Cross-linking of starch with bifunctional precursors of nitroalkenes

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

Research output: Contribution to journalArticleAcademicpeer-review

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

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
Heeres, André ; Van Doren, Henk A. ; Gotlieb, Kees F. ; Kellogg, R. M. ; Bleeker, Ido Pieter. / Cross-linking of starch with bifunctional precursors of nitroalkenes. In: Carbohydrate research. 1998 ; Vol. 310, No. 3. pp. 191-201.
@article{7a33e6247ab74c5495752610846214a4,
title = "Cross-linking of starch with bifunctional precursors of nitroalkenes",
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.",
keywords = "Cross-linked 2-nitroalkyl starches, Starch, cross-linking",
author = "Andr{\'e} Heeres and {Van Doren}, {Henk A.} and Gotlieb, {Kees F.} and Kellogg, {R. M.} and Bleeker, {Ido Pieter}",
year = "1998",
month = "8",
doi = "10.1016/S0008-6215(98)00171-2",
language = "English",
volume = "310",
pages = "191--201",
journal = "Carbohydrate research",
issn = "0008-6215",
publisher = "Elsevier",
number = "3",

}

Heeres, A, Van Doren, HA, Gotlieb, KF, Kellogg, RM & Bleeker, IP 1998, 'Cross-linking of starch with bifunctional precursors of nitroalkenes' Carbohydrate research, vol. 310, no. 3, pp. 191-201. https://doi.org/10.1016/S0008-6215(98)00171-2

Cross-linking of starch with bifunctional precursors of nitroalkenes. / Heeres, André; Van Doren, Henk A.; Gotlieb, Kees F.; Kellogg, R. M.; Bleeker, Ido Pieter.

In: Carbohydrate research, Vol. 310, No. 3, 08.1998, p. 191-201.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Cross-linking of starch with bifunctional precursors of nitroalkenes

AU - Heeres, André

AU - Van Doren, Henk A.

AU - Gotlieb, Kees F.

AU - Kellogg, R. M.

AU - Bleeker, Ido Pieter

PY - 1998/8

Y1 - 1998/8

N2 - 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.

AB - 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.

KW - Cross-linked 2-nitroalkyl starches

KW - Starch, cross-linking

U2 - 10.1016/S0008-6215(98)00171-2

DO - 10.1016/S0008-6215(98)00171-2

M3 - Article

VL - 310

SP - 191

EP - 201

JO - Carbohydrate research

JF - Carbohydrate research

SN - 0008-6215

IS - 3

ER -