Kinetic and equilibrium studies by 19F nuclear magnetic resonance of the formation of acetyl fluoride from acetyl chloride and tetraethylammonium fluoride in acetic acid

Abstract

The formation of acetyl fluoride from acetyl chloride and tetraethylammonium fluoride in glacial acetic acid has been studied by ¹⁹F n.m.r. The results show that an equilibrium is established slowly at 298 K. For example, a solution initially containing 0.476 mol dm^–3 each of acetyl chloride and tetraethylammonium fluoride attains 68% conversion into acetyl fluoride after 21 h, whereas the equilibrium position corresponds to 87% conversion. Evidence is provided to show that the reaction involves rapid formation of acetic anhydride and hydrogen fluoride, which then react slowly to give acetyl fluoride.