Diacetylene
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| Names | |
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| Preferred IUPAC name
Buta-1,3-diyne | |
| Other names
1,3-Butadiyne
Biacetylene Butadiyne | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.641 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C4H2 | |
| Molar mass | 50.060 g·mol−1 |
| Appearance | Gas |
| Boiling point | 10 °C (50 °F; 283 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Highly flammable |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diacetylene (also known as butadiyne) is the organic compound with the formula (C2H)2. It is the simplest compound containing two triple bonds. 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 and the ethynyl radical (C2H), which is produced when acetylene undergoes photolysis. 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.[1]
Preparation
This compound may be made by the dehydrohalogenation of 1,4-dichloro-2-butyne by potassium hydroxide at low temperature:[2]
- ClCH2C≡CCH2Cl + 2 KOH → HC≡C-C≡CH + 2 KCl + 2 H2O
The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene:[3]
- 2 TMS-C≡CH → TMS-C≡C-C≡C-TMS
See also
References
- ^ "The Multiplying Mystery of Moonwater", March 18, 2010. Retrieved on 2010-03-18.
- ^ Verkruijsse, H. D.; Brandsma, L. (1991). "A Detailed Procedure for the Preparation of Butadiyne". Synthetic Communications. 21 (5): 657. doi:10.1080/00397919108020833.
- ^ Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1993). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Organic Syntheses. doi:10.15227/orgsyn.065.0052
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 63.
Further reading
- Maretina, Irina A; Trofimov, Boris A (2000). "Diacetylene: a candidate for industrially important reactions". Russian Chemical Reviews. 69 (7): 591. doi:10.1070/RC2000v069n07ABEH000564.
