Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants

Chin.J.Chem.Eng. ›› 2011, Vol. 19 ›› Issue (3): 397-403.

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Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants

TANG Kewen¹, MIAO Jiabing², ZHOU Tao², LIU Yongbing¹

1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

Received:2010-08-30 Revised:2010-11-17 Online:2011-06-28 Published:2011-06-28
Supported by:
Supported by the National Natural Science Foundation of China(20976041);the Program for New Century Excellent Talents in University,the Natural Science Foundation of Hunan Province(10JJ1004);the Open Fund Project of Key Laboratory in Hunan University(09K095)

Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants

唐课文¹, 苗家兵², 周涛², 刘永兵¹

1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

通讯作者: TANG Kewen, E-mail: tangkewen@sina.com
基金资助:
Supported by the National Natural Science Foundation of China(20976041);the Program for New Century Excellent Talents in University,the Natural Science Foundation of Hunan Province(10JJ1004);the Open Fund Project of Key Laboratory in Hunan University(09K095)

Abstract

Abstract: This paper deals with the enantioseparation of phenylsuccinic acid(H₂A)enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin derivatives are not soluble in organic liquids,but highly soluble in water.In this work,hydroxypropyl-β-cyclodextrin(HP-β-CD),hydroxyethyl β-cyclodextrin(HE-β-CD)and methyl-β-cyclodextrin(Me-β-CD)were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase.The results show that the efficiency of the extraction depends,often strongly,on a number of process variables,including the types of organic solvents and β-CD derivatives,the concentrations of the extractants and H₂A enantiomers,pH and temperature.HP-β-CD,HE-β-CD and Me-β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid.Among the three kinds of β-CD derivatives,HP-β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5℃ with a maximum enantioselectivity(a)of 2.38.Reactive extraction of enantiomers with hydrophilic β-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale.

Key words: solvent extraction, enantiomer resolution, &beta, -CD derivatives, phenylsuccinic acid enantiomers

摘要： This paper deals with the enantioseparation of phenylsuccinic acid(H₂A)enantiomers by liquid-liquid reactive extraction using β-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin derivatives are not soluble in organic liquids,but highly soluble in water.In this work,hydroxypropyl-β-cyclodextrin(HP-β-CD),hydroxyethylβ-cyclodextrin(HE-β-CD)and methyl-β-cyclodextrin(Me-β-CD)were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase.The results show that the efficiency of the extraction depends,often strongly,on a number of process variables,including the types of organic solvents and β-CD derivatives,the concentrations of the extractants and H₂A enantiomers,pH and temperature.HP-β-CD,HE-β-CD and Me-β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid.Among the three kinds of β-CD derivatives,HP-β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5℃ with a maximum enantioselectivity(a)of 2.38.Reactive extraction of enantiomers with hydrophilic β-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale.

关键词: solvent extraction, enantiomer resolution, &beta, -CD derivatives, phenylsuccinic acid enantiomers

TANG Kewen, MIAO Jiabing, ZHOU Tao, LIU Yongbing. Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants[J]. Chin.J.Chem.Eng., 2011, 19(3): 397-403.

唐课文, 苗家兵, 周涛, 刘永兵. Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants[J]. Chinese Journal of Chemical Engineering, 2011, 19(3): 397-403.

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Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants

Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilic β-CD Derivatives Extractants

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