Oxidative degradation of decabromodiphenyl ether (BDE 209) by potassium permanganate: reaction pathways, kinetics, and mechanisms assisted by density functional theory calculations

Environmental Science & Technology
Jiaqi ShiZunyao Wang

Abstract

This study found that decabromodiphenyl ether (BDE 209) could be oxidized effectively by potassium permanganate (KMnO4) in sulfuric acid medium. A total of 15 intermediate oxidative products were detected. The reaction pathways were proposed, which primarily included cleavage of the ether bond to form pentabromophenol. Direct oxidation on the benzene ring also played an important role because hydroxylated polybrominated diphenyl ethers (PBDEs) were produced during the oxidation process. The degradation occurred dramatically in the first few minutes and fitted pseudo-first-order kinetics. Increasing the water content decelerated the reaction rate, whereas increasing the temperature facilitated the reaction. In addition, density functional theory (DFT) was employed to determine the frontier molecular orbital (FMO) and frontier electron density (FED) of BDE 209 and the oxidative products. The theoretical calculation results confirmed the proposed reaction pathways.

References

Apr 2, 1998·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·U Orn, E Klasson-Wehler
Sep 15, 1988·Physical Review A: General Physics·A D Becke
May 16, 2000·Environmental Health Perspectives·K Hooper, T A McDonald
Apr 12, 2003·Water Research·Sierra RayneMacMurray D Whale
Jun 20, 2003·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Anna MorckEva Klasson Wehler
Jul 10, 2003·Environment International·J Ebert, M Bahadir
Jul 10, 2003·Environment International·Heldur Hakk, Robert J Letcher
Jul 10, 2003·Environment International·Per Ola Darnerud
Feb 19, 2004·Environmental Science & Technology·Ashraf HassaninKevin C Jones
Jul 1, 2004·Environmental Science & Technology·Johan ErikssonAke Bergman
Aug 7, 2004·Environmental Science & Technology·Amy L ChiuchioloHugh W Ducklow
Aug 25, 2004·Marine Pollution Bulletin·Michael MartinBruce J Richardson
Nov 17, 2004·Environmental Science & Technology·Arnold SchecterLinda Birnbaum
May 6, 2005·Environmental Science & Technology·Kaj ThuressonKristina Jakobsson
Oct 6, 2005·Environmental Science & Technology·Jennie R ChristensenPeter S Ross
Feb 7, 2006·Chemosphere·Cynthia A de WitDerek C G Muir
Apr 14, 2007·The Journal of Chemical Physics·De-en JiangSheng Dai
May 13, 2008·Environmental Health Perspectives·Milou M L DingemansRemco H S Westerink
Feb 26, 2009·Environmental Science & Technology·Lanhua HuTimothy I Strathmann
Apr 11, 2009·Environmental Science and Pollution Research International·Anna ChristianssonAke Bergman
Nov 26, 2009·Environment International·Chang'er ChenLinke Ge
Mar 23, 2011·Environmental Science & Technology·Lanhua HuTimothy J Strathmann
Dec 10, 2013·Environment International·Natàlia Garcia-ReyeroDemetrio Raldúa

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Citations

Sep 24, 2015·International Journal of Environmental Research and Public Health·Yu LiuFu-Kai Li
Nov 15, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jiangchi FeiShuang Luo
Oct 31, 2019·International Journal of Environmental Research and Public Health·Meijin DuYu Li
Feb 18, 2020·Rapid Communications in Mass Spectrometry : RCM·Xifen ZhuPing'an Peng
Oct 30, 2020·Environmental Science and Pollution Research International·Minghao LiYu Li
Mar 20, 2021·The Science of the Total Environment·Yanhui SunXiaochen Zhang
Aug 27, 2021·The Science of the Total Environment·Zhezheng DingQingzhu Zhang
Aug 31, 2021·The Journal of Physical Chemistry. a·Yanru HuoMaoxia He

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