1-Butyne

1-Butyne
	Full displayed formula
	Space-filling model
Names
	Preferred IUPAC name But-1-yne
	Other names Ethylacetylene; Ethylethyne, UN 2452
Identifiers
CAS Number	107-00-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48087 ;
ChemSpider	7558 ;
ECHA InfoCard	100.003.139
EC Number	203-451-3;
PubChem CID	7846;
UNII	A6B47CPN6W ;
UN number	2452
CompTox Dashboard (EPA)	DTXSID4029141 ;
	InChI InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYSA-N ; InChI=1/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYAI;
	SMILES C#CCC;
Properties
Chemical formula	C4H6
Molar mass	54.091 g/mol
Odor	Acetylenic
Density	0.6783 g cm−3
Melting point	−125.7 °C (−194.3 °F; 147.5 K)
Boiling point	8.08 °C (46.54 °F; 281.23 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	P210, P377, P381, P403
Flash point	7°C (45°F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[2] 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 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]

^ "Safety Data Sheet: Ethyl Acetylene" (PDF). Airgas. 19 August 2019. Retrieved 2 April 2025.
^ ^a ^b ^c ^d ^e Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–84. ISBN 978-0-8493-0488-0.
^ 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.

[sds-1] "Safety Data Sheet: Ethyl Acetylene" (PDF). Airgas. 19 August 2019. Retrieved 2 April 2025.

[CRC-2] Lide, David R. (2008). CRC Handbook of Chemistry and Physics, 89th Edition. CRC Press. pp. 3–84. ISBN 978-0-8493-0488-0.

[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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Names
${\ce {H-C#C}}{-}{\ce {\overset {\displaystyle {H} \atop \|}{\underset {\| \atop \displaystyle {H}}{C}}}}{-}{\ce {\overset {\displaystyle {H} \atop \|}{\underset {\| \atop \displaystyle {H}}{C}}}}{\ce {-H}}$
Full displayed formula
Space-filling model
Preferred IUPAC name But-1-yne
Other names Ethylacetylene Ethylethyne, UN 2452
Identifiers
CAS Number	107-00-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48087^Y
ChemSpider	7558^Y
ECHA InfoCard	100.003.139
EC Number	203-451-3
PubChem CID	7846
UNII	A6B47CPN6W^Y
UN number	2452
CompTox Dashboard (EPA)	DTXSID4029141
InChI InChI=1S/C4H6/c1-3-4-2/h1H,4H2,2H3^Y Key: KDKYADYSIPSCCQ-UHFFFAOYSA-N^Y InChI=1/C4H6/c1-3-4-2/h1H,4H2,2H3 Key: KDKYADYSIPSCCQ-UHFFFAOYAI
SMILES C#CCC
Properties^[2]
Chemical formula	C₄H₆
Molar mass	54.091 g/mol
Odor	Acetylenic^[1]
Density	0.6783 g cm⁻³^[2]
Melting point	−125.7 °C (−194.3 °F; 147.5 K)^[2]
Boiling point	8.08 °C (46.54 °F; 281.23 K)^[2]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H220
Precautionary statements	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). Y verify (what is ^YN ?) Infobox references

1-Butyne

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