acetylene

Also known as ethyne, narcylen, acetylen, ethine, vinylene

Acetylene (systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution. Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as divinyl sulfide and phosphine.

AI overview

Acetylene is a colorless gas made of hydrogen and carbon that serves as both a fuel and a key ingredient for making other chemicals. Because pure acetylene is unstable and dangerous to handle, it's typically stored and transported dissolved in a solution, and commercial versions have a strong smell added to help detect leaks.

AI-generated from the Wikipedia summary — may contain errors.

Chemical data

Formula: C2H2
Molecular weight: 26.04 g/mol
IUPAC name: acetylene
SMILES: C#C
InChIKey: HSFWRNGVRCDJHI-UHFFFAOYSA-N
XLogP: 0.4
Polar surface area: 0 Å²
H-bond donors: 0
H-bond acceptors: 0
Formal charge: 0

via PubChem

Research

43,218 papers

Acetylene in Organic Synthesis: Recent Progress and New Uses.ReviewMolecules (Basel, Switzerland) · 2018Voronin VV, Ledovskaya MS, Bogachenkov AS et al.DOI: 10.3390/molecules23102442
Thiol-Yne click chemistry of acetylene-enabled macrocyclization.Nature communications · 2022Lü S, Wang Z, Zhu SDOI: 10.1038/s41467-022-32723-0
Acetylene-based materials in organic photovoltaics.ReviewInternational journal of molecular sciences · 2010Silvestri F, Marrocchi ADOI: 10.3390/ijms11041471
Acetylene Group, Friend or Foe in Medicinal Chemistry.Journal of medicinal chemistry · 2020Talele TTDOI: 10.1021/acs.jmedchem.9b01617
Synthesis of functional poly(disubstituted acetylene)s through the post-polymerization modification route.ReviewChemical record (New York, N.Y.) · 2015Gao Y, Wang X, Sun JZ et al.DOI: 10.1002/tcr.201402064
Dichloroacetylene.ReviewIARC monographs on the evaluation of carcinogenic risks to humans · 1999
Isolation and characterization of a bis(dithiolene)-supported tungsten-acetylenic complex as a model for acetylene hydratase.Journal of inorganic biochemistry · 2024Cranswick MA, Sperber EC, Houser RP et al.DOI: 10.1016/j.jinorgbio.2024.112543
Detection of Diazotrophy in the Acetylene-Fermenting Anaerobe Pelobacter sp. Strain SFB93.Applied and environmental microbiology · 2017Akob DM, Baesman SM, Sutton JM et al.DOI: 10.1128/AEM.01198-17

via PubMed

Wikidata facts

Mass: 26.016
Autonomy: 305

Show 19 more facts

Commons category: Acetylene
canonical SMILES: C#C
chemical formula: C₂H₂
pKa: 25
NIOSH Pocket Guide ID: 0008
sublimation temperature: -84.72
density: 1.0896
vapor pressure: 44.2
solubility: 2
lower flammable limit: 2.5
upper flammable limit: 100
ionization energy: 11.4
ceiling exposure limit: 2662
standard enthalpy of formation: -227.4
combustion enthalpy: 1302
melting point: -80.75
electric dipole moment: 0
minimal lethal concentration: 900000
median lethal concentration (LC50): 850000

Sources (8)

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~16 min read

Article

23 sections

Contents

Discovery
Preparation
Partial combustion of hydrocarbons
Dehydrogenation of alkanes
Carbochemical method
Bonding
Physical properties
Changes of state
Other
Applications
Welding
Chemicals
Historical uses
Niche applications
Natural occurrence
Reactions
Vinylation reactions
Organometallic chemistry
Acid–base reactions
Hydrogenation
Safety and handling
References
External links

As an alkyne, acetylene is unsaturated because its two carbon atoms are bonded together in a triple bond. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°. The triple bond in acetylene results in a high energy content that is released when acetylene is burned.