Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

doi:10.1016/j.cjche.2023.08.003

中国化学工程学报 ›› 2024, Vol. 65 ›› Issue (1): 188-199.DOI: 10.1016/j.cjche.2023.08.003

• Full Length Article • 上一篇下一篇

Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

Xudong Zhang, Yanhua Liu, Jun Shen, Yugao Wang, Gang Liu, Yanxia Niu, Qingtao Sheng

College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, China

收稿日期:2023-07-02 修回日期:2023-08-23 出版日期:2024-01-28 发布日期:2024-04-17
通讯作者: Jun Shen,E-mail:shenjun@tyut.edu.cn
基金资助:
This work was financially supported by Shanxi Province Natural Science Foundation of China (20210302123167); NSFC-Shanxi joint fund for coal-based low carbon (U1610223); and ShanxiZheda Institute of Advanced Materials and Chemical Engineering (2021SX-TD006).

Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

Xudong Zhang, Yanhua Liu, Jun Shen, Yugao Wang, Gang Liu, Yanxia Niu, Qingtao Sheng

College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, China

Received:2023-07-02 Revised:2023-08-23 Online:2024-01-28 Published:2024-04-17
Contact: Jun Shen,E-mail:shenjun@tyut.edu.cn
Supported by:
This work was financially supported by Shanxi Province Natural Science Foundation of China (20210302123167); NSFC-Shanxi joint fund for coal-based low carbon (U1610223); and ShanxiZheda Institute of Advanced Materials and Chemical Engineering (2021SX-TD006).

摘要/Abstract

摘要： Carbazole is an irreplaceable basic organic chemical raw material and intermediate in industry. The separation of carbazole from anthracene oil by environmental benign solvents is important but still a challenge in chemical engineering. Deep eutectic solvents (DESs) as a sustainable green separation solvent have been proposed for the separation of carbazole from model anthracene oil. In this research, three quaternary ammonium-based DESs were prepared using ethylene glycol (EG) as hydrogen bond donor and tetrabutylammonium chloride (TBAC), tetrabutylammonium bromide or choline chloride as hydrogen bond acceptors. To explore their extraction performance of carbazole, the conductor-like screening model for real solvents (COSMO-RS) model was used to predict the activity coefficient at infinite dilution (γ^∞) of carbazole in DESs, and the result indicated TBAC:EG (1:2) had the stronger extraction ability for carbazole due to the higher capacity at infinite dilution (C^∞) value. Then, the separation performance of these three DESs was evaluated by experiments, and the experimental results were in good agreement with the COSMO-RS prediction results. The TBAC:EG (1:2) was determined as the most promising solvent. Additionally, the extraction conditions of TBAC:EG (1:2) were optimized, and the extraction efficiency, distribution coefficient and selectivity of carbazole could reach up to 85.74%, 30.18 and 66.10%, respectively. Moreover, the TBAC:EG (1:2) could be recycled by using environmentally friendly water as antisolvent. In addition, the separation performance of TBAC:EG (1:2) was also evaluated by real crude anthracene, the carbazole was obtained with purity and yield of 85.32%, 60.27%, respectively. Lastly, the extraction mechanism was elucidated by σ-profiles and interaction energy analysis. Theoretical calculation results showed that the main driving force for the extraction process was the hydrogen bonding ((N-H…Cl) and van der Waals interactions (C-H…O and C-H…π), which corresponding to the blue and green isosurfaces in IGMH analysis. This work presented a novel method for separating carbazole from crude anthracene oil, and will provide an important reference for the separation of other high value-added products from coal tar.

关键词: Carbazole, Model anthracene oil, Deep eutectic solvents, COSMO-RS, Extraction mechanism

Abstract: Carbazole is an irreplaceable basic organic chemical raw material and intermediate in industry. The separation of carbazole from anthracene oil by environmental benign solvents is important but still a challenge in chemical engineering. Deep eutectic solvents (DESs) as a sustainable green separation solvent have been proposed for the separation of carbazole from model anthracene oil. In this research, three quaternary ammonium-based DESs were prepared using ethylene glycol (EG) as hydrogen bond donor and tetrabutylammonium chloride (TBAC), tetrabutylammonium bromide or choline chloride as hydrogen bond acceptors. To explore their extraction performance of carbazole, the conductor-like screening model for real solvents (COSMO-RS) model was used to predict the activity coefficient at infinite dilution (γ^∞) of carbazole in DESs, and the result indicated TBAC:EG (1:2) had the stronger extraction ability for carbazole due to the higher capacity at infinite dilution (C^∞) value. Then, the separation performance of these three DESs was evaluated by experiments, and the experimental results were in good agreement with the COSMO-RS prediction results. The TBAC:EG (1:2) was determined as the most promising solvent. Additionally, the extraction conditions of TBAC:EG (1:2) were optimized, and the extraction efficiency, distribution coefficient and selectivity of carbazole could reach up to 85.74%, 30.18 and 66.10%, respectively. Moreover, the TBAC:EG (1:2) could be recycled by using environmentally friendly water as antisolvent. In addition, the separation performance of TBAC:EG (1:2) was also evaluated by real crude anthracene, the carbazole was obtained with purity and yield of 85.32%, 60.27%, respectively. Lastly, the extraction mechanism was elucidated by σ-profiles and interaction energy analysis. Theoretical calculation results showed that the main driving force for the extraction process was the hydrogen bonding ((N-H…Cl) and van der Waals interactions (C-H…O and C-H…π), which corresponding to the blue and green isosurfaces in IGMH analysis. This work presented a novel method for separating carbazole from crude anthracene oil, and will provide an important reference for the separation of other high value-added products from coal tar.

Key words: Carbazole, Model anthracene oil, Deep eutectic solvents, COSMO-RS, Extraction mechanism

Xudong Zhang, Yanhua Liu, Jun Shen, Yugao Wang, Gang Liu, Yanxia Niu, Qingtao Sheng. Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents[J]. 中国化学工程学报, 2024, 65(1): 188-199.

参考文献

[1] Z.H. Ma, X.Y. Wei, G.H. Liu, F.J. Liu, Z.M. Zong, Value-added utilization of hightemperature coal tar:A review, Fuel 292(2021)119954.
[2] S.L. Li, D.L. Cao, Z.Y. Hu, Z.C. Li, X.J. Meng, X.H. Han, W.B. Ma, Synthesis and spectral properties of carbazole-coumarin hybrid dyes, Chem. Heterocycl. Compd. 56(2)(2020)219-225.
[3] Y.J. Xue, M.Y. Li, X.J. Jin, C.J. Zheng, H.R. Piao, Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents, J. Enzyme Inhib. Med. Chem. 36(1)(2021)295-306.
[4] L. Wan, K.K. Guo, J.L. Zhu, F. Wang, Y.P. Zhu, S.F. Deng, H.M. Qi, Improvement of the oxidation resistance of silicon-containing arylacetylene resins upon the introduction of carbazoles, J. Appl. Polym. Sci. 138(1)(2021)49642.
[5] B. Zhang, B. Li, Z.G. Wang, Creation of carbazole-based fluorescent porous polymers for recognition and detection of various pesticides in water, ACS Sens. 5(1)(2020)162-170.
[6] P.L. Gao, J.N. Wang, L.H. Wang, D. Wang, W. Peng, S.H. Zou, Y.Q. Mo, Y. Zhang, Highly efficient and stable blue quantum-dot light-emitting diodes based on polyfluorenes with carbazole pendent groups as hole-transporting materials, Org. Electron. 92(2021)106138.
[7] A.W. Schmidt, K.R. Reddy, H.J. Knölker, Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids, Chem. Rev. 112(6)(2012)3193-3328.
[8] A.A. Umar, I. Bin Mohd Saaid, A.A. Sulaimon, R.B.M. Pilus, A review of petroleum emulsions and recent progress on water-in-crude oil emulsions stabilized by natural surfactants and solids, J. Petrol. Sci. Eng. 165(2018)673-690.
[9] M. Tachibana, M. Furusawa, Zone-melting separation of carbazole and anthracene from polynuclear aromatic compounds using biphenyl as a medium, followed by the synchronous fluorometric determination, Bull. Chem. Soc. Jpn. 62(7)(1989)2179-2183.
[10] I. Goodarznia, F. Esmaeilzadeh, Solubility of an anthracene, phenanthrene, and carbazole mixture in supercritical carbon dioxide, J. Chem. Eng. Data 47(2)(2002)333-338.
[11] C.P. Ye, H.A. Zheng, T.T. Wu, M.M. Fan, J.E. Feng, W.Y. Li, Optimization of solvent crystallization process in obtaining high purity anthracene and carbazole from crude anthracene, AIChE J. 60(1)(2014)275-281.
[12] C.P. Ye, X.X. Ding, W.Y. Li, T.T. Wu, M.M. Fan, J.E. Feng, Highly efficient solvent screening for separating carbazole from crude anthracene, Energy Fuels. 30(4)(2016)3529-3534.
[13] P. Gao, J. Zhang, Z.Q. Guo, J. Gao, D.M. Xu, Y.X. Ma, L.Z. Zhang, Y.L. Wang, Experimental and quantum chemical calculations investigations of morpholine-based ionic liquids as extractants for efficient extraction of nitrogen heterocyclic neutral compounds, Fuel 333(2023)126446.
[14] Q. Liu, Q. Liu, X.L. Zhang, Separation of m-cresol from model oil by pyridiniumbased ionic liquids:COSMO-RS screening, experimental study, and process simulation, J. Environ. Chem. Eng. 10(6)(2022)108874.
[15] P. Gao, T. Zhang, J.X. Wang, J. Gao, D.M. Xu, Y.X. Ma, Y.L. Wang, L.Z. Zhang, Theoretical insight and experimental exploration of designing biocompatible functionalized ionic liquids for efficient separation of typical organic Lewis acid compound indole from coal-based fuel pyrolysis product, J. Mol. Liq. 367(2022)120439.
[16] D. Wang, T. Zhang, L. Yang, L.Z. Zhang, D.M. Xu, J. Gao, Y.L. Wang, Molecular mechanism and extraction explorations for separation of pyridine from coal pyrolysis model mixture using protic ionic liquid[Hnmp] [HSO₄], Fuel 309(2022)122130.
[17] T. Zhang, D. Wang, R.R. Fang, X.J. Tian, L.Z. Zhang, D.M. Xu, Y.X. Ma, J. Gao, Y.L. Wang, Intermolecular interaction and extraction explorations for separation of high-boiling neutral nitrogen compounds using biodegradable ionic liquids, ACS Sustain. Chem. Eng. 9(47)(2021)15839-15848.
[18] Y. Zhao, J. Tong, Investigation of the extraction ability and mechanism of environmentally friendly ionic liquids for phenol in the model oil, Fuel 341(2023)127673.
[19] P. Gao, L. Yang, J.X. Wang, J. Gao, D.M. Xu, L.Z. Ma, L.Z. Zhang, Y.L. Wang, Integrated investigation for extractive denitrogenation of fuel oils with ecofriendly piperazine-based ionic liquids, Fuel 337(2023)127187.
[20] T.T. Jiao, X.L. Zhuang, H.Y. He, L.H. Zhao, C.S. Li, H.N. Chen, S.J. Zhang, An ionic liquid extraction process for the separation of indole from wash oil, Green Chemistry 17(7)(2015)3783-3790.
[21] Y.A. Ji, Y.C. Hou, S.H. Ren, W.Z. Wu, Highly efficient separation of indole from model wash oil using tetraethyl ammonium amino acid ionic liquids, Sep. Purif. Technol. 258(2021)117997.
[22] D. Zhao, C. Liu, Y.G. Wang, H.Y. Zhang, Ionic liquids design for efficient separation of anthracene and carbazole, Sep. Purif. Technol. 281(2022)119892.
[23] D. Zhao, Y. Xiong, Y.G. Wang, B.B. Lu, H.Y. Zhang, Separation of anthracene and carbazole from crude anthracene via imidazolium-based ionic liquids, Fuel 331(2023)125704.
[24] J.M. Yin, J.P. Wang, Z. Li, D. Li, G. Yang, Y.N. Cui, A.L. Wang, C.P. Li, Deep desulfurization of fuels based on an oxidation/extraction process with acidic deep eutectic solvents, Green Chemistry 17(9)(2015)4552-4559.
[25] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Novel solvent properties of choline chloride/urea mixtures, Chem. Commun. 1(2003)70-71.
[26] A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, R.K. Rasheed, Deep eutectic solvents formed between choline chloride and carboxylic acids:Versatile alternatives to ionic liquids, J. Am. Chem. Soc. 126(29)(2004)9142-9147.
[27] E.L. Smith, A.P. Abbott, K.S. Ryder, Deep eutectic solvents (DESs) and their applications, Chem. Rev. 114(21)(2014)11060-11082.
[28] B.B. Hansen, S. Spittle, B. Chen, D. Poe, Y. Zhang, J.M. Klein, A. Horton, L. Adhikari, T. Zelovich, B.W. Doherty, B. Gurkan, E.J. Maginn, A. Ragauskas, M. Dadmun, T.A. Zawodzinski, G.A. Baker, M.E. Tuckerman, R.F. Savinell, J.R. Sangoro, Deep eutectic solvents:A review of fundamentals and applications, Chem. Rev. 121(3)(2021)1232-1285.
[29] P. López-Porfiri, J.F. Brennecke, M. Gonzalez-Miquel, Excess molar enthalpies of deep eutectic solvents (DESs) composed of quaternary ammonium salts and glycerol or ethylene glycol, J. Chem. Eng. Data 61(12)(2016)4245-4251.
[30] E.A. Mernissi Cherigui, K. Sentosun, P. Bouckenooge, H. Vanrompay, S. Bals, H. Terryn, J. Ustarroz, Comprehensive study of the electrodeposition of nickel nanostructures from deep eutectic solvents:Self-limiting growth by electrolysis of residual water, J. Phys. Chem. C 121(17)(2017)9337-9347.
[31] J.P. Bittner, N.N. Zhang, L. Huang, P.D. de María, S. Jakobtorweihen, S. Kara, Impact of deep eutectic solvents (DESs) and individual DES components on alcohol dehydrogenase catalysis:Connecting experimental data and molecular dynamics simulations, Green Chemistry 24(3)(2022)1120-1131.
[32] T. Zhang, T. Doert, H. Wang, S.J. Zhang, M. Ruck, Inorganic synthesis based on reactions of ionic liquids and deep eutectic solvents, Angew. Chem. Int. Ed. 60(41)(2021)22148-22165.
[33] E.R. Parnham, E.A. Drylie, P.S. Wheatley, A.M.Z. Slawin, R.E. Morris, Ionothermal materials synthesis using unstable deep-eutectic solvents as template-delivery agents, Angew. Chem. Int. Ed. 45(30)(2006)4962-4966.
[34] Z. Song, X.T. Hu, H.Y. Wu, M.C. Mei, S. Linke, T. Zhou, Z.W. Qi, K. Sundmacher, Systematic screening of deep eutectic solvents as sustainable separation media exemplified by the CO₂ capture process, ACS Sustain. Chem. Eng. 8(23)(2020)8741-8751.
[35] X.D. Zhang, J.Y. Wang, J. Shen, Y.G. Wang, G. Liu, Y.X. Niu, Q.T. Sheng, Highly efficient extraction of indole from model wash oil by using environmentally benign deep eutectic solvents, Sep. Purif. Technol. 285(2022)120381.
[36] W.W. Yan, X.Y. Wei, M.X. Wang, Z.M. Zong, Overview:Effective separation of oxygen-, nitrogen-, and sulfur-containing aromatics in high-temperature coal tar by ionic liquids and deep eutectic solvents:Experimental and computational, Ind. Eng. Chem. Res. 61(13)(2022)4481-4492.
[37] H.Y. Cheng, Z.W. Qi, Applications of deep eutectic solvents for hard-to-separate liquid systems, Sep. Purif. Technol. 274(2021)119027.
[38] G.X. Li, Q.H. Liu, C.M. Gui, Z.G. Lei, Thermodynamic and molecular insights into natural gas dehydration using choline chloride-based deep eutectic solvents, AIChE. J. 68(7)(2022) -17662.
[39] G.X. Li, C.M. Gui, R.S. Zhu, Z.G. Lei, Deep eutectic solvents for efficient capture of cyclohexane in volatile organic compounds:Thermodynamic and molecular mechanism, AIChE. J. 68(3)(2022) -17535.
[40] X.D. Zhang, W.B. Zhao, J. Shen, Y.G. Wang, G. Liu, Y.X. Niu, Q.T. Sheng, Theoretical and experimental exploration for efficient separation of carbazole from anthracene oil with quaternary ammonium salts via forming deep eutectic solvents, J. Mol. Liq. 368(2022)120831.
[41] M.Y. Wu, H.Y. Cheng, L.F. Chen, Z.W. Qi, Extractive deterpenation of citrus essential oils using quaternary ammonium-based deep eutectic solvents, J. Mol. Liq. 336(2021)116868.
[42] Y.S. Dai, X.J. Chu, Y.Y. Jiao, Y.N. Li, F.L. Shan, S. Zhao, G.X. Li, Z.G. Lei, P.Z. Cui, Z.Y. Zhu, Y.L. Wang, Molecular insights into azeotrope separation in the methyl tert-butyl ether production process using ChCl-based deep eutectic solvents, Chem. Eng. Sci. 264(2022)118179.
[43] M.K. Hadj-Kali, H.F. Hizaddin, I. Wazeer, L. El blidi, S. Mulyono, M. Ali Hashim, Liquid-liquid separation of azeotropic mixtures of ethanol/alkanes using deep eutectic solvents:COSMO-RS prediction and experimental validation, Fluid Phase Equilibria 448(2017)105-115.
[44] Q. Liu, X.L. Zhang, Systematic method of screening deep eutectic solvents as extractive solvents for m-cresol/cumene separation, Sep. Purif. Technol. 291(2022)120853.
[45] W.W. Yan, Z.M. Zong, Z.X. Li, J. Li, G.H. Liu, Z.H. Ma, Y.Y. Zhang, M.L. Xu, F.J. Liu, X.Y. Wei, Effective separation and purification of nitrogen-containing aromatics from the light portion of a high-temperature coal tar using choline chloride and malonic acid:Experimental and molecular dynamics simulation, ACS Sustain. Chem. Eng. 8(25)(2020)9464-9471.
[46] Z.X. Qin, H.Y. Cheng, Z. Song, L.J. Ji, L.F. Chen, Z.W. Qi, Selection of deep eutectic solvents for extractive deterpenation of lemon essential oil, J. Mol. Liq. 350(2022)118524.
[47] X.Y. Liu, Y.J. Li, J.F. Xing, Y.N. Li, Z.H. Su, X.M. Qiu, Z.R. Chen, Y.L. Wang, P.Z. Cui, Liquid-liquid extraction and mechanism analysis of extracting fuel additive isopropanol from mixture with choline-based deep eutectic solvents as efficient extractants, Fuel 326(2022)125048.
[48] T. Lemaoui, Y. Benguerba, A.S. Darwish, F. Abu Hatab, S.E.E. Warrag, M.C. Kroon, I.M. Alnashef, Simultaneous dearomatization, desulfurization, and denitrogenation of diesel fuels using acidic deep eutectic solvents as extractive agents:A parametric study, Sep. Purif. Technol. 256(2021)117861.
[49] H. Lee, S. Kang, Y. Jin, D. Jung, K. Park, K. Li, J. Lee, Systematic investigation of the extractive desulfurization of fuel using deep eutectic solvents from multifarious aspects, Fuel 264(2020)116848.
[50] Y.F. Chen, Z.M. Zong, X.K. Li, G.H. Liu, Z. Yang, X.G. Jiang, F.J. Liu, X.Y. Wei, Q.J. Guo, T.S. Zhao, H.C. Bai, B.J. Wang, An effective approach for separating carbazole and its derivates from coal-tar-derived anthracene oil using ionic liquids, Energy Fuels. 33(1)(2019)513-522.
[51] A. Klamt, Conductor-like screening model for real solvents:A new approach to the quantitative calculation of solvation phenomena, J. Phys. Chem. 99(7)(1995)2224-2235.
[52] A. Klamt, COSMO-RS:From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design, Elsevier, Amsterdam, 2005.
[53] A. Klamt, F. Eckert, COSMO-RS:A novel and efficient method for the a priori prediction of thermophysical data of liquids, Fluid Phase Equilibria 172(1)(2000)43-72.
[54] M.S. Shannon, J.M. Tedstone, S.P.O. Danielsen, M.S. Hindman, A.C. Irvin, J.E. Bara, Free volume as the basis of gas solubility and selectivity in imidazoliumbased ionic liquids, Ind. Eng. Chem. Res. 51(15)(2012)5565-5576.
[55] M. Larriba, M. Ayuso, P. Navarro, N. Delgado-Mellado, M. Gonzalez-Miquel, J. García, F. Rodríguez, Choline chloride-based deep eutectic solvents in the dearomatization of gasolines, ACS Sustain. Chem. Eng. 6(1)(2018)1039-1047.
[56] Y.F. Song, S. Chen, F. Luo, L.Y. Sun, Absorption of toluene using deep eutectic solvents:Quantum chemical calculations and experimental investigation, Ind. Eng. Chem. Res. 59(52)(2020)22605-22618.
[57] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, Gaussian 09, Revision D. 01, Gaussian, Inc., Wallingford CT, See also URL http//www.Gaussian.Com.(2009).
[58] T. Lu, Q.X. Chen, Independent gradient model based on Hirshfeld partition:A new method for visual study of interactions in chemical systems, J. Comput. Chem. 43(8)(2022)539-555.
[59] T. Lu, F.W. Chen, Multiwfn:A multifunctional wavefunction analyzer, J. Comput. Chem. 33(5)(2012)580-592.
[60] W. Humphrey, A. Dalke, K. Schulten, VMD:Visual molecular dynamics, J. Mol. Graph. 14(1)(1996)33-38, 27-28.
[61] A.P. Abbott, G. Capper, S. Gray, Design of improved deep eutectic solvents using hole theory, ChemPhysChem 7(4)(2006)803-806.
[62] 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.
[63] T.T. Jiao, C.H. Ren, S.J. Lin, L.Z. Zhang, X.Z. Xu, Y.Q. Zhang, W.R. Zhang, P. Liang, The extraction mechanism research for the separation of indole through the formation of deep eutectic solvents with quaternary ammonium salts, J. Mol. Liq. 347(2022)118325.
[64] H. Passos, D.J.P. Tavares, A.M. Ferreira, M.G. Freire, J.A.P. Coutinho, Are aqueous biphasic systems composed of deep eutectic solvents ternary or quaternary systems, ACS Sustain. Chem. Eng. 4(2016)2881-2886.
[65] M. Bisht, I.P.E. Macário, M.C. Neves, J.L. Pereira, S. Pandey, R.D. Rogers, J.A.P. Coutinho, S.P.M. Ventura, Enhanced dissolution of chitin using acidic deep eutectic solvents:A sustainable and simple approach to extract chitin from crayfish shell wastes as alternative feedstocks, ACS Sustain. Chem. Eng. 9(48)(2021)16073-16081.
[66] F.O. Farias, H. Passos, Á. Lima, M.R. Mafra, J.A.P. Coutinho, Is it possible to create ternary-like aqueous biphasic systems with deep eutectic solvents?ACS Sustain. Chem. Eng. 5(2017)9402-9411.

Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 14

编辑推荐

Metrics

本文评价

[1]	Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang. Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation[J]. 中国化学工程学报, 2023, 59(7): 160-168.
[2]	Yinglin Mai, Xiaoling Xian, Lei Hu, Xiaodong Zhang, Xiaojie Zheng, Shunhui Tao, Xiaoqing Lin. Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent[J]. 中国化学工程学报, 2023, 54(2): 248-256.
[3]	Hemayat Shekaari, Fariba Ghaffari, Masumeh Mokhtarpour. Volumetricand ultrasonic properties of thiamine hydrochloride drug in aqueous solutions of choline-based deep eutectic solvents at different temperatures[J]. 中国化学工程学报, 2023, 62(10): 21-30.
[4]	Youqi Li, Xiaopeng Chen, Linlin Wang, Xiaojie Wei, Weijian Nong, Xuejuan Wei, Jiezhen Liang. Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems[J]. 中国化学工程学报, 2023, 53(1): 155-169.
[5]	Linlan Wu, Zhengxin Jiao, Suhang Xun, Minqiang He, Lei Fan, Chao Wang, Wenshu Yang, Wenshuai Zhu, Huaming Li. Photocatalytic oxidative of Keggin-type polyoxometalate ionic liquid for enhanced extractive desulfurization in binary deep eutectic solvents[J]. 中国化学工程学报, 2022, 44(4): 205-211.
[6]	Cui-Ping Ye, Ya-Fei Qiao, Rui-Nan Wang, Wen-Ying Li. Purification of carbazole by solvent crystallization under two forced cooling modes[J]. 中国化学工程学报, 2021, 35(7): 173-179.
[7]	Zhengxing Dai, Yifeng Chen, Chang Liu, Xiaohua Lu, Yanrong Liu, Xiaoyan Ji. Prediction and verification of heat capacities for pure ionic liquids[J]. 中国化学工程学报, 2021, 29(3): 169-176.
[8]	Khatereh Ali Pishro, Ghulam Murshid, Farouq Sabri Mjalli, Jamil Naser. Investigation of CO₂ solubility in monoethanolamine hydrochloride based deep eutectic solvents and physical properties measurements[J]. 中国化学工程学报, 2020, 28(11): 2848-2856.
[9]	Zhigang Lei, Yifan Jiang, Yao Liu, Yichun Dong, Gangqiang Yu, Yanyong Sun, Ruili Guo. Solubility and mass transfer of H₂, CH₄, and their mixtures in vacuum gas oil: An experimental and modeling study[J]. 中国化学工程学报, 2019, 27(12): 3000-3009.
[10]	Qian Liu, Xianglan Zhang, Wei Li. Separation of m-cresol from aromatic hydrocarbon and alkane using ionic liquids via hydrogen bond interaction[J]. 中国化学工程学报, 2019, 27(11): 2675-2686.
[11]	Zhen Song, Dian Yu, Qian Zeng, Jingjing Zhang, Hongye Cheng, Lifang Chen, Zhiwen Qi. Effect of water on extractive desulfurization of fuel oils using ionic liquids: A COSMO-RS and experimental study[J]. , 2017, 25(2): 159-165.
[12]	Zhigang Lei, Yaru Guo, Yanyan Guo, Xinxin Li, Chengna Dai. H₂ solubility and mass transfer in anthraquinone working solution: Experimental and modeling study[J]. , 2017, 25(2): 143-148.
[13]	Cornelius B. Bavoh, Bhajan Lal, Omar Nashed, Muhammad S. Khan, Lau K. Keong, Mohd. Azmi Bustam. COSMO-RS: An ionic liquid prescreening tool for gas hydrate mitigation[J]. Chinese Journal of Chemical Engineering, 2016, 24(11): 1619-1624.
[14]	杨磊, 王胜强, 王瑞聪, 于宏兵. Selective Removal of Nitrogen-Containing Heterocyclic Compounds from Transportation Diesel Fuels with Reactive Adsorbent[J]. Chinese Journal of Chemical Engineering, 2013, 21(5): 558-563.