Vinylacetylene

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IUPACName=but-1-en-3-yne
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Section1=Chembox Identifiers
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PubChem=12720
SMILES=C=CC#C
Section2=Chembox Properties
Formula=C₄H₄
MolarMass=52.07456 g/mol
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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. [cite journal | author = J. A. Nieuwland, W. S. Calcott, F. B. Downing, and A. S. Carter | title = Acetylene Polymers and Their Derivatives. I. The Controlled Polymerization of Acetylene | journal = J. Am. Chem. Soc. | volume = 53 | pages = 4197-4202 | year = 1931 | doi = 10.1021/ja01362a041] Its synthesis entails dehydrohalogenation of 1,3-dichloro-2-butene. [OrgSynth | author = G. F. Hennion, Charles C. Price, and Thomas F. McKeon, Jr. | title = Monovinylacetylene | collvol = 4 | collvolpages = 683 | year = 1963 | prep = cv4p0683] The original industrial synthesis of chloroprene (2-chloro-1,3-butadiene) entailed the production of vinyl acetylene. [cite journal | author = Wallace H. Carothers, Ira Williams, Arnold M. Collins, and James E. Kirby | title = Acetylene Polymers and their Derivatives. II. A New Synthetic Rubber: Chloroprene and its Polymers | journal = J. Am. Chem. Soc. | year = 1937 | volume = 53 | pages = 4203-4225 | doi = 10.1021/ja01362a042] 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.

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