Carbohydrate Research p. 225 - 236 (1985)
Update date:2022-08-17
Topics:
Makkee, Michiel
Kieboom, P. G.
Bekkum, Herman van
D-Fructose and D-fructode/D-glucose mixtures have been hydrogenated in water at 60-80 deg and 20-75 atm. of hydrogen with Ni, Cu, Ru, Rh, Pd, Os, Ir, and Pt severally as catalysts.The selectivity for the formation of D-mannitol from D-fructose as well as the selectivity for the hydrogenation of D-fructose in the presence of D-glucose with Cu/silica as the catalyst are substantially higher than those for the other catalysts.With Cu/silica as the catalyst, the hydrogenation of D-fructose is first order with respect to the amount of catalyst and the hydrogen pressure, whereas a shift from first- to zero-order kinetics occurs on going from low (<0.3M) to high (>0.8) concentrations of D-fructose.D-Fructose is preferentially hydrogenated via its furanose forms, presumably by attack of a copper hydride-like species at the anomeric carbon atom with inversion of configuration.Preferential adsorption of pyranose with respect to furanose forms occurs, whereas the furanose forms show a much higher reactivity.The mechanism proposed for the copper-catalyzed hydrogenation reaction explains both the enhanced yield of D-mannitol from boric esters of D-fructose and the diastereoselectivity of the hydrogeantion of seven other ketoses.
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