Title
Synthesis and reduction of 2-nitroalkyl polysaccharide ethers
Author
Heeres, A.
Spoelma, F.F.
van Doren, H.A.
Gotlieb, K.F.
Bleeker, I.P.
Kellogg, R.M.
Centraal Instituut voor Voedingsonderzoek TNO
Publication year
2000
Abstract
Several 2-nitroalkyl polysaccharide ethers (from pullulan (1), guar (2), agarose (3), inulin (4), cellulose (5), Na-α-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-2-13C 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.
Subject
Nutrition
Addition reactions
Derivatives
Graft copolymers
Nitrogen compounds
Olefins
Polyethers
Reduction
Solutions
Suspensions (fluids)
Synthesis (chemical)
Agarose
Hydroxyethyl cellulose
Inulin
Na-polyglucuronate
Nitroalkyl polysaccharide ethers
Nitroalkylation
Polysaccharides
To reference this document use:
http://resolver.tudelft.nl/uuid:62765072-9d62-44ce-9144-20d688ea35c1
DOI
https://doi.org/10.1016/s0144-8617(99)00123-x
TNO identifier
86983
ISSN
0144-8617
Source
Carbohydrate Polymers, 42 (1), 33-43
Document type
article