Skip to main content
Log in

TEMPO-oxidation of cellulose: Synthesis and characterisation of polyglucuronans

  • Published:
Cellulose Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Blumenkrantz, N. and Asboe-Hansen, G. (1973) New method for quantitative determination of uronic acids. Anal. Biochem. 54, 484-489.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Google Scholar 

  • Isogai, A. and Attala, R. H. (1998) Dissolution of cellulose in aqueous NaOH solutions. Cellulose 5, 309-319.

    Google Scholar 

  • Isogai, A. and Kato, Y. (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5, 153-164.

    Google Scholar 

  • Marx-Figini, M. (1969) On the biosynthesis of cellulose in higher and lower plants. J. Polymer Sci. part C 28, 57-67.

    Google Scholar 

  • 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.

    Google Scholar 

  • Maurer, K. and Reiff, G. (1943) Oxidation of cellulose with NO2. J. Makromol. Chem. 1, 27-34.

    Google Scholar 

  • Painter, T. J. (1977) Preparation and periodate oxidation of C-6-oxycellulose: conformational interpretation of hemiacetal stability. Carbohydr. Res. 55, 95-103.

    Google Scholar 

  • Rinaudo, M. (1968). Etudes physico-chimiques des solutions de cellulose dans le FeTNa. La Papeterie 90, 479-487.

    Google Scholar 

  • Yackel, E. C. and Kenyon, W. O. (1942) Oxidation of cellulose by nitrogen dioxide. J. Am. Chem. Soc. 64, 121-127.

    Google Scholar 

  • Yalpani, M. (1985) A survey of recent advances in selective chemical and enzymic polysaccharide modifications. Tetrahedron. 41, 2957-3020.

    Google Scholar 

  • Yamane C., Saitoh M. and Okajima K. (1996) Industrial preparation method of cellulose-alkali dope with high solubility. Sen-i Gakkaishi 52, 310-317.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009276009711

Navigation