Abstract
A series of pseudo amorphous cellulose samples were reacted with catalytic amounts of 2,2,6,6-tetramethyl-1-piperidine oxoammonium salt (TEMPO), sodium hypochlorite and sodium bromide in water. In all samples the primary alcohol groups were selectively oxidised into carboxyl groups, and several water-soluble polyglucuronic acid sodium salts were obtained with different molecular weights. With this reaction system, the degradation of the amorphous cellulose samples may be minimized, provided the oxidation is performed at 4 °C and at constant pH 10, with controlled amounts of TEMPO and sodium hypochlorite.
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Blumenkrantz, N. and Asboe-Hansen, G. (1973) New method for quantitative determination of uronic acids. Anal. Biochem. 54, 484-489.
Chang, P. S. and Robyt, J. F. (1996) Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion. J. Carbohydr. Chem. 15, 819-830.
de Nooy, A. E., Besemer, A. C. and van Bekkum, H. (1994) Highly selective TEMPO mediated oxidation of primary alcohol groups in polysaccharides. Recl. Trav. Chim. Pays-Bas 113, 165-166.
de Nooy, A. E., Besemer, A. C. and van Bekkum, H. (1995) Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr. Res. 269, 89-98.
de Nooy, A. E., Besemer, A. C., van Bekkum, H., van Dijk, J. A. P. P. and Smit, J. A. M. (1996) TEMPO mediated oxidation of pullulan and influence of ionic strength and linear charge density on the dimensions of the obtained polyelectrolyte chains. Macromolecules 29, 6541-6547.
Heyraud, A., Courtois, J., Dantas, L., Colin-Morel, Ph. and Courtois, B. (1993) Structural characterisation and rheological properties of an extracellular glucuronan produced by a Rhizobium meliloti M5N1 mutant strain. Carbohydr. Res. 240, 71-78.
Isogai, A. and Attala, R. H. (1998) Dissolution of cellulose in aqueous NaOH solutions. Cellulose 5, 309-319.
Isogai, A. and Kato, Y. (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5, 153-164.
Marx-Figini, M. (1969) On the biosynthesis of cellulose in higher and lower plants. J. Polymer Sci. part C 28, 57-67.
Marx-Figini, M. and Pion, B. (1976) Kinetic investigations on biosynthesis of bacterial cellulose. Distribution of the degree of polymerisation for different numbers of bacterial generations. Makromol. Chem. 177, 1013-1020.
Maurer, K. and Reiff, G. (1943) Oxidation of cellulose with NO2. J. Makromol. Chem. 1, 27-34.
Painter, T. J. (1977) Preparation and periodate oxidation of C-6-oxycellulose: conformational interpretation of hemiacetal stability. Carbohydr. Res. 55, 95-103.
Rinaudo, M. (1968). Etudes physico-chimiques des solutions de cellulose dans le FeTNa. La Papeterie 90, 479-487.
Yackel, E. C. and Kenyon, W. O. (1942) Oxidation of cellulose by nitrogen dioxide. J. Am. Chem. Soc. 64, 121-127.
Yalpani, M. (1985) A survey of recent advances in selective chemical and enzymic polysaccharide modifications. Tetrahedron. 41, 2957-3020.
Yamane C., Saitoh M. and Okajima K. (1996) Industrial preparation method of cellulose-alkali dope with high solubility. Sen-i Gakkaishi 52, 310-317.
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Tahiri, C., Vignon, M.R. TEMPO-oxidation of cellulose: Synthesis and characterisation of polyglucuronans. Cellulose 7, 177–188 (2000). https://doi.org/10.1023/A:1009276009711
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DOI: https://doi.org/10.1023/A:1009276009711