The Complex of crosslinked chitosan with 4′-formal benzo-15-crown-5 and palladium used as catalyst for asymmetric hydrogenation of α-phenylethanone

Abstract

The crosslinked chitosan was grafted by 4′-formal benzo-15-crown-5 to obtaine crosslinked chitosan with 4′-formal benzo-15-crown-5(CCTS-N=CH-B-15-C-5). Then it was loaded with palldium chloride to gain the heterogeneous catalyst, which was easily isolated from the reaction system. The influences of the Pd content of the catalyst, solvent, and temperature on asymmetric hydrogenation of α-phenylethanone have been studied. The catalyst has been found to catalyze the hydrogenation of α-phenylethanone into the chiral alcohol, α-phenyl ethanol under the mild condition. The optical yield of (R)-1-phenylethanol could be obtained as 97.1% under the following conditions: temperature, 30 °C; solvent, ethanol; Pd content, 1.43 mmol/g; substrate concentration, 0.02 g /mL due to the cooperative effect of crown ether and chitosan polymer. The stability of this catalyst was also studied at the same time. This chiral natural crosslinked chitosan-palladium complex catalyst could be reused without appreciable change in optical catalytic activity, which will be useful for designing crosslinked-chitosan-based adsorption for metal ions for asymmetric hydrogenation.

Keywords

asymmetric hydrogenation / α-phenylethanone / catalysis / crosslinked chitosan with crown ether / palladium chloride

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