Synthesis and properties of thermoplastic starch laurates

Sascha Blohm; Thomas Heinze

doi:10.1016/j.carres.2019.107833

Synthesis and properties of thermoplastic starch laurates

Carbohydr Res. 2019 Dec 1:486:107833. doi: 10.1016/j.carres.2019.107833. Epub 2019 Oct 9.

Authors

Sascha Blohm¹, Thomas Heinze²

Affiliations

¹ Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Center of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743, Jena, Germany.
² Institute for Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Center of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743, Jena, Germany. Electronic address: thomas.heinze@uni-jena.de.

PMID: 31622867
DOI: 10.1016/j.carres.2019.107833

Abstract

Maize starch was allowed to react homogeneously in N,N-dimethylacetamide (DMAc)/LiCl with lauric acid activated with 4-toluenesulfonyl chloride, N,N'-dicyclohexylcarbodiimide/4-(1-pyrrolidinyl)pyridine, 1,1'-carbonyldiimidazole, and N,N-dimethylformamide (DMF) combined with oxalyl chloride. Characterization of the products by means of ¹³C NMR spectroscopy revealed different substitution patterns depending on the activation agent. The activation of lauric acid with DMF in combination with oxalyl chloride gave starch laurates of highest degree of substitution (DS), yield and reaction efficiency. The melting temperatures and the solubility of the thermoplastic starch laurates were found to depend on the DS, the substitution pattern, and on the molar mass of the starch esters.

Keywords: Esterification; In situ activation; Lauric acid; Substitution pattern; Thermoplastic starch.

MeSH terms

Animals
Carboxylic Acids / chemistry
Chemistry Techniques, Synthetic
Lauric Acids / chemistry
Plastics / chemistry*
Solubility
Starch / chemical synthesis*
Starch / chemistry*
Temperature*
Zea mays / chemistry

Substances

Carboxylic Acids
Lauric Acids
Plastics
lauric acid
Starch