Skip to main content
Log in

Evaluating the Possibility of Using Ionic Liquids in the Synthesis and Separation of Cyclohexanone

  • TECHNOLOGY OF ORGANIC COMPOUNDS
  • Published:
Theoretical Foundations of Chemical Engineering Aims and scope Submit manuscript

Abstract

Using gas–liquid chromatography, the activity coefficients upon the infinite dilution of the components of the reaction mixture for obtaining cyclohexanone in the presence of various ionic liquids are determined. Activity coefficients have been calculated at three temperatures based on experimental data on the retention times of the components. The extractive effect of the ionic liquid in respect to the binary azeotropes of the reaction system is noted. The increase in selectivity of a traditional solvent (ethylene glycol) while adding small amounts of ionic liquid is shown.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. Temkin, O.N., Bruk, L.G., Zakharova, D.S., Odintsov, K.Yu., Katsman, E.A., Petrov, I.V., and Istomina, O.Yu., Kinetics of cyclohexene oxidation by p-quinones in aqueous-organic solutions of cationic palladium(II) complexes, Kinet. Catal., 2010, vol. 51, no. 5, pp. 691–703. https://doi.org/10.1134/S0023158410050101

    Article  CAS  Google Scholar 

  2. Temkin, O.N., Bruk, L.G., Frolkova, A.V., and Zakharova, D.S., Effect of the composition of the CH3CN–H2O binary solvent on the kinetics of the oxidation of cyclohexene with p-benzoquinone in solutions of the cationic complexes of palladium(II), Tonkie Khim. Tekhnol., 2015, vol. 10, no. 3, pp. 77–84.

    Google Scholar 

  3. Frolkova, A., Zakharova, D., Frolkova, A., and Balbenov, S., Liquid–liquid and liquid–liquid equilibrium for ternary system water–acetonitrile–cyclohexene at 298.15 K, Fluid Phase Equilib., 2016, vol. 408, pp. 10–14. https://doi.org/10.1016/j.fluid.2015.06.039

    Article  CAS  Google Scholar 

  4. Frolkova, A.V., Balbenov, S.A., Frolkova, A.K., and Akishina, A.A., Phase equilibrium in the system water–acetonitrile–cyclohexene–cyclohexanone, Russ. Chem. Bull., 2015, vol. 64, no. 10, pp. 2330–2336. https://doi.org/10.1007/s11172-015-1160-7

    Article  CAS  Google Scholar 

  5. Efremov, G.E., Bovyrina, E.A., Podtyagina, A.V., Oshanina, I.V., and Temkin, O.N., Ethylene and cyclohexene oxidation by p-benzoquinone, hydrogen peroxide, and oxygen in the solutions of cationic Pd(II) complexes in acetonitrile–water and ionic liquid–water binary solvents, Kinet. Catal., 2019, vol. 60, no. 1, pp. 52–61. https://doi.org/10.1134/S0023158419010051

    Article  CAS  Google Scholar 

  6. Domańska, U. and Paduszyński, K., Gas–liquid chromatography measurements of activity coefficients at infinite dilution of various organic solutes and water in tri-iso-butylmethylphosphonium tosylate ionic liquid, J. Chem. Thermodyn., 2010, vol. 42, no. 6, pp. 707–711. https://doi.org/10.1016/j.jct.2010.01.004

    Article  CAS  Google Scholar 

  7. Marciniak, A., Influence of cation and anion structure of the ionic liquid on extraction processes based on activity coefficients at infinite dilution. A review, Fluid Phase Equilib., 2010, vol. 294, nos. 1–2, pp. 213–233. https://doi.org/10.1016/j.fluid.2009.12.025

    Article  CAS  Google Scholar 

  8. Zhuchkov, V.I., Raeva, V.M., and Frolkova, A.K., The choice of selective agents for extractive distillation by gas–liquid chromatography, Theor. Found. Chem. Eng., 2017, vol. 51, no. 6, pp. 1047–1054. https://doi.org/10.1134/S0040579517060185

    Article  CAS  Google Scholar 

  9. Lei, Z., Li, C., and Chen, B., Extractive distillation: A review, Sep. Purif. Rev., 2003, vol. 32, no. 2, pp. 121–213. https://doi.org/10.1081/SPM-120026627

    Article  CAS  Google Scholar 

  10. Rumyantsev, P.G., Zhuchkov, V.I., Frolkova, A.K., and Anisimov, A.V., Selection of separating agents using gas–liquid chromatography for extractive distillation of a benzene–perfluorobenzene biazeotropic mixture, Vestn. MITKHT, 2010, vol. 5, no. 3, p. 3.

    Google Scholar 

  11. Zhuchkov, V., Frolkova, A., and Rum’yantsev, P., Ionic liquids as separating agents in extractive rectification, Chem. Eng. Res. Des., 2015, vol. 99, pp. 215–219. https://doi.org/10.1016/j.cherd.2015.06.004

    Article  CAS  Google Scholar 

  12. Kogan, V.B., Azeotropnaya i ekstraktivnaya rektifikatsiya (Azeotropic and Extractive Distillation), Leningrad: Khimiya, 1971.

  13. Frolkova, A., Zhuchkov, V., and Nazansky, S., Evaluation of the possibility of using ionic liquids in synthesis and extraction of cyclohexanone, Proc. 45th International Conference of SSCHE, Tatranské Matliare, Slovakia, 2018, pp. 113–116.

  14. Zhuchkov, V., Frolkova, A., and Nazanskiy, S., Experimental measurements of mutual solubility of cyclohexanone, cyclohexene and ionic liquid, Chem. Pap., 2018, vol. 72, no. 5, pp. 1107–1113. https://doi.org/10.1007/s11696-018-0416-8

    Article  CAS  Google Scholar 

  15. Frolkova, A.V., Mayevskiy, M.A., and Frolkova, A.K., Analysis of phase equilibrium diagrams of cyclohexene + water + cyclohexanone + solvent system, J. Chem. Eng. Data, 2018, vol. 63, no. 3, pp. 679–683. https://doi.org/10.1021/acs.jced.7b00870

    Article  CAS  Google Scholar 

  16. Frolkova, A.V., Mayevskiy, M.A., and Smirnov, A.Yu., Phase equilibrium of systems cyclohexene + water + cyclohexanone + N-methyl-2-pyrrolidone (+acetonitrile), J. Chem. Eng. Data, 2019, vol. 64, no. 6, pp. 2888–2893. https://doi.org/10.1021/acs.jced.9b00245

    Article  CAS  Google Scholar 

  17. Raeva, V.M., Sazonova, A.Yu., and Frolkova, A.K., Synergetic effect of binary separating agents in extractive rectification of homogeneous mixtures, Theor. Found. Chem. Eng., 2013, vol. 47, no. 5, pp. 649–659. https://doi.org/10.1134/S0040579513050096

    Article  CAS  Google Scholar 

Download references

Funding

This research was carried out with financial support from the Russian Science Foundation, project no. 16-19-10632.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. I. Zhuchkov.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhuchkov, V.I., Nazansky, S.L., Frolkova, A.K. et al. Evaluating the Possibility of Using Ionic Liquids in the Synthesis and Separation of Cyclohexanone. Theor Found Chem Eng 55, 786–791 (2021). https://doi.org/10.1134/S0040579521040199

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0040579521040199

Keywords:

Navigation