Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes

doi:10.1016/j.cjche.2014.01.001

Chinese Journal of Chemical Engineering ›› 2015, Vol. 23 ›› Issue (1): 57-63.DOI: 10.1016/j.cjche.2014.01.001

Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes

Kewen Tang^1,2, Jingjing Luo², Panliang Zhang¹, Jianmin Yi^1,2, Jie Hua¹, Chang'an Yang¹

1 Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2 College of Chemistry, Xiangtan University, Xiangtan 411105, China

收稿日期:2013-07-23 修回日期:2014-01-10 出版日期:2015-01-28 发布日期:2015-01-24
通讯作者: Kewen Tang
基金资助:
Supported by the National Natural Science Foundation of China (21171054), the Open Fund Project of Key Laboratory in Hunan University (11K029), and the Key Laboratory of Hunan Province and Aid program for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province.

Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes

Kewen Tang^1,2, Jingjing Luo², Panliang Zhang¹, Jianmin Yi^1,2, Jie Hua¹, Chang'an Yang¹

1 Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2 College of Chemistry, Xiangtan University, Xiangtan 411105, China

Received:2013-07-23 Revised:2014-01-10 Online:2015-01-28 Published:2015-01-24
Contact: Kewen Tang
Supported by:
Supported by the National Natural Science Foundation of China (21171054), the Open Fund Project of Key Laboratory in Hunan University (11K029), and the Key Laboratory of Hunan Province and Aid program for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province.

摘要/Abstract

摘要： Enantioselective liquid-liquid extraction has attracted considerable attention for its potential use in largescale production. Kinetic data are needed for the reliable scale-up of the process. This paper reports the kinetic study of reactive extraction of phenylalanine (Phe) enantiomers with BINAP-copper complex (BINAP-Cu) as a chiral selector. The theory of extraction accompanied by a chemical reaction was applied. The effects of agitation speed, interfacial area, pH value of aqueous phase, initial concentration of Phe enantiomers and initial concentration of BINAP-Cu on the specific rate of extraction were investigated. The forward rate constants of the reactions in the reactive extraction process are 7.93 × 10^-5m^5/2·mol^-1/2·s^-1 for D-Phe and 1.29 × 10^-4 m^5/2·mol^-1/2·s^-1 for L-Phe.

关键词: Kinetics, Amino acids, Modeling, Liquid-liquid extraction, Enantiomers

Abstract: Enantioselective liquid-liquid extraction has attracted considerable attention for its potential use in largescale production. Kinetic data are needed for the reliable scale-up of the process. This paper reports the kinetic study of reactive extraction of phenylalanine (Phe) enantiomers with BINAP-copper complex (BINAP-Cu) as a chiral selector. The theory of extraction accompanied by a chemical reaction was applied. The effects of agitation speed, interfacial area, pH value of aqueous phase, initial concentration of Phe enantiomers and initial concentration of BINAP-Cu on the specific rate of extraction were investigated. The forward rate constants of the reactions in the reactive extraction process are 7.93 × 10^-5m^5/2·mol^-1/2·s^-1 for D-Phe and 1.29 × 10^-4 m^5/2·mol^-1/2·s^-1 for L-Phe.

Key words: Kinetics, Amino acids, Modeling, Liquid-liquid extraction, Enantiomers

Kewen Tang, Jingjing Luo, Panliang Zhang, Jianmin Yi, Jie Hua, Chang'an Yang. Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes[J]. Chinese Journal of Chemical Engineering, 2015, 23(1): 57-63.

参考文献

[1] S.K. Tulashie, H. Kaemmerer, H. Lorenz, A. Seidel-Morgenstern, Solid-liquid equilibria of mandelic acid enantiomers in two chiral solvents: Experimental determination and model correlation, J. Chem. Eng. Data 55 (2010) 333-340.

[2] S. Houlton, Resolution and racemisation of chiral drugs, Manuf. Chem. 72 (2001) 16-17.

[3] E. Gavioli, N.M. Maier, C. Minguillon,W. Lindner, Preparative enantiomer separation of dichlorprop with a cinchona-derived chiral selector employing centrifugal partition chromatography and high-performance liquid chromatography: A comparative study, Anal. Chem. 76 (2004) 5837-5848.

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

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

[6] M. Balawejder, B.Mossety-Leszczak, I. Poplewska, H. Lorenz, A. Seidel-Morgenstern, W. Piatkowski, D. Antos, Modeling and predictions of solid-liquid equilibria for citalopram oxalate as a representative of a solid solution forming system, Fluid Phase Equilib. 346 (2013) 8-19.

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

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

[9] B.J.V. 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.

[10] T.B. Reeve, J.P. Cros, C. Gennari, U. Piarulli, J.G. de Vries, A practical approach to the resolution of racemic N-benzyl-α-amino acids by liquid-liquid extraction with a lipophilic chiral salen-cobalt(III) complex, Angew. Chem. Int. Ed. 45 (2006) 2449-2453.

[11] K. Konishi, K. Yahara, H. Toshishige, T. Aida, S.J. Inoue, A novel anion-binding chiral receptor based on metalloporphyrin with molecular asymmetry. Highly enantioselective recognition of amino acid derivatives, J. Am. Chem. Soc. 116 (1994) 1337-1344.

[12] H. Tsukube, S. Shinoda, J. Uenishi, T. Kanatani, H. Itoh, M. Shiode, T. Iwachido, O. Yonemitsu, Molecular recognition with lanthanide(III) tris(β-diketonate) complexes: Extraction, transport, and chiral recognition of unprotected amino acids, Inorg. Chem. 37 (1998) 1585-1591.

[13] T. Takeuchi, R. Horikawa, T. Tanimura, Enantioselective solvent extraction of neutral DL-amino acids in two-phase systems containing N-n-alkyl-L-proline derivatives and copper(II) ion, Anal. Chem. 56 (1984) 1152-1155.

[14] P.J. Pickering, J.B. Chaudhuri, Emulsion liquid membranes for chiral separations: Selective extraction of rac-phenylalanine enantiomers, Chirality 9 (1997) 261-267.

[15] B.J.V. Verkuijl, S. Boelo, A.J.Minnaard, J.G. de Vries, B.L. Feringa, Chiral separation of substituted phenylalanine analogues using chiral palladium phosphine complexes with enantioselective liquid-liquid extraction, Org. Biomol. Chem. 8 (2010) 3045-3054.

[16] K.W. Tang, T. Fu, P.L. Zhang, Equilibrium studies on enantioselective liquid-liquid extraction of phenylalanine enantiomers using BINAP-metal complexes, J. Chem. Eng. Data 57 (2012) 3628-3635.

[17] K.W. Tang, J. Cai, C.A. Yang, Y.J. Liu, P.L. Zhang, Y.B. Liu, Kinetic study on reactive extraction for chiral separation of oxybutynin enantiomers, Sep. Purif. Technol. 92 (2012) 30-35.

[18] K.W. Tang, T. Fu, P.L. Zhang, Equilibrium studies on enantioselective liquid-liquid extraction of homophenylalanine enantiomers with metal-BINAP complexes, Process Biochem. 47 (2012) 2275-2283.

[19] M. Minier, D.M. Ayad, Y. Wei, A.A. Sarhan, Preparation of cross-linked chitosan/glyoxal molecularly imprinted resin for efficient chiral resolution of aspartic acid isomers, Biochem. Eng. J. 51 (2010) 140-146.

[20] M.D. Gourlay, J. Kendrick, F.J.J. Leusen, Predicting the spontaneous chiral resolution by crystallization of a pair of flexible nitroxide radicals, Cryst. Growth Des. 8 (2008) 2899-2905.

[21] F.P. Jiao, X.Q. Chen, L. Yang, Y.H. Hu, Enantioselective extraction of mandelic acid enantiomers using ester alcohol L-tartrate as chiral selector, Lat. Am. Appl. Res. 61 (2007) 326-328.

[22] K.W. Tang, J.B. Miao, T. Zhou, Y.B. Liu, Equilibrium studies on liquid-liquid reactive extraction of phenylsuccinic acid enantiomers using hydrophilic β-CD derivatives extractants, Chin. J. Chem. Eng. 19 (2011) 397-403.

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

[24] M. Colera, A.M. Costero, P. Gaviña, S. Gil, Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates, Tetrahedron Asymmetry 16 (2005) 2673-2679.

[25] M. Steensma, N.J.M. Kuipers, A.B. de Haan, G. Kwant, Modelling and experimental evaluation of reaction kinetics in reactive extraction for chiral separation of amines, amino acids and amino alcohols, Chem. Eng. Sci. 62 (2007) 1395-1407.

[26] K.W. Tang, J. Cai, P.L. Zhang, Equilibrium and kinetics of reactive extraction of ibuprofen enantiomers from organic solution by HP-β-CD, Ind. Eng. Chem. Res. 51 (2012) 964-971.

[27] 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. Eur. J. 15 (2009) 2111-2120.

[28] B. Schuur, J.G.M. Winkelman, J.G. de Vries, H.J. Heeres, Experimental and modeling studies on the enantio-separation of 3,5-dinitrobenzoyl-(R), (S)-leucine by continuous liquid-liquid extraction in a cascade of centrifugal contactor separators, Chem. Eng. Sci. 65 (2010) 4682-4690.

[29] K.W. Tang, L.T. Song, Y.B. Liu, Y. Pan, X.Y. Jiang, Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction, Chem. Eng. J. 158 (2010) 411-417.

[30] P. Dimitrova, H.J. Bart, Extraction of amino acid enantiomers with microemulsions, Chem. Eng. Technol. 32 (2009) 1527-1534.

[31] E. Kocabas, A. Karakucuk, A. Sirit, M. Yilmaz, Synthesis of new chiral calixarene diamide derivatives for liquid phase extraction of α-amino acid methylesters, Tetrahedron Asymmetry 17 (2006) 1514-1520.

[32] L. Tang, S. Choi, R. Nandhakumar, H. Park, H. Chung, J. Chin, K.M. Kim, Reactive extraction of enantiomers of 1,2-amino alcohols via stereoselective thermodynamic and kinetic processes, J. Org. Chem. 73 (2008) 5996-5999.

[33] P.J. Pickering, J.B. Chaudhuri, Equilibrium and kinetic studies of the enantioselective complexation of (D/L)-phenylalanine with copper(II) N-decyl-(L)-hydroxyproline, Chem. Eng. Sci. 3 (1997) 377-386.

[34] J. Lu, J. Liu, Y. Sun, C. Li, Kinetics of forward extraction of boric acid from salt lake brine by 2-ethyl-1,3-hexanediol in toluene using single drop technique, Chin. J. Chem. Eng. 22 (2014) 496-502.

[35] Y.Wang, L. Zheng, S. Ni, Z. Fan, R. Yao, K. Chen, J. Wang, Kinetic study on extraction of red pepper seed oil with supercritical CO₂, Chin. J. Chem. Eng. 22 (2014) 44-50.

[36] H.K. Gaidhani, K.L.Wasewar, V.G. Pangarkar, Intensification of enzymatic hydrolysis of penicillin G: part 1. Equilibria and kinetics of extraction of phenyl acetic acid by alamine 336, Chem. Eng. Sci. 57 (2002) 1979-1984.

[37] V. Zimmermann, I. Masuck, U. Kragl, Reactive extraction of N-acetylneuraminic acid kinetic model and simulation of integrated product removal, Sep. Purif. Technol. 63 (2008) 129-137.

[38] Y.S. Jun, E.Z. Lee, Y.S. Huh, Y.K. Hong, W.H. Hong, Kinetic study for the extraction of succinic acid with TOA in fermentation broth; effects of pH, salt and contaminated acid, Biochem. Eng. J. 36 (2007) 8-13.

[39] K.W. Tang, J.B. Miao, T. Zhou, Y.B. Liu, L.T. Song, Reaction kinetics in reactive extraction for chiral separation of α-cyclohexyl-mandelic acid enantiomers with hydroxypropyl-β-cyclodextrin, Chem. Eng. Sci. 66 (2011) 397-404.

Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes

Kinetic study on reactive extraction of phenylalanine enantiomers with BINAP-copper complexes

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]	Xiaolin Guo, Zhaoyang Zhang, Pengfei Xing, Shuai Wang, Yibing Guo, Yanxin Zhuang. Kinetic mechanism of copper extraction from methylchlorosilane slurry residue using hydrogen peroxide as oxidant[J]. 中国化学工程学报, 2023, 60(8): 228-234.
[2]	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.
[3]	Xun Tao, Fan Zhou, Xinlei Yu, Songling Guo, Yunfei Gao, Lu Ding, Guangsuo Yu, Zhenghua Dai, Fuchen Wang. Effect of carbon dioxide on oxy-fuel combustion of hydrogen sulfide: An experimental and kinetic modeling[J]. 中国化学工程学报, 2023, 59(7): 105-117.
[4]	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.
[5]	Junyang Liu, Luming Wang, Yuhang Bian, Chunshan Li, Zengxi Li, Jie Li. Liquid-phase esterification of methacrylic acid with methanol catalyzed by cation-exchange resin in a fixed bed reactor: Experimental and kinetic studies[J]. 中国化学工程学报, 2023, 58(6): 1-10.
[6]	Wei Wang, Romain Lemaire, Ammar Bensakhria, Denis Luart. Thermogravimetric analysis and kinetic modeling of the co-pyrolysis of a bituminous coal and poplar wood[J]. 中国化学工程学报, 2023, 58(6): 53-68.
[7]	Bing Liu, Yingjiao Li, Moses Arowo, Guangwen Chu, Yong Luo, Liangliang Zhang, Haikui Zou, Baochang Sun. Sulfonation of 1, 4-diaminoanthraquinone leuco by chlorosulfonic acid: Kinetics and process intensification[J]. 中国化学工程学报, 2023, 58(6): 163-169.
[8]	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.
[9]	Xinyu Liu, Hongliang Sheng, Song He, Chunhua Du, Yuansheng Ma, Chichi Ruan, Chunxiang He, Huaming Dai, Yajun Huang, Yuelei Pan. Insight into pyrolysis of hydrophobic silica aerogels: Kinetics, reaction mechanism and effect on the aerogels[J]. 中国化学工程学报, 2023, 58(6): 266-281.
[10]	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.
[11]	Shujun Peng, Song Lei, Sisi Wen, Jian Xue, Haihui Wang. A Ruddlesden–Popper oxide as a carbon dioxide tolerant cathode for solid oxide fuel cells that operate at intermediate temperatures[J]. 中国化学工程学报, 2023, 56(4): 25-32.
[12]	Bowen Jiang, Jia Liu, Guoqiang Yang, Zhibing Zhang. Efficient conversion of CO₂ into cyclic carbonates under atmospheric by halogen and metal-free poly(ionic liquid)s[J]. 中国化学工程学报, 2023, 55(3): 202-211.
[13]	Hany M. Abd El-Lateef, Mai M. Khalaf, K. Shalabi, Antar A. Abdelhamid. Multicomponent synthesis and designing of tetrasubstituted imidazole compounds catalyzed via ionic-liquid for acid steel corrosion protection: Experimental exploration and theoretical calculations[J]. 中国化学工程学报, 2023, 55(3): 304-319.
[14]	Zhiwei Wang, Yu Zhang, Zhi Zhang, Daowei Zhou, Zhikai Cao, Yong Sha. Investigation on catalytic distillation for ethyl acetate production with different catalytic packing structures[J]. 中国化学工程学报, 2023, 53(1): 63-72.
[15]	Xibao Zhang, Zhenghong Luo. Bubble size modeling approach for the simulation of bubble columns[J]. 中国化学工程学报, 2023, 53(1): 194-200.