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

Research output: Contribution to journalArticleAcademicpeer-review


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
Issue number2
Publication statusPublished - 30 Jan 2001


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


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