Abstract
The applicability of 1-alkyl-imidazoluim-based ionic liquids (ILs) for the extraction of ethanol from hexadecane by solvent extraction was studied by determining the liquid–liquid equilibrium (LLE) data for the ternary systems: {hexadecane (1) + ethanol (2) + 1,3-dimethylimidazolium methyl sulfate, [MMIM][MeSO4] (3) or 1-ethyl-3-methylimidazolium methyl sulfate, [EMIM][MeSO4] (3), or 1-butyl-3-methylimidazolium methyl sulfate, [BMIM][MeSO4] (3)} at T = 298.15 K and p = 1 atm. The selectivities and distribution coefficients of the solute, derived from the measured tie-line data, were used to examine the ability of these ILs as solvents to extract ethanol from a hexadecane-ethanol mixture. The temperature dependency was investigated by measuring the LLE data for {hexadecane (1) + ethanol (2) + [MMIM][MeSO4] (3)} at T = 313.15 K and p = 1 atm. The Othmer–Tobias and Hand equations were used to establish the quality of the LLE data. Finally, the experimental tie-line data were correlated using the Non-Random Two Liquid model.
Similar content being viewed by others
References
Poole, C.F.: Chromatographic and spectroscopic methods for the determination of solvent properties of room temperature ionic liquids. J. Chromatogr. A 1037, 49–82 (2004)
Sheldon, R.: Catalytic reactions in ionic liquids. Chem. Commun. 23, 2399–2407 (2001)
Earle, M.J., Seddon, K.R.: Ionic liquids. Green solvents for the future. Pure Appl. Chem. 72, 1391–1398 (2000)
Freemantle, M.: Designer solvents: ionic liquids may boost clean technology development. Chem. Eng. News 76, 32–37 (1998)
Brennecke, J.F., Maginn, E.J.: Ionic liquids: innovative fluids for chemical processing. AIChE J. 47, 2384–2389 (2001)
Welton, T.: Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2084 (1999)
Ganjali, M.R., Khoshsafar, H., Shirzadmehr, A., Javanbakht, M., Faridbod, F.: Improvement of carbon paste ion selective electrode response by using room temperature ionic liquids (RTILs) and multi-walled carbon nanotubes (MWCNTs). Int. J. Electrochem. Sci. 4, 435–443 (2009)
Baranyai, K.J., Deacon, G.B., Macfarlane, D.R., Pringle, J.M., Scott, J.L.: Thermal degradation of ionic liquids at elevated temperatures. Aust. J. Chem. 57, 145–147 (2004)
Smiglak, M., Reichert, W.M., Holbrey, J.D., Wilkes, J.S., Sun, L.Y., Thrasher, J.S., Kirichenko, K., Singh, S., Katritzky, A.R., Rogers, R.D.: Combustible ionic liquids by design: is laboratory safety another ionic liquid myth? Chem. Commun. 24, 2554–2556 (2006)
Marsh, K.N., Boxall, J.A., Lichtenthaler, R.: Room temperature ionic liquids and their mixtures—a review. Fluid Phase Equilib. 219, 93–98 (2004)
Rebelo, L.P.N., Lopes, J.N.C., Esperancua, J.M.S.S., Filipe, E.: On the critical temperature, normal boiling point, and vapour pressure of ionic liquids. J. Phys. Chem. B 109, 6040–6043 (2005)
Seddon, K.R.: Ionic liquids for clean technology. J. Chem. Technol. Biotechnol. 68, 351–356 (1997)
Plechkova, N.V., Seddon, K.R.: Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 37, 123–150 (2008)
Matsumoto, K., Hagiwara, R., Ito, Y.: Room-temperature ionic liquids with high conductivities and wide electrochemical windows: N-Alkyl-N-methylpyrrolidinium and N-alkyl-N-methylpiperidinium fluorohydrogenates. Electrochem. Solid-State. Lett. 7, 41–44 (2004)
Kuang, D., Ito, S., Wenger, B., Klein, C., Moser, J.E., Humphry-Baker, R., Zakeeruddin, S.M., Gratzel, M.: The performance and stability of ambient temperature molten salts for solar cell applications. J. Electrochem. Soc. 143, 3099–3108 (1996)
Lewandowski, A., Galinski, M.: Carbon–ionic liquid double-layer capacitors. J. Phys. Chem. Solids 65, 281–286 (2004)
Huang, J.F., Luo, H., Liang, C., Sun, I.-W., Baker, G.A., Dai, S.: Hydrophobic Brønsted acid–base ionic liquids based on PAMAM dendrimers with high proton conductivity and blue photoluminescence. J. Am. Chem. Soc. 37, 12784–12785 (2005)
Ding, J., Zhou, D., Spinks, G., Wallace, G., Forsyth, S., Forsyth, M., Macfarlane, D.R.: Use of ionic liquids as electrolytes in electromechanical actuator systems based on inherently conducting polymers. Chem. Mater. 15, 2392–2398 (2003)
Nakagawa, H., Izuchi, S., Kuwana, K., Nukuda, T., Nihara, Y.J.: Liquid and polymer gel electrolytes for lithium batteries composed of room-temperature molten salt doped by lithium salt. Electrochem. Soc. 150, 695–700 (2003)
Kedra-Krolik, K., Fabrice, M., Jaubert, J.N.: Extraction of thiophene or pyridine from gasoline and diesel desulfurization. Ind. Eng. Chem. Res. 50, 2296–2306 (2011)
Pereiro, A.B., Deivea, F.J., Esperanc, J.M.S.S., Rodriguez, A.: Alkylsulfate-based ionic liquids to separate azeotropic mixtures. Fluid Phase Equilib. 291, 13–17 (2010)
Pereiro, A.B., Rodriguez, A.: Effective extraction in packed column of ethanol from the azeotropic mixture ethanol + hexane with an ionic liquid as solvent. Chem. Eng. J. 153, 80–85 (2009)
Pereiro, A.B., Rodriguez, A.: Purification of hexane with effective extraction using ionic liquid as solvent. Green Chem. 11, 346–350 (2009)
Corderi, S., Gonzalez, B.: Ethanol extraction from its azeotropic mixture with hexane employing different ionic liquids as solvents. Chem. Thermodyn. 55, 138–143 (2012)
Seoane, R.G., Gonzalez, E.J., Gonzalez, B.: 1-Alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids as solvents in the separation of azeotropic mixtures. J. Chem. Thermodyn. 53, 152–157 (2012)
Letcher, T.M., Deenadayalu, N., Soko, B., Ramjugernath, D., Naicker, P.K.: Ternary liquid–liquid equilibria for mixtures of 1-methyl-3-octyl-imidazolium chloride + an alkanol + an alkane at 298.2 K and 1 atm. J. Chem. Eng. Data 48, 904–907 (2003)
Renon, H., Prausnitz, J.M.: Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 14, 135–144 (1968)
Othmer, D., Tobias, P.: Liquid–liquid extraction data—the line correlation. Ind. Eng. Chem. 34, 693–696 (1942)
Hand, D.B.: Dineric distribution. J. Phys. Chem. 34, 1961–2000 (1930)
Pereiro, A.B., Canosa, J., Rodriguez, A.: Liquid–liquid equilibria of 1,3-dimethylimidazolium methyl sulfate with ketones, dialkyl carbonates and acetates. Fluid Phase Equilb. 254, 150–157 (2007)
Pereiro, A.B., Rodriguez, A.: Ternary (liquid + liquid) equilibria of the azeotrope (ethyl acetate + 2-propanol) with different ionic liquids at T = 298.15 K. J. Chem. Thermodyn. 39, 1608–1613 (2007)
Tomé, L.I.N., Carvalho, P.J., Freire, M.G., Marrucho, I.M., Fonseca, I.M.A., Ferreira, A.G.M., Coutinho, J.A.P., Gardas, R.L.: Measurements and correlation of high pressure densities of imidazolium-based ionic liquids. J. Chem. Eng. Data 53, 1914–1921 (2008)
Acre, A., Rodríguez, H., Soto, A.: Use of a green and cheap ionic liquid to purify gasoline octane boosters. Green Chem. 9, 247–253 (2007)
Requejo, P.F., Gonzalez, E.J., Macedo, E.A., Dominguez, A.: Effect of the temperature on the physical properties of the pure ionic liquids on 1-ethyl-3methyl imidazolium methyl sulfate and characterisation of its binary mixtures with alcohols. J. Chem. Thermodyn. 74, 193–200 (2014)
Matsuda, H., Ochi, K.: Liquid–liquid equilibrium data for binary alcohol + n-alkane (C10–C16) systems: methanol + decane, ethanol + tetradecane, and ethanol + hexadecane. Fluid Phase Equil. 224, 31–37 (2004)
Atkins, M.P., Manan, N.A., Jacquemin, J., Hardacre, C., Rooney, D.: Phase equilibria of binary and ternary systems containing ILs, dodecane, and cyclohexane carboxylic acid. Sep. Sci. Technol. 47, 312–324 (2012)
Crosthwaite, J.M., Aki, S.N.V.K., Maginn, E.J., Brennecke, J.F.: Liquid-phase behaviour of imidazolium-based ionic liquids with alcohols. J. Phys. Chem. B 108, 5113–5119 (2004)
Chapeaux, A., Simoni, L.D., Stadtherr, M.A., Brennecke, J.F.: Liquid phase behavior of ionic liquids with water and 1-octanol and modeling of 1-octanol/water partition coefficients. J. Chem. Eng. Data 52, 2462–2467 (2007)
Garcia, J., Fernandez, A., Torrecilla, J.S., Oliet, M., Rodriguez, F.: Liquid–liquid equilibria for hexane + benzene + 1-ethyl-3-methylimidazolium ethylsulfate at (298.2, 313.2 and 328.2) K. Fluid Phase Equilib. 282, 117–120 (2009)
Garcia, J., Fernandez, A., Torrecilla, J.S., Oliet, M., Rodriguez, F.: Ternary liquid–liquid equilibria measurement for hexane and benzene with the ionic liquid 1-butyl-3-methylimidazolium methylsulfate at T = (298.2, 313.2, and 328.2) K. J. Chem. Eng. Data 55, 258–261 (2010)
Lu, Y., Yang, X., Luo, G., Yang, X.C., Luo, G.S.: Liquid–liquid equilibria for benzene plus cyclohexane + 1-butyl-3-methylimidazolium hexafluorophosphate. J. Chem. Eng. Data 55, 510–512 (2010)
Gonzalez, E.J., Calvar, N., Gomez, E., Dominguez, A.: Separation of benzene from alkanes using 1-ethyl-3-methylpyridinium ethylsulfate ionic liquid at several temperatures and atmospheric pressure: effect of the size of the aliphatic hydrocarbons. J. Chem. Thermodyn. 42, 104–109 (2010)
Santiago, R.S., Aznar, M.: Liquid–liquid equilibrium in ternary ionic liquid systems by UNIFAC: new volume, surface area and interaction parameters. Part II. Fluid Phase Equilib. 303, 111–114 (2011)
Acknowledgments
The authors would like to thank the National Research Foundation (NRF) through the Thuthuka program and the SARChI South African Research Chairs Initiative - NRF-DST for their financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mungar Ram, N., Bahadur, I., Letcher, T.M. et al. Liquid–Liquid Equilibria for Mixtures of Hexadecane and Ethanol with Imidazolium-Based Ionic Liquids. J Solution Chem 44, 593–605 (2015). https://doi.org/10.1007/s10953-015-0294-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10953-015-0294-4