Vinylacetylene
| Vinylacetylene | |
|---|---|
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| Identifiers | |
| CAS number | 689-97-4 |
| PubChem | 12720 |
| ChemSpider | 12197 |
| Properties | |
| Molecular formula | C4H4 |
| Molar mass | 52.07456 g/mol |
| Appearance | colourless gas |
| Boiling point | 0–6 °C |
| Solubility in water | low |
| Hazards | |
| Main hazards | flammable |
| Flash point | < -5 °C |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
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:
- [(CH 3) 3NCH 2CH=CHCH 2N(CH 3) 3]I 2 → 2 [(CH 3) 3NH]I + HC≡C-CH=CH 2
It is usually synthesized by dehydrohalogenation of 1,3-dichloro-2-butene. It also arise 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
- Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). doi:10.1002/cber.19130460172
- G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. (1963), "Monovinylacetylene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0683; Coll. Vol. 4: 683
- 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.
- 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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