Abstract
Esterification in an aqueous micellar medium is catalyzed by a commercially available lipase in the absence of any co-factors. The presence of only 2 wt% designer surfactant, TPGS-750-M, assists in a 100% selective enzymatic process in which only primary alcohols participate (in a 1 : 1 ratio with carboxylic acid). An unexpected finding is also disclosed where the simple additive, PhCF3 (1 equiv. vs. substrate), appears to significantly extend the scope of usable acid/alcohol combinations. Taken together, several chemo- and bio-catalyzed 1-pot, multi-step reactions can now be performed in water.
Highlights
Textbook and related chemical methods continue to discuss the fundamental preparation of esters from acids and alcohols, typically performed in organic solvents, that require removal of water.[1]
We report that use of an economical, commercially available lipase can, catalyze esterification in water as the reaction medium, and do so using a 1:1 stoichiometric ratio of acid and alcohol
The key to successful levels of conversion is the presence of the designer surfactant TPGS-750-M (DL-a-tocopherol methoxypolyethylene glycol succinate) in the reaction medium.[16]
Summary
Textbook and related chemical methods continue to discuss the fundamental preparation of esters from acids and alcohols, typically performed in organic solvents, that require removal of water.[1]. The key to successful levels of conversion is the presence of the designer surfactant TPGS-750-M (DL-a-tocopherol methoxypolyethylene glycol succinate) in the reaction medium.[16] Even further levels of conversion can be anticipated by the presence of a simple additive (1 equiv), as disclosed . Applications of this new esterification, together with chemocatalysis, leads to unprecedented tandem, 1-pot processes illustrative of the potential for organic synthesis to be conducted in sequential fashion, all done in water
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