Synthesis of Sucrose Fatty Acid Esters by Using Mixed Carboxylic-fatty Anhydrides

J Oleo Sci. 2020;69(7):693-701. doi: 10.5650/jos.ess19239.

Abstract

Fatty acid sugar esters are non-ionic surfactant active agents with excellent performance and many uses. This work is devoted to the synthesis of sugar esters by the esterification reaction of sugar with mixed carboxylicpalmitic anhydrides using resin Amberlyst-15 as heterogeneous acid catalyst. These anhydrides should be stable and react as acylating agents. Influence of different reaction parameters, such as the molar ratio (sucrose/anhydride), the type of solvent and the reaction time on the yield of the esterification reaction were studied. The esterification reaction of sucrose with mixed palmitic benzoic anhydride leads to a mixture of sucrose esters of palmitic acid with a good percentage of conversion. The mixed anhydride was both reactive and selective for the preparation of fatty acid ester.

Keywords: fatty acid; acylation of sucrose; esterification; heterogeneous acid catalyst; mixed anhydride; resin Amberlyst-15; sucrose; sucrose fatty acid esters (SEs).

MeSH terms

  • Acylation
  • Benzoates / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic / methods*
  • Esterification
  • Esters / chemical synthesis*
  • Fatty Acids / chemical synthesis*
  • Palmitic Acid / chemistry*
  • Solvents
  • Styrenes
  • Sucrose / chemical synthesis*
  • Surface-Active Agents / chemical synthesis
  • Time Factors

Substances

  • Benzoates
  • Carboxylic Acids
  • Esters
  • Fatty Acids
  • Solvents
  • Styrenes
  • Surface-Active Agents
  • amberlyst-15
  • Palmitic Acid
  • Sucrose
  • benzoic anhydride