Manganese meso-tetra-4-carboxyphenylporphyrin immobilized on MCM-41 as catalyst for oxidation of olefins with different oxygen donors in stoichiometric conditions

Abstract

Oxidation of olefins with tert-butyl hydroperoxide (TBHP), tetra-n-butylammonium periodate (TBAP) and potassium peroxomonosulfate (Oxone) in the presence of MCM-41 immobilized meso-tetra-4-carboxyphenylporphyrinatomanganese(III) acetate has been studied. The results of this study show better catalytic performance of the heterogonous catalyst using TBHP as oxidant in comparison with Oxone and TBAP in oxidation of the used olefins with the exception of cyclooctene. However, different order of reactivity of various olefins has been observed in the presence of Oxone and TBHP. In spite of the absence of good electron-withdrawing groups at the periphery of porphyrin ligand, the catalyst was recovered and reused (at least four times) without detectable catalyst leaching or a significant loss of the catalytic efficiency. All results have been obtained in the absence of using excess molar ratios of olefin to the oxidant, commonly employed as a strategy to overcome the instability of metalloporphyrins in oxidative conditions.