Triptane

Last updated
Triptane
Skeletal formula of triptane Triptane.png
Skeletal formula of triptane
Ball-and-Stick model of triptane 2,2,3trimethylbutane.png
Ball-and-Stick model of triptane
Names
Preferred IUPAC name
2,2,3-Trimethylbutane [1]
Identifiers
3D model (JSmol)
1730756
ChemSpider
ECHA InfoCard 100.006.680 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-346-3
PubChem CID
UNII
UN number 1206
  • InChI=1S/C7H16/c1-6(2)7(3,4)5/h6H,1-5H3 Yes check.svgY
    Key: ZISSAWUMDACLOM-UHFFFAOYSA-N Yes check.svgY
  • CC(C)C(C)(C)C
Properties
C7H16
Molar mass 100.205 g·mol−1
AppearanceColorless liquid
Odor Odorless
Density 0.693 g mL−1
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)
4.1 nmol Pa−1 kg−1
-88.36·10−6 cm3/mol
1.389
Thermochemistry
213.51 J K−1 mol−1
Std molar
entropy
(S298)
292.25 J K−1 mol−1
−238.0 – −235.8 kJ mol−1
−4.80449 – −4.80349 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H225, H302, H305, H315, H336, H400
P210, P261, P273, P301+P310, P331
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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)
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 [77 °F], 100 kPa).

Triptane, or 2,2,3-trimethylbutane, is an organic chemical compound with the molecular formula C 7 H 16 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. [2] [3]

Due to its high octane rating (112–113 RON, 101 MON [4] [5] ) triptane was produced on alkylation units starting from 1943 [6] 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. [7]

As of 2011, it was not a significant component of US automobile gasoline, present only in trace amounts (0.05–0.1%). [8]

See also

Related Research Articles

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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.