1-Butyne

Last updated
1-Butyne
Simplified skeletal formula Ethylacetylene.svg
Simplified skeletal formula
Full displayed formula But-1-yne-2D-skeletal.svg
Full displayed formula
Space-filling model 1-Butyne-3D-vdW.png
Space-filling model
Names
Preferred IUPAC name
But-1-yne
Other names
Ethylacetylene
Ethylethyne, UN 2452
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.139 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-451-3
PubChem CID
UNII
UN number 2452
  • InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3 Yes check.svgY
    Key: KDKYADYSIPSCCQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H6/c1-3-4-2/h1H,4H2,2H3
    Key: KDKYADYSIPSCCQ-UHFFFAOYAI
  • C#CCC
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:
GHS-pictogram-flamme.svg
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).
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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]

Contents

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 pre-cursor 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

References

  1. 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.
  2. ↑ "Safety Data Sheet: Ethyl Acetylene" (PDF). Airgas. 19 August 2019. Retrieved 2 April 2025.
  3. ↑ Gangolli, S.. (2005). Dictionary of Substances and Their Effects (DOSE, 3rd Electronic Edition). Royal Society of Chemistry (RSC). Retrieved from here
  4. ↑ EPA, US. "US EPA: Chemical Data Reporting: 1-Butyne". chemview.epa.gov. Retrieved 2 April 2025.
  5. ↑ 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.
  6. ↑ 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 .
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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 .
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