Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction

doi:10.1016/j.cjche.2021.01.008

Chinese Journal of Chemical Engineering ›› 2021, Vol. 35 ›› Issue (7): 180-188.DOI: 10.1016/j.cjche.2021.01.008

• Separation Science and Engineering • Previous Articles Next Articles

Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction

Yonglin Li¹, He'an Luo^1,2, Qiuhong Ai^1,2, Kuiyi You^1,2, Fei Zhao¹, Wenlong Xiao¹

1. School of Chemical Engineering, Xiangtan University, Xiangtan 411105, China;
2. National & Local United Engineering Research Center for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan 411105, China

Received:2020-09-15 Revised:2021-01-19 Online:2021-09-30 Published:2021-07-28
Contact: He'an Luo, Qiuhong Ai
Supported by:
We are grateful for the financial support by the National Natural Science Foundation of China (21676226, 21606186), the Natural Science Foundation for Distinguished Young Scholars in Hunan Province (2018JJ1023), Key Research and Development Program in Hunan Province (2019GK2041), and Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization.

Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction

Yonglin Li¹, He'an Luo^1,2, Qiuhong Ai^1,2, Kuiyi You^1,2, Fei Zhao¹, Wenlong Xiao¹

1. School of Chemical Engineering, Xiangtan University, Xiangtan 411105, China;
2. National & Local United Engineering Research Center for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan 411105, China

通讯作者: He'an Luo, Qiuhong Ai
基金资助:
We are grateful for the financial support by the National Natural Science Foundation of China (21676226, 21606186), the Natural Science Foundation for Distinguished Young Scholars in Hunan Province (2018JJ1023), Key Research and Development Program in Hunan Province (2019GK2041), and Collaborative Innovation Center of New Chemical Technologies for Environmental Benignity and Efficient Resource Utilization.

Abstract

Abstract: In this paper, a method of extracting phenols from coal tar by amines aqueous solution was proposed. The effects of various amines on the extraction properties of phenols in coal tar were researched from the views of molecular structure. The parameters such as molar ratio, concentration, extraction time and temperature for the extraction of coal tar by the monoethanolamine and ethylenediamine aqueous solution were examined. The results show that the organic amine with more amino groups, hydroxyl structure and strong electronegativity exhibited better extraction performance. Under the optimal conditions, the extraction yields of phenols in coal tar by the monoethanolamine or ethylenediamine aqueous solution are above 80%, and the recovery yields of amines reach 99%. Furthermore, the probable geometries of complexes formed by the combination of phenols and organic amines were calculated by density function theory. In addition, several thermodynamic models were evaluated through comparing the relative deviation of simulation results by ASPEN PLUS to the experimental ones, which provide feasibility thermodynamic models for the simulation of extraction process. The present work affords a mild, efficient and green approach for the extraction of phenols from coal tar by an aqueous solution of amines in industry application.

Key words: Amines, Coal tar, Liquid-liquid equilibrium, Thermodynamic model

摘要： In this paper, a method of extracting phenols from coal tar by amines aqueous solution was proposed. The effects of various amines on the extraction properties of phenols in coal tar were researched from the views of molecular structure. The parameters such as molar ratio, concentration, extraction time and temperature for the extraction of coal tar by the monoethanolamine and ethylenediamine aqueous solution were examined. The results show that the organic amine with more amino groups, hydroxyl structure and strong electronegativity exhibited better extraction performance. Under the optimal conditions, the extraction yields of phenols in coal tar by the monoethanolamine or ethylenediamine aqueous solution are above 80%, and the recovery yields of amines reach 99%. Furthermore, the probable geometries of complexes formed by the combination of phenols and organic amines were calculated by density function theory. In addition, several thermodynamic models were evaluated through comparing the relative deviation of simulation results by ASPEN PLUS to the experimental ones, which provide feasibility thermodynamic models for the simulation of extraction process. The present work affords a mild, efficient and green approach for the extraction of phenols from coal tar by an aqueous solution of amines in industry application.

关键词: Amines, Coal tar, Liquid-liquid equilibrium, Thermodynamic model

Yonglin Li, He'an Luo, Qiuhong Ai, Kuiyi You, Fei Zhao, Wenlong Xiao. Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction[J]. Chinese Journal of Chemical Engineering, 2021, 35(7): 180-188.

References

[1] C.F. Yao, Y.C. Hou, S.H. Ren, W.Z. Wu, K. Zhang, Y.A. Ji, H. Liu, Efficient separation of phenol from model oils using environmentally benign quaternary ammonium-based zwitterions via forming deep eutectic solvents, Chem. Eng. J. 326(2017) 620-626.
[2] L. Cesari, L. Canabady-Rochelle, F. Mutelet, Extraction of phenolic compounds from aqueous solution using choline bis(trifluoromethylsulfonyl) imide, Fluid Phase Equilibr. 446(2017) 28-35.
[3] Y.A. Ji, Y.C. Hou, S.H. Ren, C.F. Yao, W.Z. Wu, Highly efficient extraction of phenolic compounds from oil mixtures by trimethylamine-based dicationic ionic liquids via forming deep eutectic solvents, Fuel Process. Technol. 171(2018) 183-191.
[4] R. Gingell, J. O'Donoghue, R.J. Staab, I.W. Daly, B.K. Bernard, A. Ranpuria, E.J. Wikinson, D. Woltering, P.A. Johns, S.B. Montgomery, L.E. Hannond, M.L. Leng, Phenol and Phenolics, American Cancer Society, California, 2001.
[5] M. Sun, Y.B. Li, S. Sha, J.W. Gao, R.C. Wang, Y.J. Zhang, Q.Q. Hao, H.Y. Chen, Q.X. Yao, X.X. Ma, The composition and structure of n-hexane insoluble-hot benzene soluble fraction and hot benzene insoluble fraction from low temperature coal tar, Fuel 262(2020) 116511.
[6] D. Li, Z. Li, W.H. Li, Q.C. Liu, Z.L. Feng, Z. Fan, Hydrotreating of low temperature coal tar to produce clean liquid fuels, J. Anal. Appl. Pyrol. 100(2013) 245-252.
[7] W. Tang, M.X. Fang, H.Y. Wang, P.L. Yu, Q.H. Wang, Z.Y. Luo, Mild hydrotreatment of low temperature coal tar distillate:Product composition, Chem. Eng. J. 236(2014) 529-537.
[8] Y. Zhang, Z.Y. Li, H.Y. Wang, X.P. Xuan, J.J. Wang, Efficient separation of phenolic compounds from model oil by the formation of choline derivativebased deep eutectic solvents, Sep. Purif. Technol. 163(2016) 310-318.
[9] K.F. Chasib, Extraction of phenolic pollutants (phenol and pChlorophenol) from industrial wastewater, J. Chem. Eng. Data 58(2013) 1549-1564.
[10] X.Y. Yang, B.J. Wang, H.Q. Luo, S.L. Yan, J. Dai, Z.S. Bai, Efficient recovery of phenol from coal tar processing wastewater with tributylphosphane/diethyl carbonate/cyclohexane:Extraction cycle and mechanism study, Chem. Eng. Res. Des. 157(2020) 104-113.
[11] W.J. Guo, Y.C. Hou, S.H. Ren, S.D. Tian, W.Z. Wu, Formation of deep eutectic solvents by phenols and choline chloride and their physical properties, J. Chem. Eng. Data 58(2013) 866-872.
[12] Y.C. Hou, J. Kong, Y.H. Ren, S.H. Ren, W.Z. Wu, Mass transfer dynamics in the separation of phenol from model oil with quaternary ammonium salts via forming deep eutectic solvents, Sep. Purif. Technol. 174(2017) 554-560.
[13] T.T. Jiao, M.M. Gong, X.L. Zhuang, C.S. Li, S.J. Zhang, A new separation method for phenolic compounds from low-temperature coal tar with urea by complex formation, J. Ind. Eng. Chem. 29(2015) 344-348.
[14] J. Barbieri, C. Goltz, F.B. Cavalheiro, A. Toci, L. Igarashi-Mafra, M. Mafra, Deep eutectic solvents applied in the extraction and stabilization of rosemary (Rosmarinus officinalis L.) phenolic compounds, Ind. Crop. Prod., 144(2020) 112049.
[15] T.T. Jiao, X.Z. Qin, H.W. Zhang, W.R. Zhang, Y.Q. Zhang, P. Liang, Separation of phenol and pyridine from coal tar via liquid-liquid extraction using deep eutectic solvents, Chem. Eng. Res. Des. 145(2019) 112-121.
[16] S.H. Ren, Y. Xiao, Y.M. Wang, J. Kong, Y.C. Hou, W.Z. Wu, Effect of water on the separation of phenol from model oil with choline chloride via forming deep eutectic solvent, Fuel Process. Technol. 137(2015) 104-108.
[17] Y.A. Ji, Y.C. Hou, S.H. Ren, C.F. Yao, W.Z. Wu, Removal of the neutral oil entrained in deep eutectic solvents using an anti-extraction method, Fuel Process. Technol. 160(2017) 27-33.
[18] Y.T. Dai, G.J. Witkamp, R. Verpoorte, Y.H. Choi, Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L, Anal. Chem. 85(2013) 6272-6278.
[19] H. Amirfirouzkouhi, A.N. Kharat, Application of ionic liquids as recyclable green catalysts for selective alkylation of phenol, Sep. Purif. Technol. 196(2018) 132-139.
[20] L. Zhang, D. Xu, J. Gao, S. Zhou, L. Zhao, Z. Zhang, Extraction and mechanism for the separation of neutral N-compounds from coal tar by ionic liquids, Fuel 194(2017) 27-35.
[21] Q. Liu, X.L. Zhang, W. Li, Separation of m-cresol from aromatic hydrocarbon and alkane using ionic liquids via hydrogen bond interaction, Chin J. Chem. Eng. 27(2018) 2675-2686.
[22] X. Xu, A. Li, T. Zhang, L.Z. Zhang, D.M. Xu, J. Gao, Y.L. Wang, Efficient extraction of phenol from low-temperature coal tar model oil via imidazolium-based ionic liquid and mechanism analysis, J. Mol. Liq. 306(2020) 112911.
[23] B.N. Bhadra, I. Ahmed, S.H. Jhung, Remarkable adsorbent for phenol removal from fuel:Functionalized metal-organic framework, Fuel 174(2016) 43-48.
[24] J.J. Gao, Y.F. Dai, W.Y. Ma, H.H. Xu, C.X. Li, Efficient separation of phenol from oil by acid-base complexing adsorption, Chem. Eng. J. 281(2015) 749-758.
[25] K. Mohanty, D. Das, M.N. Biswas, Adsorption of phenol from aqueous solutions using activated carbons prepared from Tectona grandis sawdust by ZnCl₂ activation, Chem. Eng. J. 115(2005) 121-131.
[26] Y.C. Hou, Y.H. Ren, W. Peng, S.H. Ren, W.Z. Wu, Separation of phenols from oil using imidazolium-based ionic liquids, Ind. Eng. Chem. Res. 52(2013) 18071-18075.
[27] H. Meng, C.T. Ge, N.N. Ren, W.Y. Ma, Y.Z. Lu, C.X. Li, Complex extraction of phenol and cresol from model coal tar with polyols, ethanol amines, and ionic liquids thereof, Ind. Eng. Chem. Res. 53(2014) 355-362.
[28] H.J. Gai, L. Qiao, C.Y. Zhong, X.W. Zhang, M. Xiao, H.B. Song, A solvent based separation method for phenolic compounds from low-temperature coal tar, J. Clean. Prod. 223(2019) 1-11.
[29] W. Conway, S. Bruggink, Y. Beyad, W.L. Luo, I. Melián-Cabrera, G. Puxty, P. Feron, CO₂ absorption into aqueous amine blended solutions containing monoethanolamine (MEA), N, N-dimethylethanolamine (DMEA), N, Ndiethylethanolamine (DEEA) and 2-amino-2-methyl-1-propanol (AMP) for post-combustion capture processes, Chem. Eng. Sci. 126(2015) 446-454.
[30] X. Luo, A. Hartono, S. Hussain, H.F. Svendsen, Mass transfer and kinetics of carbon dioxide absorption into loaded aqueous monoethanolamine solutions, Chem. Eng. Sci. 123(2015) 57-69.
[31] Y. Yuan, G.T. Rochelle, CO₂ absorption rate in semi-aqueous monoethanolamine, Chem. Eng. Sci. 182(2018) 56-66.
[32] H. Lepaumier, D. Picq, P.L. Carrette, New amines for CO₂ capture. I. Mechanisms of amine degradation in the presence of CO₂, Ind. Eng. Chem. Res. 48(2009) 9061-9067.
[33] H.A. Luo, Y.L. Li, Q.H. Ai, K.Y. You, S. Yan, A method of extracting phenols from coal tar or coal liquefaction oil, China Pat., 106986750(2017).
[34] M. Sun, J. Chen, X.M. Dai, X.L. Zhao, K. Liu, X.X. Ma, Controlled separation of low temperature coal tar based on solvent extraction-column chromatography, Fuel Process. Technol. 136(2015) 41-49.
[35] N.R. Dhumal, Electronic structure, molecular electrostatic potential and hydrogen bonding in DMSO-X complexes (X=ethanol, methanol and water), Spectrochim. Acta A. 79(3) (2011) 654-660.
[36] M.K. Rofouei, E. Fereyduni, N. Sohrabi, M. Shamsipur, J.A. Gharamaleki, N. Sundaraganesan, Synthesis, X-ray crystallography characterization, vibrational spectroscopic, molecular electrostatic potential maps, thermodynamic properties studies of N, N'-di(p-thiazole) formamidine, Spectrochim. Acta A. 78(1) (2011) 88-95.
[37] J. Gmehling, J.D. Li, M. Schiller, A modified UNIFAC model. 2. Present parameter matrix and results for different thermodynamic properties, Ind. Eng. Chem. Res. 32(1993) 178-193.
[38] B.L. Larsen, P. Rasmussen, A. FredensluLnd, A modified UNIFAC groupcontribution model for prediction of phase equilibria and heats of mixing, Ind. Eng. Chem. Res. 26(11) (1987) 2274-2286.

Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction

Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction

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