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Diacetylene (also known as butadiyne) is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula C4H2. It is the simplest compound containing two
triple bond A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order o ...
s. It is first in the series of polyynes, which are of theoretical but not of practical interest.


Occurrence

Diacetylene has been identified in the atmosphere of Titan and in the protoplanetary nebula CRL 618 by its characteristic vibrational spectrum. It is proposed to arise by a reaction between
acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...
and the
ethynyl radical The ethynyl radical (systematically named λ3-ethyne and hydridodicarbon(''C''—''C'')) is an organic compound with the chemical formula C≡CH (also written CHor ). It is a simple molecule that does not occur naturally on Earth but is abundant ...
(C2H), which is produced when acetylene undergoes
photolysis Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by photons. It is defined as the interaction of one or more photons with one target molecule. ...
. This radical can in turn attack the triple bond in acetylene and react efficiently even at low temperatures. Diacetylene has also been detected on the
Moon The Moon is Earth's only natural satellite. It is the fifth largest satellite in the Solar System and the largest and most massive relative to its parent planet, with a diameter about one-quarter that of Earth (comparable to the width of ...
.


Preparation

This compound may be made by the
dehydrohalogenation In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halid ...
of 1,4-dichloro-2-butyne by
potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...
(in alcoholic medium) at ~70°C: : ClCH2C#CCH2Cl + 2 KOH -> HC#C-C#CH + 2 KCl + 2 H2O The bis(
trimethylsilyl A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom minus;Si(CH3)3 which is in turn bonded to the rest of a molecule. This structural group is ch ...
)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene: :2 Me3Si-C#CH -> Me3Si-C#C-C#C-SiMe3


See also

*
Acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...
* Diiodobutadiyne * Butenyne *
Hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...


References


Further reading

* {{Molecules detected in outer space Conjugated diynes