Abstract
The vapor–liquid equilibrium of the tetrahydrofuran–acetonitrile system, the equimolar tetrahydrofuran–acetonitrile–chloroform mixture is experimentally studied. The effect of various amounts of dimethyl sulfoxide on the relative volatilities of the components at 101.32 kPa is investigated. The extractive distillation flowsheets of the tetrahydrofuran–acetonitrile–chloroform mixture with dimethyl sulfoxide are calculated.
REFERENCES
Serafimov, L.A. and Frolkova, A.K., Fundamental principle of concentration-field redistribution between separation regions as a basis for the design of technological systems, Theor. Found. Chem. Eng., 1997, vol. 31, no. 2, pp. 159–166.
Frolkova, A.K., Razdelenie azeotropnykh smesei: Fiziko-khimicheskie osnovy i tekhnologicheskie priemy (Separation of Azeotropic Mixtures: Physicochemical Principles and Techniques), Moscow: VLADOS, 2010.
Mahdi, T., Ahmad, A., Nasef, M.M., and Ripin, A., State-of-the-art technologies for separation of azeotropic mixtures, Sep. Purif. Rev., 2015, vol. 44, no. 4, pp. 308–330. https://doi.org/10.1080/15422119.2014.963607
Zaretskii, M.I., Rusak, V.V., and Chartov, E.M., Extractive distillation in chemical technology: A review, Coke Chem., 2010, vol. 53, no. 3, pp. 110–113. https://doi.org/10.3103/S1068364X10030075
Bittrikh, G.I., Gaile, A.A., Lempe, D., Proskuryakov, V.A., and Semenov, L.V., Razdelenie uglevodorodov s ispol’zovaniem selektivnykh rastvoritelei (Separation of Hydrocarbons by Using Selective Solvents), Leningrad: Khimiya, 1987.
Gaile, A.A. and Zalishchevskii, G.D., N-metilpirrolidon: poluchenie, svoistva i primenenie v kachestve selektivnogo rastvoritelya (N-Methylpyrrolidone: Preparation, Properties and Application as Selective Solvent), St. Petersburg: Khimizdat, 2005.
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
Kiss, A.A., Distillation. Extractive distillation, in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2013. https://www.researchgate.net/publication/285671337_Distillation_Extractive_Distillation. Cited February, 08, 2023.
Gerbaud, V., Rodriguez-Donis, I., Hegely, L., Lang, P., Denes, F., and You, X., Review of extractive distillation. Process design, operation, optimization and control, Chem. Eng. Res. Des., 2019, vol. 141, pp. 229–271. https://doi.org/10.1016/j.cherd.2018.09.020
Teng, Z., Zhen, S., Xiang, Z., Rafiqul, G., and Kai, S., Optimal solvent design for extractive distillation processes: A multiobjective optimization-based hierarchical framework, Ind. Eng. Chem. Res., 2019, vol. 58, no. 15, pp. 5777–5786. https://doi.org/10.1021/acs.iecr.8b04245
Anokhina, E.A., Energy saving in extractive distillation, Fine Chem. Technol., 2013, vol. 8, no. 5, pp. 3–19.
Momoh, S.O., Assessing the accuracy of selectivity as a basis for solvent screening in extractive distillation processes, Sep. Sci. Technol., 1991, vol. 26, no. 5, pp. 729–742. https://doi.org/10.1080/01496399108049911
Raeva, V.M. and Sazonova, A.Yu., Separation of ternary mixtures by extractive distillation with 1,2-ethandiol and glycerol, Chem. Eng. Res. Des., 2015, vol. 99, pp. 125–131. https://doi.org/10.1016/j.cherd.2015.04.032
Raeva, V.M. and Kapranova, A.S., Comparison efficiency of extractive agents at the separation of mixture acetone–methanol, Khim. Prom-st. Segodnya, 2015, no. 3, pp. 33–46.
Myul'khi, E.P., Khristenko, M.S., and Andryukhova, M.V., Choice of an extractive separating agent for the 1-pentanol–cyclohexanone binary mixture, Russ. J. Appl. Chem., 2006, vol. 79, no. 7, pp. 1076–1082. https://doi.org/10.1134/S1070427206070068
Song, Y., Du, Y., Wang, R., Yan, H., Luo, F., and Sun, L., Vapor–liquid equilibria and conceptual design of extractive distillation for separating ethanol and ethyl propionate, J. Chem. Eng. Data, 2020, vol. 65, no. 7, pp. 3428–3437. https://doi.org/10.1021/acs.jced.9b01162
Kogan, V.B., Azeotropnaya i ekstraktivnaya rektifikatsiya (Azeotropic and Extractive Rectification), Leningrad: Khimiya, 1971.
Serafimov, L.A., Frolkova, A.K., and Bushina, D.I., Extractive distillation of binary azeotropic mixtures, Theor. Found. Chem. Eng., 2008, vol. 42, no. 5, pp. 507–516. https://doi.org/10.1134/S0040579508050059
Kossack, S., Kraemer, K., Gani, R., and Marquardt, W.A., A systematic synthesis framework for extractive distillation processes, Chem. Eng. Res. Des., 2008, vol. 86, no. 7, pp. 781–792. https://doi.org/10.1016/j.cherd.2008.01.008
Benyounes, H. and Frolkova, A.K., Aspects of multicomponent mixture separation in the presence of selective solvents, Chem. Eng. Commun., 2010, vol. 197, no. 7, pp. 901–918. https://doi.org/10.1080/00986440903088561
Raeva, V.M. and Sukhov, D.I., Selection of extractive agents for the separation of chloroform–methanol–tetrahydrofuran mixture, Fine Chem. Technol., 2018, vol. 13, no. 3, pp. 30–40. https://doi.org/10.32362/24106593-2018-13-3-30-40
Frolkova, A.K., Frolkova, A.V., Raeva, V.M., and Zhuchkov, V.I., Features of distillation separation of multicomponent mixtures, Fine Chem. Technol., 2022, vol. 17, no. 2, pp. 87–106. https://doi.org/10.32362/2410-6593-2022-17-2-87-106
Kiva, V.N., Hilmen, E.K., and Skogestad, S., Azeotropic phase equilibrium diagrams: A survey, Chem. Eng. Sci., 2003, vol. 58, no. 10, pp. 1903–1953. https://doi.org/10.1016/S0009-2509(03)00018-6
Raeva, V.M. and Sazonova, A.Yu., Separation of ternary mixtures by extractive distillation with 1,2-ethandiol and glycerol, Chem. Eng. Res. Des., 2015, vol. 99, pp. 125–131. https://doi.org/10.1016/j.cherd.2015.04.032
Wang, Yi., Bu, G., Geng, X., Zhu, Z., Cui, P., and Liao, Z., Design optimization and operating pressure effects in the separation of acetonitrile/methanol/water mixture by ternary extractive distillation, J. Cleaner Prod., 2019, vol. 218, pp. 212–224. https://doi.org/10.1016/j.jclepro.2019.01.324
Raeva, V.M. and Dubrovsky, A.M., Comparison of extractive distillation flowsheets for methanol–tetrahydrofuran–water mixtures, Fine Chem. Technol., 2020, vol. 15, no. 3, pp. 21–30. https://doi.org/10.32362/2410-6593-2020-15-3-21-30
Zhu, Z., Wang, Y., Hu, J., Qi, X., and Wang, Y., Extractive distillation process combined with decanter for separating ternary azeotropic mixture of toluene–methanol–water, Chem. Eng. Trans., 2017, vol. 61, pp. 763–768. https://doi.org/10.3303/CET1761125
Yang, A., Su, Y., Shi, T., Ren, J., Shen, W., and Zhou, T., Energy-efficient recovery of tetrahydrofuran and ethyl acetate by triple-column extractive distillation: Entrainer design and process optimization, Front. Chem. Sci. Eng., 2022, vol. 16, no. 2, pp. 303–315. https://doi.org/10.1007/s11705-021-2044-z
Shi, X., Zhu, X., Zhao, X., and Zhang, Z., Performance evaluation of different extractive distillation processes for separating ethanol/tert-butanol/water mixture, Process Saf. Environ. Prot., 2020, vol. 137, pp. 246–260. https://doi.org/10.1016/j.psep.2020.02.015
Raeva, V.M. and Gromova, O.V., Separation of water–formic acid–acetic acid mixtures in the presence of sulfolane, Fine Chem. Technol., 2019, vol. 14, no. 4, pp. 24–32. https://doi.org/10.32362/2410-6593-2019-14-4-24-32
Yang, A., Zou, H., Chien, I.-L., Wang, D., Wei, S., Ren, J., and Shen, W., Optimal design and effective control of triple-column extractive distillation for separating ethyl acetate/ethanol/water with multiazeotrope, Ind. Eng. Chem. Res., 2019, vol. 58, no. 17, pp. 7265–7283. https://doi.org/10.1021/acs.iecr.9b00466
Jian, X., Li, J., Ye, Q., Yan, L., Li, X., Xie, L., and Zhang, J., Intensification and analysis of extractive distillation processes with preconcentration for separating ethyl acetate, isopropanol and water azeotropic mixtures, Sep. Purif. Technol., 2022, vol. 287, article no. 120499. https://doi.org/10.1016/j.seppur.2022.120499
Ma, Z., Yao, D., Zhao, J., Li, H., Chen, Z., Cui, P., Zhu, Z., Wang, L., Wang, Y., Ma, Y., and Gao, L., Efficient recovery of benzene and n-propanol from wastewater via vapor recompression assisted extractive distillation based on techno-economic and environmental analysis, Process Saf. Environ. Prot., 2021, vol. 148, pp. 462–472. https://doi.org/10.1016/j.psep.2020.10.033
Shan, B., Zheng, Qi., Chen, Z., Shen, Y., Zhang, F., Wang, Y., and Zhu, Z., Dynamic control and performance comparison of conventional and dividing wall extractive distillation for benzene/isopropanol/water separation, J. Taiwan Inst. Chem. Eng., 2021, vol. 128, pp. 73–86. https://doi.org/10.1016/j.jtice.2021.08.005
Yang, A., Chun, W., Sun, S., Shi, T., Ren, J., and Shen, W., Dynamic study in enhancing the controllability of an energy-efficient double side-stream ternary extractive distillation of acetonitrile/methanol/benzene with three azeotropes, Sep. Purif. Technol., 2020. vol. 242, article no. 116830. https://doi.org/10.1016/j.seppur.2020.116830
Zhao, Y., Zhao, T., Jia, H., Li, X., Zhu, Z., and Wang, Y., Optimization of the composition of mixed entrainer for economic extractive distillation process in view of the separation of tetrahydrofuran/ethanol/water ternary azeotrope, J. Chem. Technol. Biotechnol., 2017, vol. 92, no. 9, pp. 2433–2444. https://doi.org/10.1002/jctb.5254
Zhao, Y., Ma, K., Bai, W., Du, D., Zhu, Z., Wang, Y., Gao, J., Energy-saving thermally coupled ternary extractive distillation process by combining with mixed entrainer for separating ternary mixture containing bioethanol, Energy, 2018, vol. 148, pp. 296–308. https://doi.org/10.1016/j.energy.2018.01.161
Berg, L., Yeh, A.-I., and Ratanapupech, P., The recovery of ethyl acetate by extractive distillation, Chem. Eng. Commun., 1985, vol. 39, nos. 1–6, pp. 193–199. https://doi.org/10.1080/00986448508911670
Berg, L. and Yeh, A.-I., The breaking of ternary acetate–alcohol–water azeotropes by extractive distillation, Chem. Eng. Commun., 1986, vol. 48, nos. 1–3, pp. 93–101. https://doi.org/10.1080/00986448608911779
Raeva, V.M. and Stoyakina, I.E., Selecting extractive agents on the basis of composition–excess Gibbs energy data, Russ. J. Phys. Chem. A, 2021, vol. 95, no. 9, pp. 1779–1790. https://doi.org/10.1134/S003602442109020X
Sólimo, H.N. and Gómez Marigliano, A.C., Excess properties and vapor–liquid equilibrium data for the chloroform + tetrahydrofuran binary system at 30°C, J. Solution Chem., 1993, vol. 22, no. 10, pp. 951–962. https://doi.org/10.1007/bf00646606
Nagata, I. and Kawamura, Y., Excess thermodynamic functions and complex formation in binary liquid mixtures containing acetonitrile, Fluid Phase Equilib., 1979, vol. 3, no. 1, pp. 1–11. https://doi.org/10.1016/0378-3812(79)80023-0
Govindan, A.P., Varma, Y.B.G., and Ananth, M.S., Isothermal (vapor + liquid) equilibria of four binary mixtures, J. Chem. Thermodyn., 1984, vol. 16, no. 1, pp. 1–5. https://doi.org/10.1016/0021-9614(84)90068-5
Lazarte, M., Gómez Marigliano, A.C., and Sólimo, H.N., Excess molar volume, viscosity, and molar refraction deviations, and liquid–vapor equilibrium at 303.15 K for chloroform + acetonitrile binary mixture. An infrared study, J. Solution Chem., 2004, vol. 33, no. 12, pp. 1549–1563. https://doi.org/10.1007/s10953-004-1393-9
Gmehling, J. and Bölts, R., Azeotropic data for binary and ternary systems at moderate pressures, J. Chem. Eng. Data, 1996, vol. 41, no. 2, pp. 202–209. https://doi.org/10.1021/je950228f
Ogorodnikov, S.K. Lesteva, T.M., and Kogan, V.B., Azeotropnye smesi. Spravochnik (Azeotropic Mixtures. Handbook), Kogan, V.B. Ed., Leningrad: Khimiya, 1971.
Susarev, M.P., Kudryavtseva L.S., and Eizen O.G., Troinye azeotropnye sistemy (Ternary Azeotropic Systems), Tallinn: Valgus, 1973.
Frolkova, A.V., Fertikova, V.G., Rytova, E.V., and Frolkova, A.K., Evaluation of the adequacy of phase equilibria modeling based on various sets of experimental data, Fine Chem. Technol., 2021, vol. 16, no. 6, pp. 457–464. https://doi.org/10.32362/2410-6593-2021-16-6-457-464
Swietoslawski, W., Azeotropy and Polyazeotropy, Oxford: Pergamon Press, 1963.
Sun, Y., Fu, D., Ma, S., Ma, Z., and Sun, L., Isobaric vapor–liquid equilibrium data for two binary systems n-hexane + 1,2-dimethoxyethane and methylcyclopentane + 1,2-dimethoxyethane at 101.3 kPa. J. Chem. Eng. Data, 2018, vol. 63, no. 2, pp. 395–401. https://doi.org/10.1021/acs.jced.7b00802
Song, Y., Du, Y., Wang, R., Yan, H., Luo, F., and Sun, L., Vapor–liquid equilibria and conceptual design of extractive distillation for separating ethanol and ethyl propionate, J. Chem. Eng. Data, 2020, vol. 65, no. 7, pp. 3428–3437. https://doi.org/10.1021/acs.jced.9b01162
Herington, E.F.G., Tests for the consistency of experimental isobaric vapour–liquid equilibrium data, J. Inst. Petrol., 1951, vol. 37, pp. 457–470.
Walas, S.M., Phase Equilibria in Chemical Engineering, Boston: Butterworth-Heinemann, 1985.
Funding
This work was supported by the Russian Science Foundation (project no. 19-19-00620-p).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by V. Glyanchenko
Rights and permissions
About this article
Cite this article
Zhuchkov, V.I., Ryzhkin, D.A. & Raeva, V.M. Extractive Distillation of the Tetrahydrofuran–Acetonitrile–Chloroform Mixture. Theor Found Chem Eng 57, 119–129 (2023). https://doi.org/10.1134/S0040579523010153
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0040579523010153