Vinylacetylene
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Vinylacetylene or butenyne is the organic compound with the formula C4H4. This easily condensed, colorless gas (b.p. 5.5 °C) was discovered by workers at duPont.[1] Its synthesis entails dehydrohalogenation of 1,3-dichloro-2-butene.[2] The original industrial synthesis of chloroprene (2-chloro-1,3-butadiene) entailed the production of vinyl acetylene.[3] 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.
[edit] References
- ^ 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.
- ^ 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.
- ^ 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
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