Preparation of cellouronic acids and partially acetylated cellouronic acids by TEMPO/NaClO oxidation of water-soluble cellulose acetate.
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.
Gomez-Bujedo
Silvia
S
Centre de Recherches sur les Macromolécules Végétales, CNRS, and Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.
Fleury
Etienne
E
Vignon
Michel R
MR
D000107:Acetylation; D002482:Cellulose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003497:Cyclic N-Oxides / Q000138:chemical synthesis*; D005965:Glucuronates / Q000737:chemistry; D010084:Oxidation-Reduction; D012973:Sodium Hypochlorite / Q000138:chemical synthesis*; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared; D013113:Spin Labels / Q000138:chemical synthesis; D014867:Water
D003497:Cyclic N-Oxides; D005965:Glucuronates; D013113:Spin Labels; D014867:Water; C005062:acetylcellulose; D002482:Cellulose; D012973:Sodium Hypochlorite; C003959:TEMPO