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Triptane

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(Redirected from 2,2,3-trimethylbutane) Not to be confused with triptan, a type of anti-migraine drug, Tryptan, a trade name of tryptophan, or triplane.
Triptane
Skeletal formula of triptane
Skeletal formula of triptane
Ball-and-Stick model of triptane
Ball-and-Stick model of triptane
Names
Preferred IUPAC name 2,2,3-Trimethylbutane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1730756
ChemSpider
ECHA InfoCard 100.006.680 Edit this at Wikidata
EC Number
  • 207-346-3
PubChem CID
UNII
UN number 1206
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H16/c1-6(2)7(3,4)5/h6H,1-5H3Key: ZISSAWUMDACLOM-UHFFFAOYSA-N
SMILES
  • CC(C)C(C)(C)C
Properties
Chemical formula C7H16
Molar mass 100.205 g·mol
Appearance Colorless liquid
Odor Odorless
Density 0.693 g mL
Melting point −26 to −24 °C; −15 to −11 °F; 247 to 249 K
Boiling point 80.8 to 81.2 °C; 177.3 to 178.1 °F; 353.9 to 354.3 K
Vapor pressure 23.2286 kPa (at 37.7 °C)
Henry's law
constant (kH) 		4.1 nmol Pa kg
Magnetic susceptibility (χ) -88.36·10 cm/mol
Refractive index (nD) 1.389
Thermochemistry
Heat capacity (C) 213.51 J K mol
Std molar
entropy (S298) 		292.25 J K mol
Std enthalpy of
formation (ΔfH298) 		−238.0 – −235.8 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−4.80449 – −4.80349 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Signal word Danger
Hazard statements H225, H302, H305, H315, H336, H400
Precautionary statements P210, P261, P273, P301+P310, P331
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0 3 0
Flash point −7 °C (19 °F; 266 K)
Autoignition
temperature 		450 °C (842 °F; 723 K)
Explosive limits 1–7%
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Triptane, or 2,2,3-trimethylbutane, is an organic chemical compound with the molecular formula C7H16 or (H3C-)3C-C(-CH3)2H. It is therefore an alkane, specifically the most compact and heavily branched of the heptane isomers, the only one with a butane (C4) backbone.

It was first synthesized in 1922 by Belgian chemists Georges Chavanne (1875–1941) and B. Lejeune, who called it trimethylisopropylmethane.

Due to its high octane rating (112–113 RON, 101 MON) triptane was produced on alkylation units starting from 1943 for use as an anti-knock additive in gasoline. It was extensively researched for this role and received the modern name in the late 1930s at a joint laboratory of NACA, National Bureau of Standards, US Army Air Corps and the Bureau of Aeronautics.

As of 2011, it was not a significant component of US automobile gasoline, present only in trace amounts (0.05–0.1%).

See also

References

  1. "Triptan - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 11 March 2012.
  2. Chavanne, G.; Lejeune, B. (March 1922). "Un nouvel heptane : le triméthylisopropylméthane". Bulletin de la Société Chimique de Belgique. 31 (3): 99–102 – via Internet Archive.
  3. https://webbook.nist.gov/cgi/cbook.cgi?Source=1922CHA%2FLEJ98
  4. Nash, Connor P.; Dupuis, Daniel P.; Kumar, Anurag; Farberow, Carrie A.; To, Anh T.; Yang, Ce; Wegener, Evan C.; Miller, Jeffrey T.; Unocic, Kinga A.; Christensen, Earl; Hensley, Jesse E.; Schaidle, Joshua A.; Habas, Susan E.; Ruddy, Daniel A. (2022-02-01). "Catalyst design to direct high-octane gasoline fuel properties for improved engine efficiency". Applied Catalysis B: Environmental. 301: 120801. Bibcode:2022AppCB.30120801N. doi:10.1016/j.apcatb.2021.120801. ISSN 0926-3373. OSTI 1827631.
  5. Perdih, A.; Perdih, F. (2006). "Chemical Interpretation of Octane Number". Acta Chimica Slovenica. S2CID 55494502.
  6. stason.org, Stas Bekman: stas (at). "10.1 The myth of Triptane". stason.org. Retrieved 2024-11-16.
  7. Annual Report of the National Advisory Committee for Aeronautics. U.S. Government Printing Office. 1938. p. 28.
  8. "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
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