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Volumetric Properties of Binary Mixtures of the Ionic Liquid 1-Butyl-3-Methylimidazolium Tetrafluoroborate with Aniline

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Abstract

The densities of binary mixtures of an ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF4], with an aromatic compound, aniline, have been determined over the full range of compositions and over the temperature range 298.15 to 313.15 K at atmospheric pressure using a vibrating-tube densimeter (DMA4500). Excess molar volumes ( \(V_{\mathrm{m}}^{\mathrm{E}}\) ) have been obtained from these experimental results, and were fitted by the fourth-order Redlich–Kister equation. In addition, partial molar volumes, apparent molar volumes and partial molar volumes at infinite dilution have been calculated for each component. Our results show that values of \(V_{\mathrm{m}}^{\mathrm{E}}\) decrease slightly when the temperature increases in this system. The results have been interpreted in terms of ion-dipole interactions and structural factors of the ionic liquid and the organic molecular liquid.

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References

  1. Brennecke, J.F., Maginn, E.J.: Ionic liquids: Innovative fluids for chemical processing. AIChE J. 47, 2384–2389 (2001)

    Article  CAS  Google Scholar 

  2. Earle, M.J., Seddon, K.R.: Ionic liquids. Green solvents for the future. Pure Appl. Chem. 72, 1391–1398 (2000)

    Article  CAS  Google Scholar 

  3. 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)

    Article  CAS  Google Scholar 

  4. Sheldon, R.: Catalytic reactions in ionic liquids. Chem. Commun. 23, 2399–2407 (2001)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Wasserscheid, P., Keim, W.: Ionic liquids—new “solutions” for transition metal catalysis. Angew. Chem., Int. Ed. 39, 3772–3789 (2000)

    Article  CAS  Google Scholar 

  7. Wilkes, J.S.: Properties of ionic liquid solvents for catalysis. J. Mol. Catal. A 214, 11–17 (2004)

    Article  CAS  Google Scholar 

  8. Koch, V.R., Dominey, L.A., Nanjundiah, C.: The intrinsic anodic stability of several anions comprising solvent-free ionic liquids. J. Electrochem. Soc. 143, 798–803 (1996)

    Article  CAS  Google Scholar 

  9. Every, H., Bishop, A.G., Forsyth, M., MacFarlane, D.R.: Ion diffusion in molten salt mixtures. Electrochim. Acta 45, 1279–1284 (2000)

    Article  CAS  Google Scholar 

  10. Doyle, M., Choi, S.K., Proulx, G.: High-temperature proton conducting membranes based on perfluorinated ionomer membrane-ionic liquid composites. J. Electrochem. Soc. 147, 34–37 (2000)

    Article  CAS  Google Scholar 

  11. Sheldon, R.A., Lau, R.M., Sorgedrager, M.J., van Rantwijk, F., Seddon, K.R.: Biocatalysis in ionic liquids. Green Chem. 4, 147–151 (2002)

    Article  CAS  Google Scholar 

  12. Najdanovic-Visak, V., Esperanca, J.M.S.S., Rebelo, L.P.N., da Ponte, M.N., Guedes, H.J.R., Seddon, K.R., Szydlowski, J.: Phase behaviour of room temperature ionic liquid solutions: an unusually large co-solvent effect in (water + ethanol). Phys. Chem. Chem. Phys. 4, 1701–1703 (2002)

    Article  CAS  Google Scholar 

  13. Marczak, W., Verevkin, S.P., Heintz, A.: Enthalpies of solution of organic solutes in the ionic liquid 1-methyl-3-ethyl-imidazolium bis-(trifluoromethyl-sulfonyl) amide. J. Solution Chem. 32, 519–526 (2003)

    Article  CAS  Google Scholar 

  14. Heintz, A., Kulikov, D.V., Verevkin, S.P.: Thermodynamic properties of mixtures containing ionic liquids. 1. Activity coefficients at infinite dilution of alkanes, alkenes, and alkylbenzenes in 4-methyl-n-butylpyridinium tetrafluoroborate using gas–liquid chromatography. J. Chem. Eng. Data 46, 1526–1529 (2001)

    Article  CAS  Google Scholar 

  15. Domanska, U., Marciniak, A.: Solubility of ionic liquid [emim][PF6] in alcohols. J. Phys. Chem. B 108, 2376–2382 (2004)

    Article  CAS  Google Scholar 

  16. Kabo, G.J., Blokhin, A.V., Paulechka, Y.U., Kabo, A.G., Shymanovich, M.P., Magee, J.W.: Thermodynamic properties of 1-butyl-3-methylimidazolium hexafluorophosphate in the condensed state. J. Chem. Eng. Data 49, 453–461 (2004)

    Article  CAS  Google Scholar 

  17. Fredlake, C.P., Crosthwaite, J.M., Hert, D.G., Aki, S.N.V.K., Brennecke, J.F.: Thermophysical properties of imidazolium-based ionic liquids. J. Chem. Eng. Data 49, 954–961 (2004)

    Article  CAS  Google Scholar 

  18. Harris, K.R., Woolf, L.A.: Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate. J. Chem. Eng. Data 50, 1777–1782 (2005)

    Article  CAS  Google Scholar 

  19. Branco, L.C., Afnoso, C.A.A.: Ionic liquids as recyclable reaction media for the tetrahydropyranylation of alcohols. Tetrahedron 57, 4405–4410 (2001)

    Article  CAS  Google Scholar 

  20. Zhao, G., Jiang, T., Wu, W., Han, B., Liu, Z., Gao, H.: Electro-oxidation of benzyl alcohol in a biphasic system consisting of supercritical CO2 and ionic liquids. J. Phys. Chem. B 108, 13052–13057 (2004)

    Article  CAS  Google Scholar 

  21. Chandrasekhar, S., Narasihmulu, Ch., Jagadeshwar, V., Venkatram Reddy, K.: The first Corey–Chaykovsky epoxidation and cyclopropanation in ionic liquids. Tetrahedron Lett. 44, 3629–3630 (2003)

    Article  CAS  Google Scholar 

  22. Howarth, J.: Oxidation of aromatic aldehydes in the ionic liquid [bmim]PF6. Tetrahedron Lett. 41, 6627–6629 (2000)

    Article  CAS  Google Scholar 

  23. Jiang, N., Ragauskas, A.J.: TEMPO-catalyzed oxidation of benzylic alcohols to aldehydes with the H2O2/HBr/ionic liquid [bmim]PF6 system. Tetrahedron Lett. 46, 3323–3326 (2005)

    Article  CAS  Google Scholar 

  24. Yadav, J.S., Reddy, B.V.S., Basak, A.K., Venkat Narsaiah, A.: Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents. Tetrahedron 60, 2131–2135 (2004)

    Article  CAS  Google Scholar 

  25. Fonseca, G.S., Scholten, J.D., Dupont, J.: Iridium nanoparticles prepared in ionic liquids: an efficient catalytic system for the hydrogenation of ketones. Synlett 9, 1525–1528 (2004)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  27. Gao, H., Qi, F., Wang, H.: Densities and volumetric properties of binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate with benzaldehyde at T=(298.15 to 313.15) K. J. Chem. Thermodyn. 41, 888–892 (2009)

    Article  CAS  Google Scholar 

  28. Fang, D., Shi, Q.-R., Gong, K., Liu, Z.-L.: Study on green synthesis of 1,3-dialkyl-imidazolium ionic liquids. Huaxue Shiji 29, 4–6 (2007)

    CAS  Google Scholar 

  29. Timmermans, J.: Physico-Chemical Constants of Pure Organic Compounds. Elsevier, Amsterdam (1950)

    Google Scholar 

  30. Wang, J., Tian, Y., Zhao, Y., Zhuo, K.: A volumetric and viscosity study for the mixtures of 1-n-butyl-3-methylimidazolium tetrafluoroborate ionic liquid with acetonitrile, dichloromethane, 2-butanone and N,N-dimethylformamide. Green Chem. 5, 618–622 (2003)

    Article  CAS  Google Scholar 

  31. Takenaka, M., Tanaka, R., Murakami, S.: Determination of the excess volumes of (cyclohexane + benzene) between 293.15 and 303.15 K by use of a vibrating densimeter. J. Chem. Thermodyn. 12, 849–855 (1980)

    Article  CAS  Google Scholar 

  32. IUPAC Commission: Atomic weights of the elements 1985. Pure Appl. Chem. 58, 1677–1692 (1986)

    Article  Google Scholar 

  33. 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 

  34. Zafarani-Moattar, M.T., Shekaari, H.: Volumetric and speed of sound of ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate with acetonitrile and methanol at T=(298.15 to 318.15) K. J. Chem. Eng. Data 50, 1694–1699 (2005)

    Article  CAS  Google Scholar 

  35. Holbrey, J.D., Seddon, K.R.: The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. J. Chem. Soc., Dalton Trans. 13, 2133–2139 (1999)

    Article  Google Scholar 

  36. Holbrey, J.D., Reichert, W.M., Nieuwenhuyzen, M., Sheppard, O., Hardacre, C., Rogers, R.D.: Liquid clathrate formation in ionic liquid–aromatic mixtures. Chem. Commun. 14, 476–477 (2003)

    Article  Google Scholar 

  37. Wang, J., Zhu, A., Zhao, Y., Zhuo, K.: Excess molar volumes and excess logarithm viscosities for binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium hexaflurophosphate with some organic compounds. J. Solution Chem. 34, 585–596 (2005)

    Article  CAS  Google Scholar 

  38. Iglesias-Otero, M.A., Troncoso, J., Carballo, E., Romaní, L.: Density and refractive index for binary systems of the ionic liquid [Bmim][BF4] with methanol, 1,3-dichloropropane, and dimethyl carbonate. J. Solution Chem. 36, 1219–1230 (2007)

    Article  CAS  Google Scholar 

  39. Bhujrajh, P., Deenadayalu, N.: Liquid densities and excess molar volumes for binary systems (ionic liquids + methanol or water) at 298.15, 303.15 and 313.15 K, and at atmospheric pressure. J. Solution Chem. 36, 631–642 (2007)

    Article  CAS  Google Scholar 

  40. Alonso, L., Arce, A., Francisco, M., Soto, A.: Liquid-liquid equilibria of ([C2mim][EtSO4]+thiophene+2,2,4-trimethylpentane) and ([C2mim][EtSO4]+thiophene+toluene): Experimental data and correlation. J. Solution Chem. 37, 1355–1363 (2008)

    Article  CAS  Google Scholar 

  41. 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 

  42. Arce, A., Rodil, E., Soto, A.: Physical and excess properties for binary mixtures of 1-methyl-3-octylimidazolium tetrafluoroborate, [Omim][BF4], ionic liquid with different alcohols. J. Solution Chem. 35, 63–78 (2006)

    Article  CAS  Google Scholar 

  43. Dománska, U., Laskowska, M.: Phase equilibria and volumetric properties of (1-ethyl-3-methylimidazolium ethylsulfate + alcohol or water) binary systems. J. Solution Chem. 37, 1271–1287 (2008)

    Article  Google Scholar 

  44. Calvar, N., González, B., Domínguez, A., Tojo, J.: Physical properties of the ternary mixture ethanol + water + 1-butyl-3-methylimidazolium chloride at 298.15 K. J. Solution Chem. 35, 1217–1225 (2006)

    Article  CAS  Google Scholar 

  45. Navia, P., Troncoso, J., Romaní, L.: Viscosities for ionic liquid binary mixtures with a common ion. J. Solution Chem. 37, 677–688 (2008)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Management, Zhejiang Pharmaceutical College, Ningbo, Zhejiang, 315100, China

    Yan Li & Pingli Zeng

  2. Center of Experiment, Zhejiang Pharmaceutical College, Ningbo, Zhejiang, 315100, China

    Hong Ye

  3. Department of Chemistry, Jinan University, Wuxi, Jiangsu, 214122, China

    Feng Qi

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Correspondence to Yan Li.

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Li, Y., Ye, H., Zeng, P. et al. Volumetric Properties of Binary Mixtures of the Ionic Liquid 1-Butyl-3-Methylimidazolium Tetrafluoroborate with Aniline. J Solution Chem 39, 219–230 (2010). https://doi.org/10.1007/s10953-009-9494-0

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  • DOI: https://doi.org/10.1007/s10953-009-9494-0

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