title: Photodecomposition of tetrabromobisphenol A in aqueous humic acid suspension by irradiation with light of various wavelengths.
abstract: The reactive species generated in aqueous 3,3',5,5'-tetrabromobisphenol A (TBBPA)/humic acid (HA) suspensions above the TBBPA pKa (∼7.4), under various light-irradiation conditions, namely ambient and ultraviolet light, were investigated using electron paramagnetic resonance (EPR) spectroscopy and liquid chromatography-mass spectrometry (LC-MS). We confirmed that singlet oxygen and OH radicals are the key reactive oxygen species generated at wavelengths greater than 400 and 300 nm, respectively. The amount of 2,6-dibromo-p-benzosemiquinone anion radicals (2,6-DBSQ(•-)) formed under irradiation at 400 nm increased linearly with respect to irradiation time; the initial reaction rate was 7.03 × 10(-9) mol g(-1) HA s(-1). The rate increased with increasing pH and light intensity. LC-MS and EPR spectroscopy showed that tribromohydroxybisphenol A was formed under irradiation at 300 nm via reaction of OH radicals with TBBPA. This study, for the first time, shows that the main byproducts formed during irradiation at wavelengths above 300 nm are 2,6-DBSQ(•-) and tribromohydroxybisphenol A, generated from singlet oxygen ((1)O2) and OH radicals, respectively. Photodecomposition of TBBPA in the environment may occur by formation of (1)O2 and OH radicals.
authors.affiliation: Department of Environmental Engineering and Biotechnology, Mokpo National Maritime University, 91 Haeyangdaehang-ro, Mokpo, Jeollanam-do 530-729, Republic of Korea.
authors.forename: Sang Kuk
authors.initials: SK
authors.lastname: Han
authors.affiliation: Department of Bio-functional Science, Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan.
authors.forename: Toshihide
authors.initials: T
authors.lastname: Yamasaki
authors.affiliation: Department of Bio-functional Science, Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan; JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan. Electronic address: kenyamada@phar.kyushu-u.ac.jp.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
mesh_terms: D002853:Chromatography, Liquid; D004578:Electron Spin Resonance Spectroscopy / Q000379:methods; D006812:Humic Substances / Q000528:radiation effects*; D008027:Light; D013058:Mass Spectrometry; D010782:Photolysis; D011075:Polybrominated Biphenyls / Q000737:chemistry / Q000528:radiation effects*; D017382:Reactive Oxygen Species / Q000737:chemistry; D013535:Suspensions
chemical_list: D006812:Humic Substances; D011075:Polybrominated Biphenyls; D017382:Reactive Oxygen Species; D013535:Suspensions; C020806:tetrabromobisphenol A
keywords: 2,6-Dibromo-p-benzosemiquinone radical; Electron paramagnetic resonance; Humic acid; Photodecomposition; Tetrabromobisphenol A; Tribromohydroxybisphenol A