1,2-Dichloroethylene

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1,2-Dichloroethylene
Skeletal formula of cis-1,2-dichloroethene Cis-1,2-dichloroethene.png
Skeletal formula of cis-1,2-dichloroethene
Skeletal formula of trans-1,2-dichloroethene Trans-1,2-dichloroethene.png
Skeletal formula of trans-1,2-dichloroethene
Ball-and-stick model of cis-1,2-dichloroethene Cis-1,2-dichloroethene-3D-balls.png
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-3D-balls.png
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.956 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-750-2
KEGG
PubChem CID
UNII
  • InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H Yes check.svgY
    Key: KFUSEUYYWQURPO-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless liquid
Odor sweet [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
  • −51.0·10−6 cm3/mol (cis)
  • −48.9·10−6 cm3/mol (trans)
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% [2]
Lethal dose or concentration (LD, LC):
770 mg/kg (oral, rat)
1275 mg/kg (oral, rat, trans-isomer) [3]
21,273 ppm (mouse, 6 hr, trans-isomer) [3]
16,000 ppm (rat, 6 hr, cis-isomer) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (790 mg/m3) [2]
REL (Recommended)
TWA 200 ppm (790 mg/m3) [2]
IDLH (Immediate danger)
1000 ppm [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula (CH2Cl)2. 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]

Contents

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]

See also

Related Research Articles

<i>Cis</i>–<i>trans</i> isomerism Pairs of molecules with same chemical formula showing different spatial orientations

Cistrans isomerism, also known as geometric isomerism, describes certain arrangements of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides. Cistrans isomers are stereoisomers, that is, pairs of molecules which have the same formula but whose functional groups are in different orientations in three-dimensional space. Cis and trans isomers occur both in organic molecules and in inorganic coordination complexes. Cis and trans descriptors are not used for cases of conformational isomerism where the two geometric forms easily interconvert, such as most open-chain single-bonded structures; instead, the terms "syn" and "anti" are used.

<span class="mw-page-title-main">1,4-Dichlorobenzene</span> Chemical compound

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc", and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a mild sweet, sharp odor, detectable by most people at a concentration of 50 ppm.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

IARC group 3 substances, chemical mixtures and exposure circumstances are those that can not be classified in regard to their carcinogenicity to humans by the International Agency for Research on Cancer (IARC). This category is used most commonly for agents, mixtures and exposure circumstances for which the level of evidence of carcinogenicity is inadequate in humans and inadequate or limited in experimental animals. Exceptionally, agents (mixtures) for which the evidence of carcinogenicity is inadequate in humans, but sufficient in experimental animals may be placed in this category when there is strong evidence that the mechanism of carcinogenicity in experimental animals does not operate in humans. Agents, mixtures and exposure circumstances that do not fall into any other group are also placed in this category.

<span class="mw-page-title-main">Cyclodecapentaene</span> Chemical compound

Cyclodecapentaene or [10]annulene is an annulene with molecular formula C10H10. This organic compound is a conjugated 10 pi electron cyclic system and according to Huckel's rule it should display aromaticity. It is not aromatic, however, because various types of ring strain destabilize an all-planar geometry.

1,1-Dichloroethane is a chlorinated hydrocarbon. It is a colorless oily liquid with a chloroform-like odor. It is not easily soluble in water, but miscible with most organic solvents.

Organohalide respiration (OHR) (previously named halorespiration or dehalorespiration) is the use of halogenated compounds as terminal electron acceptors in anaerobic respiration. Organohalide respiration can play a part in microbial biodegradation. The most common substrates are chlorinated aliphatics (PCE, TCE, chloroform) and chlorinated phenols. Organohalide-respiring bacteria are highly diverse. This trait is found in some Campylobacterota, Thermodesulfobacteriota, Chloroflexota (green nonsulfur bacteria), low G+C gram positive Clostridia, and ultramicrobacteria.

1,1-Dichloroethylene, commonly called vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula CHClCl2CH3. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water but soluble in organic solvents. 1,1-DCE was the precursor to the original clingwrap, Saran, for food, but this application has been phased out.

A dichlorodifluoroethylene is one of three compounds with the chemical formula C
2
Cl
2
F
2
. Dichlorodifluoroethylenes are colourless gases, and are some of the simplest chlorodifluoroalkenes.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">1,1'-Azobis-1,2,3-triazole</span> Chemical compound

1,1'-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable chemical compound which contains a long continuous chain of nitrogen atoms, with an unbroken chain of eight nitrogen atoms cyclised into two 1,2,3-triazole rings. It is stable up to 194 °C. The compound exhibits cistrans isomerism at the central azo group: the trans isomer is more stable and is yellow, while the cis isomer is less stable and is blue. The two rings are aromatic and form a conjugated system with the azo linkage. This chromophore allows the trans compound to be isomerised to the cis when treated with an appropriate wavelength of ultraviolet light.

<span class="mw-page-title-main">Pentachloroethane</span> Chemical compound

Pentachloroethane is a chemical compound of chlorine, hydrogen, and carbon with the chemical formula C2HCl5. It is a colourless non-flammable liquid that is used as a solvent for oil and grease, in metal cleaning, and in the separation of coal from impurities.

<span class="mw-page-title-main">1,2-Dimethyldiborane</span> Chemical compound

1,2-Dimethyldiborane is an organoboron compound with the formula [(CH3)BH2]2. Structurally, it is related to diborane, but with methyl groups replacing terminal hydrides on each boron. It is the dimer of methylborane, CH3BH2, the simplest alkylborane. 1,2-Dimethyldiborane can exist in a cis- and a trans arrangement. 1,2-Dimethyldiborane is an easily condensed, colorless gas that ignites spontaneously in air.

1,2-Difluoroethylene, also known as 1,2-difluoroethene, is an organofluoride with the molecular formula C2H2F2. It can exist as either of two geometric isomers, cis-1,2-difluoroethylene or trans-1,2-difluoroethylene.

<span class="mw-page-title-main">Indenofluorene</span> Class of chemical compounds

An indenofluorene (IF) is any of five hydrocarbons with formula C
20
H
12
, whose carbon skeleton is a sequence of five fused rings with 6, 5, 6, 5, and 6 carbon atoms; an arrangement that can be described as the fusion of an indene core and a fluorene core.

cis-1,2-Bis(diphenylphosphino)ethylene (dppv) is an organophosphorus compound with the formula C2H2(PPh2)2 (Ph = C6H5). Both the cis and trans isomers are known, but the cis isomer is of primary interest. Classified as a diphosphine ligand, it is a bidentate ligand in coordination chemistry. For example it gives rise to the complex Ni(dppv)2 and the coordination polymer [Ni(dppv)]n. As a chelating ligand, dppv is very similar to 1,2-bis(diphenylphosphino)benzene.

References

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  2. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 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.