Synthesis of Imidazolium Derivatives Comprising a Fatty Acid Methyl Ester Structure

The synthesis of new imidazolium derivatives is discussed in this work that are substituted with a fatty acid methyl ester structure. These new compounds were made from methyl oleate. The synthetic way started with epoxidation of methyl oleate followed by epoxy ring opening reaction using imidazole. 4-Iodomethyl styrene was used for quaternization of the resulting imidazole substituent bound at the fatty acid methyl ester on the one hand. Reaction of the hydroxy group with methacrylic anhydride followed by quaternization of the imidazole substituent using benzyl bromide was carried out on the other hand. Halide exchange by bis(trifluoromethylsulfonyl) imide resulted in two new imidazolium compounds comprising a fatty acid methyl ester structure. These new imidazolium compounds exhibit low glass transition temperatures that are typical for ionic liquids. They may be interesting as surfactants, as starting materials for polyelectrolyte manufacturing, as barrier materials for coatings, and as source for N-heterocyclic carbenes.