Separations

Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic β-cyclodextrin derivatives

  1. Kewen Tang1,*,
  2. Panliang Zhang2,
  3. Chunyue Pan2,
  4. Hongjian Li2

Article first published online: 1 FEB 2011

DOI: 10.1002/aic.12513

Issue

AIChE Journal

AIChE Journal

Volume 57, Issue 11, pages 3027–3036, November 2011

Additional Information

How to Cite

Tang, K., Zhang, P., Pan, C. and Li, H. (2011), Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic β-cyclodextrin derivatives. AIChE J., 57: 3027–3036. doi: 10.1002/aic.12513

Author Information

  1. 1

    Dept. of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, Hunan, China

  2. 2

    College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, Hunan, China

*Dept. of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, Hunan, China

Publication History

  1. Issue published online: 10 OCT 2011
  2. Article first published online: 1 FEB 2011
  3. Accepted manuscript online: 13 DEC 2010 11:21AM EST
  4. Manuscript Revised: 13 NOV 2010
  5. Manuscript Received: 9 JUL 2010

Funded by

  • National Natural Science Foundation of China. Grant Number: 20976041
  • Program for New Century Excellent Talents in University, Project supported by Hunan Provincial Natural Science Foundation of China. Grant Number: 10JJ1004
  • Open Fund Project of Key Laboratory in Hunan University. Grant Number: 09K095

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Keywords:

  • reactive extraction;
  • chiral separation;
  • oxybutynin enantiomers;
  • β-cyclodextrin;
  • modeling

Abstract

The enantioselective extraction of hydrophobic oxybutynin (OBN) enantiomers by hydrophilic β-cyclodextrin (β-CD) derivatives was studied. The efficiency of extraction depends strongly on a number of process variables such as types of organic solvents and β-CD derivatives, concentration of selector, pH, and temperature. The experimental data were described by a reactive extraction model with a homogeneous aqueous phase reaction of R,S-OBN with β-CD. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic OBN were 4.96 × 10−3 and 9.52, respectively. The equilibrium constants of the complexation reactions were 1770 and 1340 L/mol for S- and R-OBN, respectively. By modeling and experiment, an optimal extraction condition with pH of 5 and HP-β-CD concentration of 0.1 mol/L was obtained with enantioselectivity (α) of 1.26, which was close to the theoretical maximum of 1.32 and performance factor (pfi) of 0.036. The model was verified experimentally with excellent results. © 2011 American Institute of Chemical Engineers AIChE J, 2011

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