Aqueous heterogeneous oxygenation of hydrocarbons and sulfides catalyzed by recoverable magnetite nanoparticles coated with copper(ii) phthalocyanine

Abstract

In this work, a novel magnetically recoverable phthalocyanine catalyst was prepared by immobilization of the Cu(II) phthalocyanine-tetrasulfonic acid tetrasodium complex (CuPcS) on the silica coated magnetic nanoparticles (Fe₃O₄@SiO₂, SMNP) via the amine functionality (ASMNP). The epoxidation of olefins and the oxidation of saturated hydrocarbons to the related ketones and also sulfides to the sulfones by an aqueous solution of tetra-n-butylammonium peroxomonosulfate (n-Bu₄NHSO₅, TBAOX) were efficiently enhanced with excellent selectivity under the influence of the catalytic activity of the magnetically separable catalyst. Sulfoxides could also be selectively produced in the mixture of water–ethanol, which makes the title methodology a good alternative for both sulfoxide and sulfone production. The separation and recycling of the catalyst and the reduced form of the oxidant were simple, effective and economical in this clean oxidation method. The FT-IR and leaching experiments after seven successive cycles showed that the catalyst was most strongly anchored to the magnetite nanoparticles.