Dichloroacetylene

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Dichloroacetylene
Structure of dichloroacetylene

Dichloroacetylene
(with tetrachloroethylene as the stabiliser)
Names
IUPAC name
Dichloroethyne
Other names
DCA, dichloroethyne
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.149.197 Edit this at Wikidata
RTECS number
  • AP1080000
UNII
  • InChI=1S/C2Cl2/c3-1-2-4
    Key: ZMJOVJSTYLQINE-UHFFFAOYSA-N
  • InChI=1/C2Cl2/c3-1-2-4
    Key: ZMJOVJSTYLQINE-UHFFFAOYAO
  • C(#CCl)Cl
Properties
C2Cl2
Molar mass 94.927[1]
Appearance colorless oily liquid[1]
Odor disagreeable, sweetish
Density 1.26 g/cm3
Melting point −66 to −64 °C (−87 to −83 °F; 207 to 209 K)
Boiling point 33 °C (91 °F; 306 K) explodes
insoluble
Solubility soluble in acetone, ethanol, ether
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 explosive, potential carcinogen[1]
GHS labelling:
GHS01: ExplosiveGHS08: Health hazardGHS02: FlammableGHS07: Exclamation mark
H200, H319, H330, H335, H351, H370, H372, H373
P260, P261, P264, P270, P271, P280, P284, P304+P340, P310, P312, P320, P321, P337+P313, P403+P233, P405, P501
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 Ca C 0.1 ppm (0.4 mg/m3)[1]
IDLH
(Immediate danger)
 Ca (N.D.)[1]
Related compounds
Other anions
 Acetylene, Dibromoacetylene, Difluoroacetylene, Diiodoacetylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichloroacetylene (DCA) is an

organochlorine compound with the formula C2Cl2.[2] It is a colorless, explosive liquid that has a sweet and "disagreeable" odor.[3]

Production

Dichloroacetylene was first synthesized in 1930.[2]

Ether solutions of dichloroacetylene are relatively stable, and such solution can be safely generated by dehydrochlorination of trichlorethylene. A popular procedure uses potassium hydride as the base:[4]

Cl2C=CHCl + KH → ClC≡CCl + KCl + H2

A trace of methanol is required.

It has also been generated (and used in situ) using lithium diisopropylamide under anhydrous conditions[5] as well as potassium hydroxide.[6] Dichloroacetylene can occur and be stable in

air at concentrations of up to 200 parts per million if certain other compounds, such as ether, with which it forms an azeotrope (boiling point of 32 °C), and trichloroethylene,[7] are also present.[8]

Adventitious routes

It is a

vinylidene chloride.[9] For instance, it can be formed from trichloroethylene.[10][11] It is also possible to produce dichloroacetylene from trichloroethylene at low concentrations by running the trichloroethylene through nitrogen at 120 °C in the presence of dry potassium hydroxide.[12]

Reactions

Dichloroacetylene reacts with oxygen to give phosgene:[12]

ClC≡CCl + O2 → Cl2CO + CO

Dichloroacetylene, being electrophilic, adds nucleophiles, such as amines:

ClC≡CCl + R2NH → Cl(H)C=CCl(NR2)

Biological role and toxicity

Dichloroacetylene causes neurological disorders,[9] among other problems.[13][14] Studies on male

nephrotoxic in rats, it does not show any signs of nephrotoxicity in humans.[7]

Dichloroacetylene has

Salmonella typhimurium.[9]

The maximum safe concentration of dichloroacetylene in

powder.[3]

Like trichloroethylene, dichloroacetylene is metabolized to S-(1,2-dichlorovinyl)-L-cysteine (DCVC) in vivo.[16][17]

According to the

ship dichloroacetylene.[3]

Additional reading

See also

References

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0188". National Institute for Occupational Safety and Health (NIOSH).
  2. ^
    ISBN 9783527615261
    .
  3. ^
    ISBN 9781437778694[page needed
    ]
  4. doi:10.1021/jo00391a059
    .
  5. doi:10.15227/orgsyn.064.0073
    .
  6. doi:10.1021/jo00834a090
    .
  7. ^
    ISBN 9781402083990[page needed
    ]
  8. ^ Proceedings, Aerospace Medical Research Laboratory, 1966[page needed]
  9. ^
    PMID 3465694
  10. ISBN 978-0-309-05629-8
    , retrieved July 3, 2013
  11. S2CID 19576314
  12. ^
    PMID 1201833
  13. ^ a b Dichloroacetylene, November 18, 2010, retrieved July 3, 2013
  14. ^ Dichloroacetylene, retrieved July 3, 2013
  15. ^ Hazardous Material Fact Sheet (PDF), April 1997, retrieved July 4, 2013
  16. ISBN 9780470123973[page needed
    ]
  17. PMID 2519231
    .
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