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International Journal of the Biology, Chemistry, Physics, and Technology of Wood

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Polyoxometalate (POM) oxidation of lignin model compounds

Yong Sik Kim1 / Hou-min Chang2 / John F. Kadla3

1Biomaterials Chemistry, Faculty of Forestry, University of British Columbia, Vancouver, BC, Canada

2College of Natural Resources, North Carolina State University, Raleigh, NC 27695-8005, USA

3Biomaterials Chemistry, Faculty of Forestry, University of British Columbia, Vancouver, BC, Canada

Corresponding author. Biomaterials Chemistry, Faculty of Forestry, University of British Columbia, Vancouver, BC, Canada Phone: +1-604-822-5254, Fax: +1-604-822-9104,

Citation Information: Holzforschung. Volume 62, Issue 1, Pages 38–49, ISSN (Online) 1437434X, ISSN (Print) 00183830, DOI: https://doi.org/10.1515/HF.2008.006, December 2007

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Various lignin model compounds were oxidized with polyoxometalate (POM), K5[SiVW11O40]·12 H2O, in sodium acetate buffer (I=0.2 M, pH 5.0) and the reaction kinetics were investigated. The reactions were found to have second order reaction rates, first order with regards to both lignin model compound and POM. A dramatic increase in reactivity was observed upon addition of methoxyl groups in ortho-positions to the phenolic hydroxyl group. Syringyl units reacted faster than guaiacyl units. Reaction rates of para-substituted guaiacyl and syringyl model compounds showed a strong dependency on the nature of the substituents. The reaction rate of a 5-5′ dimer lignin model compound was extremely fast. The addition of the ortho-phenol substituent not only increased the electron density of the aromatic ring, but also helped stabilize the intermediate phenoxy radical through resonance stabilization and delocalization.

Keywords: kinetics; lignin model compounds; oxidation; polyoxometalate (POM)

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