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1-Butyne

Ethylethyne, UN 2452

1-Butyne is an organic compound with the formula . It is a terminal alkyne. The compound is a common terminal alkyne substrate in diverse studies of catalysis. It is a colorless combustible gas. In 2017, 3.9 e6lbs was produced in the USA.

1-Butyne participates in reactions typical for terminal alkynes, such as alkyne metathesis, hydrogenation, condensation with formaldehyde. Based on its heat of combustion, it is slightly more stable than its isomer 2-butyne.

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.

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. Usually the catalyst is palladium, operated with liquid hydrocarbon and hydrogen gas at 20-60°C and pressures up to 10 bar.

References

References

  1. (19 August 2019). "Safety Data Sheet: Ethyl Acetylene". Airgas.
  2. Gangolli, S.. (2005). Dictionary of Substances and Their Effects (DOSE, 3rd Electronic Edition). Royal Society of Chemistry (RSC). [https://app.knovel.com/hotlink/toc/id:kpDSTEDOS3/dictionary-substances/dictionary-substances Retrieved from here]
  3. Lide, David R.. (2008). "CRC Handbook of Chemistry and Physics, 89th Edition". [[CRC Press]].
  4. "US EPA: Chemical Data Reporting: 1-Butyne".
  5. (2004). "Highly Active Trialkoxymolybdenum(VI) Alkylidyne Catalysts Synthesized by a Reductive Recycle Strategy". Journal of the American Chemical Society.
  6. (1951). "Heats of combustion, formation, and insomerization of ten C4 hydrocarbons". Journal of Research of the National Bureau of Standards.
  7. (1 January 2023). "A wide-range experimental and kinetic modeling study of the pyrolysis and oxidation of 1-butyne". Proceedings of the Combustion Institute.
  8. (1 August 2019). "Application of a catalytic membrane reactor to the selective hydrogenation of 1-Butyne". Chemical Engineering and Processing - Process Intensification.
  9. (15 January 2007). "Kinetic study of the liquid-phase hydrogenation of 1-butyne over a commercial palladium/alumina catalyst". Chemical Engineering Journal.
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