Low-temperature chemical synthesis of high-purity diacylglycerols (DAG) from monoacylglycerols (MAG)

Lipids. 2015 Feb;50(2):219-26. doi: 10.1007/s11745-014-3980-x. Epub 2014 Dec 24.

Abstract

A chemical method was developed for low-temperature synthesis of DAG from MAG followed by an easy purification procedure in order to obtain high-purity DAG. Solvent-assisted and solvent-free reaction conditions were used, combined with different catalysts (sodium methoxide, p-toluenesulfonic acid, methanesulfonic acid, and sulfuric acid). All reactions were performed at 35 and 70 °C. By increasing both acidity and polarity of the catalyst the equilibrium shifts towards the formation of DAG. When using sulfuric acid in solvent-assisted condition at 70 °C, 88% conversion was obtained after 20 min of reaction (77% w/w DAG in the reaction mixture after evaporation of the solvent). After purifying by means of column chromatography, 96% pure DAG were obtained. The overall yield of DAG was 81%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cold Temperature
  • Diglycerides / chemical synthesis*
  • Esterification
  • Monoglycerides / chemical synthesis
  • Monoglycerides / chemistry*
  • Solvents / chemistry
  • Sulfuric Acids / chemistry

Substances

  • Diglycerides
  • Monoglycerides
  • Solvents
  • Sulfuric Acids
  • sulfuric acid