Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

A. Heeres; F. F. Spoelma; H. A. Van Doren; K. F. Gotlieb; R. M. Kellogg; Ido Pieter Bleeker

doi:10.1016/S0144-8617(99)00123-X

Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

A. Heeres, F. F. Spoelma, H. A. Van Doren, K. F. Gotlieb, R. M. Kellogg, Ido Pieter Bleeker

Biobased Ingredients and Materials

Research output: Contribution to journal › Article › Academic › peer-review

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 Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.

Original language	English
Pages (from-to)	33-43
Journal	Carbohydrate polymers
Volume	42
Issue number	1
DOIs	https://doi.org/10.1016/S0144-8617(99)00123-X
Publication status	Published - 2000

Keywords

polymeres

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@article{c56c67288bdd4b1a99be2d1b540de242,

title = "Synthesis and reduction of 2-nitroalkyl polysaccharide ethers",

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 Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.",

keywords = "polymeres, polymeren",

author = "A. Heeres and Spoelma, {F. F.} and {Van Doren}, {H. A.} and Gotlieb, {K. F.} and Kellogg, {R. M.} and Bleeker, {Ido Pieter}",

year = "2000",

doi = "10.1016/S0144-8617(99)00123-X",

language = "English",

volume = "42",

pages = "33--43",

journal = "Carbohydrate polymers",

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publisher = "Elsevier Science",

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TY - JOUR

T1 - Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

AU - Heeres, A.

AU - Spoelma, F. F.

AU - Van Doren, H. A.

AU - Gotlieb, K. F.

AU - Kellogg, R. M.

AU - Bleeker, Ido Pieter

PY - 2000

Y1 - 2000

N2 - 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 Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.

AB - 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 Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.

KW - polymeres

KW - polymeren

U2 - 10.1016/S0144-8617(99)00123-X

DO - 10.1016/S0144-8617(99)00123-X

M3 - Article

VL - 42

SP - 33

EP - 43

JO - Carbohydrate polymers

JF - Carbohydrate polymers

SN - 0144-8617

IS - 1

ER -