Abstract
2,5-Dihydroxy-[1,4]-benzoquinone is one of the three key chromophores found in aged cellulosics. Knowledge of the general reactivity and chemistry of this compound is helpful for a better understanding of cellulose aging and yellowing as well as bleaching of cellulosic materials - processes which also have considerable economic importance. This paper reviews the reactions reported for 2,5-dihydroxy-[1,4]-benzoquinone, from the viewpoints of both synthesis and general reactivity. The exhibits a rich chemistry because of the presence of both carbonyl and enol motifs, and is able to undergo both nucleophilic and electrophilic substitutions. Other major pathways are the condensation with amines, derivatization of the hydroxyl groups, reductions, and oxidative degradation.
Keywords: 2, 5-dihydroxy-1, 4-benzoquinone, benzoquinones, substitution, condensation, alkylation, reduction, cellulose, chromophores, yellowing.
Mini-Reviews in Organic Chemistry
Title:Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a Key Chromophore in Aged Cellulosics
Volume: 10 Issue: 3
Author(s): Takashi Hosoya, Alfred D. French and Thomas Rosenau
Affiliation:
Keywords: 2, 5-dihydroxy-1, 4-benzoquinone, benzoquinones, substitution, condensation, alkylation, reduction, cellulose, chromophores, yellowing.
Abstract: 2,5-Dihydroxy-[1,4]-benzoquinone is one of the three key chromophores found in aged cellulosics. Knowledge of the general reactivity and chemistry of this compound is helpful for a better understanding of cellulose aging and yellowing as well as bleaching of cellulosic materials - processes which also have considerable economic importance. This paper reviews the reactions reported for 2,5-dihydroxy-[1,4]-benzoquinone, from the viewpoints of both synthesis and general reactivity. The exhibits a rich chemistry because of the presence of both carbonyl and enol motifs, and is able to undergo both nucleophilic and electrophilic substitutions. Other major pathways are the condensation with amines, derivatization of the hydroxyl groups, reductions, and oxidative degradation.
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Hosoya Takashi, French D. Alfred and Rosenau Thomas, Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a Key Chromophore in Aged Cellulosics, Mini-Reviews in Organic Chemistry 2013; 10 (3) . https://dx.doi.org/10.2174/1570193X11310030009
DOI https://dx.doi.org/10.2174/1570193X11310030009 |
Print ISSN 1570-193X |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6298 |
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