Formation and properties of partially fluorinated amines, a detailed study of triethylamine electrochemical fluorination

Abstract

In the course of many electrochemical fluorination (ECF) experiments, aimed at the synthesis of perfluorinated compounds for blood substitutes, we repeatedly observed phenomena indicating the occurrence of surface-active compounds in the HF. Indeed, the electrochemical perfluorination is linked with the formation of partially fluorinated, HF-soluble intermediates and by- products, which must be responsible for these phenomena. To obtain further information on the nature and properties of the partially fluorinated compounds in the HF phase, ECF of 2-phenyl-3,4-dimethylmorpholine and triethylamine (TEA) was studied. In ECF of TEA we could isolate for the first time a number of defined partially fluorinated TEAs. Their formation and properties as well as their possible role in ECF will be discussed.