Skip to main content
SpringerLink
Log in

Density and Viscosity of Ionic Liquid Binary Mixtures of 1-n-Butyl-3-methylimidazolium Tetrafluoroborate with Acetonitrile, N,N-Dimethylacetamide, Methanol, and N-Methyl-2-pyrrolidone

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

In this study, thermodynamic properties of the binary mixtures of ionic liquid with an organic compound, as potential solvent systems in pharmaceutical industry applications, are studied. The densities and viscosities of the binary mixtures of 1-butyl-3-methylimidazolium tetrafluoroborate ([C4mim][BF4]) with acetonitrile, N,N-dimethylacetamide, methanol, and N-methyl-2-pyrrolidone were measured at atmospheric pressure over the [C4mim][BF4] mole fraction range from 0.1 to 0.9 and at temperatures from 303.15 to 333.15 K at intervals of 10 K. The densities were measured using a vibrating-tube digital density meter and the viscosities were measured using a capillary viscometer. The excess molar volumes (V E) and viscosity deviations (Δη) were calculated from densities and viscosities of mixture, respectively, and fitted to the Redlich–Kister polynomial. The optimally fitted parameters are also determined and the correlation results are in satisfactory agreement with the experimental data. In addition, the excess molar volumes of binary mixtures of ionic liquid with different organic compounds are compared and discussed using the Hansen solubility parameter.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Rogers, R.D., Seddon, K.R.: Ionic liquids—solvents of the future. Science 302, 792–793 (2003)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. An, J.H., Kim, W.S.: Antisolvent crystallization using ionic liquids as solvent and antisolvent for polymorphic design of active pharmaceutical ingredient. Cryst. Growth Des. 13, 31–39 (2013)

    Article  CAS  Google Scholar 

  4. An, J.H., Kim, J.M., Chang, S.M., Kim, W.S.: Application of ionic liquid to polymorphic design of pharmaceutical ingredients. Cryst. Growth Des. 10, 3044–3050 (2010)

    Article  CAS  Google Scholar 

  5. McCrary, P.D., Beasley, P.A., Gurau, G., Narita, A., Barber, P.S., Cojocaru, O.A., Rogers, R.D.: Drug specific, tuning of an ionic liquid’s hydrophilic-lipophilic balance to improve water solubility of poorly soluble active pharmaceutical ingredients. New J. Chem. 37, 2196–2202 (2013)

    Article  CAS  Google Scholar 

  6. Zuo, L., Meng, H., Wu, J., Jiang, Z., Xu, S., Guo, X.: Combined use of ionic liquid and β-CD for enantioseparation of 12 pharmaceuticals using CE. J. Sep. Sci. 36, 517–523 (2013)

    Article  CAS  Google Scholar 

  7. Ribeiro, B.D., Coelho, M.A.Z., Rebelo, L.P.N., Marrucho, I.M.: Ionic liquids as additives for extraction of saponins and polyphenols from mate (Ilex paraguariensis) and tea (Camellia sinensis). Ind. Eng. Chem. Res. 52, 12146–12153 (2013)

    Article  CAS  Google Scholar 

  8. Grinberg, N., Albu, F., Fandrick, K., Iorgulescu, E., Medvedovici, A.: Assay at low ppm level of dimethyl sulfate in starting materials for API synthesis using derivatization in ionic liquid media and LC-MS. J. Pharm. Biomed. Anal. 75, 1–6 (2013)

    Article  CAS  Google Scholar 

  9. Cojocaru, O.A., Bica, K., Gurau, G., Narita, A., McCrary, P.D., Shamshina, J.L., Barber, P.S., Rogers, R.D.: Prodrug ionic liquids: functionalizing neutral active pharmaceutical ingredients to take advantage of the ionic liquid form. Med. Chem. Commun. 4, 559–563 (2013)

    Article  CAS  Google Scholar 

  10. Marszall, M.P., Sroka, W.D., Balinowska, A.: Ionic liquids as mobile phase additives for feasible assay of naphazoline in pharmaceutical formulation by HPTLC–UV–densitometric method. J. Chromatogr. Sci. 51, 560–565 (2013)

    Article  CAS  Google Scholar 

  11. ICH official website, http://www.ich.org/

  12. Hansen, C.M.: Hansen Solubility Parameters: a User Handbook. CRC Press, Boca Raton (2000)

    Google Scholar 

  13. Huo, Y., Xia, S., Ma, P.: Densities of ionic liquids, 1-butyl-3- methylimidazolium hexafluorophosphate and 1-butyl-3- methylimidazolium tetrafluoroborate, with benzene, acetonitrile, and 1-propanol at T = (293.15 to 343.15) K. J. Chem. Eng. Data 52, 2077–2082 (2007)

    Article  CAS  Google Scholar 

  14. 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 hexafluorophosphate or 1-n-butyl-3- methylimidazolium tetrafluoroborate in methanol and acetonitrile. J. Chem. Thermodyn. 38, 1377–1384 (2006)

    Article  CAS  Google Scholar 

  15. Shekaari, H., Zafarani-Moattar, M.T.: Volumetric properties of the ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate, in organic solvents at T = 298.15 K. Int. J. Thermophys. 29, 534–545 (2008)

    Article  CAS  Google Scholar 

  16. 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 

  17. Stoppa, A., Hunger, J., Buchner, R.: Conductivities of binary mixtures of ionic liquids with polar solvents. J. Chem. Eng. Data 54, 472–479 (2009)

    Article  CAS  Google Scholar 

  18. Iglesias-Otero, M.A., Troncoso, J., Carballo, E., Romaní, L.: Density and refractive index for binary systems of the ionic liquid [C4mim][BF4] with methanol, 1,3-dichloropropane, and dimethyl carbonate. J. Solution Chem. 36, 1219–1230 (2007)

    Article  CAS  Google Scholar 

  19. Kim, H.D., Hwang, I.C., Park, S.J.: Isothermal vapor–liquid equilibrium data at T = 333.15 K and excess molar volumes and refractive Indices at T = 298.15 K for the dimethyl carbonate + methanol and isopropanol + water with ionic liquids. J. Chem. Eng. Data 55, 2474–2481 (2010)

    Article  CAS  Google Scholar 

  20. Tian, S., Hou, Y., Wu, W., Ren, S., Pang, K.: Physical properties of 1-butyl-3-methylimidazolium tetrafluoroborate/N-methyl-2-pyrrolidone mixtures and the solubility of CO2 in the system at elevated pressures. J. Chem. Eng. Data 57, 756–763 (2012)

    Article  CAS  Google Scholar 

  21. Qi, F., Wang, H.: Application of Prigogine–Flory–Patterson theory to excess molar volume of mixtures of 1-butyl-3-methylimidazolium ionic liquids with N-methyl-2-pyrrolidinone. J. Chem. Thermodyn. 41, 265–272 (2009)

    Article  CAS  Google Scholar 

  22. Geppert-Rybczyńska, M., Lehmann, J.K., Heintz, A.: Physicochemical properties of two 1-alkyl-1-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl] imide ionic liquids and of binary mixtures of 1-butyl-1-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl] imide with methanol or acetonitrile. J. Chem. Thermodyn. 71, 171–181 (2014)

    Article  Google Scholar 

  23. 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 

  24. 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 

  25. Roy, M.N., Chanda, R., Ghosh, G.: Molar volumes, viscosity and isentropic compressibility of some primary monoalkanols in aqueous N,N-dimethylformamide solutions. Phys. Chem. Solut. 83, 1331–1341 (2009)

    CAS  Google Scholar 

  26. Zafarani-Moattar, M.T., Majdan-Cegincara, R.: Viscosity, density, speed of sound, and refractive index of binary mixtures of organic solvent + ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate at 298.15 K. J. Chem. Eng. Data 52, 2359–2364 (2007)

    Article  CAS  Google Scholar 

  27. Glasstone, S., Laidler, K.J., Eyring, H.: The Theory of Rate Process. McGraw–Hill, New York (1941)

    Google Scholar 

  28. Salgado, J., Regueira, T., Lugo, L., Vijande, J., Fernández, J., García, J.: Density and viscosity of three (2,2,2-trifluoroethanol + 1-butyl-3- methylimidazolium) ionic liquid binary systems. J. Chem. Thermodyn. 70, 101–110 (2014)

    Article  CAS  Google Scholar 

  29. Vraneš, M., Zec, N., Tot, A., Papović, S., Dožić, S., Gadžurić, S.: Density, electrical conductivity, viscosity and excess properties of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide + propylene carbonate binary mixtures. J. Chem. Thermodyn. 68, 98–108 (2014)

    Article  Google Scholar 

  30. Królikowska, M., Zawadzki, M., Królikowski, M.: Physicochemical and thermodynamic study on aqueous solutions of dicyanamide-based ionic liquids. J. Chem. Thermodyn. 70, 127–137 (2014)

    Article  Google Scholar 

  31. Harris, K.R., Kanakubo, M., Woolf, L.A.: Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate: viscosity and density relationships in ionic liquids. J. Chem. Eng. Data 52, 2425–2430 (2007)

    Article  CAS  Google Scholar 

  32. Ku, H.C., Tu, C.H.: Density and viscosity of binary mixtures of propan-2-ol, 1-chlorobutane, and acetonitrile. J. Chem. Eng. Data 43, 465–468 (1998)

    Article  CAS  Google Scholar 

  33. Krakowiak, J., Koziel, H., Grzybkowski, W.: Apparent molar volumes of divalent transition metal perchlorates and chlorides in N,N-dimethylacetamide. J. Mol. Liq. 118, 57–65 (2005)

    Article  CAS  Google Scholar 

  34. Oswal, S.L., Patel, N.B.: Speed of sound, isentropic compressibility, viscosity, and excess volume of binary mixtures. 2. Alkanenitriles + dimethylformamide, + dimethylacetamide, and + dimethyl sulfoxide. J. Chem. Eng. Data 40, 845–849 (1995)

    Article  CAS  Google Scholar 

  35. Yang, C., Sun, Y., He, Y., Ma, P.: Volumetric properties and viscosities of binary mixtures of N, N-dimethylformamide with methanol and ethanol in the temperature range (293.15 to 333.15) K. J. Chem. Eng. Data 53, 293–297 (2008)

    Article  CAS  Google Scholar 

  36. Gong, Y., Shen, C., Lu, Y., Meng, H., Li, C.: Viscosity and density measurements for six binary mixtures of water (methanol or ethanol) with an ionic liquid ([C4mim][DMP] or [EMIM][DMP]) at atmospheric pressure in the temperature range of (293.15 to 333.15) K. J. Chem. Eng. Data 57, 33–39 (2012)

    Article  CAS  Google Scholar 

  37. 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 

  38. Yang, C., Xu, W., Ma, P.: Thermodynamic properties of binary mixtures of p-xylene with cyclohexane, heptane, octane, and N-methyl-2-pyrrolidone at several temperatures. J. Chem. Eng. Data 49, 1794–1801 (2004)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei, Taiwan

    Jheng-Yu Wu & Chie-Shaan Su

  2. Department of Chemical Engineering, National Taiwan University, Taipei, Taiwan

    Yan-Ping Chen

Authors
  1. Jheng-Yu Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yan-Ping Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chie-Shaan Su
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chie-Shaan Su.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 220 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, JY., Chen, YP. & Su, CS. Density and Viscosity of Ionic Liquid Binary Mixtures of 1-n-Butyl-3-methylimidazolium Tetrafluoroborate with Acetonitrile, N,N-Dimethylacetamide, Methanol, and N-Methyl-2-pyrrolidone. J Solution Chem 44, 395–412 (2015). https://doi.org/10.1007/s10953-014-0273-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-014-0273-1

Keywords

Search

Navigation