title: One-step preparation of 2,3,6-tricarboxy cellulose.
abstract: Water-soluble sodium 2,3,6-tricarboxylate cellulose (NaTCC) or sodium mesotartarate/monohydrated glyoxilate alternating co-polyacetal was prepared from regenerated cellulose in a yield of 82% by one-step oxidation with catalytic amounts of 2-azaadamantane N-oxyl (AZADO), NaBr, and excess NaOCl in water at room temperature under alkaline conditions. The AZADO-oxidized product was shown to have an almost homogeneous NaTCC chemical structure by its 1H and 13C NMR spectra. The weight- and number-average molecular masses of the obtained NaTCC were 10,700 and 7000. When AZADO-mediated oxidation was applied to softwood bleached kraft pulp, a water-soluble oxidized product was obtained. However, it had a more heterogeneous chemical structure showing that the complete oxidation of the C2, C3, and C6 hydroxyls to carboxyls is difficult to achieve in native cellulose.
authors.affiliation: Department of Biomaterial Sciences, The University of Tokyo, Tokyo 113-8657, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Takaichi
authors.affiliation: Department of Biomaterial Sciences, The University of Tokyo, Tokyo 113-8657, Japan.
authors.forename: Ryoya
authors.initials: R
authors.lastname: Hiraoki
authors.affiliation: Department of Biomaterial Sciences, The University of Tokyo, Tokyo 113-8657, Japan.
authors.forename: Toru
authors.initials: T
authors.lastname: Inamochi
authors.affiliation: Department of Biomaterial Sciences, The University of Tokyo, Tokyo 113-8657, Japan. Electronic address: aisogai@mail.ecc.u-tokyo.ac.jp.
authors.forename: Akira
authors.initials: A
authors.lastname: Isogai
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D002482:Cellulose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002850:Chromatography, Gel; D003497:Cyclic N-Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D014233:Tricarboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: C522607:2-azaadamantane N-oxyl; D003497:Cyclic N-Oxides; D014233:Tricarboxylic Acids; D014867:Water; D002482:Cellulose; D000218:Adamantane
keywords: 2,3,6-Tricarboxy cellulose; AZADO; Azaadamantane N-oxyl; Mesotartaric acid/hydrated glyoxilic acid alternating co-polyacetal; Size-exclusion chromatography