Cross-linking of starch with bifunctional precursors of nitroalkenes

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

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Abstract

Granular starch was cross-linked with 1,3-di-O-acetyl-2-nitro-1,3-propanediol (1), 1,3-di-O-pivaloyl-2-nitro-1,3-propanediol (2), 2-nitro-3-O-pivaloyl-1-propene-3-ol (3), 1,3-di-O-acetyl-aci-2-nitro-1,3-propanediol (4), 1,3-di-O-pivaloyl-aci-2-nitro-1,3-propanediol (5) and 1,6-di-O-acetyl-2,5-dinitro-1,6-hexanediol (6). The bifunctional precursors for the nitro-alkenes 1, 2, 3, and 4 were readily synthesized in high yields from nitromethane, paraformaldehyde and acetic anhydride (1, 3) or pivaloyl chloride (2, 4), respectively. The reaction rate for the cross-linking was very high, and for 1 and 3, the reaction reached completion within 1 h (at room temperature). The swelling capacities of the products obtained when starch was cross-linked with precursors for the nitroalkenes 1-4 and 6 were lower in comparison to epichlorohydrin cross-linked starch. These results indicate a high reaction efficiency at low degrees of substitution. Cross-linked 2-nitroalkyl starch ethers were synthesized in a one-pot synthesis by addition of 1 or 3 and 2-nitroalkyl acetates to granular suspensions of starch. Copyright (C) 1998 Elsevier Science Ltd.
Original languageEnglish
Pages (from-to)191-201
JournalCarbohydrate research
Volume310
Issue number3
DOIs
Publication statusPublished - Aug 1998

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Keywords

  • Cross-linked 2-nitroalkyl starches
  • Starch, cross-linking

Cite this

Heeres, A., Van Doren, H. A., Gotlieb, K. F., Kellogg, R. M., & Bleeker, I. P. (1998). Cross-linking of starch with bifunctional precursors of nitroalkenes. Carbohydrate research, 310(3), 191-201. https://doi.org/10.1016/S0008-6215(98)00171-2