Solvent Isotope Effect on Transfer Hydrogenation of H2O with Glycerine under Alkaline Hydrothermal Conditions

Zheng Shen, Minyan Gu, Shiyang Liu, Wenjie Dong, Yalei Zhang

Abstract


Solvent isotope effect was investigated with 1H-, 2H-NMR, LC-MS and Gas-MS analyses on transfer hydrogenation of H2O with glycerine under alkaline hydrothermal conditions. The results from solvent isotope studies showed that (1) the H on the β-C of lactate was almost exchanged by D2O, which suggests that the hydroxyl (-OH) group on the 2-C of glycerine was first transformed into a carbonyl (C=O) group and then was converted back into a -OH group to form lactate; (2) The presence of large amounts of D was found in the produced hydrogen gas, which shows that the water molecules acted as a reactant; and (3) D% in the produced hydrogen gas was far more than 50%, which straightforwardly shows that acetol was formed in the first place as the most probable intermediate by undergoing a dehydration reaction rather than a dehydrogenation reaction.

Keywords


Solvent isotope effect, transfer hydrogenation, glycerine, hydrothermal reaction.

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ISSN: 1929-6002