J. Chem. Eng. Data 24, 363–377 (1979)
Maher, P.J., Smith, B.D.: Vapor–liquid equilibrium data for binary systems of aniline with acetone, acetonitrile, chlorobenzene, methanol, and 1-pentene. J. Chem. Eng. Data 25, 61–68 (1980)
Safarov, J., Kul, I., Talibov, M., Shahverdiyev, A., Hassel, E.: Vapor pressures and activity coefficients of methanol in binary mixtures with 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. J. Chem. Eng. Data 60, 1648–1663 (2015)
Giles, N.F., Wilson, H.L., Wilding, W.V.: Phase equilibrium measurements on twelve binary mixtures. J. Chem. Eng. Data 41, 1223–1238 (1996)
Vercher, E., Orchillés, A.V., Miguel, P.J., González-Alfaro, V., Martínez-Andreu, A.: Isobaric vapor–liquid equilibria for acetone + methanol + lithium nitrate at 100 kPa. Fluid Phase Equilib. 250, 131–137 (2006)
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 43, 264–268 (1998)
Mock, B., Evans, L.B., Chen, C.-C.: Thermodynamic representation of phase equilibria of mixed-solvent electrolyte systems. AIChE J. 32, 1655–1664 (1986)
Vercher, E., Rojo, F.J., Martínez-Andreu, A.: Isobaric vapor–liquid equilibria for 1-propanol + water + calcium nitrate. J. Chem. Eng. Data 44, 1216–1221 (1999)
Prausnitz, J., Lichtenthaler, R.N., de Azevedo, E.G.: Molecular Thermodynamic of Fluid Phase Equilibria, 3rd edn. Prentice Hall, Upper Saddle River (1999)
Van Ness, H.C., Byer, S.M., Gibbs, R.E.: Vapor–liquid equilibrium: part I. An appraisal of data reduction methods. AIChE J. 19, 238–244 (1973)
Lei, Z., Alrt, W., Wasserscheid, P.: Separation of 1-hexene and n-hexane by ionic liquids. Fluid Phase Equilib. 241, 290–299 (2006)
Lei, Z., Dai, C., Zhu, J., Chen, B.: Extractive distillation with ionic liquids: a review. AIChE J. 60, 3312–3329 (2014)
Spange, S., Lungwitz, R., Schade, A.: Correlation of molecular structure and polarity of ionic liquids. J. Mol. Liq. 192, 137–143 (2014)
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Mortaheb, H.R., Mokhtarani, B., Shafiee, N. et al. Experimental Study of Vapor–Liquid Equilibrium Data for Acetone + Methanol + 1-Methyl-3-octylimidazolium Thiocyanate. J Solution Chem 47, 2007–2020 (2018). https://doi.org/10.1007/s10953-018-0827-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-018-0827-8