Carbonyl fluoride is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

COF₂. It is a

carbon oxohalide Carbon oxohalides are a group of chemical compounds that contain only carbon, oxygen and halogen atoms: fluorine, chlorine, bromine and iodine. They include carbonyl halides, COX2, and oxalyl halides, C2X2O2, where X = F, Cl, Br or I. The halogen ...

. This gas, like its analog

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...

, is colourless and highly toxic. The molecule is

planar Planar is an adjective meaning "relating to a plane (geometry)". Planar may also refer to: Science and technology * Planar (computer graphics), computer graphics pixel information from several bitplanes * Planar (transmission line technologies), ...

with ''C''_2v

symmetry Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definit ...

bond length In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of ...

s of 1.174 Å (C=O) and 1.312 Å (C–F), and an F–C–F

bond angle Bond or bonds may refer to: Common meanings * Bond (finance), a type of debt security * Bail bond, a commercial third-party guarantor of surety bonds in the United States * Chemical bond, the attraction of atoms, ions or molecules to form chemical ...

of 108.0°.

Preparation and properties

Carbonyl fluoride is usually produced as a decomposition product of fluorinated hydrocarbons in the thermal decomposition thereof, for example from

trifluoromethanol Trifluoromethanol is the organic compound with the formula . It is also referred to as perfluoromethanol or trifluoromethyl alcohol. The compound is the simplest perfluoroalcohol. The substance is a colorless gas, which is unstable at room temper ...

tetrafluoromethane Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon ( C F4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a ...

in the presence of water: : + → + 2 Carbonyl fluoride can also be prepared by reaction of phosgene with

hydrogen fluoride Hydrogen fluoride (fluorane) is an inorganic compound with the chemical formula . This colorless gas or liquid is the principal industrial source of fluorine, often as an aqueous solution called hydrofluoric acid. It is an important feedstock i ...

and the oxidation of

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

, although the latter tends to result in over-oxidation to

carbon tetrafluoride Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon ( C F4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a ...

. The oxidation of carbon monoxide with

silver difluoride Silver(II) fluoride is a chemical compound with the formula AgF2. It is a rare example of a silver(II) compound. Silver usually exists in its +1 oxidation state In chemistry, the oxidation state, or oxidation number, is the hypothetical char ...

is convenient: : + 2 → + 2 Carbonyl fluoride is unstable in the presence of water, hydrolyzing to carbon dioxide and

: : + → + 2

Safety

Carbonyl fluoride is toxic with a

recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...

of 2 ppm as an 8-hour time weighted average and a 5 ppm as a short-term (15-minute average) exposure.

References

{{reflist Carbonyl compounds Fluorine compounds Nonmetal halides Carbon oxohalides