Abstract
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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Villeneuve, P., Foglia, T.A., Mangos, T.J. et al. Synthesis of polyfunctional glycerol esters: Lipase-Catalyzed esterification of glycerol with diesters. J Amer Oil Chem Soc 75, 1545–1549 (1998). https://doi.org/10.1007/s11746-998-0092-x
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DOI: https://doi.org/10.1007/s11746-998-0092-x