Journal
JOURNAL OF WOOD SCIENCE
Volume 58, Issue 3, Pages 243-250Publisher
SPRINGER JAPAN KK
DOI: 10.1007/s10086-011-1244-4
Keywords
Alkyl-aryl ether; Bleaching; Lignin; Oxygen; Phenolic
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Funding
- Grants-in-Aid for Scientific Research [20688007] Funding Source: KAKEN
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To examine whether non-phenolic lignin moiety is converted into the new phenolic counterpart by the participation of active oxygen species (AOS) under oxygen bleaching conditions, a beta-O-4 type dimeric lignin model compound, 2-(2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol (I), 2-(3,5-difluorophenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (III), or 2-(3,5-difluorophenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol (IV), was treated under conditions similar to those for oxygen bleaching. A phenolic compound, 4-hydroxy-3-methoxybenzyl alcohol, was added together to generate AOS in the reaction of compound I or IV. The results obtained suggested that AOS attack the side chains of compounds I, III, and IV accompanied by the beta-O-4 bond cleavages and the liberations of the corresponding phenolic compounds, 2-methoxyphenol (II), 3,5-difluorophenol (V), and compound V, respectively. However, the rapid liberation of compound V in the oxygen-alkali treatment of compound III may mainly be caused by alkaline-induced reactions and/or some oxidation reactions of the primary degradation product of compound III, a muconic acid derivative.
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