Journal
AICHE JOURNAL
Volume 57, Issue 11, Pages 3027-3036Publisher
WILEY-BLACKWELL
DOI: 10.1002/aic.12513
Keywords
reactive extraction; chiral separation; oxybutynin enantiomers; beta-cyclodextrin; modeling
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Funding
- National Natural Science Foundation of China [20976041]
- Hunan Provincial Natural Science Foundation of China [10JJ1004]
- Key Laboratory in Hunan University [09K095]
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The enantioselective extraction of hydrophobic oxybutynin (OBN) enantiomers by hydrophilic beta-cyclodextrin (beta-CD) derivatives was studied. The efficiency of extraction depends strongly on a number of process variables such as types of organic solvents and beta-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 beta-CD. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic OBN were 4.96 x 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-beta-CD concentration of 0.1 mol/L was obtained with enantioselectivity (alpha) of 1.26, which was close to the theoretical maximum of 1.32 and performance factor (pf(i)) of 0.036. The model was verified experimentally with excellent results. (C) 2011 American Institute of Chemical Engineers AIChE J, 57: 3027-3036, 2011
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