1,1,1,2-Tetrachloroethane

Chemical compound From Wikipedia, the free encyclopedia

1,1,1,2-Tetrachloroethane is a chlorinated hydrocarbon. It is a colorless liquid with a sweet chloroform-like odor. It is used as a solvent and in the production of wood stains and varnishes. It is an isomer of 1,1,2,2-tetrachloroethane.

Quick facts Names, Identifiers ...
1,1,1,2-Tetrachloroethane[1]
Skeletal formula of 1,1,1,2-tetrachloroethane
Skeletal formula of 1,1,1,2-tetrachloroethane
Ball-and-stick model of 1,1,1,2-tetrachloroethane
Ball-and-stick model of 1,1,1,2-tetrachloroethane
Names
Preferred IUPAC name
1,1,1,2-Tetrachloroethane
Other names
R-130a, acetylidene tetrachloride, asymmetrical tetrachloroethane, perchloride of formyl or terchlorinated hydrochloric ether (archaic)[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.124 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H2Cl4/c3-1-2(4,5)6/h1H2 checkY
    Key: QVLAWKAXOMEXPM-UHFFFAOYSA-N checkY
  • InChI=1/C2H2Cl4/c3-1-2(4,5)6/h1H2
    Key: QVLAWKAXOMEXPM-UHFFFAOYAE
  • C(C(Cl)(Cl)Cl)Cl
  • ClCC(Cl)(Cl)Cl
Properties
C2H2Cl4
Molar mass 167.84 g·mol−1
Appearance Clear liquid
Density 1.5532 g/cm3
Melting point −70.2 Â°C (−94.4 Â°F; 203.0 K)
Boiling point 130.5 Â°C (266.9 Â°F; 403.6 K)
0.1% (20°C)[3]
Vapor pressure 14 mmHg (25°C)[3]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 Handle with caution in the workplace.[3]
IDLH (Immediate danger)
 N.D.[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Close

It was likely discovered by Auguste Laurent along with the 1,1,2,2-tetrachloroethane isomer and trichloroethylene in 1836.[4][2] 1,1,1,2-Tetrachloroethane was named "perchloride of formyl" in Leopold Gmelin's Hand-book of Chemistry,[2] the same name was also used for chloroform.[5]

Production

1,1,1,2-Tetrachloroethane can be obtained by a two-step addition reaction of acetylene with chlorine (via dichloroethylene), but this mainly produces 1,1,2,2-tetrachloroethane.

C2H2 + Cl2 → C2H2Cl2
C2H2Cl2 + Cl2 → C2H2Cl4

It can be obtained directly by chlorination of 1,1,2-trichloroethane:[6]

CHCl2−CH2Cl + Cl2 → CCl3−CH2Cl + HCl

Safety

IARC has classified 1,1,1,2-tetrachloroethane as a possible carcinogen for humans in 2014.[7]

See also

References

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