Kinetics and efficiency of chitosan reacetylation

Carbohydrate Polymers

Volumn 87, Issue 2, 2012, Pages 1192-1198

  Lavertu, Marc ^a   Darras, Vincent ^a   Buschmann, Michael D ^a  

^a ÉCOLE POLYTECHNIQUE DE MONTRÉAL   (Canada)

Author keywords

Acetic anhydride; Biomaterial; Chitosan; Efficiency; Hydrolysis; Kinetics; Polysaccharide; Reacetylation

Indexed keywords

ACETIC ANHYDRIDES; ACETYL GROUPS; ACID BASE; CONDUCTIVITY MEASUREMENTS; REACETYLATION; REACTION EFFICIENCY; SECOND ORDER KINETICS; STERIC HINDRANCES; WATER-METHANOL;

ACETIC ACID; BIOLOGICAL MATERIALS; BIOMATERIALS; CHITOSAN; DISSOCIATION; EFFICIENCY; ENZYME KINETICS; HYDROLYSIS; KINETICS; METHANOL; PH; POLYSACCHARIDES; RATE CONSTANTS;

REACTION KINETICS;

EID: 81255141924     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.08.096     Document Type: Article

References (33)

1. S. Aiba Studies on chitosan. 3. Evidence for the presence of random and block copolymer structures in partially N-acetylated chitosans International Journal of Biological Macromolecules 13 1 1991 40 44
2. S. Aiba Studies on chitosan. 4. Lysozymic hydrolysis of partially N-acetylated chitosans International Journal of Biological Macromolecules 14 4 1992 225 228
3. S. Aiba Preparation of N-acetylchito-oligosaccharides from lysozymic hydrolyzates of partially N-acetylated chitosans Carbohydrate Research 261 2 1994 297 306 (Pubitemid 24257651)
4. P.S. Albright, and L.J. Gosting Dielectric constants of the methanol-water system from 5 to 55 Deg Journal of the American Chemical Society 68 1946 1061 1063
5. S.P. Asprey, B.W. Wojciechowski, N.M. Rice, and A. Dorcas Applications of temperature scanning in kinetic investigations: The hydrolysis of acetic anhydride Chemical Engineering Science 51 20 1996 4681 4692 (Pubitemid 27108607)
6. a values for carboxylic acids and anilinium ions Journal of Organic Chemistry 20 1955 747 762
7. J. Berger, A. Reist, A. Chenite, O. Felt-Baeyens, J.M. Mayer, and R. Gurny Pseudo-thermosetting chitosan hydrogels for biomedical application International Journal of Pharmaceutics 288 2 2005 197 206 (Pubitemid 40038572)
8. E. Bosch, P. Bou, H. Allemann, and M. Roses Retention of ionizable compounds on HPLC. pH scale in methanol-water and the pK and pH values of buffers Analytical Chemistry 68 20 1996 3651 3657
9. I. Canals, F.Z. Oumada, M. Roses, and E. Bosch Retention of ionizable compounds on HPLC. 6. pH measurements with the glass electrode in methanol-water mixtures Journal of Chromatography A 911 2 2001 191 202 (Pubitemid 32166996)
10. F.A. Cleland, and R.H. Wilhelm Diffusion and reaction in viscous-flow tubular reactor AIChE Journal 2 1956 489 497
11. A. Dal Pozzo, L. Vanini, M. Fagnoni, M. Guerrini, A. De Benedittis, and R.A.A. Muzzarelli Preparation and characterization of poly(ethylene glycol)-crosslinked reacetylated chitosans Carbohydrate Polymers 42 2 2000 201 206 (Pubitemid 32133077)
12. D. Filion, M. Lavertu, and M.D. Buschmann Ionization and solubility of chitosan solutions related to thermosensitive chitosan/glycerol-phosphate systems Biomacromolecules 8 10 2007 3224 3234 (Pubitemid 350011646)
13. S. Hirano, S. Kondo, and Y. Ohe Chitosan gel. A novel polysaccharide gel Polymer 16 8 1975 622
14. J. Inczédy, T. Lengyel, A.M. Ure International Union of Pure and Applied Chemistry Compendium of analytical nomenclature: Definitive rules 1997 1998 Blackwell Science Osney Mead, Oxford; Malden, MA
15. J.Z. Knaul, M.R. Kasaai, V.T. Bui, and K.A.M. Creber Characterization of deacetylated chitosan and chitosan molecular weight review Canadian Journal of Chemistry-Revue Canadienne De Chimie 76 11 1998 1699 1706 (Pubitemid 29165617)
16. K. Kurita, T. Sannan, and Y. Iwakura Studies on chitin. 4. Evidence for formation of block and random copolymers of N-acetyl-d-glucosamine and d-glucosamine by hetero- and homogeneous hydrolyses Makromolekulare Chemie 178 12 1977 3197 3202
17. M. Lavertu, D. Filion, and M.D. Buschmann Heat-induced transfer of protons from chitosan to glycerol phosphate produces chitosan precipitation and gelation Biomacromolecules 9 2 2008 640 650 (Pubitemid 351298489)
18. M. Lavertu, Z. Xia, A.N. Serreqi, M. Berrada, A. Rodrigues, and D. Wang A validated H-1 NMR method for the determination of the degree of deacetylation of chitosan Journal of Pharmaceutical and Biomedical Analysis 32 6 2003 1149 1158 (Pubitemid 36930101)
19. G.G. Maghami, and G.A.F. Roberts Evaluation of the viscometric constants for chitosan Makromolekulare Chemie 189 1 1988 195 200
20. J. March Advanced organic chemistry: Reactions, mechanisms and structure Fourth Edition 1992
21. A. Martinez, E. Chornet, and D. Rodrigue Steady-shear rheology of concentrated chitosan solutions Journal of Texture Studies 35 1 2004 53 74 (Pubitemid 38770685)
22. G.K. Moore, and G.A.F. Roberts Chitosan gels. 2. Mechanism of gelation International Journal of Biological Macromolecules 2 2 1980 78 80
23. S. Nguyen, F.M. Winnik, and M.D. Buschmann Improved reproducibility in the determination of the molecular weight of chitosan by analytical size exclusion chromatography Carbohydrate Polymers 75 3 2009 528 533
24. M.H. Ottoy, K.M. Varum, and O. Smidsrod Compositional heterogeneity of heterogeneously deacetylated chitosans Carbohydrate Polymers 29 1 1996 17 24 (Pubitemid 126347502)
25. J.W. Park, K.H. Choi, and K.K. Park Acid-base equilibriums and related properties of chitosan Bulletin of the Korean Chemical Society 4 2 1983 68 72
26. G. Qun, W. Ajun, and Z. Yong Effect of reacetylation and degradation on the chemical and crystal structures of chitosan Journal of Applied Polymer Science 104 4 2007 2720 2728 (Pubitemid 46591322)
27. H. Sashiwa, H. Saimoto, Y. Shigemasa, R. Ogawa, and S. Tokura Distribution of the acetamide group in partially deacetylated chitins Carbohydrate Polymers 16 3 1991 291 296 (Pubitemid 21733464)
28. H. Sashiwa, H. Saimoto, Y. Shigemasa, and S. Tokura N-acetyl group distribution in partially deacetylated chitins prepared under homogeneous conditions Carbohydrate Research 242 1993 167 172 (Pubitemid 23107509)
29. T. Shedlovsky, and R.L. Kay The ionization constant of acetic acid in water-methanol mixtures at 25 Deg from conductance measurements Journal of Physical Chemistry 60 1956 151 155
30. Y. Shigemasa, K. Saito, H. Sashiwa, and H. Saimoto Enzymatic degradation of chitins and partially deacetylated chitins International Journal of Biological Macromolecules 16 1 1994 43 49 (Pubitemid 24051857)
31. L. Vachoud, N. Zydowicz, and A. Domard Formation and characterisation of a physical chitin gel Carbohydrate Research 302 3-4 1997 169 177 (Pubitemid 27339002)
32. K.M. Varum, M.W. Anthonsen, H. Grasdalen, and O. Smidsrod Determination of the degree of N-acetylation and the distribution of N-acetyl groups in partially N-deacetylated chitins (chitosans) by high-field N.M.R. spectroscopy Carbohydrate Research 211 1 1991 17 23
33. X.L. Xu, H.Q. Li, Z.D. Zhang, and X. Qi Hydrodynamic properties of aqueous dextrin solutions Journal of Applied Polymer Science 111 3 2009 1523 1529