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Smokefoot/sandbox4
Skeletal formula of trans-1,2-dichloroethene
Ball-and-stick model of trans-1,2-dichloroethene
Names
Other names
trans-1,2-Dichloroethylene
1,2-DCE
sym-Dichloroethylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1+
    Key: KFUSEUYYWQURPO-OWOJBTEDSA-N
  • C(=C/Cl)\Cl
Properties
C2H2Cl2
Molar mass 96.95 g/mol
Appearance colorless liquid[1]
Odor sweet[2]
Density 1.26 g/cm3
Melting point −49.44 °C
Boiling point 48.5 °C
  • −48.9·10−6 cm3/mol (trans)
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)[3]
21,273 ppm (mouse, 6 hr)[3]
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 ?)
Tracking categories (test):

trans-1,2-Dichloroethene is an organochloride with the molecular formula C2H2Cl2. It is a geometric isomer of cis-1,2-dichloroethene. The two are often used as a mixture. Both have modest solubility in water, are colorless liquids, and have sweet odors. The trans compound is mainly used as a specialized degreaser.[2] 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 and reactions

[edit]

Industrially both isomers of 1,2-dichloroethene arise as byproducts of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, neither isomer of 1,2-dichloroethene polymerizes.[2]

trans-DCE is used for cleaning of electronics and other speciallized cleaning applications.[5]

trans-1,2-Dichloroethene participates in cycloaddition reactions.[6]

Safety

[edit]

The isomers of 1,2-dichloroethene compounds have "moderate oral toxicity to rats".[2]

See also

[edit]

References

[edit]
  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ 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.
  3. ^ a b "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.
[edit]


Category:Chloroalkenes Category:Halogenated solvents


Smokefoot/sandbox4
Skeletal formula of cis-1,2-dichloroethene
Ball-and-stick model of cis-1,2-dichloroethene
Names
Other names
cis-1,2-Dichloroethene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C2H2Cl2/c3-1-2-4/h1-2H/b2-1-
    Key: KFUSEUYYWQURPO-UPHRSURJSA-N
  • C(=C\Cl)\Cl
Properties
C2H2Cl2
Molar mass 96.95 g/mol
Appearance colorless liquid
Odor sweet[1]
Density 1.28 g/cm3
Melting point −81.47 °C
Boiling point 60.2 °C
  • −51.0·10−6 cm3/mol (cis)
1.9 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):
16,000 ppm (rat, 6 hr, cis-isomer)ref name=Ullmann/>
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).
Tracking categories (test):

cis-1,2-Dichloroethene is an organochloride with the molecular formula C2H2Cl2. It is a geometric isomer of trans-1,2-dichloroethene. The two are often used as a mixture. Both have low solubility in water, are colorless liquids, and have sweet odors. The trans compound finds some applications as a specialized degreaser,[1] whereas the cis compound is a specialized reagent in organic synthesis.

Production

[edit]

Industrially both isomers of 1,2-dichloroethene arise as byproducts of the production of vinyl chloride, which is produced on a vast scale. Unlike vinyl chloride, neither isomer of 1,2-dichloroethene polymerizes.[1]

E-Z relative stability

[edit]

In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.[3]

Safety

[edit]

The isomers of 1,2-dichloroethene compounds have "moderate oral toxicity to rats".[1]

See also

[edit]

References

[edit]
  1. ^ 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.
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0195". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ 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.
[edit]


Category:Chloroalkenes Category:Halogenated solvents

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