156967-55-4Relevant articles and documents
Oxidation of methyl and n-octyl α-D-glucopyranoside over graphite-supported platinum catalysts: Effect of the alkyl substituent on activity and selectivity
Vleeming, Johannes H.,Kuster, Ben F.M.,Marin, Guy B.
, p. 175 - 183 (1997)
The oxidation of methyl and n-octyl α-D-glucopyranoside to methyl and n-octyl α-D-glucopyranosiduronate with molecular oxygen over a graphite-supported platinum catalyst was investigated. An increase of the length of the n-alkyl substituent from methyl to n-octyl resulted in a ten-fold decrease of the catalyst activity and an increase of the selectivity at pH 8.0 and 323 K. The selectivity decreased with increasing pH. The lower activity for a longer n-alkyl substituent is attributed to steric effects upon adsorption on the platinum surface and not to internal diffusion limitations. A tentative reaction scheme is presented, which describes the formation of side products through oxidation of secondary hydroxyl groups, ring cleavage and hydrolysis. Major side products are mono- and di-carboxylates with 2, 4, and 6 carbon atoms and mono-carboxylates, resulting from the oxidation of the alkyl substituent. C-C-Bond cleavage mainly occurs between C-2 and C-3 or C-4 and C-5, the former being less important for a longer alkyl substituent. The higher selectivity for a longer alkyl substituent is attributed to its protecting ability against hydrolysis and the exposition of neighboring hydroxyl groups to the platinum surface.
Oxidation of octyl-α-D-glucopyranoside, catalysed by (2+) or (2+) (azpy = 2-(phenyl)azopyridine), produces octyl-α-D-glucuronic acid
Boelrijk, Alexandra E. M.,Reedijk, Jan
, p. 411 - 412 (2007/10/02)
Highly stable ruthenium-2-(phenyl)azopyridine catalysts effect an oxidation of octyl-α-D-glucopyranoside in aqueous conditions with NaBrO3 as a co-oxidant.The oxidation processes involve a two-electron transfer step.
