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1,1,1-Trichloroethane

1,1,1-Trichloroethane
Skeletal formula of 1,1,1-trichloroethane
Space-filling model of 1,1,1-trichloroethane
Names
IUPAC name
1,1,1-trichloroethane
Other names
methyl chloroform, chlorothene, Solvent 111, Genklene, R-140a
Identifiers
71-55-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:36015 YesY
ChEMBL ChEMBL16080 YesY
ChemSpider 6042 YesY
ECHA InfoCard 100.000.688
5482
KEGG C18246 YesY
PubChem 6278
UNII 113C650IR1 YesY
Properties
C2H3Cl3 or CH3CCl3
Molar mass 133.40 g/mol
Appearance Colorless liquid
Odor mild, chloroform-like
Density 1.32 g/cm3
Melting point −33 °C (−27 °F; 240 K)
Boiling point 74 °C (165 °F; 347 K)
0.4% (20°C)
Vapor pressure 100 mmHg (20°C)
Hazards
Main hazards Irritant to the upper respiratory tract. Causes severe irritation and swelling to eyes.
R-phrases R19 R20 R40 R59 R66
S-phrases S9 S16 S24 S25 S46 S59 S61
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Explosive limits 7.5%-12.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
9600 mg/kg (oral, rat)
6000 mg/kg (oral, mouse)
5660 mg/kg (oral, rabbit)
3911 ppm (mouse, 2 hr)
18000 ppm (rat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 350 ppm (1900 mg/m3)
REL (Recommended)
C 350 ppm (1900 mg/m3) [15-minute]
IDLH (Immediate danger)
700 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colourless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the as an ozone-depleting substance and its use is being rapidly phased out.

1,1,1-Trichloroethane was first reported by Henri Victor Regnault in 1840. Industrially, it is usually produced in a two-step process from vinyl chloride. In the first step, vinyl chloride reacts with hydrogen chloride at 20-50 °C to produce 1,1-dichloroethane:

This reaction is catalyzed by a variety of Lewis acids, mainly aluminium chloride, iron(III) chloride, or zinc chloride. The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction with chlorine under ultraviolet irradiation:

This reaction proceeds at 80-90% yield, and the hydrogen chloride byproduct can be recycled to the first step in the process. The major side-product is the related compound 1,1,2-trichloroethane, from which the 1,1,1-trichloroethane can be separated by distillation.

A somewhat smaller amount of 1,1,1-trichloroethane is produced from the reaction of vinylidene chloride and hydrogen chloride in the presence of an iron(III) chloride catalyst:

1,1,1-Trichloroethane is marketed with stabilizers since it is unstable with respect to dehydrochlorination and attacks some metals. Stabilizers comprise up to 8% of the formulation, including acid scavengers (epoxides, amines) and complexants. The Montreal Protocol targeted 1,1,1-trichloroethane as one of those compounds responsible for ozone depletion and banned its use beginning in 1996. Since then, its manufacture and use has been phased out throughout most of the world.


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