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Alkali-catalyzed oxidation ofd-glucose with sodium 2-anthraquinonesulfonate in ethanol-water solutions

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
116
Issue
1
Identifiers
DOI: 10.1016/s0008-6215(00)90953-4

Abstract

Abstract The kinetics of oxidation of d-glucose with 0.01-10m m 2-anthraquinonesulfonic acid in 0.001-1 m sodium hydroxide in ethanol-water of up to 61% (w/w) concentration of ethanol were studied over a temperature range of 25–45°. At high concentrations of the quinone, the rate of oxidation of d-glucose was determined by its rate of enolization, which was higher in ethanol-water solutions than in water. The oxidation of the enolized d-glucose was first-order with respect to the quinone, and it competed with isomerization to d-fructose. The ratio of the rates of oxidation and isomerization was increased with decreasing ethanol concentration and increasing hydroxyl-ion concentration. d-Glucosone was proved to be the only primary oxidation product of d-glucose.

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