Triptane

{{distinguish|text=triptan, a type of anti-migraine drug, Tryptan, a trade name of tryptophan, or 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⁻¹ | MeltingPtK = 247 to 249 | BoilingPtK = 353.9 to 354.3 | VaporPressure = 23.2286 kPa (at 37.7 °C) | HenryConstant = 4.1 nmol Pa⁻¹ kg⁻¹ | RefractIndex = 1.389 | MagSus = −88.36·10⁻⁶ cm³/mol }} |Section3={{Chembox Thermochemistry | DeltaHf = −238.0 – −235.8 kJ mol⁻¹ | DeltaHc = −4.80449 – −4.80349 MJ mol⁻¹ | Entropy = 292.25 J K⁻¹ mol⁻¹ | HeatCapacity = 213.51 J K⁻¹ mol⁻¹ }} |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|2,2-Dimethylbutane|2,3-Dimethylbutane|Tetramethylbutane|Tetraethylmethane|2,2,4-Trimethylpentane|2,3,3-Trimethylpentane|2,3,4-Trimethylpentane|Tetra-''tert''-butylmethane}} }} }} '''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'''.<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 (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 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 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.<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 ==References== {{Reflist}}

Category:Alkanes