Abstract
Triclocarban (TCC) reductive dechlorination was investigated using a combination of field and laboratory experiments. Field monitoring revealed that TCC reductive dechlorination in river sediments leads to formation of two isomers of its lesser chlorinated congener namely 3,4'-dichlorocarbanilide and 4,4'-dichlorocarbanilide. Monochlorocarbanilide was not detected in sediments supporting that transformation of dichlorocarbanilide into monochlorocarbanilide is the rate limiting step of TCC dechlorination. In~vitro experiments were conducted to study TCC potential reductive dechlorination mechanisms. These experiments demonstrated that 4,4'-dichlorocarbanilide was specifically formed upon a nucleophilic addition reaction under anaerobic conditions. The 3,4'-diclorocarbanilide was formed upon a two steps radical mechanism under aerobic conditions which includes TCC activation by one electron oxidation followed by a nucleophilic substitution reaction with glutathione. In~vitro results suggested that strict anaerobic conditions might not be required for TCC reductive dechlorination in the environment. Moreover, in~vitro reactions were performed using biomimetic or enzymatic systems supposing that TCC dechlorination might occur through microbial action in situ. Measured dichlorocarbanilide isomers/triclocarban ratios were used to evaluate the relative significance of both dechlorination pathways and the pathway leading to 3,4'-dichlorocarbanilide was found significant in all investigated river sediment samples.