Vinylacetylene 2874515 224775196 2008-07-10T10:46:24Z 155.250.128.25 +de [[Image:Vinylacetylene-2D.png|thumb|right|Chemical structure of '''vinylacetylene''']] [[Image:Vinylacetylene-2D-skeletal.png|thumb|right|Skeletal structure of '''vinylacetylene''']] [[Image:Vinylacetylene-3D-vdW.png|thumb|right|Space-filling model of '''vinylacetylene''']] '''Vinylacetylene''' or '''butenyne''' is the [[organic compound]] with the formula C<sub>4</sub>H<sub>4</sub>. This easily condensed, colorless gas ([[boiling point|b.p.]] 5.5 °C) was discovered by workers at duPont.<ref>J. A. Nieuwland, W. S. Calcott, F. B. Downing, and A. S. Carter, “Acetylene Polymers and Their Derivatives. I. The Controlled Polymerization of Acetylene” Journal of the American Chemical Society, volume 53, 4197ff (1931). DOI: 10.1021/ja01362a041.</ref> Its synthesis entails [[dehydrohalogenation]] of 1,3-dichloro-2-butene.<ref>G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. “Monovinylacetylene” Organic Syntheses, Collected Volume 4, p.683 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0683.pdf.</ref> The original industrial synthesis of [[chloroprene]] (2-chloro-1,3-butadiene) entailed the production of vinyl acetylene.<ref>[[Wallace H. Carothers]], Ira Williams, Arnold M. Collins, and James E. Kirby “Acetylene Polymers and their Derivatives. II. A New Synthetic Rubber: Chloroprene and its Polymers” Journal of the American Chemical Society, 1937, volume 53, pp 4203 - 4225. DOI: 10.1021/ja01362a042</ref> In this process, [[acetylene]] is dimerized to give vinyl acetylene, which is then combine with [[hydrogen chloride]] to afford in succession vinyl acetylene, 3-chloro-1,2-butadiene, which, finally in the presence of [[cuprous chloride]], rearranges to the targeted 2-chloro-1,3-butadiene. ==References== <references/> [[Category:Hydrocarbons]] [[de:Butenin]] {{hydrocarbon-stub}}