Chlorodifluoromethane
IUPAC name	Chlorodifluoromethane
Other names	Difluoromonochloromethane, Monochlorodifluoromethane, HCFC-22, R-22, Genetron 22, Freon 22, Arcton 4, Arcton 22, UN 1018,
Identifiers
CAS number	75-45-6 Y
PubChem	6372
EC number	200-871-9
KEGG	D03789
RTECS number	PA6390000
SMILES	C(F)(F)Cl
InChI	1/CHClF2/c2-1(3)4/h1H
Properties
Molecular formula	CHClF2
Molar mass	86.47 g/mol
Appearance	Colorless gas
Density	3.66 kg/m3 at 15°C, gas
Melting point	-175.42°C (97.73 K)
Boiling point	-40.7 C (232.45 K)
Solubility in water	0.7799 vol/vol at 25°C; 3.628 g/l
log P	1.08
Vapor pressure	908 kPa at 20 °C
kH	0.033 mol.kg-1.bar-1
Structure
Molecular shape	Tetrahedral
Hazards
R-phrases	R59
S-phrases	S23, S24, S25, S59
NFPA 704	0 1 1
Autoignition temperature	632 °C
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chlorodifluoromethane or difluoromonochloromethane is a hydrochlorofluorocarbon (HCFC). This colorless gas is better known as HCFC-22, R-22. It was once commonly used as a propellant and in air conditioning applications. These applications are being phased out due to ozone depletion potential and status as a potent greenhouse gas. R22 is a versatile intermediate in industrial organofluorine chemistry, e.g. as a precursor to tetrafluoroethylene.

Contents 1 Production and current applications 2 Environmental effects 3 Physical Properties 4 External links 5 References

[edit] Production and current applications

Chlorodifluoromethane is prepared from chloroform:

HCCl₃ + 2 HF → HCF₂Cl + 2 HCl

The main application of R22 is as a precursor to tetrafluoroethylene. This conversion involves pyrolysis to give difluorocarbene, which dimerizes:^[1]

2 CHClF2 → C2F4 + 2 HCl

The compound also yields difluorocarbene upon treatment with strong base and is used in the laboratory as a source of this reactive intermediate.

The pyrolysis of R22 in the presence of chlorofluoromethane gives hexafluorobenzene.

[edit] Environmental effects

Chlorodifluoromethane was used as an alternative to the highly ozone-depleting CFC-11 and CFC-12, because of its relatively low ozone depletion potential of 0.055,^[2] among the lowest for chlorine-containing haloalkanes. However, even this lower ozone depletion potential is no longer considered acceptable. It will be phased out soon under the Montreal Protocol, to be replaced by other refrigerants with lower ozone depletion potential such as propane (R-290), R-410A (an azeotropic mixture of difluoromethane and pentafluoroethane), R-507A, R-134a (1,1,1,2-tetrafluroethane) and R-409A.

As an additional environmental concern, chlorodifluoromethane has a global warming potential that is 1810 (1810 times that of carbon dioxide).^[3] HFCs such as R-410A have high global warming potential, whereas that of propane (R-290) is only 3.

Beginning in 2010 in the U.S., the production and importing of HCFC-22 will be limited to 25% of each country's 1989 consumption level. New and imported HCFC-22 will be available only for use in equipment manufactured before 1/1/2010.

On January 1st, 2010, it will be illegal to import, produce, or sell R-22 for use in new equipment or pre-charged in new equipment. In 2015, the production and importing of HCFC-22 will be limited to 10% of each country's 1989 consumption level and in 2020, production and importing of HCFC-22 will be illegal. Re-use of recovered HCFC-22 will be permitted until 2015.

[edit] Physical Properties

Property	Value
Density (ρ) at -69 °C (liquid)	1.49 g.cm-3
Density (ρ) at -41 °C (liquid)	1.413 g.cm-3
Density (ρ) at -41 °C (gas)	4.706 kg.m-3
Density (ρ) at 15 °C (gas)	3.66 kg.m-3
Specific gravity at 21 °C (gas)	3.08 (air = 1)
Specific volume (ν) at 21 °C (gas)	0.275 m³.kg-1
Density (ρ) at 15 °C (gas)	3.66 kg.m-3
Triple point temperature (Tt)	-157.39 °C (115.76 K)
Critical temperature (Tc)	96.2 °C (369.3 K)
Critical pressure (pc)	4.936 MPa (49.36 bar)
Critical density (ρc)	6.1 mol.l-1
Latent heat of vaporization (lv) at boiling point (-40.7 °C)	233.95 kJ.kg-1
Heat capacity at constant pressure (Cp) at 30 °C (86 °F)	0.057 kJ.mol-1.K-1
Heat capacity at constant volume (Cv) at 30 °C (86 °F)	0.048 kJ.mol-1.K-1
Heat capacity ratio (γ) at 30 °C (86 °F)	1.178253
Compressibility factor (Z) at 15 °C	0.9831
Acentric factor (ω)	0.22082
Dipole moment	1.458 D
Viscosity (η) at 0 °C	12.56 µPa.s (0.1256 cP)
Ozone depletion potential (ODP)	0.055 (CCl3F = 1)
Global warming potential (GWP)	1810 (CO2 = 1)

It has two allotropes: crystaline II below 59 K and crystaline I above 59 K to 115.73 K.

[edit] External links

• MSDS at Oxford University
• International Chemical Safety Card 0049
• Data at Integrated Risk Information System: IRIS 0657
• Phase change data at webbook.nist.gov
• IR absorption spectra
• IARC Summaries & Evaluations: Vol. 41 (1986), Suppl. 7 (1987), Vol. 71 (1999)

[edit] References

1. ^ Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a11_349
2. ^ The Montreal Protocol on Substances that Deplete the Ozone Layer. UNEP, 2000. ISBN 92-807-1888-6
3. ^ IPCC (2007), Changes in Atmospheric Constituentsand in Radiative Forcing, http://www.ipcc.ch/pdf/assessment-report/ar4/wg1/ar4-wg1-chapter2.pdf

v • d • e Halomethanes Monosubstituted CH3F · CH3Cl · CH3Br · CH3I Disubstituted CH2F2 · CH2ClF · CH2BrF · CH2FI · CH2Cl2 · CH2BrCl · CH2ClI · CH2Br2 · CH2BrI · CH2I2 Trisubstituted CHF3 · CHClF2 · CHBrF2 · CHF2I · CHCl2F · C*HBrClF · C*HClFI · CHBr2F · C*HBrFI · CHFI2 · CHCl3 · CHBrCl2 · CHCl2I · CHBr2Cl · C*HBrClI · CHClI2 · CHBr3 · CHBr2I · CHBrI2 · CHI3 Tetrasubstituted CF4 · CClF3 · CBrF3 · CF3I · CCl2F2 · CBrClF2 · CClF2I · CBr2F2 · CBrF2I · CF2I2 · CCl3F · CBrCl2F · CCl2FI · CBr2ClF · C*BrClFI · CClFI2 · CBr3F · CBr2FI · CBrFI2 · CFI3 · CCl4 · CBrCl3 · CCl3I · CBr2Cl2 · CBrCl2I · CCl2I2 · CBr3Cl · CBr2ClI · CBrClI2 · CClI3 · CBr4 · CBr3I · CBr2I2 · CBrI3 · CI4 * Chiral compound.