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Cross-linking of starch with bifunctional precursors of nitroalkenes

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Author: Heeres, A. · Doren, H.A. van · Gotlieb, K.F. · Bleeker, I.P. · Kellogg, R.M.
Type:article
Date:1998
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Carbohydrate Research, 3, 310, 191-201
Identifier: 71234
Keywords: Nutrition · Cross-linked 2-nitroalkyl starches · Starch, cross-linking · Starch · Chemical reaction · Controlled study · Cross linking · Drug synthesis · Esterification · Nonhuman · Priority journal · Alkylation · Carbohydrate Sequence · Cross-Linking Reagents · Molecular Sequence Data · Nitro Compounds · Starch · Viscosity

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