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Comparison of the oxidation products produced by tetrahalobisphenol A flame retardants as a result of potassium monopersulfate oxidation with an iron(III)-tetrakis(p-sulfonatophenyl)porphyrin in the presence of humic acid
| Title: | Comparison of the oxidation products produced by tetrahalobisphenol A flame retardants as a result of potassium monopersulfate oxidation with an iron(III)-tetrakis(p-sulfonatophenyl)porphyrin in the presence of humic acid |
| Authors: | Mizutani, Yusuke Browse this author | | Maeno, Shohei Browse this author | | Zhu, Qianqian Browse this author | | Fukushima, Masami Browse this author →KAKEN DB |
| Keywords: | Humic acid | | tetrabromobisphenol A | | tetrachlorobisphenol A | | catalytic oxidation | | oxidative coupling | | iron(III)-5,10,15,20-tetrakis(p-sulfonatophenyl)porphyrin |
| Issue Date: | 21-Mar-2014 |
| Publisher: | Taylor & francis inc |
| Journal Title: | Journal of environmental science and health part a-toxic/hazardous substances & environmental engineering |
| Volume: | 49 |
| Issue: | 4 |
| Start Page: | 365 |
| End Page: | 375 |
| Publisher DOI: | 10.1080/10934529.2014.854148 |
| PMID: | 24345234 |
| 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 -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 system. These results suggest that TCBPA is incorporated into HA more readily than TBBPA. The coupling compounds between HA and halogenated intermediates from TBBPA or TCBPA were assigned by pyrolysis-gas chromatography/mass spectrometry. |
| Rights: | This is an Author's Accepted Manuscript of an article published in Journal of Environmental Science and Health, Part A (Published in Dec 2013), available online at: http://www.tandfonline.com/doi/abs/10.1080/10934529.2014.854148. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/58147 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 福嶋 正巳
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