Abstract
Tetrabromobisphenol A (TBBPA) and tetrachlorobisphenol A (TCBPA), commercially used halogenated flame retardants, can be found in leachates from landfills, because hydrophobic interactions with humic acids (HAs), major organic components in landfills, result in an increase in their solubility. The oxidation characteristics of TBBPA and TCBPA in the presence of HA were compared using a catalytic system comprised of a combination of iron(III)-tetrakis(p-sulfophenyl)porphyrin (FeTPPS) and KHSO5 that can mimic the enzymatic reactions that occur in landfills. The levels of degradation and dehalogenation of TBBPA and TCBPA at pH 4 were significantly lower than at pH 8, which is a typical pH value for landfill leachates. In the presence of HA at pH 8, 2-hydroxyisopropyl-2,6 -dihalophenols (2HIP-26DXPs) were detected as major by-products. These compounds are likely produced via the β-carbon scission of the substrates, and their levels decreased with increasing reaction time. The levels of coupling compounds between 2,6-dihalopnenols and TBBPA or TCBPA increased with reaction time. The 27% of Br in the degraded TBBPA and 50% of Cl in the degraded TCBPA were incorporated into the HA as a result of catalytic oxidation via the FeTPPS/KHSO5...Continue Reading
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