Mechanisms for the formation of polychlorinated dibenzo-p-dioxins and furans (PCDD/Fs) from chlorinated toluenes
Rawadieh, S., Altarawneh, M., Altarawneh, I. and Al-Shaweesh, M.A. (2014) Mechanisms for the formation of polychlorinated dibenzo-p-dioxins and furans (PCDD/Fs) from chlorinated toluenes. Reaction Kinetics, Mechanisms and Catalysis, 112 (2). pp. 321-333.
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In this contribution, we study a new mechanism of the formation of PCDD/F polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDD/F) from chlorinated toluenes, using quantum chemical calculations. Pathways involving 2-chlorotoluene incur high activation barriers which diminish its direct role in the formation of PCDD/F. Alternatively, the 2-chlorobenzyl and 2-methylphenoxy radicals, which are important intermediates in the early stages of the 2-chlorotoluene oxidation, yield PCDD/F through a less energy demanding pathway. The proposed mechanisms resemble the well-established pathways for the oxidative coupling of chlorinated phenols. It is predicted that the presence of an ortho methyl-bearing site facilitates initial coupling over that of an ortho chlorine-bearing site. Furthermore, chlorinated toluenes may initially be oxidized to phenoxy and phenolic intermediates to form PCDD/F. Results presented herein should be instrumental for gaining a better understanding of general formation routes of PCDD/F.
|Publication Type:||Journal Article|
|Murdoch Affiliation:||School of Engineering and Information Technology|
|Copyright:||© 2014 Akadémiai Kiadó, Budapest, Hungary.|
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