Catalytic activity of carbon nanotube supported iron(III) and manganese(III) porphyrins in oxidation of olefins with tert-butyl hydroperoxide: Higher activity of the iron(III) porphyrin

Oxidation of olefins with tert-butyl hydroperoxide (TBHP) catalyzed by carbon nanotube supported iron(III) and manganese(III) complexes of meso-tetrakis(4-hydroxyphenyl)porphyrin is reported. The results show higher catalytic activity of the Fe(III) complex compared to the Mn(III) one. With the exception of cyclooctene which gives cyclooctene oxide as the sole product, oxidation of styrene, alpha-methyl styrene and cyclohexene leads to the formation of benzaldehyde, acetophenone and cyclohexene-1-one as the major product, respectively. In this study, acetonitrile has been found to be the best solvent for reaction performed in the presence of the manganese and iron porphyrin. In comparison of the two metalloporphyrins, catalytic activity of the manganese porphyrin is more sensitive to the type of solvent than the iron one. In spite of the crucial role of imidazole (ImH) on catalytic performance of the manganese porphyrin, the presence of ImH has a negative effect on the activity of the iron porphyrin. The nano-tube supported iron porphyrin may be recovered and reused at least four times without significant loss of the catalytic activity. (c) 2012 Elsevier B.V. All rights reserved.