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Ternary (Liquid–Liquid) Equilibrium Experiment and Thermodynamic Modeling for Extraction of Phenol from Water with Different Solvents at Several Temperatures

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Abstract

In order to separate phenol from water, at 101.3 kPa, the liquid-liquid equilibria (LLE) data of water + phenol + solvents (trichloromethane, isoamyl alcohol) were obtained at 298.15, 303.15, and 313.15 K. The ability of the extractant to extract phenol from water was evaluated by the distribution coefficient (D) and selectivity coefficient (S). The Bachman and Hand equations were used to verify the reliability of the LLE data with the linear coefficient was greater than 0.98%. The LLE data was correlated with the NRTL and UNIQUAC models to obtain a binary interaction parameter with an RMSD not greater than 0.36%.

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References

  1. Heng jun, G., Hong yue, G., Hong bing, S.: Measurement and correlation of liquid–liquid equilibrium data for mesityl oxide-water-phenol ternary system-phenol ternary systems. J. Chem. Eng. Chinese Univ. 29, 1320–1324 (2015)

    Google Scholar 

  2. Chen, Q.: Study on phenolic wastewater treatment technology. D. East China University of Science and Technology, 5 (2012)

  3. Xu, J., Duan, W., Zhou, X., Zhou, J.: Extraction of phenol in wastewater with annular centrifugal contactors. J. Hazard. Mater. 131, 98–102 (2006)

    Article  CAS  PubMed  Google Scholar 

  4. Chufen, Y., Yu, Q., Lijuan, Z., Yanbin, J.: Measurement and correlation of liquid–liquid equilibrium data for methyl isobutyl ketone-water-phenol ternary system. J. Chem. Ind. Eng. 58, 805–809 (2007)

    Google Scholar 

  5. Bai, W., Dai, Y., Pan, X., Zhu, Z., Wang, Y., Gao, J.: Liquid–liquid equilibria for azeotropic mixture of methyl tert-butyl ether and methanol with ionic liquids at different temperatures. J. Chem. Thermodyn. 132, 76–82 (2019)

    Article  CAS  Google Scholar 

  6. Yu, Y., Zhang, L., Zhu, C., Huang, X., Liao, Z., Li, Q.: Experimental determination and correlation of liquid–liquid Equilibria Data for the Ternary Systems of water + 1-Butanol + solvents (isophorone and mesityl oxide) at different temperatures. J. Solution. Chem. 49, 1–15 (2020)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. Jiang, M., Shen, S., Chen, Y.: Experimental measurement and thermodynamic model of liquid–liquid equilibrium for the Ternary System of 1-decanol–phenol–water. J. Chem. Eng. Data. 64, 2801–2808 (2019)

    Article  CAS  Google Scholar 

  9. Narasimhan, K.S., Reddy, C.C., Chari, K.S.: Solubility and equilibrium data of phenol–water–n-Butyl acetate system at 30 °. J. Chem. Eng. Data. 7, 340–343 (1962)

    Article  CAS  Google Scholar 

  10. Teng, Y., Qi, M.: The study on the liquid–liquid phase equilibrium of methylethylketoxime–water–isooctyl alcohol system. Shanghai Chem. Ind. 39, 4–6 (2014)

    CAS  Google Scholar 

  11. Tang, C., Bao, Y., Hu, G., Dong, L., Zhang, L.: Liquid–liquid equilibrium for the ternary system of 3-mercaptopropionic acid + water + trichloromethane. J. Chem. Eng. Data. 64, 2380–2387 (2019)

    Article  CAS  Google Scholar 

  12. Meng, X., Liu, X., Gao, J., Xu, D., Zhang, L., Wang, Y.: Liquid–liquid equilibrium of isobutyl acetate + isobutyl alcohol + imidazolium-based ionic liquids at 298.15 and 308.15 K. J. Chem. Eng. Data. 64, 778–783 (2019)

    Article  CAS  Google Scholar 

  13. Zhang, L., Liao, Z., Zhu, C., Yu, Y., Li, Q.: Determination and correlation of liquid–liquid equilibria data for ternary system isopropyl acetate + isopropanol + water at different temperatures. J. Chem. Eng. Data. 64, 972–978 (2019)

    Article  CAS  Google Scholar 

  14. Wang, Y., Zhou, S., Tang, J., Chen, Y., Li, L.: Measurement and correlation of phase equilibrium data of the mixtures consisting of water, resorcinol, mesityl oxide at different temperatures. Chin. J Chem Eng. 26, 2573–2580 (2018)

    Article  CAS  Google Scholar 

  15. Jia, B., Jiang, X., Chen, X., Dong, S.: Experimental determination and modeling of liquid–liquid equilibrium for ternary mixtures composed of water, epichlorohydrin and different solvents. J. Mol. Liq. 322, 114984 (2021)

    Article  CAS  Google Scholar 

  16. Yang, C., Qian, Y., Jiang, Y., Zhang, L.: Liquid–liquid equilibria for the quaternary system methyl isobutyl ketone–water–phenol-hydroquinone. Fluid Phase Equilib. 258, 73–77 (2007)

    Article  CAS  Google Scholar 

  17. Li, Q., Fan, W., Yan, H., Huang, X., Zhang, L., Ma, Z.: Experimental determination and modeling of liquid–liquid equilibrium for water + diethoxymethane + methyl tert-butyl ether (or methyl isobutyl ketone) at 298.15, 308.15, and 318.15 K. Fluid Phase Equilib. 505, 112353 (2020)

    Article  CAS  Google Scholar 

  18. Rachmawati, D., Khoiroh, I., Tetrisyanda, R., Wibawa, G.: Atmospheric ternary liquid–liquid equilibrium for the diethyl carbonate + 1-propanol + water system at temperature of 303.15, 313.15, 323.15, and 333.15 K. J. Chem. Eng. Data. 64, 1029–1034 (2019)

    Article  CAS  Google Scholar 

  19. Gilani, A.G., Ramezani, S.: Comparative dielectric study and molecular interactions of binary mixtures of (cyclohexanone + 1-alkanols) and (cyclopentanone or cyclohexanone + cyclohexanol or cyclohexane) at T = 298.15 K. J. Chem. Eng. Data. 63, 4703–4719 (2018)

    CAS  Google Scholar 

  20. Hongyue, G., Hui, L., Wei, W., Bing, L., Qingsong, L.: Ternary (liquid + liquid) equilibrium experiment and thermodynamic modeling for water + cyclohexanone + mesityl oxide at 298.2, 303.2 and 313.2 K under 101.3 kPa. J. Chem. Thermodyn. 160, 106509 (2021)

  21. Borecka, M., Białk-Bielińska, A., Siedlewicz, G., Kornowska, K., Kumirska, J., Stepnowski, P., Pazdro, K.: A new approach for the estimation of expanded uncertainty of results of an analytical method developed for determining antibiotics in seawater using solid-phase extraction disks and liquid chromatography coupled with tandem mass spectrometry technique. J. Chromatogr. A. 1304, 138–146 (2013)

    Article  CAS  PubMed  Google Scholar 

  22. Konieczka, P., Namieśnik, J.: Estimating uncertainty in analytical procedures based on chromatographic techniques. J. Chromatogr. A. 1217, 882–891 (2010)

    Article  CAS  PubMed  Google Scholar 

  23. Joint Committee For Guides In Metrology: Evaluation of measurement data—guide to the expression of uncertainty in measurement. Int. Organ. Stand. Geneva ISBN. 50, 134 (2008)

    Google Scholar 

  24. Fakhri, K., Ranjbar, S., Soltanabadi, A.: Liquid–liquid equilibria data and thermodynamic modeling for quaternary system of methanol, dimethyl carbonate, toluene and water at 298 to 318 K. J. Mol. Liq. 299, 112225 (2020)

    Article  CAS  Google Scholar 

  25. Shi, M., Zeng, W., Song, S., Zhou, M., Wang, W.: Measurement and correlation of ternary (liquid–liquid) equilibrium data for n-heptane + p-xylene + (furfural or dimethyl sulfoxide) system at 303.15 K and 323.15 K. J. Chem. Thermodyn. 149, 106175 (2020)

  26. Wang, C., Jia, M., Bai, Z., Shi, M., Chen, X., Fan, J., Dai, F.: The separation of isopropyl alcohol from diisopropyl ether system using glycols: Phase equilibrium and rigorous correlation. J. Chem. Thermodyn. 150, 106230 (2020)

    Article  CAS  Google Scholar 

  27. Li, Y.X., Xu, Q., Liu, S.L., Li, H.M., Zhang, F.B., Zhang, G.L., Xia, Q.: Liquid-liquid equilibrium for the ternary system of isopropyl acetate + 2-propanol + glycerol at different temperatures under atmospheric pressure. Fluid Phase Equilib. 412, 199–204 (2016)

    Article  CAS  Google Scholar 

  28. de Almeida, B.F., Waldrigui, T.M., Alves, T., de Oliveira, C., Aznar, L.H.: Experimental and calculated liquid-liquid equilibrium data for water + furfural + solvents. Fluid Phase Equilib. 334, 97–105 (2012)

    Article  Google Scholar 

  29. Treybal, R.E.: Liquid Extraction. McGraw-Hill, New York (1963)

    Google Scholar 

  30. Diky, V.: An Efficient Way of Visualization of Mutual Solubility Data in the whole range of compositions. J. Chem. Eng. Data. 62, 2920–2926 (2017)

    Article  CAS  Google Scholar 

  31. Ghanadzadeh Gilani, A., Ghanadzadeh Gilani, H., Shekarsaraee, S., Nasiri-Touli, E., Saadat, S.: Liquid-liquid equilibria study of the (water + phosphoric acid + hexyl or cyclohexyl acetate) systems at T = (298.15, 308.15, and 318.15) K: Measurement and thermodynamic modelling. J. Chem. Thermodyn. 98, 200–207 (2016)

    Article  CAS  Google Scholar 

  32. Othmer, D.D.F., Ku, P. liang: Solubility Data for Ternary Liquid Systems: Acetic Acid and Formic Acid Distributed between Chloroform and Water. J. Chem. Eng. Data. 5, 42–44 (1960). 

  33. Jae-Ik, K., So-Jin, P., Young-Yoon, C., Sang-Bae, K.: Liquid-liquid equilibrium, Solid-Liquid Equilibrium, densities, and Refractivity of a Water, Chloroform, and Acetylacetone mixture. J. Chem. Eng. Data. 56, 1798–1803 (2011)

    Article  Google Scholar 

  34. Stephenson, R.M.: Mutual solubilities: Water-Ketones, Water-Ethers, and water-gasoline-alcohols. J. Chem. Eng. Data. 37, 80–95 (1992)

    Article  CAS  Google Scholar 

  35. Stephenson, R.M., Stuart, J., Tabak, M.: Mutual solubility of water and aliphatic alcohols. J. Chem. Eng. Data. 39, 287–290 (1984)

    Article  Google Scholar 

  36. IA, K., VT, M.: The volumetric method of measurement of the mutual solubility of liquids. The mutual solubility of the systems Ethyl Ethyl-Water and Iso-amyl alcohol-water. J. Am. Chem. Soc. 47, 1553–1561 (1925)

    Article  Google Scholar 

  37. Zhou, S., Xiong, K., Li, L., Chen, Y.: Liquid-liquid equilibrium for methyl butyl ketone + o-, m-, p-cresol + water ternary systems and COSMO-SAC predictions. J. Chem. Thermodyn. 127, 17–24 (2018)

    Article  CAS  Google Scholar 

  38. Gilani, H.G., Gilani, A.G., Sangashekan, M.: Tie-line data for the aqueous solutions of phenol with organic solvents at T = 298. 2 K. J. Chem. Thermodyn. 58, 142–148 (2013)

    Article  Google Scholar 

  39. Li, H., Zhang, Y., Sun, D., Zhao, L., Gao, J., Xu, C.: Extraction of { benzene, toluene, thiophene and 3-methylthiophene } from n-hexane : Liquid-liquid equilibrium measurements and interaction exploration. J. Mol. Liq. 310, 113184 (2020)

    Article  CAS  Google Scholar 

  40. Dong, S., Sun, W., Jiang, Y., Jia, B.: Liquid-liquid equilibrium study for ternary systems of (water + furfuryl alcohol + solvents) at 298.2 K: Measurement and thermodynamic modelling. J. Chem. Thermodyn. 148, 106136 (2020)

    Article  CAS  Google Scholar 

  41. Li, H., Gao, X., Dou, Y., Xu, L., Liu, G.: Investigation of liquid-liquid equilibrium for (1-butanol or 1-pentanol + (–)-trans-Cyclohexane-1,2-diamine + water) ternary systems at 298.2 K to 318.2 K. J. Mol. Liq. 277, 990–995 (2019)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Yankuang Coal Slurry Gasification and Coal Chemical Industry National Engineering Research Center Co., Ltd, Jinan, 250100, Shandong, China

    Tao Li

  2. The State Key Lab of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum East China, Qingdao, 266580, Shandong, China

    Hongyue Guo & Qingsong Li

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  1. Tao Li
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  2. Hongyue Guo
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Contributions

The contributions of each author in this paper are as follows: TL: Writing - original draft, Validation, Visualization, Investigation, Software; HG: Conceptualization, Validation, Visualization, Investigation, Software Data curation, Formal analysis; QL: Methodology, Data curation, Supervision;

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Correspondence to Hongyue Guo or Qingsong Li.

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Li, T., Guo, H. & Li, Q. Ternary (Liquid–Liquid) Equilibrium Experiment and Thermodynamic Modeling for Extraction of Phenol from Water with Different Solvents at Several Temperatures. J Solution Chem (2024). https://doi.org/10.1007/s10953-023-01340-w

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  • DOI: https://doi.org/10.1007/s10953-023-01340-w

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