Synthesis of mixed anhydrides of fatty acids: Stability and Reactivity

Published Date
Industrial Crops and Products
March 2017, Vol.97:552–557, doi:10.1016/j.indcrop.2017.01.003

• Author 

• Iteb Trabelsi
• Kamel Essid ^,
• Mohamed Hédi Frikha

• Laboratory of Physical and Organic Chemistry: Departement of Chemistry, Faculty of sciences in Sfax, Tunisia

Received 30 October 2015. Revised 13 December 2016. Accepted 4 January 2017. Available online 9 January 2017

Highlights

• •
  Performance of mixed carboxylic fatty anhydrides as reagents to synthesize fatty esters.
• •
  The fatty acid group of the mixed anhydride was the most involved in the esterification reaction.
• •
  A preferential esterification of the fatty group was related to the stability of its leaving group in the mixed anhydride.

Abstract

Compared to carboxylic acids, carboxylic anhydrides are efficient acylating agents. Mixed anhydrides are appreciated in organic chemistry because of their high reactivity. They are finding an increasing interest in the chemical industry.

This work describes a novel and efficient method of synthesis of fatty esters by the esterification reaction with mixed carboxylic fatty anhydrides, using heterogeneous acid catalyst. These anhydrides, characterized by the general formula RCOOCOC₁₅H₃₁, can be easily prepared by the reaction of palmitic acid with the acid chloride in organic solvent and in the presence of triethylamine as acid acceptor. These anhydrides should be stable and react as acylating agents.

Keywords

Fatty acid

Mixed anhydride

Symmetrical anhydride

Stability

Heterogeneous acid catalyst

Esterification

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Fig. 1.

 Table 1

Table 1.

Scheme 1.

Scheme 2.

Scheme 3.

 Table 2

Table 2.

 Table 3

Table 3.

• ⁎ 
  Corresponding author.

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