Anaerobic biotransformation of tetrabromobisphenol A, tetrachlorobisphenol A, and bisphenol A in estuarine sediments.

Biotransformation of the flame retardants tetrabromobisphenol A and tetrachlorobisphenol A, and their ultimate biodehalogenation product, bisphenol A, was examined in anoxic estuarine sediments. Dehalogenation of tetrabromobisphenol A and tetrachlorobisphenol A was examined under conditions promoting either methanogenesis or sulfate reduction as the primary terminal electron-accepting process. Complete dehalogenation of tetrabromobisphenol A to bisphenol A with no further degradation of bisphenol A, was observed under both methanogenic and sulfate-reducing conditions. Dehalogenation of tetrachlorobisphenol A under both methanogenic and sulfate-reducing conditions resulted in the accumulation of a persistent dichlorinated bisphenol A isomer, while no bisphenol A was formed. Co-amendment of sediment enrichments with either 2,6-dibromo- or 2,6-dichlorophenol did not affect the extent of dehalogenation as compared to sediments that were amended only with the flame retardants. Sediment cultures pre-acclimated on 2-bromophenol dehalogenated the flame retardants in a manner similar to that of fresh sediments. No loss of bisphenol A was observed in separate incubations within 162 days under conditions promoting either methanogenesis, sulfate-reduction, iron(III)-reduction, or nitrate-reduction. Furthermore, identical enrichments that readily degraded 4-hydroxybenzoate, a structural analogue of bisphenol A, did not exhibit bisphenol A degradation. The dehalogenation of tetrabromo- and tetrachlorobisphenol A and the potential for accumulation of bisphenol A in anoxic sediments is significant given the widespread use of these chemicals.