Skip to main content
SpringerLink
Log in

Interactions of Imidazolium Based Ionic Liquids with Water Studied by Density and Speed of Sound Measurements: Effect of the Chain Length of an Alkyl Substituent on the Imidazolium Ion

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

Abstract

Densities and speeds of sound of three ionic liquids (ILs), 1-ethyl-3-methyl imidazoliumtetrafluoroborate (C2mimBF4), 1-butyl-3-methylimidazoliumtetrafluoroborate (C4mimBF4) and 1-hexyl-3-methylimidazoliumtetrafluoroborate (C6mimBF4) were measured in aqueous solutions at (288.15, 293.15, 298.15, 303.15 and 308.15) K. These data were used to calculate the volumetric properties apparent molar volume and apparent molar isentropic compression as a function of molality. Infinite dilution values for these properties were evaluated by an extrapolation procedure based on Redlich–Meyer type equations. Apparent molar isobaric expansions at infinite dilution were also obtained from the slopes of the apparent molar volume at infinite dilution versus temperature. All these properties are interpreted in terms of IL–water interactions. The hydrolysis of the \( {\text{BF}}_{4}^{ - } \) anion of the ILs and its effects on the results is discussed.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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. Domanska, U.: Solubilities and thermophysical properties of ionic liquids. Pure Appl. Chem. 77, 543–557 (2005)

    Article  Google Scholar 

  2. Min, G.H., Yim, T., Lee, H.Y., Huh, D.H., Lee, E., Mun, J., Oh, S.M., Kim, Y.G.: Synthesis and properties of ionic liquids: imidazolium tetrafluoroborates with unsaturated side chains. Bull. Korean Chem. Soc. 27, 847–852 (2006)

    Article  CAS  Google Scholar 

  3. Ayranci, E., Conway, B.E.: Size shape and charge effects in the partial molal volume compressibility and electrostriction behavior of sulfur and chlorine oxyanions in water. J. Chem. Soc. Faraday Trans. I 79, 1357–1372 (1983)

    Article  CAS  Google Scholar 

  4. Singh, G., Banipal, T.S.: Partial molar adiabatic compressibilities and viscosities of some amino acids in aqueous glycerol solutions at 298.15 K. Indian J. Chem. A 47, 1355–1369 (2008)

    Google Scholar 

  5. Sembira-Nahum, Y., Apelblat, A., Manzurola, E.: Volumetric properties of aqueous solutions of l-glutamic acid and magnesium-L-glutamate. J. Solution Chem. 37, 391–401 (2008)

    Article  CAS  Google Scholar 

  6. Conway, B.E., Ayranci, G., Ayranci, E.: Molecular structure effects in the adsorption behaviour of some aromatic heterocyclic compounds at high-area carbon-cloth in relation to waste-water purification. Z. Phys. Chem. 217, 315–331 (2003)

    Article  CAS  Google Scholar 

  7. Lal, B., Sahin, M., Ayranci, E.: Volumetric studies to examine the interactions of imidazolium based ionic liquids with water by means of density and speed of sound measurements. J. Chem. Thermodyn. 54, 142–147 (2012)

    Article  CAS  Google Scholar 

  8. Singh, T., Kumar, A.: Thermodynamics of dilute aqueous solutions of imidazolium based ionic liquids. J. Chem. Thermodyn. 43, 958–965 (2011)

    Article  CAS  Google Scholar 

  9. Gardas, R.L., Dagade, D.H., Terdale, S.S., Coutinho, J.A.P., Patil, K.J.: Acoustic and volumetric properties of aqueous solutions of imidazolium based ionic liquids at 298.15 K. J. Chem. Thermodyn. 40, 695–701 (2008)

    Article  CAS  Google Scholar 

  10. Zhou, Q., Wang, L.S., Chen, H.P.: Densities and viscosities of 1-butyl-3-methylimidazolium tetrafluoroborate + H2O binary mixtures from (303.15 to 353.15) K. J. Chem. Eng. Data 51, 905–908 (2006)

    Article  CAS  Google Scholar 

  11. Sahin, E.M., Lal, B., Ayranci, E.: Densimetric and ultraacoustic study of LiCl in 1-butyl-3-methylimidazolium tetrafluoroborate and in water: a comparative interaction analysis. J. Chem. Thermodyn. 110, 51–56 (2017)

    Article  CAS  Google Scholar 

  12. Sahin, M., Erkan, N., Ayranci, E.: Solution behavior of p-coumaric, caffeic and ferulic acids in methanol as determined from volumetric properties: attempts to explore a correlation with antioxidant activities. J. Solution Chem. 45, 52–66 (2016)

    Article  CAS  Google Scholar 

  13. Bhagour, S., Solanki, S., Hooda, N., Sharma, D., Sharma, V.K.: Thermodynamic properties of binary mixtures of the ionic liquid [emim][BF4] with acetone and dimethylsulphoxide. J. Chem. Thermodyn. 60, 76–86 (2013)

    Article  CAS  Google Scholar 

  14. Curras, M.R., Gomes, M.F.C., Husson, P., Padua, A.A.H., Garcia, J.: Calorimetric and volumetric study on binary mixtures 2,2,2-trifluoroethanol + (1-butyl-3-methylimidazolium tetrafluoroborate or 1-ethyl-3-methylimidazolium tetrafluoroborate). J. Chem. Eng. Data 55, 5504–5512 (2010)

    Article  CAS  Google Scholar 

  15. Srinivasa Rao, V., Vijaya Krishna, T., Madhu Mohan, T., Madhusudana Rao, P.: Physicochemical properties of green solvent 1-ethyl-3-methylimidazolium tetrafluoroborate with aniline from T = (293.15 to 323.15) K at atmospheric pressure. J. Chem. Thermodyn. 104, 150–161 (2017)

    Article  CAS  Google Scholar 

  16. Taguchi, R., Machida, H., Sato, Y., Smith, R.L.: High-pressure densities of 1-alkyl-3-methylimidazolium hexafluorophosphates and 1-alkyl-3-methylimidazolium tetrafluoroborates at temperaturess from (313 to 473) K and pressures up to 200 MPa. J. Chem. Eng. Data 54, 22–27 (2009)

    Article  CAS  Google Scholar 

  17. Navia, P., Troncoso, J., Romani, L.: Excess magnitudes for ionic liquid binary mixtures with a common ion. J. Chem. Eng. Data 52, 1369–1374 (2007)

    Article  CAS  Google Scholar 

  18. Riloa, E., Picoa, J., García-Garabal, S., Varela, L.M., Cabeza, O.: Density and surface tension in binary mixtures of CnMIM–BF4 ionic liquids with water and ethanol. Fluid Phase Equilib. 285, 83–89 (2009)

    Article  Google Scholar 

  19. Wei-Guo, X., Long, L., Xiao-Xue, M., Jie, W., Wen-Bin, D., Wei, G., Jia-Zhen, Y.: Density, surface tension, and refractive index of ionic liquids homologue of 1-alkyl-3-methylimidazolium tetrafluoroborate [C n mim][BF4] (n = 2,3,4,5,6). J. Chem. Eng. Data 57, 2177–2184 (2012)

    Article  Google Scholar 

  20. Seki, S., Tsuzuki, S., Hayamizu, K., Umebayashi, Y., Serizawa, N., Takei, K., Miyashiro, H.: Comprehensive refractive index property for room-temperature ionic liquids. J. Chem. Eng. Data 57, 2211–2216 (2012)

    Article  CAS  Google Scholar 

  21. Stoppa, A., Zech, O., Kunz, W., Buchner, R.: The conductivity of imidazolium-based ionic liquids from (−35 to 195) °C. A. Variation of cation’s alkyl chain. J. Chem. Eng. Data 55, 1768–1773 (2010)

    Article  CAS  Google Scholar 

  22. Vakili-Nezhaad, G., Vatani, M., Asghari, M., Ashour, I.: Effect of temperature on the physical properties of 1-butyl-3-methylimidazolium based ionic liquids with thiocyanate and tetrafluoroborate anions, and 1-hexyl-3-methylimidazolium with tetrafluoroborate and hexafluorophosphate anions. J. Chem. Thermodyn. 54, 148–154 (2012)

    Article  CAS  Google Scholar 

  23. Malham, I.B., Letellier, P., Mayaffre, A., Turmine, M.: Part I: thermodynamic analysis of volumetric properties of concentrated aqueous solutions of 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, and ethylammonium nitrate based on pseudo-lattice theory. J. Chem. Thermodyn. 39, 1132–1143 (2007)

    Article  Google Scholar 

  24. Govardhana-Rao, S., Madhu Mohan, T., Vijaya, Krishna T., Narendra, K., Subba Rao, B.: Thermophysical properties of 1-butyl-3-methylimidazolium tetrafluoroborate and N-methyl-2-pyrrolidinone as a function of temperature. J. Mol. Liq. 211, 1009–1017 (2015)

    Article  CAS  Google Scholar 

  25. Kavitha, T., Vasantha, T., Venkatesu, P., Rama Devi, R.S., Hofman, T.: Thermophysical properties for the mixed solvents of N-methyl-2-pyrrolidone with some of the imidazolium-based ionic liquids. J. Mol. Liq. 198, 11–20 (2014)

    Article  CAS  Google Scholar 

  26. Taib, M.M., Murugesan, T.: Density, refractive index and excess properties of 1-butyl- 3-methylimidazolium tetrafluoroborate with water and monoethanolamine. J. Chem. Eng. Data 57, 120–126 (2012)

    Article  CAS  Google Scholar 

  27. 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 

  28. Kumar, A.: Estimates of internal pressure and molar refraction of imidazolium based ionic liquids as a function of temperature. J. Solution Chem. 37, 203–214 (2008)

    Article  CAS  Google Scholar 

  29. Moattar, M.T.Z., 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  Google Scholar 

  30. Muhammad, A., Abdul Mutalib, M.I., Wilfred, C.D., Murugesan, T., Shafeeq, A.: Thermophysical properties of 1-hexyl-3-methylimidazolium based ionic liquids with tetrafluoroborate, hexafluorophosphate and bis(trifluoromethylsulfonyl)imide anions. J. Chem. Thermodyn. 40, 1433–1438 (2008)

    Article  CAS  Google Scholar 

  31. Zhu, A., Wang, J., Liu, R.: A volumetric and vicosity studyfor the binary mixtures of 1-hexyl-3-methylimidazolium tetrafluoroborate with some molecular solvents. J. Chem. Thermodyn. 43, 796–799 (2011)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. Akbar, M.M., Murugesan, T.: Thermophysical properties of 1-hexyl-3-methylimidazolium tetrafluoroborate [hmim][BF4] + N-methyldiethanolamine (MDEA) at temperatures (303.15 to 323.15) K. J. Mol. Liq. 177, 54–59 (2013)

    Article  CAS  Google Scholar 

  34. Miran Beigi, A.A., Abdouss, M., Yousefi, M., Pourmortazavi, S.M., Vahid, A.: Investigation on physical and electrochemical properties of three imidazolium based ionic liquids (1-hexyl-3-methylimidazoliumtetrafluoroborate, 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonylimidde and 1-butyl-3-methylimidazolium methylsulfate). J. Mol. Liq. 177, 361–368 (2013)

    Article  CAS  Google Scholar 

  35. Millero, F.J.: The partial molal volumes of electrolytes in aqueous solutions. In: Horne, R.A. (ed.) Structure and Transport Process in Water and Aqueous Solutions, chap. 13, pp. 519–595. Wiley, New York (1972)

  36. Pitzer, K.S.: Activity Coefficients in Electrolyte Solutions, 2nd edn. CRC Press, London (1991)

    Google Scholar 

  37. Harned, H.S., Owen, B.B.: The Physical Chemistry of Electrolyte Solutions. ACS, New York (1958)

    Google Scholar 

  38. Mathieson, J.G., Conway, B.E.: Partial molal compressibilities of salts in aqueous solution and assignment of ionic contributions. J. Solution Chem. 3, 455–477 (1974)

    Article  CAS  Google Scholar 

  39. Wang, J., Wang, H.: Zhang, Zhang, S.H., Zhao Y.: conductivities, volumes, fluorescence, and aggregation behavior of ionic liquids [C4mim][BF4] and [C n mim]Br (n = 4, 6, 8, 10, 12) in aqueous solutions. J. Phys. Chem. B 111, 6181–6188 (2007)

    Article  CAS  Google Scholar 

  40. Freire, M.G., Neves, C.M.S.S., Marrucho, I.M., Cautinho, J.A.P., Fernandes, A.M.: Hydrolysis of tetrafluoroborate and hexafluorophosphate counter ions in imidazolium-based ıonic liquids. J. Phys. Chem. A 114, 3744–3749 (2010)

    Article  CAS  Google Scholar 

  41. Wamser, C.A.: Hydrolysis of fluoboric acid in aqueous solution. J. Am. Chem. Soc. 70, 1209 (1948)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The support of this work by the Scientific Research Projects Coordination Unit of Akdeniz University is acknowledged.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Akdeniz University, 07058, Antalya, Turkey

    Erol Ayranci & Elif Merve Sahin

Authors
  1. Erol Ayranci
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elif Merve Sahin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Erol Ayranci.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ayranci, E., Sahin, E.M. Interactions of Imidazolium Based Ionic Liquids with Water Studied by Density and Speed of Sound Measurements: Effect of the Chain Length of an Alkyl Substituent on the Imidazolium Ion. J Solution Chem 47, 246–261 (2018). https://doi.org/10.1007/s10953-018-0724-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-018-0724-1

Keywords

Search

Navigation