Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers

doi:10.1016/j.cjche.2015.08.015

Chinese Journal of Chemical Engineering ›› 2015, Vol. 23 ›› Issue (11): 1774-1781.DOI: 10.1016/j.cjche.2015.08.015

Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers

Ping Wen¹, Kewen Tang², Jicheng Zhou¹, Panliang Zhang²

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

收稿日期:2014-01-15 修回日期:2014-06-17 出版日期:2015-11-28 发布日期:2015-12-18
通讯作者: Jicheng Zhou, Panliang Zhang
基金资助:
Supported by the National Natural Science Foundation of China (21176062), the Natural Science Foundation of Hunan Province (12JJ2007), Scientific Research Fund of Hunan Provincial Education Department (12B053), Science and Technology Planning Project of Hunan Province (2012GK3107) and Aid Program for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province.

Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers

Ping Wen¹, Kewen Tang², Jicheng Zhou¹, Panliang Zhang²

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

Received:2014-01-15 Revised:2014-06-17 Online:2015-11-28 Published:2015-12-18
Contact: Jicheng Zhou, Panliang Zhang
Supported by:
Supported by the National Natural Science Foundation of China (21176062), the Natural Science Foundation of Hunan Province (12JJ2007), Scientific Research Fund of Hunan Provincial Education Department (12B053), Science and Technology Planning Project of Hunan Province (2012GK3107) and Aid Program for Science and Technology Innovative Research Team in Higher Educational Institutions of Hunan Province.

摘要/Abstract

摘要： Based on the interfacial ligand exchangemodel and the law of conservation ofmass, themulti-stage enantioselective liquid-liquid extraction model has been established to analyze and discuss on multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine (PGL) enantiomers. The influence of phase ratio, extractant concentration, and PF₆^- concentration on the concentrations of enantiomers in the extract and raffinate was investigated by experiment and simulation. A good agreement between model and experiment was obtained. On this basis, the influence ofmany parameters such as location of stage, concentration levels, extractant excess, and number of stages on the symmetric separation performance was simulated. The optimal location of feed stage is the middle of fractional extraction equipment. The feed flow must satisfy a restricted relationship on flow ratios and the liquid throughout of centrifugal device. For desired purity specification, the required flow ratios decrease with extractant concentration and increase with PF₆^- concentration.When the number of stages is 18 stages at extractant excess of 1.0 or 14 stages at extractant excess of 2.0, the eeeq (equal enantiomeric excess) can reach to 99%.

关键词: Fractional extraction, Multistage model, Interfacial ligand exchange, Chiral separation

Abstract: Based on the interfacial ligand exchangemodel and the law of conservation ofmass, themulti-stage enantioselective liquid-liquid extraction model has been established to analyze and discuss on multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine (PGL) enantiomers. The influence of phase ratio, extractant concentration, and PF₆^- concentration on the concentrations of enantiomers in the extract and raffinate was investigated by experiment and simulation. A good agreement between model and experiment was obtained. On this basis, the influence ofmany parameters such as location of stage, concentration levels, extractant excess, and number of stages on the symmetric separation performance was simulated. The optimal location of feed stage is the middle of fractional extraction equipment. The feed flow must satisfy a restricted relationship on flow ratios and the liquid throughout of centrifugal device. For desired purity specification, the required flow ratios decrease with extractant concentration and increase with PF₆^- concentration.When the number of stages is 18 stages at extractant excess of 1.0 or 14 stages at extractant excess of 2.0, the eeeq (equal enantiomeric excess) can reach to 99%.

Key words: Fractional extraction, Multistage model, Interfacial ligand exchange, Chiral separation

Ping Wen, Kewen Tang, Jicheng Zhou, Panliang Zhang. Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers[J]. Chinese Journal of Chemical Engineering, 2015, 23(11): 1774-1781.

参考文献

[1] E.L. Eliel, S.H.Wilen, Stereochemistry of Organic Compounds, JohnWiley & Sons Inc., 1994

[2] R.A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, Inc., New York, 1993.

[3] J. Crosby, Synthesis of optically active compounds: A large scale perspective, Tetrahedron 47 (27) (1991) 4789-4846.

[4] A.M. Rouhi, Fine chemicals companies are jockeying for position to deliver the increasingly complicated chiral small molecules of the future, Chem. Eng. News 81 (18) (2003) 45-61.

[5] 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 (8) (2008) 2899-2905.

[6] G. Zenoni, F. Quattrini, M. Mazzotti, C. Fuganti, M. Morbidelli, Scale-up of analytical chromatography to the simulated moving bed separation of the enantiomers of the flavour norterpenoids alphaionone and alpha-damascone, Flavour Fragrance J. 17 (3) (2002) 195-202.

[7] E. Francotte, T. Leutert, L. La Vecchia, F. Ossola, P. Richert, A. Schmidt, Preparative resolution of the enantiomers of tert-leucine derivatives by simulated moving bed chromatography, Chirality 14 (4) (2002) 313-317.

[8] A. Seidel-Morgenstern, L.C. Kessler, M. Kaspereit, New developments in simulated moving BED chromatography, Chem. Eng. Technol. 31 (6) (2008) 826-837.

[9] J.G. Lu, A non-linear model of simulated moving bed chromatography for chiral separations, Chin. J. Chem. Eng. 11 (2) (2003) 234-239.

[10] J.G. Lu, Numerical simulation of asynchronous simulated moving bed chromatography, Chin. J. Chem. Eng. 12 (3) (2004) 415-420.

[11] B. Hungerhoff, H. Sonnenschein, F. Theil, Separation of enantiomers by extraction based on lipase-catalyzed enantiomer selective fluorous-phase labeling, Angew. Chem. Int. Ed. 40 (13) (2001) 2492-2494.

[12] M. Okudomi, M. Shimojo, K. Matsumoto, Easy separation of optically active products by enzymatic hydrolysis of soluble polymer-supported substrates, Tetrahedron Lett. 48 (48) (2007) 8540-8543.

[13] T.X. Mei, Y.H. Ya, Y. Jing, H.G. Yang, Study on the kinetic characteristics of the asymmetric production of R-(-)-mandelic acid with immobilized Saccharomyces cerevisiae FD11b, Biochem. Eng. J. 39 (2) (2008) 311-318.

[14] X.J. Huo, Q.L. Zhi, C.H. Zhong, G.Z. Yu, Production of (R)-epichlorohydrin from 1,3-dichloro-2-propanol by two-step biocatalysis using haloalcohol dehalogenase and epoxide hydrolase in two-phase system, Biochem. Eng. J. 74 (15) (2013) 1-7.

[15] C.A.M. Afonso, J.G. Crespo, Recent advances in chiral resolution throughmembranebased approaches, Angew. Chem. Int. Ed. 43 (40) (2004) 5293-5295.

[16] J.T.F. Keurentjes, L.J.W.M. Nabuurs, E.A. Vegter, Liquid membrane technology for the separation of racemic mixtures, J. Membr. Sci. 113 (2) (1996) 351-360.

[17] A. Maximini, H. Chmiel, H. Holdik, N.W. Maier, Development of a supported liquid membrane process for separating enantiomers of N-protected amino acid derivatives, J. Membr. Sci. 276 (1-2) (2006) 221-231.

[18] N. Sunsandee, N. Leepipatpiboon, P. Ramakul, U. Pancharoen, The selective separation of (S)-amlodipine via a hollow fiber supported liquid membrane: Modeling and experimental verification, Chem. Eng. J. 180 (15) (2012) 299-308.

[19] L.H. Li, F.F. Li, Chiral separation of α-cyclohexyl-mandelic-acid by aqueous two phase system combined with Cu₂-β-cyclodextrin complex, Chem. Eng. J. 211-212 (2012) 240-245.

[20] J. Lacour, C. Goujon-Ginglinger, S. Torche-Haldimann, J.J. Jodry, Efficient enantioselective extraction of tris (diimine) ruthenium(II) complexes by chiral, lipophilic TRISPHAT anions, Angew. Chem. Int. Ed. 39 (20) (2000) 3695-3697.

[21] M. Colera, A.M. Costero, P. Gavina, S. Gil, Synthesis of chiral 18-crown-6 ethers containing lipophilic chains and their enantiomeric recognition of chiral ammonium picrates, Tetrahedron Asymmetry 16 (15) (2005) 2673-2679.

[22] R.M.C. Viegas, C.A.M. Afonso, J.G. Crespo, I.M. Coelhoso, Modelling of the enantioselective extraction of propranolol in a biphasic system, Sep. Purif. Technol. 53 (3) (2007) 224-234.

[23] B. Tan, G.S. Luo, J.D.Wang, Extractive separation of amino acid enantiomerswith coextractants of tartaric acid derivative and Aliquat-336, Sep. Purif. Technol. 53 (3) (2007) 330-336.

[24] 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 (18) (2009) 4081-4088.

[25] K.W. Tang, L.T. Song, Y.B. Liu, X.Y. Jiang, Y. Pan, Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction, Chem. Eng. J. 158 (3) (2010) 411-417.

[26] 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 (17) (2009) 6526-6533.

[27] C. Donze, A.W. Coleman, β-CD inclusion complexes: relative selectivity of terpene and aromatic guest molecules studied by competitive inclusion experiments, J. Incl. Phenom. Macrocycl. Chem. 16 (1) (1993) 1-15.

[28] M. Steensma, N.J.M. Kuipers, A.B. de Haan, G. Kwant, Identification of enantioselective extractants for chiral separation of amines and aminoalcohols, Chirality 18 (5) (2006) 314-328.

[29] 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 (11) (2011) 3027-3036.

[30] 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 (24) (2008) 10027-10033.

[31] J. Koska, C.A. Haynes, Modelling multiple chemical equilibria in chiral partition systems, Chem. Eng. Sci. 56 (20) (2001) 5853-5864.

[32] 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 aminoalcohols, Chem. Eng. Sci. 62 (5) (2007) 1395-1407.

[33] M. Steensma, N.J.M. Kuipers, A.B. de Haan, G. Kwant, Analysis and optimization of enantioselective extraction in a multi-product environment with a multistage equilibrium model, Chem. Eng. Proc. 46 (10) (2007) 996-1005.

[34] K.W. Tang, P.L. Zhang, Experimental and modeling studies on the enantioselective extraction of hydrophobic pranoprofen enantiomers with hydrophilic β-cyclodextrin as selectors, J. Chem. Eng. Data 56 (10) (2011) 3902-3909.

[35] 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 (3) (2011) 397-403.

[36] B. Schuur,W.J. Jansma, J.G.M.Winkelman, H.J. Heeres, Determination of the interfacial area of a continuous integrated mixer/separator (CINC) using a chemical reaction method, Chemical Engineering and Proce. 47 (9-10) (2008) 1484-1491.

[37] K.W. Tang, H. Zhang, Y.B. Liu, Experimental and simulation on enantioselective extraction in centrifugal contactor separators, AIChE J 59 (7) (2011) 2594-2602.

[38] K.W. Tang, H. Zhang, P.L. Zhang, Continuous separationofα-cyclohexyl-mandelic acid enantiomers by enantioselective liquid-liquid extraction in centrifugal contactor separators: experiments andmodeling, Ind. Eng. Chem. Res. 52 (10) (2013) 3893-3902.

[39] P.L. Zhang, C. Liu, K.W. Tang, J.J. Liu, C.S. Zhou, C.A. Yang, Studies on enantioselective liquid-liquid extraction of amino-(4-nitro-phenyl)-acetic acid enantiomers: modeling and optimization, Chirality 26 (2) (2014) 79-87.

Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers

Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 1

编辑推荐

Metrics

本文评价