Isolation and Characterization of CH 3 OC(O)OOC(O)F from the Reaction CH 3 OH + FC(O)OOC(O)F

Abstract

The synthesis of CH3OC(O)OOC(O)F is accomplished by the thermal reaction between CH3OH and FC(O)OOC(O)F at room temperature. The new peroxide is obtained in pure form after repeated trap-to-trap condensation and it is characterized by NMR and IR spectroscopy and mass spectrometry. Geometrical parameters were studied by ab initio methods [B3LYP/6-31++G(d,p)]. CH3OC(O)OOC(O)F isstable for a few hours at room temperature, and it decomposes into CO2, CO, HF, HC(O)OH, and CH2O. The boiling point is extrapolated to 366.5 K from the vapor pressure curve log p = 8.623–2061/T (p /mbar, T /K). The mechanisms for boththe formation and thermal decomposition of CH3OC(O)OOC(O)F are discussed, and some physicochemical properties are compared with those of related compounds.