Zn-containing ionic liquids as effective catalysts for the condensation of camphor with diamines

Abstract

The study is dedicated to the investigation of the catalytic activity of zinc carboxylates in the condensation reaction of camphor with aliphatic diamines. The reaction of camphor with 1,6-hexanediamine was selected as the model system. The research demonstrated that the reaction does not proceed without a catalyst, while the use of zinc carboxylates as catalysts leads to a higher conversion and selectivity compared to the classical catalyst for this reaction, Et2O∙BF3. The best results were achieved using zinc 2-ethylhexanoate, which provided an 88.4 % conversion of camphor and a 76.9 % selectivity for the formation of diimine. It was established that the catalytic activity of zinc carboxylates in the condensation reaction of camphor with diamines is related to the structure of the acid residue of the salt. Based on the obtained data, a reaction mechanism was proposed, associated with the formation of a complex between the zinc carboxylate and the initial amine, which is confirmed by FTIR and UV–vis spectroscopic data.

Keywords

• Ionic liquid
• Camphor
• Imine
• Amine
• Zn carboxylate