Porphyrin-Catalyzed Oxidation of Trichlorophenol

Porphyrin-metal complexes are potentially useful to catalyze redox reactions, which convert toxic and biologically recalcitrant compounds to compounds that are less toxic and more amenable to biotreatment. Porphyrins, in the absence of proteins as in ligninases, peroxidases, and oxidases, are potentially more robust than enzymes and microbial cultures in the treatment of inhibitory substances. 2,4,6-Trichlorophenol was used as a model compound for chlorinated phenols and as a substrate for various porphyrin-metal complexes acting as oxidation catalysts. t-Butyl hydroperoxide was the oxidizing agent. TCP was shown to be at least partially dechlorinated and the aromatic ring broken in reaction products. All porphyrins exhibited saturation kinetics with regard to the initial TCP concentration in reaction mixtures. Electron-withdrawing substituents on the porphyrins were observed to increase stability of the catalysts to inactivating ring-centered oxidation.