Journal of Organic Chemistry p. 2253 - 2259 (1993)
Update date:2022-08-11
Topics:
Seip, John E.
Fager, Susan K.
Gavagan, John E.
Gosser, Lawrence W.
Anton, David L.
DiCosimo, Robert
The production of glyoxylic acid from glycolic (hydroxyacetic) acid has been demonstrated using the soluble enzymes glycolate oxidase and catalase as catalysts.Catalase was included as cocatalyst to decompose byproduct hydrogen peroxide, thus limiting peroxide-dependent formate production and glycolate oxidase deactivation.The addition to reaction mixtures of a primary amine capable of forming the hemiaminal or imine of glyoxylate resulted in an increase in the yield of glyoxylate; hemiaminal/imine mixtures of glyoxylate were not as readily oxidized to formate and carbon dioxide by hydrogen peroxide and also limited product inhibition of glycolate oxidase at high glyoxylate concentrations.A synergistic effect was observed when using Tris or ethylenediamine (EDA) with catalase, where increases in selectivity to glyoxylate were much greater than the sum of selectivities to glyoxylate obtained when using amine or catalase alone.The inclusion of EDA in reactions produced selectivities to glyoxylic acid in excess of 98-99percent at greater than 99percent conversion of 0.25M to 1.5M glycolic acid.The technical feasibility of a biocatalytic process for the production of glyoxylic acid was demonstrated by the preparation of ca. 0.50 kg of the acid in a series of 2.0-L batch reactions.
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