Optimization of cellouronic acid synthesis by TEMPO-mediated oxidation of cellulose III from sugar beet pulp

Cellulose

Volumn 15, Issue 1, 2008, Pages 177-185

  Habibi, Youssef ^a,b   Vignon, Michel R ^a  

^a CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^b INP Grenoble EFPG   (France)

Author keywords

Cellouronic acid; Cellulose; Oxidation; TEMPO

Indexed keywords

ACIDS; OPTIMIZATION; OXIDATION; PULP; SIZE EXCLUSION CHROMATOGRAPHY; SYNTHESIS (CHEMICAL);

CELLOURONIC ACID; MICROFIBRILLATED CELLULOSE; SUGAR BEET PULP;

CELLULOSE;

ACIDS; CELLULOSE III; CHROMATOGRAPHY; FIBRILS; OPTIMIZATION; OXIDATION; PULPS; SYNTHESIS; WATER SOLUBLES;

ACID; OPTIMIZATION; OXIDATION; PULP; SYNTHESIS;

EID: 38049006980     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-007-9179-z     Document Type: Article

References (34)

1. Bragd PL, Besemer AC, van Bekkum H (2000) Bromide-free TEMPO-mediated oxidation of primary alcohol groups in starch and methyl α-D-glucopyranoside. Carbohydr Res 328(3):355-363
2. Bragd PL, van Bekkum H, Besemer AC (2004) TEMPO-mediated oxidation of polysaccharides: Survey of methods and applications. Top Catal 27(1-4):49-66
3. Bredereck K, Karstens T, Lentz H and Steinmeier H (1995) Process for the treatment of cellulose. US 0 298 399
4. Chang PS, Robyt JF (1996) Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6,-tetramethyl-1-piperidine oxoammonium ion. J Carbohydr Chem 15(7):819-830
5. Chanzy H, Henrissat B, Vuong R, Revol J-F (1986) Distortion and fragmentation of cellulose crystals during the "reversible" transformation: Cellulose I-cellulose III I in Valonia. Holzforschung 40(Suppl):25
6. Da Silva Perez D, Montanari S, Vignon MR (2003) TEMPO-mediated oxidation of cellulose III. Biomacromolecules 4(5):1417-1425
7. de Nooy AEJ, Besemer AC, van Bekkum H (1994) Highly selective TEMPO mediated oxidation of primary alcohol groups in polysaccharides. Recl Trav Chim Pays Bas 113(3):165-6
8. de Nooy AEJ, Besemer AC, van Bekkum H (1995) Highly selective nitrosyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr Res 269(1):89-98
9. de Nooy AEJ, Besemer AC, van Bekkum H, van Dijk JAPP, Smit JAM (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(20):6541-6547
10. Dimitrijevich SD, Tatarko M, Gracy RW, Linsky CB, Olsen C (1990) Biodegradation of oxidized regenerated cellulose. Carbohydr Res 195:247-256
11. Dinand E (1997) Doctoral dissertation. Joseph Fourier University of Grenoble, France
12. Dinand E, Excoffier G, Lienart Y, Vignon MR (1997) Two rhamnogalacturonide tetrasaccharides isolated from semi-retted flax fibers are signaling molecules in Rubus fruticosus L. cells. Plant Physiol 115(2):793-801
13. Dinand E, Chanzy H, Vignon MR (1999) Suspensions of cellulose microfibrils from sugar beet pulp. Food Hydrocolloid 13(3):275-283
14. Fleury E, Vignon MR and Gomez BS (2003) Method for preparation of poly- or copolyglucuronic acid. FR 2831171
15. Fraschini C, Vignon MR (2000) Selective oxidation of primary alcohol groups of β-cyclodextrin mediated by 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO). Carbohydr Res 328(4):585-589
16. Gomez-Bujedo S, Fleury E, Vignon MR (2004) Preparation of cellouronic acids and partially acetylated cellouronic acids by TEMPO/NaClO oxidation of water-soluble cellulose acetate. Biomacromolecules 5(2):565-571
17. Ibert M, Marsais F, Merbouh N, Brückner C (2002) Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid. Carbohydr Res 337:1059-1063
18. Isogai A (1998) Cellulose derivatives having glucuronic acid residues and their manufacture. JP 10251302
19. Isogai A, Kato Y (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5(3):153-164
20. Isogai A, Shibata I (2001) Chemical modifications of cellulose by TEMPO-mediated oxidation. Sen'i Gakkaishi 57(6):163-P167
21. Kato Y, Matsuo R, Kaminaga J (2002a) Gas barrier properties of polysaccharides. Cellulose Comm 9(4):221-224
22. Kato Y, Habu N, Yamaguchi J, Kobayashi Y, Shibata I, Isogai A, Samejima M (2002b) Biodegradation of β-1,4-linked polyglucuronic acid (celluronic acid). Cellulose 9(1):75-81
23. Kato Y, Matsuo R, Isogai A (2002c) Oxidation process of water-soluble starch in TEMPO-mediated system. Carbohydr Polym 51(1):69-75
24. Kato Y, Kaminaga J, Matsuo R, Isogai A (2005a) Oxygen permeability and biodegradability of polyuronic acids prepared from polysaccharides by TEMPO-mediated oxidation. J Polym Environ 13(3):261-266
25. Kato Y, Kaminaga J, Matsuo R and Abe Y (2005b) Polyglucuronic acids as bioabsorbable hemostatics. JP 1056743
26. Klemm D, Heublein B, Fink HP, Bohn A (2005) Cellulose: Fascinating biopolymer and sustainable raw material. Angew Chem 44(22):3358-3393
27. Lienart Y, Heyraud A and Sevenou O (2001) β-1,4-D-glucuronane polymers and related polysaccharide and oligosaccharide pesticides and fertilizers. WO 2001000025
28. Miyazawa T, Endo T, Okawara M (1985) New method for preparation of superoxide ion by use of amino oxide. J Org Chem 50:5389-5391
29. Montanari S, Roumani M, Heux L, Vignon MR (2005) Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation. Macromolecules 38(5):1665-1671
30. Rinaudo M (1968) Physicochemical studies of solutions of cellulose in FeTNa [sodium iron tartrate]. La Papèterie 90:479-487
31. Roche E, Chanzy H (1981) Electron microscopy study of the transformation of cellulose I into cellulose III I in Valonia. Int J Biol Macromol 3:201-206
32. Saito T, Isogai A (2004) Modification of cellulose by TEMPO-mediated oxidation. Cellulose Comm 11(4):192-196
33. Tahiri C, Vignon MR (2000) TEMPO-oxidation of cellulose: Synthesis and characterization of polyglucuronans. Cellulose 7(2):177-188
34. Vignon MR, Montanari S and Habibi Y (2004) Crystalline polysaccharide derivatives in the form of water-insoluble aggregates of microcrystals, for use e.g. as viscosity modifiers or super-absorbers, manufactured by controlled oxidation of primary alcohol groups. FR 2854161