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The Volumetric and Transport Properties of 1-Ethyl-3-Methylimidazolium Trifluoromethanesulfonate Ionic Liquid and Propylene Carbonate Binary System

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Abstract

In the present work, a new binary mixture system composed of the ionic liquid 1-ethyl-3-methylimidazolium trifluoromethanesulfonate ([Emim][CF3SO3]) and propylene carbonate (PC) was prepared. The densities, dynamic viscosities, and electrical conductivities of ([Emim][CF3SO3] + PC) were measured over the whole concentration range (mole fractions of IL from 0 to 1) for temperatures from 288.15 to 353.15 K. The excess molar volumes (VE) and viscosity deviations (Δη) of the binary systems were calculated to characterize the volume contraction and intermolecular interactions in the mixture system, and both were correlated with the Redlich–Kister polynomial equation. The Vogel–Fulcher–Tamman equation was used to describe the temperature dependences of the dynamic viscosities and the electrical conductivities of the binary system. Further, density functional theory calculations were employed to obtain the structure, energy, and COSMO charge distributions of the cation and anion of the IL and the PC molecule, and the intermolecular interactions in the binary mixture system were evaluated.

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References

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

    Article  CAS  PubMed  Google Scholar 

  2. Ye, C., Liu, W., Chen, Y., Yu, L.: Room-temperature ionic liquids: a novel versatile lubricant. Chem. Commun. 21, 2244–2245 (2001)

    Article  CAS  Google Scholar 

  3. Plechkova, N.V., Seddon, K.R.: Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 37, 123–150 (2008)

    Article  CAS  PubMed  Google Scholar 

  4. MacFarlane, D.R., Forsyth, M., Howlett, P.C., Pringle, J.M., Sun, J.Z., Annat, G., Neil, W., Izgorodina, E.I.: Ionic liquids in electrochemical devices and processes: managing interfacial electrochemistry. Acc. Chem. Res. 40, 1165–1173 (2007)

    Article  CAS  PubMed  Google Scholar 

  5. Requejo, P., González, E., Macedo, E., Domínguez, Á.: Effect of the temperature on the physical properties of the pure ionic liquid 1-ethyl-3-methylimidazolium methylsulfate and characterization of its binary mixtures with alcohols. J. Chem. Thermodyn. 74, 193–200 (2014)

    Article  CAS  Google Scholar 

  6. Zhong, Y., Wang, H., Diao, K.: Densities and excess volumes of binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate with aromatic compound at T = (298.15 to 313.15) K. J. Chem. Thermodyn. 39, 291–296 (2007)

    Article  CAS  Google Scholar 

  7. Zhao, H., Song, Z.Y., Olubajo, O.: High transesterification activities of immobilized proteases in new ether-functionalized ionic liquids. Biotechnol. Lett. 32, 1109–1116 (2010)

    Article  CAS  PubMed  Google Scholar 

  8. Buriol, L., Frizzo, C.P., Prola, L.D., Moreira, D.N., Marzari, M.R., Scapin, E., Zanatta, N., Bonacorso, H.G., Martins, M.A.: Synergic effects of ionic liquid and microwave irradiation in promoting trifluoromethylpyrazole synthesis. Catal. Lett. 141, 1130–1135 (2011)

    Article  CAS  Google Scholar 

  9. Munoz, M., Domínguez, C.M., de Pedro, Z.M., Quintanilla, A., Casas, J.A., Rodriguez, J.J.: Ionic liquids break down by Fenton oxidation. Catal. Today 240, 16–21 (2015)

    Article  CAS  Google Scholar 

  10. Liang, X.: Synthesis of a cross linked polymer with a benzyl(triphenyl)phosphonium ionic liquid moiety and its catalytic activity. RSC Adv. 120, 99448–99453 (2015)

    Article  CAS  Google Scholar 

  11. Li, H.N., Wang, Z., Chen, L.C., Wu, J., Huang, H.J., Yang, K., Wang, Y.Q., Su, L., Yang, G.: Kinetic effect on pressure-induced phase transitions of room temperature ionic liquid, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. J. Phys. Chem. B 119, 14245–14251 (2015)

    Article  CAS  PubMed  Google Scholar 

  12. Singh, D.K., Rathke, B., Kiefer, J., Materny, A.: Materny, molecular structure and interactions in the ionic liquid 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. J. Phys. Chem. A 120, 6274–6286 (2016)

    Article  CAS  PubMed  Google Scholar 

  13. Vercher, E., Orchillés, A.V., Llopis, F.J., González-Alfaro, V., Martínez-Andreu, A.: Ultrasonic and volumetric properties of 1-ethyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid with 2-propanol or tetrahydrofuran at several temperatures. J. Chem. Eng. Data 56, 4633–4642 (2011)

    Article  CAS  Google Scholar 

  14. Podgoršek, A., Jacquemin, J., Pádua, A.A.H., Gomes, M.F.C.: Mixing enthalpy for binary mixtures containing ionic liquids. Chem. Rev. 116, 6075–6106 (2016)

    Article  CAS  PubMed  Google Scholar 

  15. Reddy, M.S., Raju, K.T.S., Rao, A.S., Sharmila, N., Babu, B.H.: Study of thermophysical properties of the binary mixtures of ionic liquid 1-ethyl-3-methylimidazolium ethylsulfate and 2-propoxyethanol from T = (298.15 to 328.15) K at atmospheric pressure. J. Chem. Thermodyn. 101, 139–149 (2016)

    Article  CAS  Google Scholar 

  16. Sanchez, L.G., Espel, J.R., Onink, F., Meindersma, G.W., Haan, A.B.D.: Density, viscosity, and surface tension of synthesis grade imidazolium, pyridinium, and pyrrolidinium based room temperature ionic liquids. J. Chem. Eng. Data 54, 2803–2812 (2009)

    Article  CAS  Google Scholar 

  17. Anouti, M., Vigeant, A., Jacquemin, J., Brigouleix, C., Lemordant, D.: Volumetric properties, viscosity and refractive index of the protic ionic liquid, pyrrolidiniumoctanoate, in molecular solvents. J. Chem. Thermodyn. 42, 834–845 (2010)

    Article  CAS  Google Scholar 

  18. Vercher, E., Miguel, P.J., Llopis, F.J., Orchillés, A.V., Martínez-Andreu, A.: 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 

  19. Wolff, C., Jeong, S., Paillard, E., Balducci, A., Passerini, S.: High power, solvent-free electrochemical double layer capacitors based on pyrrolidinium dicyanamide ionic liquids. J. Power Sources 293, 65–70 (2015)

    Article  CAS  Google Scholar 

  20. Zhang, T., Fuchs, B., Secchiaroli, M., Wohlfahrt-Mehrens, M., Dsoke, S.: Electrochemical behavior and stability of a commercial activated carbon in various organic electrolyte combinations containing Li-salts. Electrochim. Acta 218, 163–173 (2016)

    Article  CAS  Google Scholar 

  21. Sekiguchi, K., Atobe, M., Fuchigami, T.: Electrooxidative polymerization of aromatic compounds in 1-ethyl-3-methylimidazolium trifluoromethanesulfonate room-temperature ionic liquid. J. Electroanal. Chem. 557, 1–7 (2003)

    Article  CAS  Google Scholar 

  22. Zhang, Q.G., Wang, N.N., Wang, S.L., Yu, Z.W.: Hydrogen bonding behaviors of binary systems containing the ionic liquid 1-butyl-3-methylimidazolium trifluoroacetate and water/methanol. J. Phys. Chem. B 115, 11127–11136 (2011)

    Article  CAS  PubMed  Google Scholar 

  23. Zhang, Q.G., Wang, N.N., Wang, S.L., Yu, Z.W.: The thermodynamic estimation and viscosity, electrical conductivity characteristics of 1-alkyl-3-methylimidazolium thiocyanate ionic liquids. Z. Phys. Chem. 228, 851–867 (2014)

    CAS  Google Scholar 

  24. Zhang, Q.G., Xu, T.T., Zhang, X.Y., Yang, H.G., Zhang, W.B.: The thermodynamic and excess properties of trialkyl-substituted imidazolium-based ionic liquids with thiocyanate and its binary systems with acetonitrile. J. Chem. Eng. Data 63, 1408–1418 (2018)

    Article  CAS  Google Scholar 

  25. Vieira, N.S.M., Luis, A., Reis, P.M., Carvalho, P.J., Lopes-da-Silva, J.A., Esperanca, J.M.S.S., Araújo, J.M.M., Rebelo, L.P.N., Freire, M.G., Pereiro, A.B.: Fluorination effects on the thermodynamic, thermophysical and surface properties of ionic liquids. J. Chem. Thermodyn. 97, 354–361 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Putnam, R., Taylor, R., Klamt, A., Eckert, F., Schiller, M.: Prediction of infinite dilution activity coefficients using COSMO-RS. Ind. Eng. Chem. Res. 42, 3635–3641 (2003)

    Article  CAS  Google Scholar 

  27. Turbomole, a development of university of Karlsruhe and Forschungszentrum Karlsruhe GmbH v6.6 2014; TURBOMOLE GmbH: 2007; available from http://www.turbomole.com. Order date: 10-11-2014 (permanent license)

  28. Jacquemin, J., Feder-Kubis, J., Zorębski, M., Grzybowska, K., Chorążewski, M., Hensel-Bielówka, S., Zorebski, E., Paluch, M., Dzida, M.: Structure and thermal properties of salicylate-based-protic ionic liquids as new heat storage media COSMO-RS structure characterization and modeling of heat capacities. Phys. Chem. Chem. Phys. 16, 3549–3557 (2014)

    Article  CAS  PubMed  Google Scholar 

  29. Nockemann, P., Thijs, B., Pittois, S., Thoen, J., Glorieux, C., Van Hecke, K., Van Meervelt, L., Kirchner, B., Binnemans, K.: Task-specific ionic liquid for solubilizing metal oxides. J. Phys. Chem. B 110, 20978–20992 (2006)

    Article  CAS  PubMed  Google Scholar 

  30. Reddy, M.S., Khan, I., Raju, K.T.S., Suresh, P., Babu, B.H.: The study of molecular interactions in 1-ethyl-3-methylimidazolium trifluoromethanesulfonate + 1-pentanol from density, speed of sound and refractive index measurements. J. Chem. Thermodyn. 98, 298–308 (2016)

    Article  CAS  Google Scholar 

  31. Zhang, Z.B., Zhou, Q., Lu, X.M., Qiao, C.Z., Zhang, S.J.: Densities and viscosities of binary mixtures containing 1,3-dimethylimidazolium dimethylphosphate and alcohols. J. Chem. Eng. Data 59, 2377–2388 (2014)

    Article  CAS  Google Scholar 

  32. Zhang, Q.G., Cai, S.Y., Zhang, W.B., Lan, Y.Y., Zhang, X.Y.: Density, viscosity, conductivity, refractive index and interaction study of binary mixtures of the ionic liquid 1-ethyl-3-methylimidazolium acetate with methyldiethanolamine. J. Mol. Liq. 233, 471–478 (2017)

    Article  CAS  Google Scholar 

  33. Castro, M.C., Arce, A., Soto, A., Rodríguez, H.: Thermophysical characterization of the mixtures of the ionic liquid 1-ethyl-3-methylimidazolium acetate with 1-propanol or 2-propanol. J. Chem. Eng. Data 61, 2299–2310 (2016)

    Article  CAS  Google Scholar 

  34. Jänes, A., Eskusson, J., Thomberg, T., Romann, T., Lust, E.: Ionic liquid-1,2-dimethoxyethane mixture as electrolyte for high power density supercapacitors. J. Energy Chem. 25, 609–614 (2016)

    Article  Google Scholar 

  35. Xu, L., Cui, X.B., Zhang, Y., Feng, T.Y., Lin, R.R., Li, X.B., Jie, H.M.: Measurement and correlation of electrical conductivity of ionic liquid [EMIM][DCA] in propylene carbonate and γ-butyrolactone. Electrochim. Acta 174, 900–907 (2015)

    Article  CAS  Google Scholar 

  36. Liu, Q.S., Li, P.P., Welz-Biermann, U., Chen, J., Liu, X.X.: Density, dynamic viscosity, and electrical conductivity of pyridinium-based hydrophobic ionic liquids. J. Chem. Thermodyn. 66, 88–94 (2013)

    Article  CAS  Google Scholar 

  37. Domańska, U., Królikowska, M.: Density and viscosity of binary mixtures of {1-butyl-3-methylimidazolium thiocyanate + 1-heptanol, 1-octanol, 1-nonanol, or 1-decanol}. J. Chem. Eng. Data 55, 2994–3004 (2010)

    Article  CAS  Google Scholar 

  38. Zhang, L.F., Lu, X.X., Ye, D.F., Guo, Y.S., Fang, W.J.: Density and viscosity for binary mixtures of the ionic liquid 2,2-diethyl-1,1,3,3-tetramethylguanidinium ethyl sulfate with water, methanol, or ethanol. J. Chem. Eng. Data 61, 1023–1031 (2016)

    Article  CAS  Google Scholar 

  39. Qian, W., Xu, Y.J., Zhu, H.Y., Yu, C.H.: Properties of pure 1-methylimidazoliumacetate ionic liquid and its binary mixtures with alcohols. J. Chem. Thermodyn. 49, 87–94 (2012)

    Article  CAS  Google Scholar 

  40. Zheng, Y.Z., Zhou, Y., Deng, G., Yu, Z.W.: Hydrogen-bonding interactions between a nitrile-based functional ionic liquid and DMSO. J. Mol. Struct. 1124, 207–215 (2016)

    Article  CAS  Google Scholar 

  41. Zhang, X.C., Huo, F., Liu, X.M., Dong, K., He, H.Y., Yao, X.Q., Zhang, S.J.: Influence of microstructure and interaction on viscosity of ionic liquids. Ind. Eng. Chem. Res. 54, 3505–3514 (2015)

    Article  CAS  Google Scholar 

  42. He, H.Y., Chen, H., Zheng, Y.Z., Zhang, S.J., Yu, Z.W.: Hydrogen-bonding interactions between a pyridinium-based ionic liquid [C4Py][SCN] and dimethyl sulfoxide. Chem. Eng. Sci. 121, 169–179 (2015)

    Article  CAS  Google Scholar 

  43. Fox, E.T., Paillard, E., Borodin, O., Henderson, W.A.: Physicochemical properties of binary ionic liquid–aprotic solvent electrolyte mixtures. J. Phys. Chem. C 117, 78–84 (2012)

    Article  CAS  Google Scholar 

  44. Aranowski, R., Cichowska-Kopczyńska, I., Dębski, B., Jasiński, P.: Conductivity and viscosity changes of imidazolium ionic liquids induced by H2O and CO2. J. Mol. Liq. 221, 541–546 (2016)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was financially supported by the National Nature Science Foundation of China (Nos. 21503020 and 21373002), the Nature Science Foundation of Liaoning Province (No. 201602016), the Doctoral Fund of Liaoning Province of China (No. 201601347), and Program for Liaoning Excellent Talents in University, China (LJQ2015099).

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Wei, Y., Zhang, W., Zhang, X. et al. The Volumetric and Transport Properties of 1-Ethyl-3-Methylimidazolium Trifluoromethanesulfonate Ionic Liquid and Propylene Carbonate Binary System. J Solution Chem 48, 125–141 (2019). https://doi.org/10.1007/s10953-019-00842-w

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