Carbonyl fluoride

Carbonyl fluoride is a chemical compound with the formula COF2. This gas, like its analog phosgene, is colourless and highly toxic. The molecule is planar with C2v symmetry.

Carbonyl fluoride
Structure of carbonyl fluoride
Space-filling model of the carbonyl fluoride molecule
Names
Preferred IUPAC name
Carbonyl difluoride
Other names
Fluorophosgene; Carbon difluoride oxide; Fluoromethanoyl fluoride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.941
EC Number
  • 206-534-2
RTECS number
  • FG6125000
UNII
UN number 2417
  • InChI=1S/CF2O/c2-1(3)4 Y
    Key: IYRWEQXVUNLMAY-UHFFFAOYSA-N Y
  • InChI=1/CF2O/c2-1(3)4
    Key: IYRWEQXVUNLMAY-UHFFFAOYAE
  • FC(F)=O
Properties
COF2
Molar mass 66.01 g mol−1
Appearance Colorless gas
Density 2.698 g/L (gas), 1.139 g/cm3 (liquid at melting point)
Melting point −111.26 °C (−168.27 °F; 161.89 K)
Boiling point −84.57 °C (−120.23 °F; 188.58 K)
reacts violently with water[1]
Vapor pressure 55.4 atm (20°C)[1]
Structure
C2v
0.95 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Fatal if inhaled, reacts with water
GHS labelling:
Danger
H280, H290, H314, H330, H331, H370
P234, P260, P261, P264, P270, P271, P280, P284, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P311, P320, P321, P363, P390, P403+P233, P404, P405, P410+P403, P501
NFPA 704 (fire diamond)
4
0
2
Flash point Non-flammable
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 2 ppm (5 mg/m3) ST 5 ppm (15 mg/m3)[1]
IDLH (Immediate danger)
 N.D.[1]
Related compounds
Related compounds
 Phosgene
Carbonyl bromide
Formyl fluoride
Thiocarbonyl chloride
Acetone
Urea
Carbonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Preparation and properties

Carbonyl fluoride is usually produced as a decomposition product of fluorinated hydrocarbons in the thermal decomposition thereof, for example from trifluoromethanol or tetrafluoromethane in the presence of water:

CF
4 + H
2O → COF
2 + 2 HF

Carbonyl fluoride can also be prepared by reaction of phosgene with hydrogen fluoride and the oxidation of carbon monoxide, although the latter tends to result in over-oxidation to carbon tetrafluoride. The oxidation of carbon monoxide with silver difluoride is convenient:

CO + 2 AgF
2 → COF
2 + 2 AgF

Carbonyl fluoride is unstable in the presence of water, hydrolyzing to carbon dioxide and hydrogen fluoride:[2]

COF
2 + H
2O → CO
2 + 2 HF

Safety

Carbonyl fluoride is 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.[3]

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0108". National Institute for Occupational Safety and Health (NIOSH).
  2. M. W. Farlow; E. H. Man; C. W. Tullock (1960). "Carbonyl Fluoride". Inorganic Syntheses. Inorganic Syntheses. Vol. 6. pp. 155–158. doi:10.1002/9780470132371.ch48. ISBN 9780470132371.
  3. "Carbonyl Fluoride". NIOSH Pocket Guide to Chemical Hazards. CDC Centers for Disease Control and Prevention. Retrieved 2013-09-10.
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