1,1,1,2-Tetrachloroethane

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1,1,1,2-Tetrachloroethane [1]
Skeletal formula of 1,1,1,2-tetrachloroethane 1,1,1,2-Tetrachloroethane.svg
Skeletal formula of 1,1,1,2-tetrachloroethane
Ball-and-stick model of 1,1,1,2-tetrachloroethane 1,1,1,2-Tetrachloroethane-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C2H2Cl4/c3-1-2(4,5)6/h1H2 Yes check.svgY
    Key: QVLAWKAXOMEXPM-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceClear liquid
Density 1.5532 g/cm3
Melting point −70.2 °C (−94.4 °F; 203.0 K)
Boiling point 130.5 °C (266.9 °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 °C [77 °F], 100 kPa).
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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.

Contents

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

  1. ↑ "National Pollutant Inventory Substance Profile". Archived from the original on 2007-08-29. Retrieved 2007-07-19.
  2. 1 2 3 The so-called Perchloride of Formyl, Gmelin, L. (translated in 1855). Hand-book of Chemistry: Organic chemistry. UK: Cavendish Society. pages 199-200
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0597". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Essai sur l'Action du Chlore sur la Liqueur des Hollandais et sur quelques Ethers in Annales de Chimie, LXIII. (1836) page 379
  5. ↑ On Chloroform and Tests for Its Purity (1865) by D. R. Brown in American Journal of Pharmacy, vol. 37, page 289
  6. ↑ Lawrance Waddams: The Petroleum chemicals Industry, S. 175.
  7. ↑ IARC Monograph 106 – 1,1,1,2-Tetrachloroethane, 2014
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