The transformation pathways of chloroanilines (CAs), chlorobenzenes (CBs) and chlorophenols (CPs) were examined in anaerobic sediment collected from the Tsurumi river, Japan. The sediment was pre-exposed to various organic chemicals from the surrounding industries and appears to be sulfidogenic. Experiments were carried out for each compound in the sediment slurry, which was spiked at a desired concentration. The transformation of the parent substrate and the appearance of its metabolites were monitored for a year. All the compounds transformed without any lag period. For CBs, the preferential Cl removal was in the order: two Cl atoms on adjacent carbon atoms > one Cl atom on adjacent carbon > no adjacent Cl atom on the carbon. In case of CPs, ortho dechlorination was the preferred pathway, while for CAs, sequential removal of ortho and para positions was observed.

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