SYNTHESES OF POLYFLUOROALKYL ESTERS OF MALEOPIMARIC ACID N-PHENYLIMIDE

Abstract

To meet the challenge of complex processing of plant material, in particular, tall oil rosin, research has been conducted on the synthesis of new polyfluroalkyl maleimides. As is well known, maleopimaric acid’s imides constitute a forward-looking class of organic compounds for pharmacology, agriculture, polymer chemistry and so on. The introduction of a fluorocarbon unit often gives high surface activity, chemical and heat resistance, hydrophobic and oleophobic properties. This paper presents the results of experiments on the synthesis of new N-phenylimides of maleopimaric acid’s polyfluoroalkyl esters by the interaction of the corresponding monosubstituted polyfluorinated maleopimarates with aniline during boiling for 10–16 h in toluene (40–52%). The starting N-phenylimide of maleopimaric acid has been obtained by two methods: by the Diels-Alder reaction from abietic acid and N-phenyl maleimide using sulfuric acid as a catalyst in the melt (40%) and by heating (MPA) with aniline in toluene (80%). 2,2,3,3,4,4,5,5-octafluoroamyl and 2,2,3,3,4,4,5,5,6,6,7,7,7- dodecaftaforpetyl ethers have been obtained by esterification of MPA with fluorinated alcohols under conditions of acid catalysis (70%). It have been identified the ester bonds are quite stable by TLC during long-term treatment of the stock (over 11 hours). The synthesized substances were analyzed with UV-, IR-, 1H NMR and 19F.