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Interaction of 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate with Ethyl Acetate/1-Butanol: Thermophysical Properties

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Abstract

Densities, speeds of sound and viscosities of pure and the binary mixtures of [BMIM][CF3SO3] + ethyl acetate or 1-butanol have been measured over the entire range of mole fractions at T = (298.15–323.15) K and at 0.1 MPa pressure using an Anton Paar density and sound velocity meter DSA 5000M and a Lovis microviscometer 2000M. The excess molar volumes (V E), viscosity deviations (Δη) and the isentropic compressibility deviations (Δκ S ) have been calculated using the experimental data. The variations in V E, Δη and Δκ S with changes in mole fraction and temperature have been interpreted in terms of ion–dipole interactions and structural effects on mixing of IL and solvents. The Redlich–Kister equation has been fitted to the V E, Δη and Δκ S values using a multi-parametric nonlinear regression method. The PFP theory has been applied to correlate the excess molar volumes. The experimental and PFP correlated values of V E are found to be quite close to each other.

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References

  1. Abdulagatov, I.M., Tekin, A., Safarov, J., Shahverdiyev, A., Hassel, E.: High-pressure densities and derived volumetric properties (excess, apparent and partial molar volumes) of binary mixtures of methanol + [BMIM][PF6]. J. Solution Chem. 37, 801–833 (2008)

    Article  CAS  Google Scholar 

  2. Holbrey, J.D., Seddon, K.R.: The phase behavior of 1-alkyl-3-methylimidazolium tetra-fluoroborates, ionic liquids and ionic liquid crystals. J. Chem. Soc. Dalton Trans. 2133–2139 (1999)

  3. Ciocirlan, O., Iulian, O.: Properties of pure 1-butyl-2,3-dimethylimidazolium tetrafluoro-borate ionic liquid and its binary mixtures with dimethyl sulfoxide and acetonitrile. J. Chem. Eng. Data 57, 3142–3148 (2012)

    Article  CAS  Google Scholar 

  4. Welton, T.: Room-temperature ionic liquids, solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2084 (1999)

    Article  CAS  Google Scholar 

  5. Kumar, A., Pawar, S.: Converting exoselective Diels–Alder reaction to endoselective in chloroloaluminate ionic liquids. J. Org. Chem. 69, 1419–1420 (2004)

    Article  CAS  Google Scholar 

  6. Freemantle, M.: Designer solvents: ionic liquids may boost clean technology development. Chem. Eng. News 76, 32–37 (1998)

    Article  Google Scholar 

  7. Fletcher, K., Pandey, S.: Surfactant aggregation within room temperature ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide. Langmuir 20, 33–36 (2004)

    Article  CAS  Google Scholar 

  8. Zhao, D., Wu, M., Kou, Y., Min, E.: Ionic liquids: Applications in catalysis. Catal. Today 74, 157–189 (2002)

    Article  CAS  Google Scholar 

  9. 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)

    Article  CAS  Google Scholar 

  10. González, E.J., Domínguez, Á., Macedo, E.A.: Physical and excess properties of eight binary mixtures containing water and ionic liquids. J. Chem. Eng. Data 57, 2165–2176 (2012)

    Article  Google Scholar 

  11. Klomfar, J., Souckova, M., Patek, J.: Temperature dependence measurements of the density at 0.1 MPa for 1-alkyl-3-methylimidazolium-based liquids with the trifluoromethane-sulfonate and tetrafluoroborate anion. J. Chem. Eng. Data 55, 4054–4057 (2010)

    Article  CAS  Google Scholar 

  12. Ge, M.L., Zhao, R.S., Yi, Y.F., Zhang, Q., Wang, L.S.: Densities and viscosities of 1-butyl-3-methylimidazolium trifluoromethanesulfonate + H2O binary mixtures at T = (303.15 to 343.15) K. J. Chem. Eng. Data 53, 2408–2411 (2008)

    Article  CAS  Google Scholar 

  13. Miaja, G.G., Troncoso, J., Romani, L.: Excess enthalpy, density and heat capacity for binary systems of alkylimidazolium-based ionic liquids + water. J. Chem. Thermodyn. 41, 161–166 (2009)

    Article  Google Scholar 

  14. Vercher, E., Llopis, F.J., Alez-Alfaro, V.G., Miguel, P.J., Andreu, A.M.: Refractive indices and deviations in refractive indices of trifluoromethanesulfonate-based ionic liquids in water. J. Chem. Eng. Data 56, 4499–4504 (2011)

    Article  CAS  Google Scholar 

  15. Tokuda, H., Hayamizu, K., Ishii, K., Susan, M.A.B.H., Watanabe, M.: Physicochemical properties and structures of room temperature ionic liquids: 1. Variation of anionic species. J. Phys. Chem. B 108, 16593–16600 (2004)

    Article  CAS  Google Scholar 

  16. Miaja, G.G., Troncoso, J., Romani, L.: Excess properties for binary systems ionic liquid + ethanol: experimental results and theoretical description using the ERAS model. Fluid Phase Equilib. 274, 59–67 (2008)

    Article  Google Scholar 

  17. Shamsipura, M., Beigi, A.A.M., Teymouri, M., Pourmortazavi, S.M., Irandoust, M.: Physical and electrochemical properties of ionic liquids 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate and 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide. J. Mol. Liquids 157, 43–50 (2010)

    Article  Google Scholar 

  18. Miaja, G.G., Troncoso, J., Romaní, L.: Excess molar properties for binary systems of alkylimidazolium-based ionic liquids + nitromethane: experimental results and ERAS-model calculations. J. Chem. Thermodyn. 41, 334–341 (2009)

    Article  Google Scholar 

  19. Zech, O., Stoppa, A., Buchner, R., Kunz, W.: The conductivity of imidazolium-based ionic liquids from (248 to 468) K. B. Variation of the anion. J. Chem. Eng. Data 55, 1774–1778 (2010)

    Article  CAS  Google Scholar 

  20. Seddon, K.R., Stark, A., Torres, M.J.: Viscosity and density of 1-alkyl-3-methyl-imidazolium ionic liquids. Am. Chem. Soc. Symp. Ser. 819, 34–49 (2002)

    CAS  Google Scholar 

  21. Arce, A., Rodriguez, O., Soto, A.: Tert-amyl ethyl-ether separation from its mixtures with ethanol using the 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid: liquid–liquid equilibrium. Ind. Eng. Chem. Res. 43, 8323–8327 (2004)

    Article  CAS  Google Scholar 

  22. Gardas, R.L., Freire, M.G., Carvalho, P.J., Marrucho, I.M., Fonseca, I.M.A., Ferreira, A.G.M., Coutinho, J.A.P.: High-pressure densities and derived thermodynamic properties of imidazolium-based ionic liquids. J. Chem. Eng. Data 52, 80–88 (2007)

    Article  CAS  Google Scholar 

  23. Vercher, E., Miguel, P.J., Llopis, F.J., Orchillés, A.V., Andreu, A.M.: Volumetric and acoustic properties of aqueous solutions of trifluoromethanesulfonate based ionic liquids at several temperatures. J. Chem. Eng. Data 57, 1953–1963 (2012)

    Article  CAS  Google Scholar 

  24. Djojoputro, H., Ismadji, S.: Density and viscosity correlation for several common fragrance and flavor esters. J. Chem. Eng. Data 50, 727–731 (2005)

    Article  CAS  Google Scholar 

  25. Mokhtarani, B., Sharifi, A., Mortaheb, H.R., Mirzaei, M., Mafi, M., Sadeghian, F.: Density and viscosity of 1-butyl-3-methylimidazolium nitrate with ethanol, 1-propanol, or 1-butanol at several temperatures. J. Chem. Thermodyn. 41, 1432–1438 (2009)

    Article  CAS  Google Scholar 

  26. Acosta, J., Arce, A., Rodil, E., Soto, A.: Densities, speeds of sound, refractive indices, and the corresponding changes of mixing at 25 °C and atmospheric pressure for systems composed of ethyl acetate, hexane, and acetone. J. Chem. Eng. Data 46, 1176–1180 (2001)

    Article  CAS  Google Scholar 

  27. Aminabhavi, T.M., Aralaguppi, M.I., Harogoppad, S.B., Balundgri, R.H.: Densities, viscosities, refractive indices, and speeds of sound for methyl acetoacetate + aliphatic alcohols (C1–C8). J. Chem. Eng. Data 38, 31–39 (1993)

    Article  CAS  Google Scholar 

  28. Gonzalez, E.J., Calvar, N., Dominguez, A., Macedo, E.A.: Osmotic and apparent molar properties of binary mixtures alcohol + 1-butyl-3-methylimidazolium trifluoromethane-sulfonate ionic liquid. J. Chem. Thermodyn. 61, 64–73 (2013)

    Article  CAS  Google Scholar 

  29. Chirico, R.D., Frenkel, M., Magee, J.W., Diky, V., Muzny, C.D., Kazakov, A.F., Kroenlein, K., Abdulagatov, I., Hardin, G.R., Acree Jr., W.E., Brenneke, J.F., Brown, P.L., Cummings, P.T., de Loos, T.W., Friend, D.G., Goodwin, A.R.H., Hansen, L.D., Haynes, W.M., Koga, N., Mandelis, A., Marsh, K.N., Mathias, P.M., McCabe, C., O’Connell, J.P., Padua, A., Rives, V., Schick, C., Trusler, J.P.M., Vyazovkin, S., Weir, R.D., Wu, J.: Improvement of quality in publication of experimental thermophysical property data: challenges, assessment tools, global implementation, and online support. J. Chem. Eng. Data 58, 2699–2716 (2013)

    Article  CAS  Google Scholar 

  30. Tejraj, M.A.: Thermodynamic interactions in binary mixture of ethyenyl benzene with methanol, ethanol, butan-1-ol in the temperature range 298.15–308.15 K. J. Chem. Eng. Data 44, 1291–1297 (1999)

    Article  Google Scholar 

  31. Gonzalez, B., Calvar, N., Gonzalez, E., Dominguez, A.: Density and viscosity experimental data of the ternary mixtures 1-propanol or 2-propanol + water + 1-ethyl-3-methylimidazolium ethylsulfate. Correlation and prediction of physical properties of the ternary systems. J. Chem. Eng. Data 53, 881–887 (2008)

    Article  CAS  Google Scholar 

  32. Pereiro, A.B., Rodriguez, A.: Study on the phase behavior and thermodynamic properties of ionic liquids containing imidazolium cation with ethanol at several temperatures. J. Chem. Thermodyn. 39, 978–989 (2007)

    Article  CAS  Google Scholar 

  33. Yao, H., Zhang, S., Wang, J., Zhou, Q., Dong, H., Zhang, X.: Densities and viscosities of the binary mixtures of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide with N-methyl-2-pyrrolidone or ethanol at T = (293.15 to 323.15) K. J. Chem. Eng. Data 57, 875–881 (2012)

    Article  CAS  Google Scholar 

  34. Redlich, O., Kister, A.T.: Algebraic representation of thermodynamic properties and the classification of solutions. Ind. Eng. Chem. 40, 345–348 (1948)

    Article  Google Scholar 

  35. Patterson, D., Delmas, G.: Corresponding states theories and liquid models. Discuss. Faraday Soc. 49, 98–105 (1970)

    Article  Google Scholar 

  36. Zafarani-Moattar, M.T., Shekaari, H.: Application of Prigogine–Flory–Patterson theory to excess molar volume and speed of sound of 1-n-butyl-3-methylimidazolium hexafluoro-phosphate or 1-n-butyl-3-methylimidazolium tetrafluoroborate in methanol, and acetonitrile. J. Chem. Thermodyn. 38, 1377–1384 (2006)

    Article  CAS  Google Scholar 

  37. Kermanpour, F., Niakan, H.Z.: Measurement and modeling the excess molar properties of binary mixtures of [C6mim][BF4] + 3-amino-1-propanol and {[C6mim][BF4] + isobutanol}: application of Prigogine–Flory–Patterson theory. J. Chem. Thermodyn. 48, 129–139 (2012)

    Article  CAS  Google Scholar 

  38. Vercher, E., Llopis, F.J., Gonzalez-Alfaro, M.V., Andreu, A.M.: Density, speed of sound, and refractive index of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate with acetone, methyl acetate, and ethyl acetate at temperatures from (278.15 to 328.15) K. J. Chem. Eng. Data 55, 1377–1388 (2010)

    Article  CAS  Google Scholar 

  39. Flory, P.J.: Statistical thermodynamics of liquid mixtures. J. Am. Chem. Soc. 87, 1833–1838 (1965)

    Article  CAS  Google Scholar 

  40. Abe, A., Flory, P.J.: The thermodynamic properties of mixtures of small, non-polar molecules. J. Am. Chem. Soc. 87, 1838–1846 (1965)

    Article  CAS  Google Scholar 

  41. Vercher, E., Orchilles, A.V., Miguel, P.J., Andreu, A.M.: Volumetric and ultrasonic studies of 1-Ethyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid with methanol, ethanol, 1-propanol, and water at several temperatures. J. Chem. Eng. Data 52, 1468–1482 (2007)

    Article  CAS  Google Scholar 

  42. Daubert, T.E., Danner, R.P., Sibul, H.M., Stebbins, C.C.: Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation. DIPPR/AIChE. Taylor & Francis, Washington, DC (1998)

    Google Scholar 

  43. Zorebski, E., Góralski, P., Godula, B., Zorebski, M.: Thermodynamic and acoustic properties of binary mixtures of 1-butanol with 1,2-butanediol. The comparison with the results for 1,3- and 1,4-butanediol. J. Chem. Thermodyn. 68, 145–152 (2014)

    Article  CAS  Google Scholar 

  44. Diedrichs, A., Gmehling, J.: Measurement of heat capacities of ionic liquids by differential scanning calorimetry. Fluid Phase Equilib. 244, 68–77 (2006)

    Article  CAS  Google Scholar 

  45. Lin, P.Y., Soriano, A.N., Caparanga, A.R., Li, M.H.: Molar heat capacity and electrolytic conductivity of aqueous solutions of [Bmim][MeSO4] and [Bmim][triflate]. Thermochim. Acta 496, 105–109 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are thankful to the Chairman, Department of Chemistry, A.M.U., Aligarh for providing the necessary facilities for the compilation of this work. Financial support from the UGC (Major Research Project) F. No. 41-240/2012(SR) scheme is acknowledged.

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Anwar, N., Riyazuddeen Interaction of 1-Butyl-3-methylimidazolium Trifluoromethanesulfonate with Ethyl Acetate/1-Butanol: Thermophysical Properties. J Solution Chem 45, 1077–1094 (2016). https://doi.org/10.1007/s10953-016-0490-x

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