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Molecules 2013, 18(5), 5360-5372; doi:10.3390/molecules18055360

Oxidative Debromination and Degradation of Tetrabromo-bisphenol A by a Functionalized Silica-Supported Iron(III)-tetrakis(p-sulfonatophenyl)porphyrin Catalyst

Laboratory of Chemical Resources, Division of Sustainable Resources Engineering, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
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Received: 15 April 2013 / Revised: 7 May 2013 / Accepted: 7 May 2013 / Published: 10 May 2013
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Abstract

Tetrabromobisphenol A (TBBPA), a commonly used brominated flame retardant, also functions as an endocrine disruptor. Thus, the degradation of TBBPA has attracted considerable interest among the scientific community. Iron(III)-porphyrin complexes are generally regarded as “green” catalysts and have been reported to catalyze the efficient degradation and dehalogenation of halogenated phenols in environmental wastewaters. However, they are quickly deactivated due to self-degradation in the presence of an oxygen donor, such as KHSO5. In the present study, an iron(III)-tetrakis (p-sulfonatophenyl)-porphyrin (FeTPPS) was immobilized on imidazole-modified silica (FeTPPS/IPS) via coordination of the Fe(III) with the nitrogen atom in imidazole to suppress self-degradation and thus enhance the catalyst reusability. The oxidative degradation and debromination of TBBPA and the influence of humic acid (HA), a major component in leachates, on the oxidation of TBBPA was investigated. More than 95% of the TBBPA was degraded in the pH range from 3 to 8 in the absence of HA, while the optimal pH for the reaction was at pH 8 in the presence of HA. Although the rate of degradation was decreased in the presence of HA, over 95% of the TBBPA was degraded within 12 h in the presence of 28 mg-C L−1 of HA. At pH 8, the FeTPPS/IPS catalyst could be reused up to 10 times without any detectable loss of activity for TBBPA for degradation and debromination, even in the presence of HA.
Keywords: iron(III)-porphyrin; humic acid; silica support; catalytic oxidation; tetrabromobisphenol A iron(III)-porphyrin; humic acid; silica support; catalytic oxidation; tetrabromobisphenol A
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MDPI and ACS Style

Zhu, Q.; Mizutani, Y.; Maeno, S.; Fukushima, M. Oxidative Debromination and Degradation of Tetrabromo-bisphenol A by a Functionalized Silica-Supported Iron(III)-tetrakis(p-sulfonatophenyl)porphyrin Catalyst. Molecules 2013, 18, 5360-5372.

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