Esterification of Mixed Carboxylic-fatty Anhydrides Using Amberlyst-15 as Heterogeneous Catalyst

J Oleo Sci. 2017;66(7):667-676. doi: 10.5650/jos.ess17008.

Abstract

The article deals with the use of mixed anhydrides for the synthesis of fatty esters. Both aliphatic and aromatic acids are involved, indicating different behaviors according to the chain length of the aliphatic acid. We describe a novel and efficient method for the synthesis of fatty esters by the esterification reaction of primary, secondary and tertiary alcohols with mixed carboxylic-palmitic anhydrides using resin Amberlyst-15 as heterogeneous acid catalyst. Influence of various reaction parameters such as molar ratio (anhydride/alcohol), catalyst amount, type of alcohol and type of mixed anhydride were studied to optimize the conditions for maximum yield. Among tested anhydrides we quote mainly the 4-chlorobenzoic palmitic anhydride because it was both reactive and selective for the preparation of palmitic acid ester. This anhydride gave a good yield of palmitic ester.

Keywords: esterification; fatty acid; heterogeneous acid catalyst; mixed anhydride; resin Amberlyst-15.

MeSH terms

  • Anhydrides / chemistry*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Chlorobenzoates / chemistry
  • Esterification
  • Esters / chemical synthesis*
  • Fatty Acids / chemistry*
  • Palmitic Acid / chemistry
  • Styrenes / chemistry*

Substances

  • Anhydrides
  • Carboxylic Acids
  • Chlorobenzoates
  • Esters
  • Fatty Acids
  • Styrenes
  • amberlyst-15
  • Palmitic Acid
  • 4-chlorobenzoic acid