Measurements and correlation of liquid-liquid equilibrium data for the ternary (methyl tert-butyl ketone + o, m, p-benzenediol + water) system at (333.2, 343.2 and 353.2) K

doi:10.1016/j.cjche.2018.09.011

Abstract

Abstract: In this work, liquid-liquid equilibria (LLE) data for the ternary system methyl tert-butyl ketone (MTBK) + o, m, p-benzenediol + water were investigated at 333.2 K, 343.2 K and 353.2 K under 101.3 kPa. The performance of MTBK to extract o, m, p-benzenediol from wastewaters was estimated by partition coefficients and separation factors. The Hand and Bachman equations were both applied to check the reliability of the experimental LLE data. Furthermore, the Non-Random Two-Liquid (NRTL) and Universal Quasi Chemical (UNIQUAC) models were applied to correlate the measured LLE data. The results showed a good agreement with the determined ternary LLE data with the root-mean-square error (RMSE) values below 0.71%. MTBK was proved to be a promising extracting agent in extracting benzenediols from effluents.

Key words: Liquid-liquid equilibrium, Methyl tert-butyl ketone, Benzenediol, NRTL model, UNIQUAC model

摘要： In this work, liquid-liquid equilibria (LLE) data for the ternary system methyl tert-butyl ketone (MTBK) + o, m, p-benzenediol + water were investigated at 333.2 K, 343.2 K and 353.2 K under 101.3 kPa. The performance of MTBK to extract o, m, p-benzenediol from wastewaters was estimated by partition coefficients and separation factors. The Hand and Bachman equations were both applied to check the reliability of the experimental LLE data. Furthermore, the Non-Random Two-Liquid (NRTL) and Universal Quasi Chemical (UNIQUAC) models were applied to correlate the measured LLE data. The results showed a good agreement with the determined ternary LLE data with the root-mean-square error (RMSE) values below 0.71%. MTBK was proved to be a promising extracting agent in extracting benzenediols from effluents.

关键词: Liquid-liquid equilibrium, Methyl tert-butyl ketone, Benzenediol, NRTL model, UNIQUAC model

Kangning Xiong, Shuai Shen, Youchang Wang, Yun Chen. Measurements and correlation of liquid-liquid equilibrium data for the ternary (methyl tert-butyl ketone + o, m, p-benzenediol + water) system at (333.2, 343.2 and 353.2) K[J]. Chinese Journal of Chemical Engineering, 2019, 27(4): 905-911.

References

[1] K. Xie, W. Li, W. Zhao, Coal chemical industry and its sustainable development in China, Energy 35(2010) 4349-4355.
[2] Q. Ji, S. Tabassum, S. Hena, C.G. Silva, G. Yu, Z. Zhang, A review on the coal gasification wastewater treatment technologies:past, present and future outlook, J. Clean. Prod. 126(2016) 38-55.
[3] W. Wang, H. Han, J. Zhang, Progress in treatment technologies of coal gasification wastewater, Chem. Eng. Prog. 32(2013) 681-686.
[4] National Environmental Protection Agency, Integrated Wastewater Discharge Standard. GB 8978-1996, 1996.
[5] A. Dabrowski, P. Podkościelny, Z. Hubicki, M. Barczak, Adsorption of phenolic compounds by activated carbon-a critical review, Chemosphere 58(2005) 1049-1070.
[6] M. Otero, M. Zabkova, A.E. Rodrigues, Comparative study of the adsorption of phenol and salicylic acid from aqueous solution onto nonionic polymeric resins, Sep. Purif. Technol. 45(2005) 86-95.
[7] M.T.A. Reis, O.M.F.D. Freitas, M.R.C. Ismael, Recovery of phenol from aqueous solutions using liquid membranes with Cyanex 923, J. Membr. Sci. 305(2007) 313-324.
[8] D. Vione, C. Minero, V. Maurino, Degradation of phenol and benzoic acid in the presence of a TiO₂-based heterogeneous photocatalyst, Appl. Catal. B Environ. 58(2005) 79-88.
[9] Z. Wang, X. Xu, Z. Gong, F. Yang, Removal of COD, phenols and ammonium from Lurgi coal gasification wastewater using A₂O-MBR system, J. Hazard. Mater. 235-236(2012) 78-84.
[10] W. Xu, G. Dai, K. Tang, Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers:experiment and model, Chin. J. Chem. Eng. 26(2018) 708-714.
[11] H. Hou, J. Xu, Y. Wang, Solvent extraction of lanthanum and cerium ions from hydrochloric acidic aqueous solutions using partly saponified 2-ethylhexyl phosphonic acid mono-2-ethylhexyl ester, Chin. J. Chem. Eng. 24(2016) 79-85.
[12] Y. Chen, S. Zhou, H. Chen, Y. Wang, L. Li, Extraction of o-, m- and p-cresol from aqueous solution with methyl isopropyl ketone:equilibrium, correlations, and COSMO-RS predictions, J. Chem. Thermodyn. 115(2017) 180-190.
[13] Y. Chen, R. Lv, F. Wang, L. Li, Determination and modeling of liquid-liquid equilibrium for ternary mixtures of methyl isopropyl ketone, cresol isomers and water, Fluid Phase Equilib. 429(2016) 107-112.
[14] S. Zhou, M. Liao, D. Liu, L. Li, Y. Chen, Liquid-liquid equilibrium for the ternary systems methyl tert-butyl ketone + o -, m -, p -cresol + water at (298.2, 313.2, and 323.2) K, J. Chem. Eng. Data 62(2017) 1929-1936.
[15] Y. Chen, H. Wang, R. Lv, L. Li, Phase equilibrium measurement and thermodynamic modeling of the 4-methylpentan-2-one/3-methylphenol, and 4-methylphenol/water ternary systems at 298.2, 313.2, and 323.2 K and 0.1 MPa, J. Chem. Eng. Data 62(2017) 141-147.
[16] R. Lv, Z. Wang, L. Li, Y. Chen, Liquid-liquid equilibria in the ternary systems water+ cresols+ methyl butyl ketone at 298.2 and 313.2 K:experimental data and correlation, Fluid Phase Equilib. 404(2015) 89-95.
[17] S. Zhou, L. Li, Y. Wang, Y. Chen, Measurement, correlation and COSMO-SAC prediction of liquid-liquid equilibrium for the ternary systems, mesityl oxide + o -, m -, p -cresol + water, at 333.2 K and 353.2 K, Fluid Phase Equilib. 440(2017) 45-53.
[18] Y. Chen, H. Wang, R. Lv, L. Li, Liquid-liquid equilibria for methyl isobutyl ketone + cresols + water at 333.15 K, 343.15 K and 353.15 K:experimental results and data correlation, Fluid Phase Equilib. 427(2016) 291-296.
[19] L. Luo, D. Liu, L. Li, Y. Chen, Measurements and thermodynamic modeling of liquid-liquid equilibria in ternary system 2-methoxy-2-methylpropane+p-cresol+water, Chin. J. Chem. Eng. 24(2016) 360-364.
[20] Teh C. Lo, M.H.I. Baird, Solvent Extraction, Encyclopedia of Physical Science and Technology, Third Edition Academic Press 2003, pp. 341-362.
[21] X. Miao, H. Zhang, Liquid-liquid equilibria of the ternary system water + acetic acid + methyl tert-butyl ether, J. Chem. Eng. Data 52(2007) 789-793.
[22] I.C. Hwang, S.J. Park, S.J. In, Liquid-liquid equilibria for ternary mixtures of methyl tert-butyl ether, ethyl tert-butyl ether, water and imidazolium-based ionic liquids at 298.15K, J. Ind. Eng. Chem. 20(2014) 3292-3296.
[23] D.M.T. Newsham, S.B. Ng, Liquid-liquid equilibriums in mixtures of water, propyl alcohol, and butyl alcohol, J. Chem. Eng. Data 17(1972) 205-207.
[24] N.V. Sastry, S.R. Patel, S.S. Soni, Excess molar volumes, excess isentropic compressibilities, excess viscosities, relative permittivity and molar polarization deviations for methyl acetate +, ethyl acetate +, butyl acetate +, isoamyl acetate +, methyl propionate +, ethyl propionate +, ethyl, J. Mol. Liq. 183(2013) 102-112.
[25] Y. Chen, Z. Wang, L. Li, 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 59(2014) 2750-2755.
[26] C. Chang, J.L. Chang, Measurement and correlation of liquid-liquid equilibrium data for water-ethanol-methyl isobutyl ketone, Chem. Eng. 42(2014) 39-60.
[27] H.S. Sang, I.C. Hwang, S.J. Park, Liquid-liquid equilibria at 298.15 K for ternary mixtures of methyl tert -butyl ether + methanol (or ethanol) + imidazolium-based ionic liquids at atmospheric pressure, Fluid Phase Equilib. 342(2013) 82-87.
[28] G. Xu, D. Yang, P. Ning, Measurements and correlation of liquid-liquid equilibrium data for the ternary (3-heptanone + phenol + water) system, J. Chem. Thermodyn. 106(2016) 295-302.
[29] R. Lv, L. Li, H. Wang, 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 61(2016) 2221-2225.
[30] H.D. Oliveira, M. Aznar, (Liquid + liquid) equilibrium of {water + phenol +(1-butanol, or 2-butanol, or tert-butanol)} systems, J. Chem. Thermodyn. 42(2010) 1379-1385.
[31] Y. Chen, K. Xiong, S. Zhou, Liquid-liquid equilibrium of ternary systems of methyl isobutyl ketone + o-cresol + water at 298.2, 313.2 and 323.2 K, J. Solut. Chem. (2017) 1-10.
[32] Y. Chen, R. Lv, H. Wang, Ternary liquid-liquid equilibria for methyl isopropyl ketone +(resorcinol or hydroquinone) + water systems at different temperatures, Fluid Phase Equilib. 429(2016) 93-97.
[33] C. Yang, Y. Jiang, Liquid-liquid equilibria for the ternary system methyl isobutyl ketone + water + hydroquinone, J. Chem. Eng. Data 51(2006) 2107-2109.
[34] Y. Chen, H. Wang, R. Lv, Liquid-liquid equilibrium for ternary systems, methyl isobutyl ketone+(catechol, resorcinol and hydroquinone)+water at 333.15K, 343.15K and 353.15K, Fluid Phase Equilib. 433(2017) 206-211.
[35] D.B. Hand, Dineric distribution, J. Phys. Chem. 34(1929) 1961-2000.
[36] I. Bachman, Tie lines in ternary liquid systems, Ind. Eng. Chem. Anal. Ed. 14(1940) 38-39.
[37] H. Renon, J.M. Prausnitz, Local compositions in thermodynamic excess functions for liquid mixtures, AIChE J. 14(1968) 135-144.
[38] D.S. Abrams, J.M. Prausnitz, Statistical thermodynamics of liquid mixtures anew expression for the excess Gibbs energy of party or completely miscible systems, AIChE J. 21(1975) 116-128.