Skip to main content
SpringerLink
Log in

Thermodynamic properties of binary mixtures of n-butylammonium-based ionic liquids with ethanol at T = (293.15–313.15) K

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

In this study, density, speed of sound and viscosity of binary mixtures of ionic liquids + ethanol have been measured as a function of composition at T = (293.15–313.15) K and atmospheric pressure. The ionic liquids studied were: {n-butylammonium acetate (N4Ace), n-butylammonium propanoate (N4Pro), n-butylammonium hexanoate (N4Hex), and n-butylammonium decanoate (N4Dec)}. Excess molar volume, \(V_{\text{m}}^{\rm{E}}\), deviation in isentropic compressibility, \(\Delta \kappa_{\text{S}}\), deviation in viscosity, \(\Delta \eta\), and excess Gibbs energy of activation of viscous flow, \(\Delta G^{ * \rm{E}}\), were obtained from experimental results and correlated with the Redlich–Kister polynomial equation. Ionic liquids were synthesized and characterized using 1H-NMR, 13C-NMR and FTIR spectroscopy techniques. For all systems studied, the values of \(V_{\text{m}}^{\rm E}\), \(\Delta \kappa_{\text{S}}\) and \(\Delta \eta\) were negative over the entire composition range, whereas \(\Delta G^{ * \rm{E}}\) values were positive over the entire composition range. The results obtained were discussed in terms of structural effects and intermolecular interactions between like and unlike molecules.

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
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Cremer T. Ionic liquid bulk and interface properties. Basel: Springer; 2013.

    Book  Google Scholar 

  2. Fang Z, Smith J, Qi RLX. Production of biofuels and chemicals with ionic liquids. New York: Springer; 2014.

    Book  Google Scholar 

  3. Yue CB, Fang D, Liu L, Yi TF. Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J Mol Liq. 2011;163:99–121.

    Article  CAS  Google Scholar 

  4. Shamsipur M, Beigi AAM, Teymouri M, Pourmortazavi SM, 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 Liq. 2010;157:43–50.

    Article  CAS  Google Scholar 

  5. Gomez E, Calvar N, Macedo EA, Dominguez A. Effect of the temperature on the physical properties of pure 1-propyl 3-methylimidazolium bis(trifluoromethylsulfonyl)imide and characterization of its binary mixtures with alcohols. J Chem Thermodyn. 2012;45:9–15.

    Article  CAS  Google Scholar 

  6. Xu YJ, Chen B, Qian W, Li HR. Properties of pure n-butylammonium nitrate ionic liquid and its binary mixtures of with alcohols at T = (293.15 to 313.15) K. J Chem Thermodyn. 2013;58:449–59.

    Article  CAS  Google Scholar 

  7. Kurnia KA, Ibrahim M, Mutalib A. Density, viscosity, speed of sound, excess property and bulk modulus of binary mixtures of gamma-butyrolactone with acetonitrile, dimethyl carbonate, and tetrahydrofuran at temperatures (293.15 to 333.15) K. J Chem Eng Data. 2011;56:79–83.

    Article  CAS  Google Scholar 

  8. Xu Y, Yao J, Wang C, Li H. Density, viscosity, and refractive index properties for the binary mixtures of n-butylammonium acetate ionic liquid plus alkanols at several temperatures. J Chem Eng Data. 2012;57:298–308.

    Article  CAS  Google Scholar 

  9. Rilo E, Varea LM, Cabeza O. Density and derived thermodynamic properties of 1-ethyl-3-methylimidazolium alkyl sulfate ionic liquid binary mixtures with water and with ethanol from 288 K to 318 K. J Chem Eng Data. 2012;57:2136–42.

    Article  CAS  Google Scholar 

  10. Pereiro AB, Rodriguez A. Study on the phase behaviour and thermodynamic properties of ionic liquids containing imidazolium cation with ethanol at several temperatures. J Chem Thermodyn. 2007;39:978–89.

    Article  CAS  Google Scholar 

  11. Gonzalez EJ, Dominguez A, Macedo EA. Excess properties of binary mixtures containing 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquid and polar organic compounds. J Chem Thermodyn. 2012;47:300–11.

    Article  CAS  Google Scholar 

  12. Qian W, Xu YJ, Zhu HY, Yu CH. Properties of pure 1-methylimidazolium acetate ionic liquid and its binary mixtures with alcohols. J Chem Thermodyn. 2012;49:87–94.

    Article  CAS  Google Scholar 

  13. Requejo PF, Gonzalez EJ, Macedo EA, Dominguez A. 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. 2014;74:193–200.

    Article  CAS  Google Scholar 

  14. Garcia-Miaja G, Troncoso J, Romani L. Excess properties for binary systems ionic liquid plus ethanol: experimental results and theoretical description using the ERAS model. Fluid Phase Equilib. 2008;274:59–67.

    Article  CAS  Google Scholar 

  15. Wang JY, Zhao FY, Liu YM, Wang XL, Hu YQ. Thermophysical properties of pure 1-ethyl-3-methylimidazolium methylsulphate and its binary mixtures with alcohols. Fluid Phase Equilib. 2011;305:114–20.

    Article  CAS  Google Scholar 

  16. Zhang ZB, Zhou Q, Lu XM, Qiao CZ, Zhang SJ. Densities and viscosities of binary mixtures containing 1,3-dimethylimidazolium dimethylphosphate and alcohols. J Chem Eng Data. 2014;59:2377–88.

    Article  CAS  Google Scholar 

  17. Garcia-Mardones M, Perez-Gregorio V, Guerrero H, Bandres I, Lafuente C. Thermodynamic study of binary mixtures containing 1-butylpyridinium tetrafluoroborate and methanol, or ethanol. J Chem Thermodyn. 2010;42:1500–5.

    Article  CAS  Google Scholar 

  18. Vasanthakumar A, Bahadur I, Redhi GG, Gengan RM, Anand K. Synthesis, characterization and thermophysical properties of ionic liquid N-methyl-N-(2′,3′-epoxypropyl)-2-oxopyrrolidinium chloride and its binary mixtures with water or ethanol at different temperatures. J Mol Liq. 2016;219:685–93.

    Article  CAS  Google Scholar 

  19. Lu XX, Wu D, Ye DF, Wang YP, Guo YS, Fang WJ. Densities and viscosities of binary mixtures of 2-ethyl-1,1,3,3-tetramethylguanidinium ionic liquids with ethanol and 1-propanol. J Chem Eng Data. 2015;60:2618–28.

    Article  CAS  Google Scholar 

  20. Zhou Q, Song YT, Yu YH, He HY, Zhang SJ. Density and excess molar volume for binary mixtures of naphthenic acid ionic liquids and ethanol. J Chem Eng Data. 2010;55:1105–8.

    Article  CAS  Google Scholar 

  21. Bittencourt SS, Hoga HE, Torres RB, d’Angelo JVH. Thermodynamic and spectroscopic properties of binary mixtures of n-butylammonium butanoate ionic liquid with alcohols at T = (293.15–313.15) K. J Chem Thermodyn. 2017;105:238–52.

    Article  CAS  Google Scholar 

  22. Olivieri GV, da Cunha CS, Martins LS, Paegle PAM, Nuncio SD, Morandim-Giannetti AA, Torres RB. Thermodynamic and spectroscopic study of binary mixtures of n-butylammonium oleate ionic liquid + alcohol at T = 288.15–308.15 K. J Therm Anal Calorim. 2018;131:2925–42.

    Article  CAS  Google Scholar 

  23. Arce A, Soto A. Physical and excess properties of binary and ternary mixtures of 1,1-dimethylethoxy-butane, methanol, ethanol and water at 298.15 K. Thermochim Acta. 2005;435:197–201.

    Article  CAS  Google Scholar 

  24. Zafarani-Moattar MT, Tohidifar N. Vapor-liquid equilibria, density, speed of sound, and viscosity for the system poly(ethylene glycol) 400 + ethanol at different temperatures. J Chem Eng Data. 2008;53:785–93.

    Article  CAS  Google Scholar 

  25. Gonzalez B, Calvar N, Gomez E, Dominguez I, Dominguez A. Synthesis and physical properties of 1-ethylpyridinium ethylsulfate and its binary mixtures with ethanol and 1-propanol at several temperatures. J Chem Eng Data. 2009;54:1353–8.

    Article  CAS  Google Scholar 

  26. Bicak N. A new ionic liquid: 2-hydroxy ethylammonium formate. J Mol Liq. 2005;116:15–8.

    Article  CAS  Google Scholar 

  27. Neto JCA, Cabral AD, Oliveira LR, Torres RB, Morandim-Giannetti AD. Synthesis and characterization of new low-cost ILs based on butylammonium cation and application to lignocellulose hydrolysis. Carbohydr Polym. 2016;143:279–87.

    Article  CAS  Google Scholar 

  28. Pavia DL, Lampman GM, Kriz GS, Vyvyan JA. Introduction to spectroscopy. Boston: Cengage Learning; 2010.

    Google Scholar 

  29. Silverstein RM, Webster FX, Kiemle DJ, Bryce DL. Spectrometric identification of organic compounds. 8th ed. New York: Wiley; 2005.

    Google Scholar 

  30. Chen JY, Chen LX, Xu YJ. Properties of pure 1,1,3,3-tetramethylguanidine imidazole ionic liquid and its binary mixtures with alcohols at T = (293.15 to 313.15) K. J Chem Thermodyn. 2015;88:110–20.

    Article  CAS  Google Scholar 

  31. Redlich O, Kister AT. Thermodinamics of nonelectrolyte solutions—X–Y–T relations in a binary system. Ind Eng Chem. 1948;40:341–5.

    Article  CAS  Google Scholar 

  32. Zhu X, Wang Y, Li HR. The structural organization in aqueous solutions of ionic liquids. AIChE J. 2009;55:198–205.

    Article  CAS  Google Scholar 

  33. Xu YJ. Volumetric, viscosity, and electrical conductivity properties of aqueous solutions of two n-butylammonium-based protic ionic liquids at several temperatures. J Chem Thermodyn. 2013;64:126–33.

    Article  CAS  Google Scholar 

  34. Chen FC, Yang ZY, Chen ZY, Hu JH, Chen C, Cai JX. Density, viscosity, speed of sound, excess property and bulk modulus of binary mixtures of gamma-butyrolactone with acetonitrile, dimethyl carbonate, and tetrahydrofuran at temperatures (293.15 to 333.15) K. J Mol Liq. 2015;209:683–92.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work has been supported by the Fundação Educacional Inaciana Padre Sabóia de Medeiros (FEI), Universidade Estadual de Campinas (UNICAMP), Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (Process No 2009/14556-5) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES). We thank Dr. Nivaldo Boralle for the NMR measurements and Dr. Andreia Morandim-Giannetti for discussion of the results.

Author information

Authors and Affiliations

  1. Department of Chemical Systems Engineering, Chemical Engineering School, University of Campinas, UNICAMP, 500, Albert Einstein Avenue, Campinas, SP, 13083-852, Brazil

    Samara Storion Bittencourt & José Vicente Hallak d’Angelo

  2. Departamento de Engenharia Química, Centro Universitário FEI, Avenida Humberto Alencar Castelo Branco, 3972, São Bernardo do Campo, SP, 09850-901, Brazil

    Heloisa Emi Hoga & Ricardo Belchior Torres

Authors
  1. Samara Storion Bittencourt
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Heloisa Emi Hoga
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ricardo Belchior Torres
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. José Vicente Hallak d’Angelo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ricardo Belchior Torres.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1033 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bittencourt, S.S., Hoga, H.E., Torres, R.B. et al. Thermodynamic properties of binary mixtures of n-butylammonium-based ionic liquids with ethanol at T = (293.15–313.15) K. J Therm Anal Calorim 135, 2519–2539 (2019). https://doi.org/10.1007/s10973-018-7399-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-018-7399-0

Keywords

Search

Navigation