Mechanistic and kinetic investigation on OH-initiated oxidation of tetrabromobisphenol A

Chemosphere. 2016 Jun:153:262-9. doi: 10.1016/j.chemosphere.2016.03.043. Epub 2016 Mar 25.

Abstract

Detailed mechanism of the OH-initiated transformation of tetrabromobisphenol A (TBBPA) has been investigated by quantum chemical methods in this paper. Abstraction reactions of hydrogen atoms from the OH groups and CH3 groups of TBBPA are the dominant pathways of the initial reactions. The produced phenolic-type radical and alkyl-type radical may transfer to 4,4'-(ethene-1,1-diyl)bis(2,6-dibromophenol), 4-acetyl-2,6-dibromophenol and 2,6-dibromobenzoquinone at high temperature. In water, major products are 2,6-dibromo-p-hydroquinone, 4-isopropylene-2,6-dibromophenol and 4-(2-hydroxyisopropyl)-2,6-dibromophenol resulting from the addition reactions. Total rate constants of the initial reaction are 1.02 × 10(-12) cm(3) molecule(-1) s(-1) in gas phase and 1.93 × 10(-12) cm(3) molecule(-1) s(-1) in water at 298 K.

Keywords: Decomposition; OH radical; Oxidation; Rate constants; TBBPA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Environmental Pollutants / chemistry*
  • Environmental Restoration and Remediation / methods*
  • Flame Retardants / analysis
  • Flame Retardants / metabolism*
  • Kinetics
  • Oxidation-Reduction
  • Phenols / chemistry*
  • Polybrominated Biphenyls / chemistry*
  • Water

Substances

  • Environmental Pollutants
  • Flame Retardants
  • Phenols
  • Polybrominated Biphenyls
  • Water
  • 2,6-dibromophenol
  • tetrabromobisphenol A