1,1,2-Trichloro-1,2,2-trifluoroethane

1,1,2-Trichloro-1,2,2-trifluoroethane

Names
Preferred IUPAC name 1,1,2-Trichloro-1,2,2-trifluoroethane
Other names Arklone P CFC-113 Freon 113 Frigen 113 TR Freon TF Valclene 1,1,2-trichlorotrifluoroethane TCTFE Solvent 113
Identifiers
CAS Number	76-13-1 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL478511 Y
ChemSpider	6188 Y
ECHA InfoCard	100.000.852
PubChem CID	6428
UNII	0739N04X3A Y
CompTox Dashboard (EPA)	DTXSID6021377
InChI InChI=1S/C2Cl3F3/c3-1(4,6)2(5,7)8 Y Key: AJDIZQLSFPQPEY-UHFFFAOYSA-N Y InChI=1/C2Cl3F3/c3-1(4,6)2(5,7)8 Key: AJDIZQLSFPQPEY-UHFFFAOYAE
SMILES ClC(F)(F)C(Cl)(Cl)F
Properties
Chemical formula	CClF2CCl2F
Molar mass	187.37 g·mol−1
Appearance	Colorless liquid
Odor	like carbon tetrachloride[1]
Density	1.56 g/mL
Melting point	−35 °C (−31 °F; 238 K)
Boiling point	47.7 °C (117.9 °F; 320.8 K)
Solubility in water	170 mg/L
Vapor pressure	285 mmHg (20 °C)[1]
Thermal conductivity	0.0729 W m−1 K−1 (300 K)[2]
Hazards
Lethal dose or concentration (LD, LC):
LCLo (lowest published)	250,000 ppm (mouse, 1.5 hr) 87,000 (rat, 6 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 1000 ppm (7600 mg/m3)[1]
REL (Recommended)	TWA 1000 ppm (7600 mg/m3) ST 1250 ppm (9500 mg/m3)[1]
IDLH (Immediate danger)	2000 ppm[1]
Hazards
GHS labelling:[4]
Pictograms
Signal word	Warning
NFPA 704 (fire diamond)	3 0 1
Safety data sheet (SDS)	https://datasheets.scbt.com/sc-251541.pdf
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane (often abbreviated as TCTFE) or CFC-113, is a chlorofluorocarbon. It has the formula Cl₂FC−CClF₂. This colorless, volatile liquid is a versatile solvent.^[5]

Production

CFC-113 can be prepared from hexachloroethane and hydrofluoric acid:^[6]

${\displaystyle {\ce {C2Cl6 + 3HF -> CF2Cl-CFCl2 + 3HCl}}}$

This reaction may require catalysts such as antimony, chromium, iron and alumina at high temperatures.^[7]

Another synthesis method uses HF on tetrachloroethylene instead.^[8]

Atmospheric reactions

CFC-113 is a very unreactive chlorofluorocarbon. It remains in the atmosphere about 90 years,^[9] sufficiently long that it will cycle out of the troposphere and into the stratosphere. In the stratosphere, CFC-113 can be broken up by ultraviolet radiation (where sunlight in the 190-225 nm (UV) range), generating chlorine radicals (Cl•), which initiate degradation of ozone requiring only a few minutes:^[10][11]

CClF₂CCl₂F → C₂F₃Cl₂ + Cl•

Cl• + O₃ → ClO• + O₂

This reaction is followed by:

ClO• + O → Cl• + O₂

The process regenerates Cl• to destroy more O₃. The Cl• will destroy an average of 100,000 O₃ molecules during its atmospheric lifetime of 1–2 years. In some parts of the world, these reactions have significantly thinned the Earth's natural stratospheric ozone layer that shields the biosphere against solar UV radiation; increased UV levels at the surface can cause skin cancer or even blindness.^[12]

Uses

CFC-113 was one of the most heavily produced CFCs. In 1989, an estimated 250,000 tons were produced.^[5] It has been used as a cleaning agent for electrical and electronic components.^[12] CFC-113’s low flammability and low toxicity made it ideal for use as a cleaner for delicate electrical equipment, fabrics, and metals. It would not harm the product it was cleaning, ignite with a spark or react with other chemicals.^[13] It was used as a dry-cleaning solvent, introduced by Du Pont in March 1961 as "Valclene"^[14] and was also marketed as the "solvent of the future" by Imperial Chemical Industries in the 1970s under the tradename Arklone. Others from this series were Perklone (Tetrachloroethylene), Triklone (Trichloroethylene), Methoklone (Dichloromethane) and Genklene (1,1,1-Trichloroethane).^[15][16]

CFC-113 is one of the three most popular CFCs, along with CFC-11 and CFC-12.^[17]

CFC-113 in laboratory analytics has been replaced by other solvents.^[18]

Reduction of CFC-113 with zinc gives chlorotrifluoroethylene:^[5]

CFCl₂−CClF₂ + Zn → CClF=CF₂ + ZnCl₂

Dangers

Aside from its immense environmental impacts, Freon 113, like most chlorofluoroalkanes, forms phosgene gas when exposed to a naked flame.^[19]

See also

• 1,1,1-Trichloro-2,2,2-trifluoroethane

References