1-Butyne
 | |
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
But-1-yne | |
| Other names
Ethylacetylene Ethylethyne, UN 2452 | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.139 |
| EC Number |
|
PubChem CID |
|
| UNII | |
| UN number | 2452 |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties[1] | |
| C4H6 | |
| Molar mass | 54.091 g/mol |
| Odor | Acetylenic[2] |
| Density | 0.6783 g cm−3[1] |
| Melting point | −125.7 °C (−194.3 °F; 147.5 K)[1] |
| Boiling point | 8.08 °C (46.54 °F; 281.23 K)[1] |
| Hazards | |
| GHS labelling: | |
 | |
| Danger | |
| H220 | |
| P210, P377, P381, P403 | |
| Flash point | 7°C (45°F)[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
1-Butyne is an organic compound with the formula CH3CH2C≡CH. It is a terminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustible gas.[1] In 2017, 3.9 million pounds (1,700 long tons) was produced in the USA.[4]
1-Butyne participates in reactions typical for terminal alkynes, such as alkyne metathesis,[5] hydrogenation, condensation with formaldehyde. Based on its heat of combustion, it is slightly more stable than its isomer 2-butyne.[6]
The combustion of 1-Butyne produces propargyl radicals, a precursor to soot and polycyclic aromatic hydrocarbons, as the propargyl radicals can form basic aromatic rings, making butyne's fuel usage a concern for emissions.[7]
1-Butyne is in unsaturated C4 petroleum cuts, and has to be separated out in industrial hydrorefining to make 1-butene, which is used to make low density polyethylene and polybutene. Distillation is impractical due to similar boiling points, so 1-butyne is removed by catalytic hydrogenation.[8] Usually the catalyst is palladium, operated with liquid hydrocarbon and hydrogen gas at 20-60°C and pressures up to 10 bar.[9]
See also
[edit]References
[edit]- 1 2 3 4 5 Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–84. ISBN 978-0-8493-0488-0.
- ↑ "Safety Data Sheet: Ethyl Acetylene" (PDF). Airgas. 19 August 2019. Retrieved 2 April 2025.
- ↑ Gangolli, S.. (2005). Dictionary of Substances and Their Effects (DOSE, 3rd Electronic Edition). Royal Society of Chemistry (RSC). Retrieved from here
- ↑ EPA, US. "US EPA: Chemical Data Reporting: 1-Butyne". chemview.epa.gov. Retrieved 2 April 2025.
- ↑ Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. (2004). "Highly Active Trialkoxymolybdenum(VI) Alkylidyne Catalysts Synthesized by a Reductive Recycle Strategy". Journal of the American Chemical Society. 126 (1): 329–335. doi:10.1021/ja0379868. PMID 14709099.
- ↑ Prosen, E.J.; Maron, F.W.; Rossini, F.D. (1951). "Heats of combustion, formation, and insomerization of ten C4 hydrocarbons". Journal of Research of the National Bureau of Standards. 46 (2): 106. doi:10.6028/jres.046.015.
- ↑ Lu, Haitao; Dong, Shijun; Liu, Fuqiang; Nagaraja, Shashank S.; Lindblade, Nathan; Turner, Mattias A.; Mathieu, Olivier; Petersen, Eric L.; Vilchez, Jesús Caravaca; Heufer, Karl Alexander; Xu, Gang; Sarathy, S. Mani; Curran, Henry J. (1 January 2023). "A wide-range experimental and kinetic modeling study of the pyrolysis and oxidation of 1-butyne". Proceedings of the Combustion Institute. 39 (1): 355–364. doi:10.1016/j.proci.2022.09.044. hdl:10754/686057. Retrieved 2 April 2025.
- ↑ García Colli, G.; Alves, J. A.; Martínez, O. M.; Barreto, G. F. (1 August 2019). "Application of a catalytic membrane reactor to the selective hydrogenation of 1-Butyne". Chemical Engineering and Processing - Process Intensification. 142: 107518. doi:10.1016/j.cep.2019.04.018.
- ↑ Alves, J. A.; Bressa, S. P.; Martínez, O. M.; Barreto, G. F. (15 January 2007). "Kinetic study of the liquid-phase hydrogenation of 1-butyne over a commercial palladium/alumina catalyst". Chemical Engineering Journal. 125 (3): 131–138. doi:10.1016/j.cej.2006.08.006. hdl:11336/54075.