Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs)

Anam Saeed, Mohammednoor Altarawneh, Bogdan Z. Dlugogorski

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)149-156
Number of pages8
JournalChemosphere
Volume137
Issue numberOctober
Early online date6 Jul 2015
DOIs
Publication statusPublished - Oct 2015
Externally publishedYes

Fingerprint

Condensation reactions
dibenzofuran
Kinetic parameters
dioxin
Phenols
Ethers
Substitution reactions
kinetics
Molecules
Kinetics
formation mechanism
ether
Ether
condensation
phenol
substitution
dibenzo(1,4)dioxin
Dibenzofurans
analysis
parameter

Cite this

Saeed, Anam ; Altarawneh, Mohammednoor ; Dlugogorski, Bogdan Z. / Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs). In: Chemosphere. 2015 ; Vol. 137, No. October. pp. 149-156.
@article{acadce7d36694c48aebcd99272dd46d8,
title = "Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs)",
abstract = "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.",
keywords = "Bromophenol, Chlorophenol, Polyhalogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs), Reaction mechanism, Reaction rate constants",
author = "Anam Saeed and Mohammednoor Altarawneh and Dlugogorski, {Bogdan Z.}",
year = "2015",
month = "10",
doi = "10.1016/j.chemosphere.2015.06.054",
language = "English",
volume = "137",
pages = "149--156",
journal = "Chemosphere",
issn = "0045-6535",
publisher = "Global Science Books",
number = "October",

}

Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs). / Saeed, Anam; Altarawneh, Mohammednoor; Dlugogorski, Bogdan Z.

In: Chemosphere, Vol. 137, No. October, 10.2015, p. 149-156.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Formation of mixed halogenated dibenzo-p-dioxins and dibenzofurans (PXDD/Fs)

AU - Saeed, Anam

AU - Altarawneh, Mohammednoor

AU - Dlugogorski, Bogdan Z.

PY - 2015/10

Y1 - 2015/10

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

UR - http://www.scopus.com/inward/record.url?scp=84955277545&partnerID=8YFLogxK

U2 - 10.1016/j.chemosphere.2015.06.054

DO - 10.1016/j.chemosphere.2015.06.054

M3 - Article

VL - 137

SP - 149

EP - 156

JO - Chemosphere

JF - Chemosphere

SN - 0045-6535

IS - October

ER -