1,2-Dichloroethylene

1,2-Dichloroethylene
Skeletal formula of cis-1,2-dichloroethene	Skeletal formula of trans-1,2-dichloroethene
Ball-and-stick model of cis-1,2-dichloroethene cis-1,2-Dichloroethene (Z)	Ball-and-stick model of trans-1,2-dichloroethene trans-1,2-Dichloroethene (E)
Names
	Preferred IUPAC name 1,2-Dichloroethene
	Other names 1,2-Dichloroethene; 1,2-DCE; Acetylene dichloride; sym-Dichloroethylene
Identifiers
CAS Number	156-59-2 (Z) ; 156-60-5 (E) ; 540-59-0 (E/Z) ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:18882 ;
ChemSpider	10438 ;
ECHA InfoCard	100.007.956
EC Number	208-750-2;
KEGG	C06792 ;
PubChem CID	643833 (Z); 638186 (E); 10900 (E/Z);
UNII	FYO9G15JYD (Z) ; 41799BI61U (E) ; XU9RUA6YUT (E/Z) ;
CompTox Dashboard (EPA)	DTXSID8024991 ;
	InChI InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H Key: KFUSEUYYWQURPO-UHFFFAOYSA-N ; 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;
	SMILES Cl[C@H]=CCl; ClC=CCl;
Properties
Chemical formula	C2H2Cl2
Molar mass	96.95 g/mol
Appearance	colorless liquid
Odor	sweet
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
Magnetic susceptibility (χ)	−51.0·10−6 cm3/mol (cis); −48.9·10−6 cm3/mol (trans);
Dipole moment	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%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	770 mg/kg (oral, rat); 1275 mg/kg (oral, rat, trans-isomer)
LC50 (median concentration)	21,273 ppm (mouse, 6 hr, trans-isomer)
LCLo (lowest published)	16,000 ppm (rat, 6 hr, cis-isomer)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 200 ppm (790 mg/m3)
REL (Recommended)	TWA 200 ppm (790 mg/m3)
IDLH (Immediate danger)	1000 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula C₂H₂Cl₂. 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.^[1] In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.^[4]

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.^[1]

trans-1,2-DCE has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.^[5]

Both isomers participate in Kumada coupling reactions. trans-1,2-Dichloroethylene participates in cycloaddition reactions.^[6]

Safety and environmental concerns

These compounds have "moderate oral toxicity to rats".^[1]

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.^[7]^[8]

References

^ ^a ^b ^c ^d 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. ISBN 978-3527306732.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c "1,2-Dichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.
^ "Chlorinated Solvents and Feed Stock - Axiall". Archived from the original on 2016-04-08. Retrieved 2016-03-23.
^ Wang, Xiao Min; Hou, Xuelong; Zhou, Zhongyuan; Mak, Thomas C. W.; Wong, Henry N. C. (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. 58 (26): 7498–7506. doi:10.1021/jo00078a031.
^ Mattes, Timothy E.; Alexander, Anne K.; Coleman, Nicholas V. (2010). "Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution". FEMS Microbiology Reviews. 34 (4): 445–475. doi:10.1111/j.1574-6976.2010.00210.x. PMID 20146755.
^ Schrick, Bettina; Blough, Jennifer L.; Jones, A. Daniel; Mallouk, Thomas E. (2002). "Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles". Chemistry of Materials. 14 (12): 5140–5147. doi:10.1021/cm020737i.

External links

International Chemical Safety Card 0436
NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-1] 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. ISBN 978-3527306732.

[NIOSH-2] NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-3] "1,2-Dichloroethylene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[4] Pitzer, Kenneth S.; Hollenberg, J. L. (1954). "cis- and trans-Dichloroethylenes. The Infrared Spectra from 130–400 Cm.^–1 and the Thermodynamic Properties". J. Am. Chem. Soc. 76 (6): 1493–1496. doi:10.1021/ja01635a010.

[5] "Chlorinated Solvents and Feed Stock - Axiall". Archived from the original on 2016-04-08. Retrieved 2016-03-23.

[6] Wang, Xiao Min; Hou, Xuelong; Zhou, Zhongyuan; Mak, Thomas C. W.; Wong, Henry N. C. (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. 58 (26): 7498–7506. doi:10.1021/jo00078a031.

[7] Mattes, Timothy E.; Alexander, Anne K.; Coleman, Nicholas V. (2010). "Aerobic biodegradation of the chloroethenes: Pathways, enzymes, ecology, and evolution". FEMS Microbiology Reviews. 34 (4): 445–475. doi:10.1111/j.1574-6976.2010.00210.x. PMID 20146755.

[8] Schrick, Bettina; Blough, Jennifer L.; Jones, A. Daniel; Mallouk, Thomas E. (2002). "Hydrodechlorination of Trichloroethylene to Hydrocarbons Using Bimetallic Nickel−Iron Nanoparticles". Chemistry of Materials. 14 (12): 5140–5147. doi:10.1021/cm020737i.

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1,2-Dichloroethylene

Contents

Production, uses and reactions

Safety and environmental concerns

See also

References

External links