Origin of the selectivity in the gold-mediated oxidation of benzyl alcohol

Juan Carlos F. Rodríguez-Reyes, Cynthia M. Friend, Robert J. Madix

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41 Citas (Scopus)

Resumen

Benzyl alcohol has received substantial attention as a probe molecule to test the selectivity and efficiency of novel metallic gold catalysts. Herein, the mechanisms of benzyl alcohol oxidation on a gold surface covered with atomic oxygen are elucidated; the results show direct correspondence to the reaction on gold-based catalysts. The selective, partial oxidation of benzyl alcohol to benzaldehyde is achieved with low oxygen surface concentrations and takes place through dehydrogenation of the alcohol to form benzaldehyde via a benzyloxy (C 6H 5-CH 2O) intermediate. While in this case atomic oxygen plays solely a dehydrogenating role, at higher concentrations it leads to the formation of intermediates from benzaldehyde, producing benzoic acid and CO 2. Facile ester (benzyl benzoate) formation also occurs at low oxygen concentrations, which indicates that benzoic acid is not a precursor of further oxidation of the ester; instead, the ester is produced by the coupling of adsorbed benzyloxy and benzaldehyde. Key to the high selectivity seen at low oxygen concentrations is the fact that the production of the aldehyde (and esters) is kinetically favored over the production of benzoic acid.

Idioma originalInglés
Páginas (desde-hasta)1129-1134
Número de páginas6
PublicaciónSurface Science
Volumen606
N.º15-16
DOI
EstadoPublicada - ago. 2012
Publicado de forma externa

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