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Carbonyl fluoride

| NFPA-H = 4 | NFPA-F = 0 | NFPA-R = 2 | NFPA-S = W

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 C2v symmetry, bond lengths of 1.174 Å (C=O) and 1.312 Å (C–F), 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: :

Reactions

Carbonyl fluoride readily hydrolyzes to carbon dioxide and hydrogen fluoride: :

When produced in situ, carbonyl fluoride converts carboxylic acids to acyl fluorides: :

Safety

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 (15-minute average) exposure, where 1 ppm = 2.70 mg of carbonyl fluoride per 1 m3 of air.

References

References

  2. {{PGCH. 0108
  3. {{Greenwood&Earnshaw2nd
  4. (2024). "Unlocking the Power of Acyl Fluorides: A Comprehensive Guide to Synthesis and Properties". European Journal of Organic Chemistry.
  5. (1960). "Inorganic Syntheses".
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carbonyl-compounds oxyfluorides nonmetal-halides carbon-oxohalides
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