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Degradation of the Cellulosic Key Chromophore 5,8-Dihydroxy-[1,4]-naphthoquinone by Hydrogen Peroxide Under Alkaline Conditions

Degradation of the Cellulosic Key Chromophore 5,8-Dihydroxy-[1,4]-naphthoquinone by Hydrogen Peroxide Under Alkaline Conditions

Nele Sophie Zwirchmayr, Takashi Hosoya, Ute Henniges, Lars Gille, Markus Bacher, Paul Furtmüller, Thomas Rosenau

J Org Chem. 2017 Nov 3;82(21):11558-11565.

PMID: 28968096

Abstract:

5,8-Dihydroxy-[1,4]-naphthoquinone (DHNQ) is one of the key chromophores in cellulosic materials. Its almost ubiquitous presence in cellulosic materials makes it a target molecule of the pulp and paper industry's bleaching efforts. In the presented study, DHNQ was treated with hydrogen peroxide under alkaline conditions at pH 10, resembling the conditions of industrial hydrogen peroxide bleaching (P stage). The reaction mechanism, reaction intermediates, and final degradation products were analyzed by UV/vis, NMR, GC-MS, and EPR. The degradation reaction yielded C1-C4 carboxylic acids as the final products. Highly relevant for pulp bleaching are the findings on intermediates of the reaction, as two of them, 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ) and 1,4,5,8-naphthalenetetrone, are potent chromophores themselves. While DHBQ is one of the three key cellulosic chromophores and its degradation by H2O2 is well-established, the second intermediate, 1,4,5,8-naphthalenetetrone, is reported for the first time in the context of cellulose discoloration.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP475387	5,8-Dihydroxy-1,4-naphthoquinone		475-38-7	Price

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