Carbonyl fluoride

Carbonyl fluoride is a chemical compound with the formula. It is a carbon oxohalide. This gas, like its analog phosgene, is colourless and highly toxic. The molecule is planar with C_2v symmetry, bond lengths of 1.174 Å and 1.312 Å, and an F–C–F bond angle of 108.0°.

Preparation

Carbonyl fluoride is produced from trifluoromethanol. The latter is produced in turn by protonation of in-situ generated trifluoromethoxide.
Of potential relevance to atmospheric chemistry, tetrafluoromethane hydrolyses to carbonyl fluoride:
Carbonyl fluoride can also be prepared by reaction of phosgene with hydrogen fluoride as well as the fluorination of carbon monoxide, although the latter tends to result in over-fluorination to carbon tetrafluoride. The fluorination of carbon monoxide with silver difluoride is convenient:

Carbonyl fluoride readily hydrolyzes to carbon dioxide and hydrogen fluoride:
When produced in situ, carbonyl fluoride converts carboxylic acids to acyl fluorides:

Carbonyl fluoride is very toxic with a recommended exposure limit of 2 ppm as an 8-hour time weighted average and a 5 ppm as a short-term exposure, where 1 ppm = 2.70 mg of carbonyl fluoride per 1 m³ of air.