Synthesis and reduction of 2-nitroalkyl polysaccharide ethers
| Autor: | André Heeres, H.A. van Doren, Ido P. Bleeker, Rm Kellogg, F.F. Spoelma, Kornelis Fester Gotlieb |
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| Přispěvatelé: | Biobased Ingredients and Materials, Molecular Inorganic Chemistry, Stratingh Institute of Chemistry, Centraal Instituut voor Voedingsonderzoek TNO |
| Rok vydání: | 2000 |
| Předmět: |
nitroalkylation
polymeres Polymers and Plastics Nitroso Compounds Na-polyglucuronate polysaccharides Nitro compound Nitroalkane reduction Nitroalkylation Nitrogen compounds Olefins Addition reactions chemistry.chemical_compound Nitroalkyl polysaccharide ethers Graft copolymers Polysaccharides Polymer chemistry Agarose Materials Chemistry Organic chemistry Cellulose Reduction Nutrition polymeren chemistry.chemical_classification modification Suspensions (fluids) Organic Chemistry Inulin Pullulan Solutions chemistry Synthesis (chemical) Michael reaction STARCH Polyethers Hydroxyethyl cellulose Derivatives |
| Zdroj: | Carbohydrate Polymers, 42(1), 33-43. Elsevier Science Carbohydrate Polymers, 42(1), 33-43. ELSEVIER SCI LTD Carbohydrate Polymers, 1, 42, 33-43 |
| ISSN: | 0144-8617 |
| DOI: | 10.1016/s0144-8617(99)00123-x |
| Popis: | Several 2-nitroalkyl polysaccharide ethers (from pullulan (1), guar (2), agarose (3), inulin (4), cellulose (5), Na-alpha-polyglucuronate (6) and hydroxyethyl cellulose (7)) were synthesized by reaction with 2-nitro-1-alkenes (2-nitro-1-propene and 2-nitro-1-butene) formed in situ from 2-nitroalkyl acetates. Moderate to high efficiencies are obtained in concentrated aqueous solution/suspension for addition to 1-4 and 7. Analysis of this new class of polysaccharide derivatives with the aid of labeled 2-nitropropyl-2-C-13 pullulan revealed that the nitrogroup is a mixture of the nitroalkane and nitronic acid tautomers. Grafting of nitroalkenes is observed and, to a lesser extent, additional reactions of the nitro group (formation of carbonyl, oxime and allyl groups) take place.Reduction of 2-nitroalkyl polysaccharide ethers with Na2S2O4 Or Na2S2O4/NaBH4 leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates. (C) 2000 Elsevier Science Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
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