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| Vinylacetylene was first prepared by ] of the related quaternary ammonium salt:<ref>Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). {{DOI|10.1002/cber.19130460172}}</ref> | Vinylacetylene was first prepared by ] of the related quaternary ammonium salt:<ref>Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). {{DOI|10.1002/cber.19130460172}}</ref> | ||
| :I<sub>2</sub> → 2 I + HC≡C-CH=CH<sub>2</sub> | :I<sub>2</sub> → 2 I + HC≡C-CH=CH<sub>2</sub> | ||
| It is usually synthesized by ] of 1,3-dichloro-2-butene.<ref name=OS>{{OrgSynth | author = G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. | title = Monovinylacetylene | collvol = 4 | collvolpages = 683 | year = 1963 | prep = cv4p0683}}</ref> It also arises via the dimerization of acetylene. | It is usually synthesized by ] of 1,3-dichloro-2-butene.<ref name=OS>{{OrgSynth | author = G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. | title = Monovinylacetylene | collvol = 4 | collvolpages = 683 | year = 1963 | prep = cv4p0683}}</ref> It also arises via the ] of ] or ] of ]. | ||
| == Application == | == Application == | ||
Revision as of 22:39, 8 November 2011
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| 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 
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| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| 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).
 Y verify (what is ?)
Infobox references
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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 or dehydrgenation of 1,3-butadiene.
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". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 4, p. 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - 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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