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Sugar fatty acid ester surfactants: Base-catalyzed hydrolysis
Authors:Irene J. A. Baker  D. Neil Furlong  Franz Grieser  Calum J. Drummond
Affiliation:(1) School of Chemistry, The University of Melbourne, 3052 Parkville, Victoria, Australia;(2) CSIRO, Molecular Science, Bag 10, 3169 Clayton South MDC, Victoria, Australia;(3) Present address: R&D Division, RMIT University, P.O. Box 71, 3083 Bundoora, Australia
Abstract:Rate constants for the base-catalyzed hydrolysis of sucrose laurate, sucrose α-sulfonyl laurate, and sucrose α-ethyl laurate were measured at several temperatures in pH 11 buffer. Activation energies and Arrhenius factors for the hydrolysis reactions were determined. At 27°C, sucrose laurate hydrolyzed fastest and sucrose α-ethyl laurate slowest. Activation energies and Arrhenius factors showed that both steric and electronic factors affect the rates of ester hydrolysis. Other work has shown that bacterial hydrolysis of sugar fatty acid esters is inhibited in the presence of either α-sulfonyl or α-alkyl groups. A kinetic study of base-catalyzed ester hydrolysis has revealed reasons for the inhibition of bacterial hydrolysis and provided information regarding ester stability at elevated pH.
Keywords:Activation energy  Arrhenius factor  base hydrolysis  ester  fatty acid  high-performance liquid chromatography  kinetics  laurate  sucrose  sulfonyl  surfactant
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