Visible light and fulvic acid assisted generation of Mn(III) to oxidize bisphenol A: The effect of tetrabromobisphenol A.
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abstract
Bisphenol A (BPA) and tetrabromobisphenol A (TBBPA), endocrine disrupting compounds (EDCs), are of increasing concerns for many years. This paper presents the elimination of BPA under visible light (VL) (420nm) irradiated solutions containing fulvic acid (FA) and MnSO4 (Mn(II)), and examines the possible effects of TBBPA on the transformation of BPA. After 72h of reaction time, the removal efficiency of BPA in the studied system was 69%. Results of different experiments to identify oxidative species suggested the dominate role of soluble manganese (III) (Mn(III)) in the conversion of BPA. The transformation of BPA by the VL/FA/Mn(II) system was through self-oligomerization in absence of co-existence of TBBPA. In the co-existence of BPA with TBBPA, the removal of BPA was largely inhibited due to the competition with available Mn(III) and the possible occurrence of cross-coupling reactions between the two EDCs. This phenomenon was further elucidated by product analyses and density functional theory (DFT) calculations. The energy difference (E) for generating a cross-coupling product was calculated as-23.4kJmol-1, much lower than the positive values of E for self-coupling products of BPA or TBBPA, demonstrating that cross-coupling reactions between BPA and TBBPA likely occurred easier than the respective self-coupling reactions. The toxicity test showed that the overall estrogenic activity of BPA reaction solution was significantly decreased by the VL/FA/Mn(II) system. In general, our study provided new insights into the transformation of co-existing EDCs by in situ formed Mn(III) in aqueous solution.
