The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration

doi:10.1016/j.cjche.2023.05.016

中国化学工程学报 ›› 2023, Vol. 64 ›› Issue (12): 117-127.DOI: 10.1016/j.cjche.2023.05.016

• Full Length Article • 上一篇下一篇

The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration

Yanjing Li¹, Shilong Dong¹, Lili Wang¹, Xiaoyan Sun¹, Wenying Zhao², Shuguang Xiang¹

1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China;
2. College of Chemistry and Chemical Engineering, Qilu Normal University, Jinan 250200, China

收稿日期:2022-11-16 修回日期:2023-05-26 出版日期:2023-12-28 发布日期:2024-02-05
通讯作者: Xiaoyan Sun,E-mail:sxy@qust.edu.cn
基金资助:
We gratefully acknowledge the support from the National Natural Science Foundation of China (22178190), and the National Youth Natural Science Foundation of China (CN) (22008129).

The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration

Yanjing Li¹, Shilong Dong¹, Lili Wang¹, Xiaoyan Sun¹, Wenying Zhao², Shuguang Xiang¹

1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China;
2. College of Chemistry and Chemical Engineering, Qilu Normal University, Jinan 250200, China

Received:2022-11-16 Revised:2023-05-26 Online:2023-12-28 Published:2024-02-05
Contact: Xiaoyan Sun,E-mail:sxy@qust.edu.cn
Supported by:
We gratefully acknowledge the support from the National Natural Science Foundation of China (22178190), and the National Youth Natural Science Foundation of China (CN) (22008129).

摘要/Abstract

摘要： LLE data of cyclooctane/3-methylpentane + benzene/toluene + N-methylpyrrolidone (NMP) at 298.15 K and 313.15 K under a pressure of 101.3 kPa were measured in this work. The Othmer-Tobias and Hand equations were adopted to validate the reliability of LLE data, where the correlation coefficients (R²) were close to unity, indicating the high reliability of the experimental data. The experimental data were analyzed using the distribution coefficient (D) and separation factor (S), and the effect of NMP extracting benzene and toluene from aromatics was explored. Meanwhile, the reason for the different extraction efficiencies of benzene and toluene using NMP was analyzed by quantum chemical calculations. The NRTL and UNIQUAC thermodynamic models were used to correlate the liquid–liquid equilibrium data, and the relevant binary interaction parameters were obtained. The calculated root mean square deviation (RMSD) were all less than 0.0063, indicating that the obtained binary interaction parameters can be used to simulate and calculate the extraction of aromatics using NMP.

关键词: Extraction, Liquid-liquid equilibrium, Thermodynamic models, Quantum chemistry calculation

Abstract: LLE data of cyclooctane/3-methylpentane + benzene/toluene + N-methylpyrrolidone (NMP) at 298.15 K and 313.15 K under a pressure of 101.3 kPa were measured in this work. The Othmer-Tobias and Hand equations were adopted to validate the reliability of LLE data, where the correlation coefficients (R²) were close to unity, indicating the high reliability of the experimental data. The experimental data were analyzed using the distribution coefficient (D) and separation factor (S), and the effect of NMP extracting benzene and toluene from aromatics was explored. Meanwhile, the reason for the different extraction efficiencies of benzene and toluene using NMP was analyzed by quantum chemical calculations. The NRTL and UNIQUAC thermodynamic models were used to correlate the liquid–liquid equilibrium data, and the relevant binary interaction parameters were obtained. The calculated root mean square deviation (RMSD) were all less than 0.0063, indicating that the obtained binary interaction parameters can be used to simulate and calculate the extraction of aromatics using NMP.

Key words: Extraction, Liquid-liquid equilibrium, Thermodynamic models, Quantum chemistry calculation

Yanjing Li, Shilong Dong, Lili Wang, Xiaoyan Sun, Wenying Zhao, Shuguang Xiang. The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration[J]. 中国化学工程学报, 2023, 64(12): 117-127.

参考文献

[1] N. Brijmohan, C. Narasigadu, Ternary liquid–liquid equilibrium data for the N-formylmorpholine + toluene +{n-nonane or n-decane}systems at (303.2, 323.2, and 343.2) K and 101.3 kPa, J. Chem. Eng. Data 65 (2) (2020) 788–792.
[2] N. Brijmohan, K. Moodley, C. Narasigadu, Identification and screening of potential organic solvents for the liquid–liquid extraction of aromatics, Org. Process Res. Dev. 25 (10) (2021) 2230–2248.
[3] Y.C. Guo, F.M. Shi, Q.P. Shu, X.Y. Yue, C. Wang, L. Tao, J.L. Li, Liquid-liquid equilibrium for n-hexane + benzene + sulfolane, + 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([EMIM][NTf2]), + 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO₄]) and + the mixtures of[EMIM][NTf2]and[EMIM][EtSO₄, Fluid Phase Equilib. 529 (2021) 112882.
[4] S.H. Feng, J.J. Sun, Z.Q. Ren, Z.Y. Zhou, F. Zhang, W. Liu, Effective separation of aromatic hydrocarbons by pyridine-based deep eutectic solvents, Can. J. Chem. Eng. 97 (12) (2019) 3138–3147.
[5] P. Wiśniewski, K. Bołoz, A. Wiśniewska, Z. Dąbrowski, D. Kubica, J. Łuczak, U. Domańska, Effect of the ionic liquids on extraction of aromatic and sulfur compounds from the model petrochemical stream, Fluid Phase Equilib. 552 (2022) 113296.
[6] M.K. Hadj-Kali, M.Z.M. Salleh, I. Wazeer, A. Alhadid, S. Mulyono, Separation of benzene and cyclohexane using eutectic solvents with aromatic structure, Molecules 27 (13) (2022) 4041.
[7] Y. Park, Separation of toluene from a toluene/n-heptane mixture using ethylene glycol containing deep eutectic solvents, Korean J. Chem. Eng. 38 (3) (2021) 604–609.
[8] A. Hosseini, R. Haghbakhsh, S. Raeissi, Experimental investigation of liquid–liquid extraction of toluene + heptane or toluene + hexane using deep eutectic solvents, J. Chem. Eng. Data 64 (9) (2019) 3811–3820.
[9] J. Mahmoudi, M.N. Lotfollahi, (Liquid + liquid) equilibria of (sulfolane + benzene + n-hexane), (N-formylmorpholine + benzene + n-hexane), and (sulfolane + N-formylmorpholine + benzene + n-hexane) at temperatures ranging from (298.15 to 318.15) K: Experimental results and correlation, J. Chem. Thermodyn. 42 (4) (2010) 466–471.
[10] I. Domínguez, E.J. González, Á. Domínguez, Liquid extraction of aromatic/cyclic aliphatic hydrocarbon mixtures using ionic liquids as solvent: literature review and new experimental LLE data, Fuel Process. Technol. 125 (2014) 207–216.
[11] R.P. Tripathi, A.R. Ram, P.B. Rao, Liquid-liquid equilibriums in ternary system toluene-n-heptane-sulfolane, J. Chem. Eng. Data 20 (3) (1975) 261–264.
[12] P. Kaur, V.C. Srivastava, I.D. Mall, Studies on Bi-cyclic aromatics extraction using furfural and N-methyl pyrrolidone (NMP) as solvent, Sep. Sci. Technol. 47 (12) (2012) 1762–1770.
[13] H. Li, Y.H. Zhang, L. Zhao, D.X. Sun, J.S. Gao, C.M. Xu, Liquid-liquid equilibria and mechanism exploration for the extraction of sulfides from FCC naphtha via organic solvent as extractant, J. Mol. Liq. 327 (2021) 114821.
[14] H. Li, Y.H. Zhang, D.X. Sun, L. Zhao, J.S. Gao, C.M. Xu, Extraction of{benzene, toluene, thiophene and 3-methylthiophene}from n-hexane: liquid-liquid equilibrium measurements and interaction exploration, J. Mol. Liq. 310 (2020) 113184.
[15] T. Lu, F.W. Chen, Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem. 33 (5) (2012) 580–592.
[16] W. Humphrey, A. Dalke, K. Schulten, VMD: visual molecular dynamics, J. Mol. Graph. 14 (1) (1996) 33–38.
[17] D. Othmer, P. Tobias, Liquid-liquid extraction data - the line correlation, Ind. Eng. Chem. 34 (6) (1942) 693–696.
[18] Y.C. Wang, S.M. Zhou, J.H. Tang, Y. Chen, L.B. Li, Measurement and correlation of phase equilibrium data of the mixtures consisting of water, resorcinol, mesityl oxide at different temperatures, Chin. J. Chem. Eng. 26 (12) (2018) 2573–2580.
[19] L.Z. Zhang, D.M. Xu, J. Gao, M. Zhang, Z.M. Xia, Y.X. Ma, S.X. Zhou, Separation of the mixture pyridine + methylbenzene via several acidic ionic liquids: phase equilibrium measurement and correlation, Fluid Phase Equilib. 440 (2017) 103–110.
[20] L. El blidi, M.K. Hadj-Kali, A.M. Al-Anazi, S.M. Alhawtali, I. Wazeer, Liquid-liquid separation of n-hexane/1-hexene and cyclohexane/cyclohexene using deep eutectic solvents, J. Mol. Liq. 344 (2021) 117776.
[21] H.R. Zhang, F. Zhao, Z.Y. Ma, X.Y. Liu, P.Z. Cui, J. Gao, Y.L. Wang, S.Q. Zheng, Design and optimization for the separation of cyclohexane-isopropanol-water using mixed extractants with thermal integration based on molecular mechanism, Sep. Purif. Technol. 266 (2021) 118541.
[22] T. Lu, Molclus program, Version 1.9.9.6, http://www.keinsci.com/research/molclus.html.
[23] R.F.W. Bader, A quantum theory of molecular structure and its applications, Chem. Rev. 91 (5) (1991) 893–928.
[24] R.F.W. Bader, P.M. Beddall, Virial field relationship for molecular charge distributions and the spatial partitioning of molecular properties, J. Chem. Phys. 56 (7) (1972) 3320–3329.
[25] Z.Y. Liu, T. Lu, Q.X. Chen, Intermolecular interaction characteristics of the all-carboatomic ring, cyclo[18]carbon: focusing on molecular adsorption and stacking, Carbon 171 (2021) 514–523.
[26] T. Lu, F.W. Chen, Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm, J. Mol. Graph. Model. 38 (2012) 314–323.
[27] A.S. Darwish, F. Abu Hatab, T. Lemaoui, O.A.Z. Ibrahim, G. Almustafa, B. Zhuman, S.E.E. Warrag, M.K. Hadj-Kali, Y. Benguerba, I.M. Alnashef, Multicomponent extraction of aromatics and heteroaromatics from diesel using acidic eutectic solvents: experimental and COSMO-RS predictions, J. Mol. Liq. 336 (2021) 116575.
[28] H. Renon, J.M. Prausnitz, Local compositions in thermodynamic excess functions for liquid mixtures, AlChE. J. 14 (1) (1968) 135–144.
[29] S. Yang, D.H. Ma, P.Z. Cui, Liquid–liquid equilibrium data and correlation for the quaternary systems water + polyphenol (hydroquinone, catechol, and resorcinol) + methyl isobutyl ketone + methylbenzene, J. Chem. Eng. Data 63 (1) (2018) 63–68.
[30] D.S. Abrams, J.M. Prausnitz, Statistical thermodynamics of liquid mixtures: a new expression for the excess Gibbs energy of partly or completely miscible systems, AlChE. J. 21 (1) (1975) 116–128.
[31] Y.H. Dou, H.X. Li, X.Q. Gao, G.J. Liu, L. Xu, Investigation of liquid-liquid equilibrium of the ternary system (water + 1, 6-diaminohexane + 2-methyl-1-propanol or 3-methyl-1-butanol) at different temperatures, Chin. J. Chem. Eng. 28 (1) (2020) 191–197.
[32] K.N. Xiong, S. Shen, Y.C. Wang, Y. 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, Chin. J. Chem. Eng. 27 (4) (2019) 905–911.
[33] T. Wongsawa, M. Hronec, T. Soták, N. Leepipatpiboon, U. Pancharoen, S. Phatanasri, Ternary (liquid–liquid) equilibrium data of furfuryl alcohol with organic solvents at T=298.2K: experimental results and thermodynamic models, Fluid Phase Equilib. 365 (2014) 88–96.
[34] U. Koch, P.L.A. Popelier, Characterization of C-H-O hydrogen bonds on the basis of the charge density, J. Phys. Chem. 99 (24) (1995) 9747–9754.
[35] D.X. Sun, Y.L. Zhao, Y.J. Cao, M.Q. Liu, Y.X. Zhang, L.A. Zhao, Y.H. Zhang, J.S. Gao, C.M. Xu, T.Z. Hao, J.L. Chen, D.W. Ji, Investigation on the interaction mechanism of the solvent extraction for mercaptan removal from liquefied petroleum gas, Energy Fuels 34 (4) (2020) 4788–4798.
[36] J.F. Peng, J.F. Liu, X.L. Hu, G.B. Jiang, Direct determination of chlorophenols in environmental water samples by hollow fiber supported ionic liquid membrane extraction coupled with high-performance liquid chromatography, J. Chromatogr. A 1139 (2) (2007) 165–170.
[37] Y.H. Zhang, H.R. Gao, M.X. Wang, L.A. Zhao, J.S. Gao, C.M. Xu, Research on the effect of the solvent structure and group on separation of 1-hexene, benzene, and thiophene, Energy Fuels 33 (6) (2019) 5162–5172.
[38] Y.H. Zhang, L. Zhao, F. Chen, Y.T. Wang, J.S. Gao, L.Y. Cao, H. Wang, C.M. Xu, High efficient separation of olefin from fluid catalytic cracking naphtha: separation mechanism and universal simulation method, AlChE. J. 67 (5) (2021) e17153.

The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration

The extraction of aromatics using N-methylpyrrolidone: Liquid-liquid equilibrium determination and mechanism exploration

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