Oxidation studies of carbohydrates using molecular oxygen and a bismuth-ruthenium oxide catalyst

The oxidation of trans-1,2-cyclohexanediol, methyl alpha-D-glucopyranoside and beta-cyclodextrin has been studied, using a heterogeneous oxidation system in water at 50-75 degrees C. Molecular oxygen at 15-20 bar was used as the oxidant, in combination with a bismuth-rich ruthenium pyrochlore oxide as the catalyst. Both oxidative cleavage of the vicinal diols and oxidation of the primary hydroxyl groups occurred. HPLC and C-13 NMR were used to analyse the complex product mixtures. The oxidation method is successful for glycol cleavage iri small carbohydrates but not for polysaccharides.