title: Formation and ecotoxicity of N-heterocyclic compounds on ammoxidation of mono- and polysaccharides.
abstract: Ammoxidation of technical lignins under mild conditions is a suitable approach to artificial humic substances. However, carbohydrates as common minor constituents of technical lignins have been demonstrated to be a potential source of N-heterocyclic ecotoxic compounds. Ethyl acetate extracts of ammoxidation mixtures of the monosaccharides glucose and xylose exhibited considerable growth inhibiting activity in the OECD 201 test, with 4-methyl-1H-imidazole, 4-(hydroxymethyl)-1H-imidazole, and 3-hydroxypyridine being the most active compounds. The amount of N-heterocyclic compounds formed at moderate ammoxidation conditions (70 °C, 0.2 MPa O2, 3 h) was significantly lower for the polysaccharides cellulose and xylan (16-30 μg/g of educt) compared to glucose (15.4 mg). Ammoxidation at higher temperature is not recommendable for carbohydrate-rich materials as much higher amounts of N-heterocyclic compounds were formed from both monosaccharides (100 °C: 122.4-160.5 mg/g of educt) and polysaccharides (140 °C: 5.52-16.03 mg/g of educt).
authors: Department of Chemistry, University of Natural Resources and Life Sciences Vienna , Konrad-Lorenz-Straße 24, A-3430 Tulln, Austria.
authors: Karl Michael
authors: KM
authors: Klinger
authors: Falk
authors: F
authors: Liebner
authors: Ines
authors: I
authors: Fritz
authors: Antje
authors: A
authors: Potthast
authors: Thomas
authors: T
authors: Rosenau
mesh_terms: D000641:Ammonia / Q000737:chemistry*; D000460:Chlorophyta / Q000187:drug effects / Q000254:growth & development; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000633:toxicity*; D009005:Monosaccharides / Q000737:chemistry* / Q000633:toxicity; D010084:Oxidation-Reduction; D011134:Polysaccharides / Q000737:chemistry* / Q000633:toxicity
chemical_list: D006571:Heterocyclic Compounds; D009005:Monosaccharides; D011134:Polysaccharides; D000641:Ammonia
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