Catalysis of the hydrolysis of ethyl mandelate and esterification of alpha-bromopropionic acid by lipase in microemulsions.
Candida cyclindracea lipase (CCL) was added to "sodium dodecyl sulfonate (AS)/n-butanol/n-octane/n-octane" water-in-oil microemulsion to catalyze the hydrolysis of ethyl mandelate and the esterification of alpha-bromopropionic acid with n-butanol, respectively. The catalytic activity of CCL in the above microemulsions was higher than that in the traditional oil/water biphasic systems. After hydrolysis for 48 h, the conversion rate of the reaction reached 90% and S-mandelic acid, [alpha]D20-149.8 (C10; H2O), optical purity ca. 97%, was isolated. While after esterification for 6 h, the conversion rate of the reaction reached 45%, and butyl-(R)-alpha-bromopropionate, [alpha]D20 18.2 (Cl; CHCl3), optical purity ca. 99%, was obtained.
Xiao
H
H
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai.
Liu
J
J
Li
Z
Z
D020001:1-Butanol; D000440:Butanols; D002175:Candida / Q000201:enzymology*; D002384:Catalysis; D004655:Emulsions; D004951:Esterification; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D008333:Mandelic Acids / Q000737:chemistry*; D009795:Octanes; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism
D000440:Butanols; D004655:Emulsions; D008333:Mandelic Acids; D009795:Octanes; D011422:Propionates; C086822:ethyl mandelate; D020001:1-Butanol; D008049:Lipase; C035775:2-bromopropionic acid; C026728:octane