Oxidation of dichloroanilines and related anilides catalyzed by iron(III) tetrasulfonatophthalocyanine

We investigated the degradation of polychlorinated pollutants, such as dich loroanilines and related anilides, catalyzed by iron(III) tetrasulfonatopht halocyanine (FePcS) with potassium monopersulfate or hydrogen peroxide as o xidant. The reaction is influenced by the positions of the two chloro-subst ituents 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 di mers (azo and azoxy compounds). The oxidation of 3,4-dichloroaniline by FeP cS/H2O2 converts this pollutant into coupling products. The formation of di mers in the catalytic oxidation of dichloroanilines can be avoided by acyla tion of the amine function.