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・ VINYL Music
・ Vinyl On Demand
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・ Vinylacetyl-CoA Delta-isomerase
Vinylacetylene
・ Vinylbital
・ Vinylcyclohexene dioxide
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・ Vinylene group
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Vinylacetylene : ウィキペディア英語版
Vinylacetylene

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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.
Vinylacetylene is extremely dangerous because in high enough concentrations (typically > 30 mole percent, but pressure dependent) it can auto-detonate (explode without air being present) especially at elevated pressures, such as those seen in chemical plants processing C4 hydrocarbons.〔Ritzert and Berthol, Chem Ing Tech 45(3), 131-136, Feb 1973, reproduced in Viduari, J Chem Eng Data 20(3), 328-333, 1975.〕 An example of such an explosion occurred at a Union Carbide plant in Texas City in 1969.〔Carver, Chemical Process Hazards V, Paper F〕
== Synthesis ==
Vinylacetylene was first synthesized by Hofmann elimination of the related quaternary ammonium salt:〔Richard Willstätter, Theodor Wirth "Über Vinyl-acetylen" Ber., volume 46, p. 535 (1913). 〕
:()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 dehydrogenation of 1,3-butadiene.

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