PMID- 25340709
OWN - NLM
STAT- MEDLINE
DCOM- 20150821
LR  - 20181202
IS  - 1520-5851 (Electronic)
IS  - 0013-936X (Linking)
VI  - 48
IP  - 24
DP  - 2014 Dec 16
TI  - Thermal decomposition of 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), a novel 
      brominated flame retardant.
PG  - 14335-43
LID - 10.1021/es5038047 [doi]
AB  - 1,2-Bis(2,4,6-tribromophenoxy)ethane (BTBPE) is currently one of the most 
      commonly applied novel brominated flame retardants. In this contribution, we 
      analyze 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  approximately  680 
      K. H atom abstraction from CH2 sites, followed by a fission of a C-C bond, 
      produce a 2,4,6-tribromophenoxy radical (M2) and a M10 molecule. Bimolecular 
      condensation reactions involving M2, M9, and M10 generate 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). Reactions of alkyl primary/secondary radicals and 
      diradical with the BTBPE molecule proceed via H abstraction from a -CH2- moiety.
FAU - Altarawneh, Mohammednoor
AU  - Altarawneh M
AD  - School of Engineering and Information Technology Murdoch University , Murdoch WA 
      6150, Australia.
FAU - Dlugogorski, Bogdan Z
AU  - Dlugogorski BZ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20141124
PL  - United States
TA  - Environ Sci Technol
JT  - Environmental science & technology
JID - 0213155
RN  - 0 (Bromobenzenes)
RN  - 0 (Dioxins)
RN  - 0 (Flame Retardants)
RN  - 0 (Furans)
RN  - 0 (Halogenated Diphenyl Ethers)
RN  - 0 (Phenols)
RN  - 34I00D6RNM (1,2-bis(2,4,6-tribromophenoxy)ethane)
RN  - YS6K3EU393 (2,4,6-tribromophenol)
SB  - IM
MH  - Bromobenzenes/*chemistry
MH  - Dioxins/chemistry
MH  - *Flame Retardants
MH  - Furans/chemistry
MH  - Halogenated Diphenyl Ethers/chemistry
MH  - Hot Temperature
MH  - Phenols/chemistry
EDAT- 2014/10/24 06:00
MHDA- 2015/08/22 06:00
CRDT- 2014/10/24 06:00
PHST- 2014/10/24 06:00 [entrez]
PHST- 2014/10/24 06:00 [pubmed]
PHST- 2015/08/22 06:00 [medline]
AID - 10.1021/es5038047 [doi]
PST - ppublish
SO  - Environ Sci Technol. 2014 Dec 16;48(24):14335-43. doi: 10.1021/es5038047. Epub 
      2014 Nov 24.