File:NFPA_704.svg · Wikimedia Commons · See Wikimedia Commons
acetylene
Sign in to saveAlso 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.
OverviewAI-generated
Acetylene is a chemical compound with the formula C₂H₂ and a molecular mass of 26.016. It has a melting point of -80.75 and sublimation temperatures of -83.9 and -84.72. The substance possesses a density of 1.0896 and a vapor pressure of 44.2. Its pKa is 25, and it has an ionization energy of 11.4. The electric dipole moment is 0, while the standard enthalpy of formation is -227.4 and the combustion enthalpy is 1302.
Safety data indicates a lower flammable limit of 2.5 and an upper flammable limit of 100. The autoignition temperature is 305, and the ceiling exposure limit is 2662. The minimal lethal concentration is 900000, with a median lethal concentration (LC50) of 850000. Acetylene has a solubility of 2. In computational chemistry, it is represented by the SMILES string C#C and has an xlogp of 0.4.
Synthesized by Vinony from 35 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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 Ų
- 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
- Has use
- fuel
Show 22 more facts
- described by source
- Granat Encyclopedic Dictionary
- 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
- different from
- ethane
- subject has role
- reducing agent
- electric dipole moment
- 0
- minimal lethal concentration
- 900000
- median lethal concentration (LC50)
- 850000
Sources (8)
via Wikidata · CC0
~16 min read
Encyclopedic overview
23 sectionsContents
- 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
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.
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.
Excerpted from Wikipedia’s “acetylene” article, available under the CC BY-SA 4.0 licence.
Gallery (230)
Available in 75 languages
- Español
- Français
- Deutsch
- 中文
- 日本語
- Русский
- Português
- Italiano
- العربية
- हिन्दी
- Afrikaans
- Albanian
- Armenian
- azb
- Azerbaijani
- Bahasa Indonesia
- Bangla
- Basque
Show 56 more
- Belarusian
- Bosnian
- Bulgarian
- Burmese
- Catalan
- Croatian
- Czech
- Danish
- Esperanto
- Estonian
- Finnish
- Galician
- Georgian
- Greek
- Hebrew
- Hungarian
- Ido
- Irish
- Javanese
- Kannada
- Kazakh
- Kyrgyz
- Latvian
- Lithuanian
- Macedonian
- Malay
- Malayalam
- Nederlands
- Nepali
- Norwegian
- Norwegian Nynorsk
- Polski
- Romanian
- Serbian
- Serbian (Latin)
- Sicilian
- simple
- Sinhala
- Slovak
- Slovenian
- Svenska
- Tajik
- Tamil
- Tatar
- Telugu
- Tiếng Việt
- Türkçe
- Ukrainian
- Urdu
- Uzbek
- Wu Chinese
- zh_classical
- zh_yue
- فارسی
- ไทย
- 한국어
via Wikidata sitelinks · CC0