Radical-induced degradation of a lignin model compound. Decomposition of 1-phenyl-2-phenoxyethanol

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DOIResolve DOI: http://doi.org/10.1139/v95-256
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TypeArticle
Journal titleCanadian Journal of Chemistry
Volume73
Issue11
Pages20792085; # of pages: 7
Subjectketyl radical; photochemical degradation; thermal degradation; lignin
AbstractReaction of 1-phenyl-2-phenoxyethanol (1) with thermally or photochemically generated tert-butoxyl radicals leads, via the intermediate ketyl radical, to the formation of the corresponding ketone, α-phenoxyacetophenone (4), as the only product at low conversion under an inert atmosphere. An approximately twofold increase in the product yield is observed when the reactions are carried out under oxygen. Under the photochemical conditions it is shown that 4 is the primary product and that acetophenone and phenol are formed as a result of secondary photolysis of 4. These data suggest that the rate constant for fragmentation of the ketyl radical derived from 1 is on the order of 10 s−1 at 298 K and contradict a report in the literature that suggests a rate constant of >10^6 s−1. The relevance of this study to the photodegradation of lignin and consequent photoyellowing is discussed and a revised mechanism for the photoyellowing of pulp is proposed. Keywords: ketyl radical, photochemical degradation, thermal degradation, lignin.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
NPARC number12328343
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Record identifier332ab2c5-7312-4b41-8d48-524ef4efff01
Record created2009-09-10
Record modified2016-05-09
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