1,2-Dichloroethylene

changed changed 477203654 Cis-1,2-dichloroethene.svg Skeletal formula of cis-1,2-dichloroethene skin-invert Trans-1,2-dichloroethene.svg Skeletal formula of trans-1,2-dichloroethene skin-invert Cis-1,2-dichloroethene-3D-balls.png Ball-and-stick model of cis-1,2-dichloroethene bg-transparent Trans-1,2-dichloroethene-3D-balls.png Ball-and-stick model of trans-1,2-dichloroethene bg-transparent cis-1,2-Dichloroethene (Z) trans-1,2-Dichloroethene (E) 1,2-Dichloroethene 1,2-Dichloroethene1,2-DCEAcetylene dichloridesym-Dichloroethylene correct chemspider correct EBI 18882 10438 208-750-2 643833 (Z) 638186 (E) 10900 (E/Z) correct kegg C06792 1/C2H2Cl2/c3-1-2-4/h1-2H/b2-1- KFUSEUYYWQURPO-UPHRSURJBI 1/C2H2Cl2/c3-1-2-4/h1-2H KFUSEUYYWQURPO-UHFFFAOYAW ClC=CCl correct chemspider 1S/C2H2Cl2/c3-1-2-4/h1-2H correct chemspider KFUSEUYYWQURPO-UHFFFAOYSA-N correct CAS 156-59-2 (Z) correct ?? 156-60-5 (E) correct ?? 540-59-0 (E/Z) correct FDA FYO9G15JYD (Z) correct FDA 41799BI61U (E) correct FDA XU9RUA6YUT (E/Z) Cl[C@H]=CCl 2 2 2 Z: 1.28 g/cm3E: 1.26 g/cm3 Z: −81.47 °CE: −49.44 °C Z: 60.2 °CE: 48.5 °C Z: 1.9 DE: 0 D colorless liquid sweet −51.0·10−6 cm3/mol (cis) −48.9·10−6 cm3/mol (trans) TWA 200 ppm (790 mg/m3)0195 36-39 5.6–12.8% 1000 ppm TWA 200 ppm (790 mg/m3) 21,273 ppm (mouse, 6 hr, trans-isomer)540590 1,2-Dichloroethylene 770 mg/kg (oral, rat)1275 mg/kg (oral, rat, trans-isomer) 16,000 ppm (rat, 6 hr, cis-isomer) 1,2-Dichloroethylene (1,2-DCE) is a pair of organochlorine compounds with the molecular formula C2H2Cl2 1. 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. E.-L. Dreher T. R. Torkelson K. K. Beutel Chlorethanes and Chloroethylenes Ullmann's Encyclopedia of Industrial Chemistry 2011 Wiley-VCH Weinheim 10.1002/14356007.o06_o01 978-3527306732 In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol. cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.–1 and the Thermodynamic Properties Kenneth S. Pitzer J. L. Hollenberg J. Am. Chem. Soc. 1954 76 6 1493–1496 10.1021/ja01635a010 Production, uses and reactions cis-DCE, the Z isomer, is obtainable by the controlled chlorination of acetylene: C2H2 + Cl2 → C2H2Cl2 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.http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ Chlorinated Solvents and Feed Stock - Axiall 2016-03-23 https://web.archive.org/web/20160408122850/http://www.axiall.com/Products/Chlorovinyls/Chlorinated-Solvents-and-Feedstock/ 2016-04-08 dead Both isomers participate in Kumada coupling reactions. trans-1,2-Dichloroethylene participates in cycloaddition reactions.10.1021/jo00078a031 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 1993 Wang Xiao Min Hou Xuelong Zhou Zhongyuan Mak Thomas C. W. Wong Henry N. C. The Journal of Organic Chemistry 58 26 7498–7506 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.10.1111/j.1574-6976.2010.00210.x Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution 2010 Mattes Timothy E. Alexander Anne K. Coleman Nicholas V. FEMS Microbiology Reviews 34 4 445–475 20146755 free 10.1021/cm020737i Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles 2002 Schrick Bettina Blough Jennifer L. Jones A. Daniel Mallouk Thomas E. Chemistry of Materials 14 12 5140–5147 See also 1,1-Dichloroethene 1,2-Dichloroethane, which is also often abbreviated as 1,2-DCE References External links 0436 04 0195 Category:Chloroalkenes Category:Halogenated solvents Category:Haloethenes