Chinese Journal of Catalysis ›› 2017, Vol. 38 ›› Issue (4): 745-757.DOI: 10.1016/S1872-2067(17)62776-1

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Nanoscale graphene oxide sheets as highly efficient carbocatalysts in green oxidation of benzylic alcohols and aromatic aldehydes

Alireza Sedrpoushana, Masoud Heidaria, Omid Akhavanb,c   

  1. a Department of Chemical Technologies, Iranian Research Organization for Science and Technology(IROST), P. O. Box 33535-111, Tehran, Iran;
    b Department of Physics, Sharif University of Technology, P. O. Box 11155-9161, Tehran, Iran;
    c Institute for Nanoscience and Nanotechnology, Sharif University of Technology, P. O. Box 14588-89694, Tehran, Iran
  • Received:2016-11-19 Revised:2016-12-22 Online:2017-04-18 Published:2017-04-12

Abstract:

Nanoscale graphene oxide (NGO) sheets were synthesized and used as carbocatalysts for effective oxidation of benzylic alcohols and aromatic aldehydes. For oxidation of alcohols in the presence of H2O2 at 80℃, the NGOs (20% mass fraction) as carbocatalysts showed selectivity toward aldehyde. The rate and yield of this reaction strongly depended on the nature of substituents on the alcohol. For 4-nitrobenzyl alcohol, <10% of it was converted into the corresponding carboxylic acid after 24 h. By contrast, 4-methoxybenzyl alcohol and diphenylmethanol were completely converted into the corresponding carboxylic acid and ketone after only 9 and 3 h, respectively. The conversion rates for oxidation of aromatic aldehydes by NGO carbocatalysts were higher than those for alcohol oxidation. For all the aldehydes, complete conversion to the corresponding carboxylic acids was achieved using 7% (mass fraction) of NGO at 70℃ within 2-3 h. Possible mechanisms for NGO carbocatalyst structure-dependent oxidation of benzyl alcohols and structure-independent oxidation of aromatic aldehydes are discussed.

Key words: Carbocatalyst, Nanoscale graphene oxide, Green chemistry, Oxidation, Metal-free catalyst, Colloidal dispersion