Liquid phase oxidation of alkenes and glycerol with molecular oxygen over mixed-ligand copper(II) complexes grafted on GO as catalysts

Abstract

[Cu(acac)(phen)(H2O)](ClO4) and [Cu(acac)(bipy)(H2O)](ClO4) catalysts were prepared by the immobilization of mixed-ligand complexes on graphene oxide derivatized with monochloroacetic acid. These catalysts were characterized through an ensemble of techniques including XRD, FTIR, Raman, and XPS while the catalytic behavior has been investigated in the oxidation of cyclohexene, 1-octene and glycerol in the presence of molecular oxygen. Cyclohexanone was the dominant product in the oxidation of cyclohexene resulting in selectivities higher than 50% for a conversion of 14.5%. The turnover frequencies were pretty high, namely, 4.5 h−1 for [Cu(acac)(phen)(H2O)](ClO4) and 2.3 h−1 for Cu(acac)(bipy)(H2O)](ClO4). The oxidation of 1-octene also occurred with a pretty high selectivity in 2-octanol as the main product. The role of copper in the oxidative dehydrogenation of glyceric acid towards tartronic acid was as well confirmed. Noteworthy, these catalysts were stable and their recycling occurred with no change in the conversion or selectivity.