Synthesis of Higher Fatty Acid Starch Esters using Vinyl Laurate and Stearate as Reactants

This paper describes the synthesis of long-chain fatty esters of corn starch (starch laurate and starch stearate) with a broad range in degree of substitution (DS = 0.24-2.96). The fatty esters were prepared by reacting the starch with vinyl laurate or vinyl stearate in the presence of basic catalysts (Na(2)HPO(4), K(2)CO(3), and Na acetate) in DMSO at 110 degrees C. The yellowish products were characterized by (1)H-, (13)C-NMR and FTIR. The DS of the products is a function of the carbon number of the fatty acid chain, vinyl ester to starch ratio and the type of catalyst. When performing the reactions using Na(2)HPO(4) as the catalyst, the DS for the starch laurate compounds is higher than for the corresponding starch stearates. For low vinyl ester to starch ratios, an increase in the vinyl ester concentration leads to higher product DS values. At higher ratios, the DS decreases, presumably due to a reduction of the polarity of the reaction medium. K(2)CO(3) and Na acetate are superior catalysts with respect to activity compared to Na(2)HPO(4) and products with DS values close to 3 were obtained.