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Extraction of Phenol from Wastewaters. Choice of Extractant in Coproduction of Phenol and Acetone (Review)

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Abstract

A comparative analysis of the effectiveness of various organic extractants (ethers, acetates, ketones, and alcohols) in phenol extraction from aqueous solutions is given. The differences in the phenol distribution coefficients, moisture contents in the extracts, and amounts of reagent remaining in the aqueous solution are shown. The choice of n-butyl acetate, methyl-tert-butyl and methyl-tert-amyl ethers is substantiated for replacement of imported diisopropyl ether, currently widely used at Russian plants.

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REFERENCES

  1. https://alto-group.ru/otchot/rossija/445-rynok-fenola-tekushhaya-situaciya-i-prognoz-2015-2019-gg.html

  2. Hodel, A.E., Butyl acetate replaces toluene to remove phenol from water, Chem. Proc., 1993.

  3. Abrams, D.S. and Prausnitz, J.M., Distribution of phenolic solutes between water and non-polar organic solvents, J. Chem. Thermodyn., 1975, vol. 7, pp. 61–72.

    Article  CAS  Google Scholar 

  4. Won, K.W. and Prausnitz, J.M., Distribution of phenolic solutes between water and polar organic solvents, J. Chem. Thermodyn., 1975, vol. 7, pp. 661–670.

    Article  CAS  Google Scholar 

  5. Mikhaleva, M.S. and Egutkin, N.L., On the mechanism of phenol extraction from aqueous solutions with diisopropyl ether, Bashkir. Khim. Zh., 2008, vol. 15, no. 2, pp. 168–170.

    CAS  Google Scholar 

  6. Smirnova, A.A., Grigor’eva, L.S., and Ostroukhov, N.N., Extraction of water-soluble phenols from water of shale chemical plants, Khim. Tverd. Topl., 2016, no. 6, pp. 40–44.

  7. Porebski, T., Zieborak, K., Bazela, Cz., and Grudzien, J., Extraction of phenols with tert-amyl methyl ether from coking plant wastewater, Nucl. Chem. Waste Manage., 1988, vol. 8, pp. 69–73.

    Article  CAS  Google Scholar 

  8. Greminger, D.G., Burns, G.P., Lynn, S., Hanson, D.N., and King, J., Solvent extraction of phenols from water, Ind. Eng. Chem. Process Des. Dev., 1982, vol. 21, pp. 51–54.

    Article  CAS  Google Scholar 

  9. Kiezyk, P.R. and Mackay, D., The screening and selection of solvents for the extraction of phenol from water, Can. J. Chem. Eng., 1973, vol. 51, pp. 741–745.

    Article  CAS  Google Scholar 

  10. Medir, M. and Mackay, D., Extraction of phenol from water with mixed solvents, Can. J. Chem. Eng., 1975, vol. 53, pp. 274–277.

    Article  CAS  Google Scholar 

  11. Abdelmonem, R.M., Hashem, M.A., and Mohmed, A.A., Further studies on phenol removal from aqueous solutions by solvent extraction, Trans. Biomed. Health, 2001, vol. 5, pp. 139–149.

    Article  Google Scholar 

  12. Mikhaleva, M.S. and Egutkin, N.L., Comparative efficiency of extractants of phenol in its extraction from aqueous solutions, Bashkir. Khim. Zh., 2008, vol. 15, no. 1, pp. 70–72.

    CAS  Google Scholar 

  13. Egutkin, N.L. and Syrkin, A.M., Extraction of phenol from aqueous solutions with methyl tert-butyl ether, Neftegazov. Delo, 2014, no. 1, pp. 193–205.

  14. Lei, Y., Chen, Y., Li, X., Qian, Y., Yang, S., and Yang, C., Liquid–liquid equilibria for the ternary system 2-methoxy-2-methylpropane + phenol + water, J. Chem. Eng. Data, 2013, vol. 58, pp. 1874–1878.

    Article  CAS  Google Scholar 

  15. Oprea, F. and Petre, M., Methyl tert-pentyl ether (TAME): A new solvent for phenol extraction from wastewater, in Proceedings of 17th International Solvent Extraction Conference, 2005, Beijing, China, pp. 1275–1280.

  16. Gonzalez, J.R., Macedo, E.A., Soares, M.E., and Medina, A.G., Liquid–liquid equlibria for ternary systems of water-phenol and solvents: Data and representation with models, Fluid Phase Equilib., 1986, vol. 26, pp. 289–302.

    Article  Google Scholar 

  17. Narasimhan, K.S., Reddy, C.C., and Chari, K.S., Solubility and equilibrium data of phenol–water–n-butyl acetate system at 30°C, J. Chem. Eng. Data, 1962, vol. 7, pp. 340–343.

    Article  CAS  Google Scholar 

  18. Ghanadzadeh Gilani, H., Ghanadzadeh Gilani, A., and Sangashekan, M., Tie-line data for the aqueous solutions of phenol with organic solvents at T = 298.2 K, J. Chem. Thermodyn., 2013, vol. 58, pp. 142–148.

    Article  CAS  Google Scholar 

  19. Rudakov, O.B., Podolina, E.A., Khorokhordina, E.A., and Kharitonova, L.A., effect of binary solvent composition on phenol extraction from aqueous solutions, Russ. J. Phys. Chem., 2007, vol. 81, no. 12, pp. 2053–2058.

    Article  CAS  Google Scholar 

  20. Zhenjing, S., Mengxiang, F., Chunguang, Z., Qinghui, W., and Zhongyang, L., Studies on the extraction of phenol from the wastewater of multi-generation system, in Proceedings of the International Conference on Computer Distributed Control and Intelligent Environment Monitoring, February 19–20, 2011, Changsha, Hunan, China, pp. 1303–1309.

  21. Mafra, M.R. and Krähenbühl, M.A., Liquid–liquid equilibrium of (water + acetone) with cumene or α‑methylstyrene or phenol at temperatures of (323.15 and 333.15) K, J. Chem. Eng. Data, 2006, vol. 51, pp. 753–756.

    Article  CAS  Google Scholar 

  22. Rogošić, M., Bakula, M., and Župan, M., Liquid–liquid equilibria in the ternary systems H2O–phenol–2-butanone and H2O–phenol–2-propanol, Chem. Biochem. Eng. Q., 2012, vol. 26, no. 3, pp. 155–162.

    Google Scholar 

  23. Lv, R., Li, L., Wang, H., and Chen, Y., Phase equilibrium for phenol extraction from aqueous solution with 2-pentanone at different temperatures, J. Solution Chem., 2016, vol. 45, pp. 1414–1424.

    Article  CAS  Google Scholar 

  24. Lv, R., Li, L., Wang, H., and Chen, Y., Experimental determination and correlation of liquid–liquid equilibria for methyl isopropyl ketone + phenol + water mixtures at 298.15, 313.15, and 323.15 K, J. Chem. Eng. Data, 2016, vol. 61, pp. 2221–2225.

    Article  CAS  Google Scholar 

  25. Chen, Y., Wang, Z., and Li, L., Liquid–liquid equilibria for ternary systems: methyl butyl ketone + phenol + water and methyl butyl ketone + hydroquinone + water at 298.15 K and 323.15 K, J. Chem. Eng. Data, 2014, vol. 59, pp. 2750–2755.

    Article  CAS  Google Scholar 

  26. Narasimhan, K.S., Reddy, C.C., and Chari, K.S., Solubility and equilibrium data of phenol–water–isoamyl acetate and phenol–water–methyl isobutyl ketone systems at 30°C, J. Chem. Eng. Data, 1962, vol. 7, pp. 457–460.

    Article  CAS  Google Scholar 

  27. Liu, D., Luo, L., Li, L., and Chen, Y., Liquid–liquid equilibria for the methyl tert-butyl ketone + phenol + water ternary system at 298.15, 313.15 and 323.15 K, J. Solution Chem., 2015, vol. 44, pp. 1891–1899.

    Article  CAS  Google Scholar 

  28. Xu, G., Yang, D., Ning, P., Wang, Q., Gong, F., and Cao, H., Measurements and correlation of liquid–liquid equilibrium data for the ternary (3-heptanone+phenol+water) system, J. Chem. Thermodyn., 2017, vol. 106, pp. 295–302.

    Article  CAS  Google Scholar 

  29. Liu, D., Li, L., Lv, R., and Chen, Y., Liquid–liquid equilibria for the ternary system mesityl oxide + phenol + water at 298.15, 313.15, and 323.15 K, J. Chem. Eng. Data, 2016, vol. 61, pp. 2493–2498.

    Article  CAS  Google Scholar 

  30. De Oliveira, L.H. and Aznar, M., (Liquid + liquid) equilibrium of {water + phenol + (1-butanol, or 2-butanol, or tert-butanol)} systems, J. Chem. Thermodyn., 2010, vol. 47, pp. 1379–1385.

    Article  Google Scholar 

  31. https://neftegaz.ru/news/neftechim/636619-rosneft-razrabotala-tekhnologiyu-polucheniya-izopropilovogo-spirta-na-sobstvennom-geterogennom-metal

  32. https://trendeconomy.ru/data/commodity_h2/291413

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This study was performed under government contract at the Institute of Petrochemical Synthesis, Russian Academy of Sciences.

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Correspondence to G. S. Dmitriev.

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Translated by L. Smolina

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Dmitriev, G.S., Zanaveskin, L.N., Terekhov, A.V. et al. Extraction of Phenol from Wastewaters. Choice of Extractant in Coproduction of Phenol and Acetone (Review). Theor Found Chem Eng 56, 859–871 (2022). https://doi.org/10.1134/S0040579522050037

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  • DOI: https://doi.org/10.1134/S0040579522050037

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