Triptane (original) (raw)
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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  Ball-and-Stick model of triptane |
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|---|---|
| Names | |
| Preferred IUPAC name 2,2,3-Trimethylbutane[1] | |
| Identifiers | |
| CAS Number | 464-06-2  Y |
| 3D model (JSmol) | Interactive image |
| Beilstein Reference | 1730756 |
| ChemSpider | 9649 Y |
| ECHA InfoCard | 100.006.680  |
| EC Number | 207-346-3 |
| PubChem CID | 10044 |
| UNII | 40V943JDGR Y |
| UN number | 1206 |
| CompTox Dashboard (EPA) | DTXSID7060047 |
| InChI InChI=1S/C7H16/c1-6(2)7(3,4)5/h6H,1-5H3 YKey: ZISSAWUMDACLOM-UHFFFAOYSA-N Y |
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| SMILES CC(C)C(C)(C)C | |
| Properties | |
| Chemical formula | C7H16 |
| Molar mass | 100.205 g·mol−1 |
| Appearance | Colorless 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) |
| Henry's law constant (_k_H) | 4.1 nmol Pa−1 kg−1 |
| Magnetic susceptibility (χ) | -88.36·10−6 cm3/mol |
| Refractive index (_n_D) | 1.389 |
| Thermochemistry | |
| Heat capacity (C) | 213.51 J K−1 mol−1 |
| Std molar entropy (_S_⦵298) | 292.25 J K−1 mol−1 |
| Std enthalpy of formation (Δf_H_⦵298) | −238.0 – −235.8 kJ mol−1 |
| Std enthalpy of combustion (Δc_H_⦵298) | −4.80449 – −4.80349 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
| Pictograms |     |
| Signal word | Danger |
| Hazard statements | H225, H302, H305, H315, H336, H400 |
| Precautionary statements | P210, P261, P273, P301+P310, P331 |
| NFPA 704 (fire diamond) |  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 | Neopentane2,2-Dimethylbutane2,3-DimethylbutaneTetramethylbutaneTetraethylmethane2,2,4-Trimethylpentane2,3,3-Trimethylpentane2,3,4-TrimethylpentaneTetra-_tert_-butylmethane |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.[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]
- ^ "Triptan - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 11 March 2012.
- ^ 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.
- ^ https://webbook.nist.gov/cgi/cbook.cgi?Source=1922CHA%2FLEJ98
- ^ 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. doi:10.1016/j.apcatb.2021.120801. ISSN 0926-3373.
- ^ Perdih, A.; Perdih, F. (2006). "Chemical Interpretation of Octane Number". Acta Chimica Slovenica.
- ^ stason.org, Stas Bekman: stas (at). "10.1 The myth of Triptane". stason.org. Retrieved 2024-11-16.
- ^ Annual Report of the National Advisory Committee for Aeronautics. U.S. Government Printing Office. 1938. p. 28.
- ^ "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.