Synthesis, analysis and reduction of 2-nitropropyl starch

André Heeres, Henk A. Van Doren, Kees F. Gotlieb, Jack Bergsma, Richard M. Kellogg, Ido Pieter Bleeker

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Abstract

Granular 2-nitropropyl potato starch was synthesized by reaction with 2-nitropropyl acetate in an aqueous suspension. Nitroalkylation occurs preferentially with the amylose fraction of potato starch, as was confirmed by leaching experiments and digestion of the modified starch with α-amylase. The 2-nitropropyl substituent is a mixture of the nitroalkane and nitronic acid tautomer. Some grafting occurs and to a lesser extent additional reactions (formation of carbonyls and oximes) of the nitro group take place. After catalytic hydrogenation of water soluble 2-nitropropyl starch only a small amount of the nitro functionality was reduced to the corresponding amine. Reduction of granular 2-nitropropyl starch with sodium dithionite did not go to completion and led to a complex mixture of starting material, several intermediates and side products (for example sulfamates). © 2001 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)191-204
JournalCarbohydrate research
Volume330
Issue number2
DOIs
Publication statusPublished - 30 Jan 2001

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Keywords

  • 2-nitropropyl starch
  • analysis
  • reduction
  • synthesis
  • topochemistry

Cite this

Heeres, A., Van Doren, H. A., Gotlieb, K. F., Bergsma, J., Kellogg, R. M., & Bleeker, I. P. (2001). Synthesis, analysis and reduction of 2-nitropropyl starch. Carbohydrate research, 330(2), 191-204. https://doi.org/10.1016/S0008-6215(00)00288-3