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Synthesis of Copper Porphyrin into SBA-16 Walls as Catalyst for Oxidation Reacti
Published: 04 November 2012 by MDPI in The 16th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: Metalloporphyrins are the most widely studied catalysts for homogeneous selective oxidation alkenes. An important area of research into their catalytic properties is associated with immobilization of the porphyrin onto a solid support, in order to make the catalyst easier to handle and to separate from the reaction medium, as well as possibly stabilize and/or modify the catalytic performance.Among the mesoporoussilicas, SBA-16 is characterized with unique pore size, high hydrothermal and chemical stability. SBA-16 has a body-centered-cubic structure (Im3m symmetry) of nearly spherical cages, in which each cage is connected with 8 neighboring cages through small openings, which facilitates diffusion and transport of various species, for these reasons they are promising candidates to be used as support for functionalization of porphyrins. The SBA-16 was synthesized in acidic medium by F127 as directing agent and Tetraethylorthosilicate as silica source, respectively and then modified by aminopropyltriethoxysilane (APTES) .The synthesis of tetrakis(4-chlorophenyl)porphyrin (TClPP) immobilized into SBA-16 (TClPP@SBA-16) was performed by using ship-in-a-bottle. The characterization of synthesized materials were identified by FT-IR, UV-vis spectroscopy, XRD, nitrogen adsorption-desorption and SEM.in oxidation of cyclohexene. Oxidation of cyclohexene with tertiary butyl-hydroperoxide (TBHP) as oxidantefficientlywas catalyzed to epoxide, ketone and alcohol in presenceacetonitrile as solvent under reflax condition. The obtained products were characterized by using gas chromatography (GC). In addition, leaching and recycling experiments revealed that the catalyst can be repeatedly applied for cyclohexene oxidation for three successive cycles.
Keywords: Metlloporphyrn, SBA-16, TClPP, Oxidation, Cyclohexene