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Title: Chemistry of 2,5-dihydroxy-(1,4)-benzoquinone, a key chromophore in aged cellulosics

Author
item HOSOYA, TAKASHI - University Of Natural Resources & Applied Life Sciences - Austria
item FRENCH, ALFRED - Retired ARS Employee
item ROSENAU, THOMAS - University Of Natural Resources & Applied Life Sciences - Austria

Submitted to: Mini Reviews in Organic Chemistry
Publication Type: Review Article
Publication Acceptance Date: 6/5/2013
Publication Date: 7/1/2013
Citation: Hosoya, T., French, A., Rosenau, T. 2013. Chemistry of 2,5-dihydroxy-(1,4)-benzoquinone, a key chromophore in aged cellulosics. Mini Reviews in Organic Chemistry. 10(3):302-308.

Interpretive Summary: Cotton or linen fabrics and paper, as well as other items composed chiefly of cellulose, tend to change to a yellow or brown color as they age. The change in color is usually accompanied by increased brittleness and loss of strength, as well. A cause of these phenomena is thought to be the formation of chemical compounds (chromophores) that originate in the individual glucose units of the cellulose which consists of many glucose residues connected together. In the present work, many aspects of the structure and chemistry of another important chromophore, 5,8-dihydroxy-[1,4]-napthoquinone are brought together along with new results from computational quantum mechanics studies to obtain new understanding of the various reaction mechanisms and potential ways to stop, or slow, the deterioration of items made from cellulose. Current attempts to change the color are by bleaching, for example, are largely futile because the benzoquinone structure is readily re-oxidized to the dihydroxy benzoquinone, a chromophore that is visible at the parts per billion level. Other chemical remedies are discussed.

Technical Abstract: Cotton or linen fabrics and paper, as well as other items composed chiefly of cellulose, tend to change to a yellow or brown color as they age. The change in color is usually accompanied by increased brittleness and loss of strength, as well. A cause of these phenomena is thought to be the formation of chemical compounds (chromophores) that originate in the individual glucose units of the cellulose which consists of many glucose residues connected together. In the present work, many aspects of the structure and chemistry of another important chromophore, 5,8-dihydroxy-[1,4]-napthoquinone are brought together along with new results from computational quantum mechanics studies to obtain new understanding of the various reaction mechanisms and potential ways to stop, or slow, the deterioration of items made from cellulose. Current attempts to change the color are by bleaching, for example, are largely futile because the benzoquinone structure is readily re-oxidized to the dihydroxy benzoquinone, a chromophore that is visible at the parts per billion level. Other chemical remedies are discussed.