TY - JOUR
T1 - Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs)
AU - Saeed, Anam
AU - Altarawneh, Mohammednoor
AU - Dlugogorski, Bogdan Z.
N1 - Funding Information:
This study has been supported by the Australian Research Council (ARC), and grants of computing time from the National Computational Infrastructure (NCI), Australia as well as the Pawsey Supercomputing Centre. A.S. thanks Murdoch University, Australia, for a postgraduate research scholarship.
Publisher Copyright:
© 2015 Elsevier Ltd.
PY - 2015
Y1 - 2015
N2 - This contribution investigates mechanistic and kinetic parameters pertinent to formation of mixed dibenzo-p-dioxins and dibenzofurans (PXDD/Fs) from the condensation reactions involving 2-chlorophenoxy (2-CPxy) and 2-bromophenoxy (2-BPxy) radicals. Keto-ether structures act as direct intermediates for the formation of DD, 1-MCDD, 1-MBDD, 1-B,6-CDD and 1-B,9-CDD molecules. Likewise, diketo adducts initiate the formation of 4-MCDF, 4-MBDF and 4-B,6-CDF compounds through interconversion and rearrangement reactions. As formation mechanisms of halogenated dibenzo-p-dioxins and dibenzofurans from precursors of brominated and chlorinated phenols are insensitive to substitution at meta and para sites, our mechanistic and kinetic analysis of reactions involving 2-BPxy and 2-CPxy should also apply to higher halogenated phenoxy radicals.
AB - This contribution investigates mechanistic and kinetic parameters pertinent to formation of mixed dibenzo-p-dioxins and dibenzofurans (PXDD/Fs) from the condensation reactions involving 2-chlorophenoxy (2-CPxy) and 2-bromophenoxy (2-BPxy) radicals. Keto-ether structures act as direct intermediates for the formation of DD, 1-MCDD, 1-MBDD, 1-B,6-CDD and 1-B,9-CDD molecules. Likewise, diketo adducts initiate the formation of 4-MCDF, 4-MBDF and 4-B,6-CDF compounds through interconversion and rearrangement reactions. As formation mechanisms of halogenated dibenzo-p-dioxins and dibenzofurans from precursors of brominated and chlorinated phenols are insensitive to substitution at meta and para sites, our mechanistic and kinetic analysis of reactions involving 2-BPxy and 2-CPxy should also apply to higher halogenated phenoxy radicals.
KW - Bromophenol
KW - Chlorophenol
KW - Polyhalogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs)
KW - Reaction mechanism
KW - Reaction rate constants
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U2 - 10.1016/j.chemosphere.2015.06.054
DO - 10.1016/j.chemosphere.2015.06.054
M3 - Article
C2 - 26159067
AN - SCOPUS:84955277545
SN - 0045-6535
VL - 137
SP - 149
EP - 156
JO - Chemosphere
JF - Chemosphere
ER -