Oxidation of Dichloroanilines and Related Anilides Catalyzed by Iron(III) Tetrasulfonatophthalocyanine

We investigated the degradation of polychlorinated pollutants, such as dichloroanilines and related anilides, catalyzed by iron(III) tetrasulfonatophthalocyanine (FePcS) with potassium monopersulfate or hydrogen peroxide as oxidant. The reaction is influenced by the positions of the two chloro-substituents and by the nature of the oxidant. The FePcS-catalyzed oxidation of 3,5-dichloroaniline with potassium monopersulfate leads to the formation of more biodegradable products (carboxylic acids) and to potentially toxic dimers (azo and azoxy compounds). The oxidation of 3,4-dichloroaniline by FePcS/H2O2 converts this pollutant into coupling products. The formation of dimers in the catalytic oxidation of dichloroanilines can be avoided by acylation of the amine function.

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