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Synthesis of polyfunctional glycerol esters: lipase-catalyzed esterification of glycerol with diesters

Villeneuve P., Foglia T.A., Mangos T.J., Nuñez A.. 1998. Journal of the American Oil Chemists' Society, 75 (11) : p. 1545-1549. Annual Meeting of the American Oil Chemists' Society. 89, 1998-05/1998-05, Chicago (Etats-Unis).

DOI: 10.1007/s11746-998-0092-x

The enzymatic esterification of glycerol with dicarboxylic acids or esters was studied to produce mono- and/or diesterified glycerol adducts. Such materials are useful synthons in the synthesis of biodegradable polymers and surfactants. In this work two strategies were studied for preparing these prepolymeric glycerol derivatives: the lipase-catalyzed esterification of free glycerol with diacids or esters and the reaction of supported or protected glycerol with diesters. For example, reaction of isopropylidene glycerol with dimethyl sebacate gave a >95% yield of isopropylidene glycerol-monomethyl sebacate ester. Reaction of glycerol supported on silica with dimethyl adipate gave a 40% yield of glycerol-monomethyl adipate ester. Best yields of glycerol-mono- and diesters (70% and 10%, respectively) were obtained by direct esterification of free glycerol with a diester in a solvent-free system containing small amounts of water (<4%).

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