Abstract

This article concerns ethanol fluorinated at carbon 2. 2-Fluoroethanol behaves like a typical alcohol in its chemical reactions and is slightly more acidic than ethanol. It is usually prepared by reaction of potassium fluoride with 2-chloroethanol or by the addition of hydrogen fluoride to ethylene oxide. It is extremely toxic due to its facile oxidation to fluoroacetic acid. 2,2-Difluoroethanol is also more acidic than ethanol. It is prepared by the hydrolysis of 2-bromo-1,1-difluoroethane. 2,2,2-Trifluoroethanol is the most acidic fluoroethanol and has the unusual property of dissolving most polyamides (nylons and polypeptides) at room temperature. It behaves like a typical alcohol and the trifluoromethyl group is inert to most reagents. It is prepared by the reduction of trifluoroacetic acid and its derivatives. Because of its excellent combination of physical and thermodynamic properties, it has been used (mixed with water) as a working fluid for recovery of energy from waste heat sources. It is the only fluorinated ethanol available in commercial quantities, and finds use as the starting material for two inhalation anesthetics.