Studies on the oxidation of 2,6-di-tert-butylphenol by molecular oxygen catalyzed by cobalt(II) tetraarylporphyrins bound to cationic latex

Abstract

A cationic latex has been prepared by emulsion copolymerization of styrene and divinylbenzene with 2 mol.% of quaternary ammonium ion surfactant monomer. The catalytic activity of cobalt(II) sulfonated tetraarylporphrins 1-5 supported on the cationic latex 6 was investigated in the autoxidation of 2,6-di-tert-butylphenol in water. All colloidal catalysts showed good catalytic activity in the autoxidation of 2,6-di-tert-butylphenol. Reaction products were identified as 2,6-di-tert-butyl-1,4-benzoquinone and the oxidative coupling product as 3,3',5,5'-tetra-tert-butyl-4,4'-diphenoquinone. The rate of autoxidation reaction catalyzed by 5 supported on cationic latex was found to increase with increasing pH in the range 7.0-10.0. At constant concentration of cobalt(II) porphyrin 5 in the reaction mixture, the rate as a function of the weight of the latex showed a maximum. The rate of autoxidation increased with increasing partial pressure of dioxygen in the range between 0.2 and 1.0 atm. 5,10,15,20-tetrakis(2,4,6-trimethyl-3,5-disulfonatopheny)porphyrinatocobalt(II) bound to the cationic latex was found to be the most reactive catalyst and the latex supported 5,10,15,20-tetrakis(2,6-dichloro-3-sulfonatophenyl)porphyrinatocobalt(II) showed the highest stability.