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

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

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
Heeres, André ; Van Doren, Henk A. ; Gotlieb, Kees F. ; Bergsma, Jack ; Kellogg, Richard M. ; Bleeker, Ido Pieter. / Synthesis, analysis and reduction of 2-nitropropyl starch. In: Carbohydrate research. 2001 ; Vol. 330, No. 2. pp. 191-204.
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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). {\circledC} 2001 Elsevier Science Ltd.",
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Heeres, A, Van Doren, HA, Gotlieb, KF, Bergsma, J, Kellogg, RM & Bleeker, IP 2001, 'Synthesis, analysis and reduction of 2-nitropropyl starch' Carbohydrate research, vol. 330, no. 2, pp. 191-204. https://doi.org/10.1016/S0008-6215(00)00288-3

Synthesis, analysis and reduction of 2-nitropropyl starch. / Heeres, André; Van Doren, Henk A.; Gotlieb, Kees F.; Bergsma, Jack; Kellogg, Richard M.; Bleeker, Ido Pieter.

In: Carbohydrate research, Vol. 330, No. 2, 30.01.2001, p. 191-204.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Synthesis, analysis and reduction of 2-nitropropyl starch

AU - Heeres, André

AU - Van Doren, Henk A.

AU - Gotlieb, Kees F.

AU - Bergsma, Jack

AU - Kellogg, Richard M.

AU - Bleeker, Ido Pieter

PY - 2001/1/30

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N2 - 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.

AB - 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.

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KW - synthesis

KW - topochemistry

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Heeres A, Van Doren HA, Gotlieb KF, Bergsma J, Kellogg RM, Bleeker IP. Synthesis, analysis and reduction of 2-nitropropyl starch. Carbohydrate research. 2001 Jan 30;330(2):191-204. https://doi.org/10.1016/S0008-6215(00)00288-3