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1,2-Dichloroethylene

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cis-1,2-Dichloroethene (Z) (left) and trans-1,2-Dichloroethene (E) (right)
Skeletal formula of cis-1,2-dichloroethene
Skeletal formula of cis-1,2-dichloroethene
Skeletal formula of trans-1,2-dichloroethene
Skeletal formula of trans-1,2-dichloroethene
Ball-and-stick model of cis-1,2-dichloroethene
Ball-and-stick model of cis-1,2-dichloroethene
Ball-and-stick model of trans-1,2-dichloroethene
Ball-and-stick model of trans-1,2-dichloroethene
Names
IUPAC name
1,2-Dichloroethene
Other names
1,2-Dichloroethylene
1,2-DCE
sym-Dichloroethylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.956 Edit this at Wikidata
KEGG
  • InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H checkY
    Key: KFUSEUYYWQURPO-UHFFFAOYSA-N checkY
  • InChI=1/C2H2Cl2/c3-1-2-4/h1-2H/b2-1-
    Key: KFUSEUYYWQURPO-UPHRSURJBI
  • InChI=1/C2H2Cl2/c3-1-2-4/h1-2H
    Key: KFUSEUYYWQURPO-UHFFFAOYAW
  • Cl[C@H]=CCl
  • ClC=CCl
Properties
C2H2Cl2
Molar mass 96.95 g/mol
Appearance clear liquid[1]
Odor acrid, chloroform-like[1]
Density Z: 1.28 g/cm³
E: 1.26 g/cm³
Melting point Z: -81.47 °C
E: -49.44 °C
Boiling point Z: 60.2 °C
E: 48.5 °C
Z: 1.9 D
E: 0 D
Hazards
Flash point 2–4 °C; 36–39 °F; 275–277 K
Explosive limits 5.6%-12.8%[1]
Lethal dose or concentration (LD, LC):
770 mg/kg (oral, rat)
1275 mg/kg (oral, rat, trans-isomer)[2]
21,273 ppm (mouse, 6 hr, trans-isomer)[2]
16,000 ppm (rat, 6 hr, cis-isomer)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 200 ppm (790 mg/m3)[1]
REL (Recommended)
 TWA 200 ppm (790 mg/m3)[1]
IDLH (Immediate danger)
 1000 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1,2-Dichloroethene, commonly called 1,2-dichloroethylene or 1,2-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a highly flammable, colorless liquid with a sharp, harsh odor. It can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two. They have modest solubility in water. These compounds have few industrial applications,[3] although they are fundamental given their simple stoichiometries.

Production

cis-DCE, the E isomer, is obtainable by the controlled chlorination of acetylene:

C2H2 + Cl2 → C2H2Cl2

Industrially both isomers arise as byproduct of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, the 1,2-dichloroethylene isomers do not polymerize.[3]

trans-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.[4]

Safety

These compounds have "moderate oral toxicity to rats."[3]

See also

References

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c "1,2-Dichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b c E.-L. Dreher, T. R. Torkelson, K. K. Beutel (2011). "Chlorethanes and Chloroethylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o06_o01.{{cite book}}: CS1 maint: multiple names: authors list (link)
  4. ^ http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/
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