Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

doi:10.1016/j.cjche.2017.09.002

Chinese Journal of Chemical Engineering ›› 2018, Vol. 26 ›› Issue (4): 708-714.DOI: 10.1016/j.cjche.2017.09.002

• Separation Science and Engineering • 上一篇下一篇

Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

Weifeng Xu, Guilin Dai, Kewen Tang, Panliang Zhang, Biquan Xiong, Yu Liu

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China

收稿日期:2017-01-17 修回日期:2017-09-01 出版日期:2018-04-28 发布日期:2018-05-19
通讯作者: Kewen Tang,E-mail addresses:tangkewen@sina.com;Panliang Zhang,E-mail addresses:qpanny@163.com
基金资助:
Supported by the National Basic Research Program of China (2014CB260407).

Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

Weifeng Xu, Guilin Dai, Kewen Tang, Panliang Zhang, Biquan Xiong, Yu Liu

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China

Received:2017-01-17 Revised:2017-09-01 Online:2018-04-28 Published:2018-05-19
Contact: Kewen Tang,E-mail addresses:tangkewen@sina.com;Panliang Zhang,E-mail addresses:qpanny@163.com
Supported by:
Supported by the National Basic Research Program of China (2014CB260407).

摘要/Abstract

摘要： The utilization of liquid-liquid extraction for the separation of 2-phenylbutyric acid (2-PBA) enantiomers was proposed. Factors affecting the extract process were investigated, including organic solvents, β-cyclodextrin derivatives, cyclodextrin concentration, pH and temperature. A model was proposed to describe the separation process based on the homogeneous phase reaction mechanism. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic 2-PBA were 0.129 and 7.455, respectively. The equilibrium constants of the complexation reactions were 89.36 and 36.78 L·mol^-1 for (+)-and (-)-2-PBA, respectively. The model was verified by experiments and proved to be an excellent means to optimize the separation system. Through modeling prediction and experiment, the best conditions (e.g., pH value of 3.00, extractant concentration of 0.1 mol·L^-1, temperature of 5.0℃) were acquired. Under this condition, the maximum enantioselectivity (2.096) was obtained.

关键词: Model, Simulation, Enantioselective extraction, 2-Phenylbutyric acid, Hydrophilic selector

Abstract: The utilization of liquid-liquid extraction for the separation of 2-phenylbutyric acid (2-PBA) enantiomers was proposed. Factors affecting the extract process were investigated, including organic solvents, β-cyclodextrin derivatives, cyclodextrin concentration, pH and temperature. A model was proposed to describe the separation process based on the homogeneous phase reaction mechanism. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic 2-PBA were 0.129 and 7.455, respectively. The equilibrium constants of the complexation reactions were 89.36 and 36.78 L·mol^-1 for (+)-and (-)-2-PBA, respectively. The model was verified by experiments and proved to be an excellent means to optimize the separation system. Through modeling prediction and experiment, the best conditions (e.g., pH value of 3.00, extractant concentration of 0.1 mol·L^-1, temperature of 5.0℃) were acquired. Under this condition, the maximum enantioselectivity (2.096) was obtained.

Key words: Model, Simulation, Enantioselective extraction, 2-Phenylbutyric acid, Hydrophilic selector

Weifeng Xu, Guilin Dai, Kewen Tang, Panliang Zhang, Biquan Xiong, Yu Liu. Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model[J]. Chinese Journal of Chemical Engineering, 2018, 26(4): 708-714.

参考文献

[1] I.W. Wainer, Drue stereochemistry, 2nd ed., Anal. Methods Pharmacol., Marcel Dekker, New York, 1993.

[2] H.Y. Aboul-Enein, I.W. Wainer, The Impact of Stereochemistry on Drug Development and Use, Wiley, New York, 1997.

[3] G.T. Liu, K. Nagahama, Application of rapid expansion of supercritical solutions in the crystallization separation, Ind. Eng. Chem. Res. 35(1996) 4626-4634.

[4] T.J. Ward, B.A. Baker, Chiral separations, Anal. Chem. 80(2008) 4363-4372.

[5] C.A.M. Afonso, J.G. Crespo, Recent advances in chiral resolution through membranebased approaches, Angew. Chem. Int. Ed. 43(2004) 5293-5295.

[6] V. Prelog, M. Kovakevic, M. Egli, Lipophilic tartaric acid esters as enantioselective ionophores, Angew. Chem. Int. Ed. Engl. 28(1989) 1147-1152.

[7] K.W. Tang, J.M. Yi, Y.B. Liu, X.Y. Jiang, Y. Pan, Enantioselective separation of R,S-phenylsuccinic acid by biphasic recognition chiral extraction, Chem. Eng. Sci. 64(2009) 4081-4088.

[8] M. Steensma, N.J. Kuipers, A.B. de Haan, G. Kwant, Influence of process parameters on extraction equilibria for the chiral separation of amines and amino-alcohols with a chiral crown ether, J. Chem. Technol. Biotechnol. 81(2006) 588-597.

[9] M. Pietraszkiewicz, M. Kozbia, O. Pietraszkiewicz, Chiral discrimination of amino acids and their potassium or sodium salts by optically active crown ether derived from D-mannose, J. Membr. Sci. 138(1998) 109-113.

[10] J. Koska, C.A. Haynes, Modelling multiple chemical equilbria in chiral partition systems, Chem. Eng. Sci. 56(2001) 5853-5864.

[11] B. Schuur, J.G.M. Winkelmam, H.J. Heeres, Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant, Ind. Eng. Chem. Res. 47(2008) 10027-10033.

[12] H.I. Kim, K.W. Lee, D. Mishra, K.M. Yi, J.H. Hong, M.K. Jun, H.K. Park, Separation of molybdenum and vanadium from oxalate leached solution of spent residue hydrodesulfurization (RHDS) catalyst by liquid-liquid extraction using amine extractant, J. Ind. Eng. Chem. 21(2015) 1265-1269.

[13] N. Sunsandee, P. Ramakul, M. Hronec, U. Pancharoen, N. Leepipatpiboon, Mathematical model and experimental validation of the synergistic effect of selective enantioseparation of (S)-amlodipine from pharmaceutical wastewater using a HFSLM, J. Ind. Eng. Chem. 20(2014) 1612-1622.

[14] A.J. Hallett, G.J. Kwant, J.G. de Vries, Continuous separation of racemic 3,5-dinitrobenzoyl-amino acids in a centrifugal contact separator with the aid of cinchona-based chiral host compounds, Chem. A Eur. J. 15(2009) 2111-2120.

[15] B. Schuur, J.G.M. Winkelmam, H.J. Heeres, Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant, Ind. Eng. Chem. Res. 47(2008) 10027-10033.

[16] X. Chen, J. Wang, F. Jiao, Efficient enantioseparation of phenylsuccinic acid enantiomers by aqueous two-phase system-based biphasic recognition chiral extraction:phase behaviors and distribution experiments, Process Biochem. 9(2015) 1468-1478.

[17] P. Zhang, J. Luo, K. Tang, J. Yi, C. Yang, Kinetics study on reactive extraction of d-p-hydroxyphenylglycine by BINAP-palladium complex in Lewis cell, Chem. Eng. Process:Process Intensif. 93(2015) 50-55.

[18] S.E. Evans, P. Davies, A. Lubben, B. Kasprzyk-Hordern, Determination of chiral pharmaceuticals and illicit drugs in wastewater and sludge using microwave assisted extraction, solid-phase extraction and chiral liquid chromatography coupled with tandem mass spectrometry, Anal. Chim. Acta 882(2015) 112-126.

[19] A. Holbach, J. Godde, R. Mahendrarajah, N. Kockmann, Enantioseparation of chiral aromatic acids in process intensified liquid-liquid extraction columns, AIChE J. 61(2015) 266-276.

[20] B.J. Verkuijl, A.J. Minnaard, J.G. de Vries, B.L. Feringa, Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes, J. Org. Chem. 74(2009) 6526-6533.

[21] K. Tang, G. Wu, P. Zhang, C. Zhou, J. Liu, Experimental and model study on enantioselective extraction of phenylglycine enantiomers with BINAP-metal complexes, Ind. Eng. Chem. Res. 51(2012) 15233-15241.

[22] M. Asztemborska, M. Miskiewicz, D. Sybilska, Separation of some chiral flavanones by micellar electrokinetic chromatography, Electrophoresis 24(2003) 2527-2531.

[23] C. Akbay, S.A.A. Rizvi, S.A. Shamsi, Simultaneous enantioseparation and tandem UV-MS detection of eight β-blockers in micellar electrokinetic chromatography using a chiral molecular micelle, Anal. Chem. 77(2005) 1672-1683.

[24] S. Fanali, Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors, J. Chromatogr. A 875(2000) 89-122.

[25] K. Tang, H. Zhang, Y. Liu, Experimental and simulation on enantioselective extraction in centrifugal contactor separators, AIChE J. 59(2013) 2594-2602.

[26] G. Wang, L. Yang, F. Wu, N. Deng, Carboxymethyl-β-cyclodextrin enhanced TiO₂ removal of acid red R and lead ions in suspended solutions, J. Chem. Technol. Biotechnol. 89(2014) 297-304.

[27] Z. Ren, Y. Zeng, Y. Hua, Y. Cheng, Z. Guo, Enantioselective liquid-liquid extraction of racemic ibuprofen by L-tartatic acid derivatives, J. Chem. Eng. Data 59(2014) 2517-2522.

[28] J. Szejtli, Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest, 1982.

[29] Y. Yamashoji, T. Ariga, S. Asano, M. Tanaka, Chiral recognition and enantiomeric separation of alanine β-naphthylamide by cyclodextrins, Anal. Chim. Acta 268(1992) 39-47.

[30] K. Tang, P. Zhang, C. Pan, H. Li, Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic-β-cyclodextrin derivatives, AIChE J. 57(2011) 3027-3036.

[31] Y. Zheng, J. Yan, S. Tong, X. Li, C. Chu, High performance liquid chromatographic enantioseparation of 2-phenylpropionic acid chiral mobile phase additive, Chin. J. Pharm. Anal. 33(2013) 827-830.

[32] T. O'Brien, L. Crocker, R. Thompson, K. Thompson, P.H. Toma, D.A. Conlon, B. Feibush, C. Moeder, G. Bicker, N. Grinberg, Mechanistic aspects of chiral discrimination on modified cellulose, Anal. Chem. 69(1997) 1999-2007.

Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Jiahao Xing, Huaizhi Han, Ruitian Yu, Wen Luo. Numerical simulation of flow and heat transfer of n-decane in sub-millimeter spiral tube at supercritical pressure[J]. 中国化学工程学报, 2023, 60(8): 173-185.
[2]	Huiqi Wang, Jianpo Ren, Shihao Zhang, Jiayu Dai, Yue Niu, Ketao Shi, Qiuxiang Yin, Ling Zhou. Measurement and correlation of solubility of 9-fluorenone in 11 pure organic solvents from T = 283.15 to 323.15 K[J]. 中国化学工程学报, 2023, 60(8): 235-241.
[3]	Jindong Dai, Chi Zhai, Jiali Ai, Guangren Yu, Haichao Lv, Wei Sun, Yongzhong Liu. A cellular automata framework for porous electrode reconstruction and reaction-diffusion simulation[J]. 中国化学工程学报, 2023, 60(8): 262-274.
[4]	Lijuan Zhao, Zhe Tan, Xiaoguang Zhang, Qijun Zhang, Wei Wang, Qiang Deng, Jie Ma, De'an Pan. Research on process modeling and simulation of spent lead paste desulfurization enhanced reactor[J]. 中国化学工程学报, 2023, 60(8): 293-303.
[5]	Borui Liu, Tao Zhang, Yi Zheng, Kailong Li, Hui Pan, Hao Ling. A dynamic control structure of liquid-only transfer stream distillation column[J]. 中国化学工程学报, 2023, 59(7): 135-145.
[6]	Jian Han, Xinhua Liu, Shanwei Hu, Nan Zhang, Jingjing Wang, Bin Liang. Optimization of decoupling combustion characteristics of coal briquettes and biomass pellets in household stoves[J]. 中国化学工程学报, 2023, 59(7): 182-192.
[7]	Zhonghao Li, Yuanyuan Yang, Huanong Cheng, Yun Teng, Chao Li, Kangkang Li, Zhou Feng, Hongwei Jin, Xinshun Tan, Shiqing Zheng. Measurement and model of density, viscosity, and hydrogen sulfide solubility in ferric chloride/trioctylmethylammonium chloride ionic liquid[J]. 中国化学工程学报, 2023, 59(7): 210-221.
[8]	Yaran Bu, Changchun Wu, Lili Zuo, Qian Chen. The calculation and optimal allocation of transmission capacity in natural gas networks with MINLP models[J]. 中国化学工程学报, 2023, 59(7): 251-261.
[9]	Junhao Wang, Shugang Ma, Peng Chen, Zhipeng Li, Zhengming Gao, J. J. Derksen. Mixing of miscible shear-thinning fluids in a lid-driven cavity[J]. 中国化学工程学报, 2023, 58(6): 112-123.
[10]	Weikai Ren, Runsong Dai, Ningde Jin. Modeling of liquid film thickness around Taylor bubbles rising in vertical stagnant and co-current slug flowing liquids[J]. 中国化学工程学报, 2023, 58(6): 179-194.
[11]	Hongwei Liang, Wenling Li, Zisheng Feng, Jianming Chen, Guangwen Chu, Yang Xiang. Numerical simulation of gas-liquid flow in the bubble column using Wray-Agarwal turbulence model coupled with population balance model[J]. 中国化学工程学报, 2023, 58(6): 205-223.
[12]	Yun-Zhang Liu, Lu-Yao Zhang, Dan He, Li-Zhen Chen, Zi-Shuai Xu, Jian-Long Wang. Solubility measurement, correlation and thermodynamic properties of 2, 3, 4-trichloro-1, 5-dinitrobenzene in fifteen mono-solvents at temperatures from 278.15 to 323.15 K[J]. 中国化学工程学报, 2023, 58(6): 224-233.
[13]	Danlei Chen, Yiqing Luo, Xigang Yuan. Cascade refrigeration system synthesis based on hybrid simulated annealing and particle swarm optimization algorithm[J]. 中国化学工程学报, 2023, 58(6): 244-255.
[14]	Wende Tian, Jiawei Zhang, Zhe Cui, Haoran Zhang, Bin Liu. Microscopic mechanism study and process optimization of dimethyl carbonate production coupled biomass chemical looping gasification system[J]. 中国化学工程学报, 2023, 58(6): 291-305.
[15]	Guangyuan Chen, Tong Zhou, Meng Zhang, Zhongxiang Ding, Zhikun Zhou, Yuanhui Ji, Haiying Tang, Changsong Wang. Effects of heavy metal ions Cu²⁺/Pb²⁺/Zn²⁺ on kinetic rate constants of struvite crystallization[J]. 中国化学工程学报, 2023, 57(5): 10-16.