Photolysis Kinetics, Mechanisms, and Pathways of Tetrabromobisphenol A in Water under Simulated Solar Light Irradiation.
The photolysis of tetrabromobisphenol A (TBBPA) in aqueous solution under simulated solar light irradiation was studied under different conditions to find out mechanisms and pathways that control the transformation of TBBPA during photoreaction. Particular attention was paid to the identification of intermediates and elucidation of the photolysis mechanism of TBBPA by UPLC, LC/MS, FT-ICR-MS, NMR, ESR, and stable isotope techniques ((13)C and (18)O). The results showed that the photolysis of TBBPA could occur under simulated solar light irradiation in both aerated and deaerated conditions. A magnetic isotope effect (MIE)-hydrolysis transformation was proposed as the predominant pathway for TBBPA photolysis in both cases. 2,6-Dibromophenol and two isopropylphenol derivatives were identified as photooxidation products of TBBPA by singlet oxygen. Reductive debromination products tribromobisphenol A and dibromobisphenol A were also observed. This is the first report of a photolysis pathway involving the formation of hydroxyl-tribromobisphenol A.
†Key Laboratory of Coastal Environmental Processes and Ecological Remediation, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shandong 264003, P.R. China.|‡University of Chinese Academy of Sciences, Beijing 100049, P.R. China.
Xiaowen
X
Wang
†Key Laboratory of Coastal Environmental Processes and Ecological Remediation, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shandong 264003, P.R. China.|‡University of Chinese Academy of Sciences, Beijing 100049, P.R. China.
Xuefeng
X
Hu
†Key Laboratory of Coastal Environmental Processes and Ecological Remediation, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shandong 264003, P.R. China.|‡University of Chinese Academy of Sciences, Beijing 100049, P.R. China.
Hua
H
Zhang
§School of Environment and Architecture, University of Shanghai for Science and Technology, Shanghai 200093, P.R. China.
Fei
F
Chang
†Key Laboratory of Coastal Environmental Processes and Ecological Remediation, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai, Shandong 264003, P.R. China.|‡University of Chinese Academy of Sciences, Beijing 100049, P.R. China.
Yongming
Y
Luo
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D017665:Hydroxyl Radical / Q000737:chemistry; D007700:Kinetics; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D010636:Phenols / Q000737:chemistry; D010782:Photolysis; D011075:Polybrominated Biphenyls / Q000737:chemistry*; D026082:Singlet Oxygen / Q000737:chemistry; D012993:Solar Energy; D014867:Water / Q000737:chemistry; D014874:Water Pollutants, Chemical / Q000737:chemistry*
D010636:Phenols; D011075:Polybrominated Biphenyls; D014874:Water Pollutants, Chemical; D014867:Water; D026082:Singlet Oxygen; C038964:2,6-dibromophenol; D017665:Hydroxyl Radical; C020806:tetrabromobisphenol A