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Mini-Reviews in Organic Chemistry


ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a Key Chromophore in Aged Cellulosics

Author(s): Takashi Hosoya, Alfred D. French and Thomas Rosenau

Volume 10, Issue 3, 2013

Page: [309 - 315] Pages: 7

DOI: 10.2174/1570193X11310030009

Price: $65


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.

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