SCI和EI收录∣中国化工学会会刊

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 Zhang1,2, Pan Jiang3, Weifeng Xu1, Yu Liu1, Biquan Xiong1, Yunren Qiu2, Kewen Tang1   

  1. 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 Zhang1,2, Pan Jiang3, Weifeng Xu1, Yu Liu1, Biquan Xiong1, Yunren Qiu2, Kewen Tang1   

  1. 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: 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