Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector

doi:10.1016/j.cjche.2017.04.001

Chin.J.Chem.Eng. ›› 2018, Vol. 26 ›› Issue (1): 67-72.DOI: 10.1016/j.cjche.2017.04.001

• Separation Science and Engineering • Previous Articles Next Articles

Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector

Panliang Zhang^1,2, Pan Jiang³, Weifeng Xu¹, Yu Liu¹, Biquan Xiong¹, Yunren Qiu², Kewen Tang¹

1 Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2 School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China;
3 College of Chemical Engineering, Xiangtan University, Xiangtan 411105, China

Received:2017-01-17 Revised:2017-04-01 Online:2018-03-01 Published:2018-01-28
Contact: Yunren Qiu,E-mail addresses:csu_tian@csu.edu.cn;Kewen Tang,E-mail addresses:tangkewen@sina.com
Supported by:
Supported by the National Basic Research Program of China (2014CB260407).

Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector

Panliang Zhang^1,2, Pan Jiang³, Weifeng Xu¹, Yu Liu¹, Biquan Xiong¹, Yunren Qiu², Kewen Tang¹

1 Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China;
2 School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China;
3 College of Chemical Engineering, Xiangtan University, Xiangtan 411105, China

通讯作者: Yunren Qiu,E-mail addresses:csu_tian@csu.edu.cn;Kewen Tang,E-mail addresses:tangkewen@sina.com
基金资助:
Supported by the National Basic Research Program of China (2014CB260407).

Abstract

Abstract: In this work, the kinetic study on reactive extraction of α-cyclopentylmandelic acid (α-CPMA) enantiomers was performed in a Lewis cell using hydroxyethyl-β-cyclodextrin (HE-β-CD) as chiral selector. The enantioselective complexation equilibrium between HE-β-CD and α-CPMA enantiomers was studied by phase solubility method. The important process parameters affecting the initial extraction rate were separately studied and the reaction rate equations were deduced. The optimal conditions for kinetic study were as follows:stirring speed of 75 r·min^-1, interfacial area of 12.56 cm², pH of 2.5, initial HE-β-CD concentration of 0.05 mol ·L^-1, initial α-CPMA concentration of 5 mmol·L^-1, and temperature of 278 K. The reaction has been found to be first order in α-CPMA and second order in HE-β-CD with the forward rate constants of 2.056×10^-3 m⁶·mol^-2·s^-1 and 1.459×10^-3 m⁶·mol^-2·s^-1 for (S)-α-CPMA and (R)-α-CPMA, respectively. The complexation equilibrium constants were evaluated as 61 L·mol^-1 and 117 L·mol^-1 for (S)-α-CPMA and (R)-α-CPMA, and the intrinsic enantioselectivity is estimated as 1.92.

Key words: Kinetics, Liquid-liquid extraction, Chiral resolution, &alpha, -Cyclopentylmandelic acid

摘要： In this work, the kinetic study on reactive extraction of α-cyclopentylmandelic acid (α-CPMA) enantiomers was performed in a Lewis cell using hydroxyethyl-β-cyclodextrin (HE-β-CD) as chiral selector. The enantioselective complexation equilibrium between HE-β-CD and α-CPMA enantiomers was studied by phase solubility method. The important process parameters affecting the initial extraction rate were separately studied and the reaction rate equations were deduced. The optimal conditions for kinetic study were as follows:stirring speed of 75 r·min^-1, interfacial area of 12.56 cm², pH of 2.5, initial HE-β-CD concentration of 0.05 mol ·L^-1, initial α-CPMA concentration of 5 mmol·L^-1, and temperature of 278 K. The reaction has been found to be first order in α-CPMA and second order in HE-β-CD with the forward rate constants of 2.056×10^-3 m⁶·mol^-2·s^-1 and 1.459×10^-3 m⁶·mol^-2·s^-1 for (S)-α-CPMA and (R)-α-CPMA, respectively. The complexation equilibrium constants were evaluated as 61 L·mol^-1 and 117 L·mol^-1 for (S)-α-CPMA and (R)-α-CPMA, and the intrinsic enantioselectivity is estimated as 1.92.

关键词: Kinetics, Liquid-liquid extraction, Chiral resolution, &alpha, -Cyclopentylmandelic acid

Panliang Zhang, Pan Jiang, Weifeng Xu, Yu Liu, Biquan Xiong, Yunren Qiu, Kewen Tang. Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector[J]. Chin.J.Chem.Eng., 2018, 26(1): 67-72.

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Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector

Study on extraction kinetics of α-cyclopentylmandelic acid enantiomers with hydroxyethyl-β-cyclodextrin as chiral selector

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