Journal of Molecular Catalysis A-Chemical, Vol.258, No.1-2, 178-184, 2006
Novel Schiff base complexes as catalysts in aerobic selective oxidation of beta-isophorone
A series of novel metal-Schiff base complexes with the general formula MLnXm (where M = Cu, Cc, Nd, etc., L = disalicylaldehyde-arginine (DSALA) and the derivatives, n = 1, 2, X = Cl, m = 1, 2, 3) have been synthesized and applied in aerobic oxidation for the first time, especially, the oxidation of beta-isophorone to keto-isophorone was explored. The MLnXm complexes were synthesized from arginine, salicylaldehyde with the derivatives and metal chloride. They were characterized by physicochemical methods such as elemental analysis, IR, H-1 NMR and C-13 NMR spectra, etc. A new practical method was studied for beta-isophorone oxidation with Cu-DSALA and the derivatives. Compared with the general ones, the catalysts described herein are much more efficient with the beta-isophorone conversion up to nearly 100% and the keto-isophorone yield exceeding 95%. Moreover, the catalysts in use were much less than that of salen catalysts, while the reaction time was relatively shorter. Additionally, the mechanism of beta-isophorone oxidation with influence factors such as temperature, catalyst, solvent, assistant solvent, etc. were also studied in detail. (c) 2006 Elsevier B.V. All rights reserved.