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

Environ Sci Technol. 2002 Feb 15;36(4):696-701. doi: 10.1021/es011081h.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Bacteria, Anaerobic / physiology*
  • Benzhydryl Compounds
  • Biotransformation
  • Chlorophenols / metabolism*
  • Estrogens, Non-Steroidal / metabolism*
  • Flame Retardants / metabolism*
  • Geologic Sediments / chemistry
  • Geologic Sediments / microbiology
  • Phenols / metabolism*
  • Polybrominated Biphenyls / metabolism*
  • Water Pollutants, Chemical / metabolism

Substances

  • Benzhydryl Compounds
  • Chlorophenols
  • Estrogens, Non-Steroidal
  • Flame Retardants
  • Phenols
  • Polybrominated Biphenyls
  • Water Pollutants, Chemical
  • tetrachlorodian
  • tetrabromobisphenol A
  • bisphenol A