Release of 3,3‘-dichlorobenzidine (DCB), an intermediate in dye manufacturing, and its congeners are of environmental concern due to their carcinogenic nature. To elucidate the fate of these compounds in sediment/water systems, sediment/water mixtures were spiked with DCB and incubated at 20 °C for 12 months under anaerobic conditions. The sediments used in this study were collected from Lake Macatawa (Holland, MI) and ranged in composition from silty-clay to sandy. Dehalogenation of DCB to benzidine appeared to take place through a transient intermediate, 3-monochlorobenzidine, which was observed in time-course analyses of the sediment/water mixtures. No metabolites were observed in autoclaved samples, sug gesting that dehalogenation of DCB in anaerobic sediment/water systems was mediated by microbial activity. The product of dehalogenation (benzidine) is more toxic to humans than the parent compound, DCB. From sediment/water distribution experiments, DCB showed greater affinity for the sediment phase than its non-chlorinated derivative, benzidine. Therefore, progressive dehalogenation of DCB in anaerobic lake sediments is expected to yield a greater total concentration of aromatic amines in the solution phase, a shift to a more toxic form, and greater potential for transport in the environment.
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Nyman et al. (1997) studied this question.
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