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Thermal decomposition of 1,2-bis-(2,4,6-tribromophenoxy)ethane (BTBPE), a novel brominated flame retardant

Altarawneh, M.ORCID: 0000-0002-2832-3886 and Dlugogorski, B.Z. (2014) Thermal decomposition of 1,2-bis-(2,4,6-tribromophenoxy)ethane (BTBPE), a novel brominated flame retardant. Environmental Science & Technology, 48 (24). pp. 14335-14343.

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1,2-bis-(2,4,6-tribromophenoxy)ethane (BTBPE) is currently one of the most utilised novel brominated flame retardants. In this contribution, we analyse in detail the mechanisms pertinent to its thermal decomposition in view of analogous experimental findings. We demonstrate that a 1,3-hydrogen shift, leading to 2,4,6-tribromophenol (M9) and 1,3,5-tribromo-2-(vinyloxy)benzene (M10) molecules, dominates direct scission of O-CH2 bonds up to a temperature of ~ 680 K. H atom abstraction from CH2 sites, followed by a fission of a C-C bond, produces a 2,4,6-tribromophenoxy radical (M2) and a M10 molecule. Bimolecular condensation reactions involving M2, M9 and M10 produce several congeners of brominated diphenyl ethers and their OH/OCHCH2 substituents, which serve as direct precursors for the formation of polybrominated dibenzo-p-dioxins. Reaction of M9 with a model compound of a hydrocarbon chain preferentially yields M2. Strong adsorption energy of the latter on a radical site of a hydrocarbon chain suggests that mechanisms such as Langmuir–Hinshelwood, Eley–Rideal and Diels-Alder might be operating during the formation of PBDD/Fs from brominated flame retardants (BFRs).

Item Type: Journal Article
Murdoch Affiliation(s): School of Engineering and Information Technology
Publisher: American Chemical Society
Copyright: © 2014 American Chemical Society
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