HAZARIKA , S and GOSWAMI , P and DUTTA , N N
(2003)
Lipase catalyzed transesterification of 2-obenzylglycercol with vinyl acetate : solvent effect.
Chemical Engineering J, 94.
pp. 1-10.
Abstract
The Pseudomonas cepacia lipase catalysed synthesis of (S)-2-o-benzylglycerol-1-acetate by transesterification of 2-o-benzylglycerol
with vinyl acetate was studied in 10 different solvents in order to deduce the solvent effect through an attempt to correlate the initial
reaction rate, selectivity for monoester formation and enantiomeric excess (ee) with such solvent properties as hydrophobicity (log P),
water solubility (log Sw), electron pair acceptance (EN
T ) and donation abilities (DNN
), polarisability and dielectric constant. The initial rate
was found to exhibit reasonable correlation with log P, log Sw, EN
T
+ DNN
, log P/polarisability and dielectric constant. The correlations for
selectivity and ee were also found to be reasonable excepting deviation of data points of certain solvents. Probable explanation for the
deviation has been put forwarded based on established hypothesis. The study revealed, in general that polar solvents favour the initial
reaction rate, selectivity and enantiomeric excess for transesterification of prochiral diol to chiral monoester
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