title: Photochemical transformations of tetrabromobisphenol A and related phenols in water.
abstract: A method was developed for studies of the phototransformation at UV irradiation of aqueous solutions of tetrabromobisphenol A (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenol at various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbance spectra of the compounds and the emission spectra of the light-source were determined and used to calculate disappearance quantum yields of the photochemical reactions that were taking place. No major differences between the disappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yield of TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8 than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC-MS analysis and by comparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via different mechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenol and 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while the major degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane.
authors.affiliation: Departments of Environmental Chemistry and Structural Chemistry, Stockholm University, SE-106 91, Sweden. johan.eriksson@mk.su.se
authors.forename: Johan
authors.initials: J
authors.lastname: Eriksson
authors.forename: Sara
authors.initials: S
authors.lastname: Rahm
authors.forename: Nicholas
authors.initials: N
authors.lastname: Green
authors.forename: Ake
authors.initials: A
authors.lastname: Bergman
authors.forename: Eva
authors.initials: E
authors.lastname: Jakobsson
mesh_terms: D008401:Gas Chromatography-Mass Spectrometry; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D010636:Phenols / Q000737:chemistry; D010777:Photochemistry / Q000379:methods*; D011075:Polybrominated Biphenyls / Q000737:chemistry* / Q000528:radiation effects; D014466:Ultraviolet Rays; D014867:Water
chemical_list: D010636:Phenols; D011075:Polybrominated Biphenyls; D014867:Water; C020806:tetrabromobisphenol A