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1,2-Dichloroethylene

1,2-DCE Acetylene dichloride sym-Dichloroethylene E: 1.26 g/cm E: −49.44 °C E: 48.5 °C E: 0 D

  • −51.0·10 cm/mol (cis)
  • −48.9·10 cm/mol (trans) 1275 mg/kg (oral, rat, trans-isomer)

1,2-Dichloroethylene (1,2-DCE) is a pair of organochlorine compounds with the molecular formula . The two compounds are isomers, each being colorless liquids with a sweet 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 some applications as a degreasing solvent. In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.

Production, uses and reactions

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

:CH + Cl → CHCl

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

trans-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.

Both isomers participate in Kumada coupling reactions. trans-1,2-Dichloroethylene participates in cycloaddition reactions.

Safety and environmental concerns

These compounds have "moderate oral toxicity to rats".

The dichloroethylene isomers occur in some polluted waters and soils, as the decomposition products of trichloroethylene. Significant attention has been paid to their further degradation, e.g. by iron particles.

References

References

  1. {{PGCH. 0195
  2. {{IDLH. 540590. 1,2-Dichloroethylene
  3. E.-L. Dreher. (2011). "Ullmann's Encyclopedia of Industrial Chemistry". Wiley-VCH.
  4. (1954). "''cis''- and ''trans''-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.{{sup". J. Am. Chem. Soc..
  5. "Chlorinated Solvents and Feed Stock - Axiall".
  6. (1993). "Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: Synthesis of 5,6-didehydro-1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene and 5,6-didehydro-10,11-methano-1H-benzo[5,6]cycloocta[1,2,3,4-def]fluorene-1,14-dione and x-ray crystal structures of 1,1,14,14-tetramethyl-10,11-methano-1H-benzo[5,6-cycloocta[1,2,3,4-def]fluorene and 1,12-dihydro-1,1,12,12-tetramethyldicyclopenta[def,JKL]tetraphenylene". The Journal of Organic Chemistry.
  7. (2010). "Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution". FEMS Microbiology Reviews.
  8. (2002). "Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles". Chemistry of Materials.
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chloroalkenes halogenated-solvents
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