# Triptane

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Triptane
> Markdown URL: https://mediated.wiki/source/Triptane.md
> Source: https://en.wikipedia.org/wiki/Triptane
> Source revision: 1330145080
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{distinguish|text=[triptan](/source/triptan), a type of anti-migraine drug, [Tryptan](/source/Tryptan), a trade name of tryptophan, or [triplane](/source/triplane)}}
{{Chembox
| ImageFileL1 = triptane.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 100
| ImageNameL1 = Skeletal formula of triptane
| ImageFileR1 = 2,2,3trimethylbutane.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageSizeR1 = 120
| ImageNameR1 = Ball-and-Stick model of triptane
| PIN = 2,2,3-Trimethylbutane<ref>{{Cite web|title=Triptan - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/compound/10044|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=11 March 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}</ref>
|Section1={{Chembox Identifiers
| CASNo = 464-06-2
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 40V943JDGR
| PubChem = 10044
| ChemSpiderID = 9649
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 207-346-3
| UNNumber = 1206
| Beilstein = 1730756
| SMILES = CC(C)C(C)(C)C
| StdInChI = 1S/C7H16/c1-6(2)7(3,4)5/h6H,1-5H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZISSAWUMDACLOM-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=7 | H=16
| Appearance = Colorless liquid
| Odor = Odorless
| Density = 0.693 g mL<sup>−1</sup>
| MeltingPtK = 247 to 249
| BoilingPtK = 353.9 to 354.3
| VaporPressure = 23.2286 kPa (at 37.7 °C)
| HenryConstant = 4.1 nmol Pa<sup>−1</sup> kg<sup>−1</sup>
| RefractIndex = 1.389
| MagSus = −88.36·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −238.0 – −235.8 kJ mol<sup>−1</sup>
| DeltaHc = −4.80449 – −4.80349 MJ mol<sup>−1</sup>
| Entropy = 292.25 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 213.51 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|302|305|315|336|400}}
| PPhrases = {{P-phrases|210|261|273|301+310|331}}
| NFPA-H = 0
| NFPA-F = 3
| NFPA-R = 0
| FlashPtC = −7
| AutoignitionPtC = 450
| ExploLimits = 1–7%
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|[Neopentane](/source/Neopentane)|[2,2-Dimethylbutane](/source/2%2C2-Dimethylbutane)|[2,3-Dimethylbutane](/source/2%2C3-Dimethylbutane)|[Tetramethylbutane](/source/Tetramethylbutane)|[Tetraethylmethane](/source/Tetraethylmethane)|[2,2,4-Trimethylpentane](/source/2%2C2%2C4-Trimethylpentane)|[2,3,3-Trimethylpentane](/source/2%2C3%2C3-Trimethylpentane)|[2,3,4-Trimethylpentane](/source/2%2C3%2C4-Trimethylpentane)|[Tetra-''tert''-butylmethane](/source/tetra-tert-butylmethane)}}
}}
}}
'''Triptane''', or '''2,2,3-trimethylbutane''', is an [organic](/source/organic_compound) [chemical compound](/source/chemical_compound) with the molecular formula [C](/source/Carbon)<sub>7</sub>[H](/source/Hydrogen)<sub>16</sub> or (H<sub>3</sub>C-)<sub>3</sub>C-C(-CH<sub>3</sub>)<sub>2</sub>H. It is therefore an [alkane](/source/alkane), specifically the most compact and heavily branched of the [heptane](/source/heptane) isomers, the only one with a [butane](/source/butane) (C<sub>4</sub>) backbone. 

It was first synthesized in 1922 by Belgian chemists Georges Chavanne (1875–1941) and B. Lejeune, who called it '''trimethylisopropylmethane'''.<ref>{{Cite journal |last1=Chavanne |first1=G. |last2=Lejeune |first2=B. |date=March 1922 |title=Un nouvel heptane: le triméthylisopropylméthane |url=https://archive.org/details/v31_1922/v31_1922/page/n99/mode/1up |journal=Bulletin de la Société Chimique de Belgique |volume=31 |issue=3 |pages=99–102 |via=Internet Archive}}</ref><ref>{{cite web | title=No Species Found | url=https://webbook.nist.gov/cgi/cbook.cgi?Source=1922CHA%2FLEJ98 }}</ref> 

Due to its high [octane rating](/source/octane_rating) (112–113 RON, 101 MON<ref>{{Cite journal |last1=Nash |first1=Connor P. |last2=Dupuis |first2=Daniel P. |last3=Kumar |first3=Anurag |last4=Farberow |first4=Carrie A. |last5=To |first5=Anh T. |last6=Yang |first6=Ce |last7=Wegener |first7=Evan C. |last8=Miller |first8=Jeffrey T. |last9=Unocic |first9=Kinga A. |last10=Christensen |first10=Earl |last11=Hensley |first11=Jesse E. |last12=Schaidle |first12=Joshua A. |last13=Habas |first13=Susan E. |last14=Ruddy |first14=Daniel A. |date=2022-02-01 |title=Catalyst design to direct high-octane gasoline fuel properties for improved engine efficiency |url=https://www.sciencedirect.com/science/article/abs/pii/S0926337321009267 |journal=Applied Catalysis B: Environmental |volume=301 |article-number=120801 |doi=10.1016/j.apcatb.2021.120801 |bibcode=2022AppCB.30120801N |osti=1827631 |issn=0926-3373}}</ref><ref>{{Cite journal |last1=Perdih |first1=A. |last2=Perdih |first2=F. |date=2006 |title=Chemical Interpretation of Octane Number |journal=Acta Chimica Slovenica|s2cid=55494502 }}</ref>) triptane was produced on [alkylation units](/source/Alkylation_unit) starting from 1943<ref>{{Cite web |last=stason.org |first=Stas Bekman: stas (at) |title=10.1 The myth of Triptane |url=https://stason.org/TULARC/vehicles/gasoline-faq/10-1-The-myth-of-Triptane.html |access-date=2024-11-16 |website=stason.org}}</ref> for use as an [anti-knock additive](/source/anti-knock_additive) in [gasoline](/source/gasoline). It was extensively researched for this role and received the modern name in the late 1930s at a joint laboratory of [NACA](/source/National_Advisory_Committee_for_Aeronautics), [National Bureau of Standards](/source/National_Bureau_of_Standards), [US Army Air Corps](/source/United_States_Army_Air_Corps) and the [Bureau of Aeronautics](/source/Bureau_of_Aeronautics).<ref>{{Cite book |last= |first= |url=https://books.google.com/books?id=9XwiAQAAMAAJ&pg=PA28 |title=Annual Report of the National Advisory Committee for Aeronautics |date=1938 |publisher=U.S. Government Printing Office |page=28 |language=en}}</ref>

As of 2011, it was not a significant component of US automobile gasoline, present only in trace amounts (0.05–0.1%).<ref>{{cite web |date=2011 |title=Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT |website=nepis.epa.gov |publisher=United States Environmental Protection Agency}}</ref>

==See also==
*[List of gasoline additives](/source/List_of_gasoline_additives)
==References==
{{Reflist}}

Category:Alkanes

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Adapted from the Wikipedia article [Triptane](https://en.wikipedia.org/wiki/Triptane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Triptane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.