, Volume 12, Issue 4, pp 435-444

First online:

Starch Derivatives of High Degree of Functionalization 11: Studies on Alternative Acylation of Starch with Long-chain Fatty Acids Homogeneously in N,N-dimethyl acetamide/LiCl

  • Carsten GroteAffiliated withKompetenzzentrum Polysaccharidforschung, Friedrich-Schiller-Universität Jena
  • , Thomas HeinzeAffiliated withKompetenzzentrum Polysaccharidforschung, Friedrich-Schiller-Universität Jena Email author 

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Starch materials of different amylose content were allowed to react with saturated and unsaturated fatty acids of varying chain length from C14 to C18 under homogeneous conditions applying the solvent N,N-dimethyl acetamide in combination with LiCl. As reagent the corresponding acid chlorides and, alternatively, carboxylic acids in situ activated with toluene-4-sulfonyl chloride and N,N′-carbonyldiimidazole (CDI) were studied. Using fatty acid chlorides (FACl) and toluene-4-sulfonyl chloride-activated acids an almost complete substitution of the starch occurs. By in situ activation of the fatty acids with CDI, products with a degree of substitution up to 2 were obtained, which, in particular, represents a simple and very mild procedure.

Key words

N,N′-Carbonyldiimidazole N,N-Dimethyl acetamide/LiCl Esterification Long-chain fatty acid Polysaccharide Starch Toluene-4-sulfonyl chloride