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.