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.
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REFERENCES
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
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.
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
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
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
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
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
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
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
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.
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
Kogan, V.B., Azeotropnaya i ekstraktivnaya rektifikatsiya (Azeotropic and Extractive Distillation), Leningrad: Khimiya, 1971.
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.
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
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
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
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
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This research was carried out with financial support from the Russian Science Foundation, project no. 16-19-10632.
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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
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DOI: https://doi.org/10.1134/S0040579521040199