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Vinylacetylene

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Vinylacetylene
Names
IUPAC name but-1-en-3-yne
Other names butenyne, 3-butene-1-yne
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.650 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H4/c1-3-4-2/h1,4H,2H2Key: WFYPICNXBKQZGB-UHFFFAOYSA-N
  • InChI=1/C4H4/c1-3-4-2/h1,4H,2H2Key: WFYPICNXBKQZGB-UHFFFAOYAE
SMILES
  • C#CC=C
Properties
Chemical formula C4H4
Molar mass 52.07456 g/mol
Appearance colourless gas
Boiling point 0–6 °C
Solubility in water low
Hazards
Occupational safety and health (OHS/OSH):
Main hazards flammable
Flash point < -5 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Vinylacetylene is the organic compound with the formula C4H4. The colourless gas was once used in the polymer industry. It is composed of both alkyne and alkene groups.

Synthesis

Vinylacetylene was first prepared by Hofmann Elimination of the related quaternary ammonium salt:

I2 → 2 I + HC≡C-CH=CH2

It is usually synthesized by dehydrohalogenation of 1,3-dichloro-2-butene. It also arises via the dimerization of acetylene.

Application

At one time, chloroprene (2-chloro-1,3-butadiene), an industrially important monomer, was produced via the intermediacy of vinyl acetylene. In this process, acetylene is dimerized to give vinyl acetylene, which is then combined with hydrogen chloride to give 4-chloro-1,2-butadiene, which, in the presence of cuprous chloride, rearranges to 2-chloro-1,3-butadiene.

References

  1. Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). doi:10.1002/cber.19130460172
  2. G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. (1963). "Monovinylacetylene". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 4, p. 683.
  3. Wallace H. Carothers, Ira Williams, Arnold M. Collins, and James E. Kirby (1937). "Acetylene Polymers and their Derivatives. II. A New Synthetic Rubber: Chloroprene and its Polymers". J. Am. Chem. Soc. 53: 4203–4225. doi:10.1021/ja01362a042.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry, 2006 John Wiley-VCH: Weinheim.doi:10.1002/14356007.a06_233.pub2
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