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Biomacromolecules. 2004 Mar-Apr;5(2):565-71.

Preparation of cellouronic acids and partially acetylated cellouronic acids by TEMPO/NaClO oxidation of water-soluble cellulose acetate.

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1
Centre de Recherches sur les Macromolécules Végétales, CNRS, and Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.

Abstract

Water-soluble cellulose acetates with a degree of substitution (DS) of 0.5, prepared by partial deacetylation of cellulose acetate of DS=2.5, were oxidized with catalytic amount of 2,2,6,6,-tetramethyl-1-piperidinyloxy radical (TEMPO), sodium hypochlorite, and sodium bromide to provide useful cellouronic acids. The oxidation was conducted at a constant pH of 10 and at 2 degrees C to avoid the occurrence of side products. Whereas only the primary hydroxyl groups of cellulose acetate were oxidized, a variable degree of oxidation (DO) resulted in a range of 0.33 to 1.0, depending on the concentration in sodium hypochlorite. Thus, polyglucuronic acid as well as partially acetylated cellouronic acid, having a range of DO were obtained.

PMID:
15003022
DOI:
10.1021/bm034405y
[Indexed for MEDLINE]
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