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.

Due to its high octane rating (112.8 RON, 101.3 MON [2] ) triptane has been produced on alkylation units since 1943 [3] for use as an anti-knock additive in gasoline.

See also

Related Research Articles

<span class="mw-page-title-main">Gasoline</span> Liquid fuel derived from petroleum

Gasoline or petrol is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When formulated as a fuel for engines, gasoline is chemically composed of organic compounds derived from the fractional distillation of petroleum and later chemically enhanced with gasoline additives. It is a high-volume profitable product produced in crude oil refineries.

Texaco, Inc. is an American oil brand owned and operated by Chevron Corporation. Its flagship product is its fuel "Texaco with Techron". It also owned the Havoline motor oil brand. Texaco was an independent company until its refining operations merged into Chevron in 2001, at which time most of its station franchises were divested to Shell plc through its American division.

<span class="mw-page-title-main">Tetraethyllead</span> Organolead compound

Tetraethyllead (commonly styled tetraethyl lead), abbreviated TEL, is an organolead compound with the formula Pb(C2H5)4. It was widely used as a fuel additive for much of the 20th century, first being mixed with gasoline beginning in the 1920s. This "leaded gasoline" had an increased octane rating that allowed engine compression to be raised substantially and in turn increased vehicle performance and fuel economy. TEL was first synthesised by German chemist Carl Jacob Löwig in 1853. American chemical engineer Thomas Midgley Jr., who was working for the U.S. corporation General Motors, was the first to discover its effectiveness as an antiknock agent in 1921, after spending several years attempting to find an additive that was both highly effective and inexpensive.

<span class="mw-page-title-main">Heptane</span> Chemical compound

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without causing engine knocking. The higher the octane number, the more compression the fuel can withstand before detonating. Octane rating does not relate directly to the power output or the energy content of the fuel per unit mass or volume, but simply indicates the resistance to detonating under pressure without a spark.

<span class="mw-page-title-main">Avgas</span> Aviation fuel

Avgas is an aviation fuel used in aircraft with spark-ignited internal combustion engines. Avgas is distinguished from conventional gasoline (petrol) used in motor vehicles, which is termed mogas in an aviation context. Unlike motor gasoline, which has been formulated without lead since the 1970s to allow the use of catalytic converters for pollution reduction, the most commonly used grades of avgas still contain tetraethyl lead, a toxic lead containing additive used to aid in lubrication of the engine, increase octane rating, and prevent engine knocking. There are ongoing efforts to reduce or eliminate the use of lead in aviation gasoline.

Methyl <i>tert</i>-butyl ether Chemical compound

Methyl tert-butyl ether (MTBE), also known as tert-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions.

<span class="mw-page-title-main">Super VGA</span> Graphics display resolution

Super VGA (SVGA) is a broad term that covers a wide range of computer display standards that extended IBM's VGA specification.

<span class="mw-page-title-main">Liquid fuel</span> Liquids that can be used to create energy

Liquid fuels are combustible or energy-generating molecules that can be harnessed to create mechanical energy, usually producing kinetic energy; they also must take the shape of their container. It is the fumes of liquid fuels that are flammable instead of the fluid. Most liquid fuels in widespread use are derived from fossil fuels; however, there are several types, such as hydrogen fuel, ethanol, and biodiesel, which are also categorized as a liquid fuel. Many liquid fuels play a primary role in transportation and the economy.

<span class="mw-page-title-main">Methylcyclopentadienyl manganese tricarbonyl</span> Chemical compound

Methylcyclopentadienyl manganese tricarbonyl (MMT or MCMT) is an organomanganese compound with the formula (C5H4CH3)Mn(CO)3. Initially marketed as a supplement for use in leaded gasoline, MMT was later used in unleaded gasoline to increase the octane rating. Following the implementation of the Clean Air Act (United States) (CAA) in 1970, MMT continued to be used alongside tetraethyl lead (TEL) in the US as leaded gasoline was phased out (prior to TEL finally being banned from US gasoline in 1995), and was also used in unleaded gasoline until 1977. Ethyl Corporation obtained a waiver from the U.S. EPA (Environmental Protection Agency) in 1995, which allows the use of MMT in US unleaded gasoline (not including reformulated gasoline) at a treat rate equivalent to 8.3 mg Mn/L (manganese per liter).

<span class="mw-page-title-main">DABCO</span> Chemical compound

DABCO (1,4-diazabicyclo[2.2.2]octane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.

<span class="mw-page-title-main">2,2,4-Trimethylpentane</span> Chemical compound

2,2,4-Trimethylpentane, also known as isooctane or iso-octane, is an organic compound with the formula (CH3)3CCH2CH(CH3)2. It is one of several isomers of octane (C8H18). This particular isomer is the standard 100 point on the octane rating scale (the zero point is n-heptane). It is an important component of gasoline, frequently used in relatively large proportions (around 10%) to increase the knock resistance of fuel.

<span class="mw-page-title-main">2,2-Dimethylbutane</span> Chemical compound

2,2-Dimethylbutane, trivially known as neohexane at William Odling's 1876 suggestion, is an organic compound with formula C6H14 or (H3C-)3-C-CH2-CH3. It is therefore an alkane, indeed the most compact and branched of the hexane isomers — the only one with a quaternary carbon and a butane (C4) backbone.

<span class="mw-page-title-main">Butanol fuel</span> Fuel for internal combustion engines

Butanol may be used as a fuel in an internal combustion engine. It is more similar to gasoline than it is to ethanol. A C4-hydrocarbon, butanol is a drop-in fuel and thus works in vehicles designed for use with gasoline without modification. Both n-butanol and isobutanol have been studied as possible fuels. Both can be produced from biomass (as "biobutanol" ) as well as from fossil fuels (as "petrobutanol"). The chemical properties depend on the isomer (n-butanol or isobutanol), not on the production method.

An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuel's octane rating by raising the temperature and pressure at which auto-ignition occurs. The mixture known as gasoline or petrol, when used in high compression internal combustion engines, has a tendency to knock and/or to ignite early before the correctly timed spark occurs.

The MTBE controversy concerns methyl tert-butyl ether (MTBE), a gasoline additive that replaced tetraethyllead. MTBE is an oxygenate and raises gasoline's octane number. Its use declined in the United States in response to environmental and health concerns. It has polluted groundwater due to MTBE-containing gasoline being spilled or leaked at gas stations. MTBE spreads more easily underground than other gasoline components due to its higher solubility in water. Cost estimates for removing MTBE from groundwater and contaminated soil range from $1 billion to $30 billion, including removing the compound from aquifers and municipal water supplies, and replacing leaky underground oil tanks. Who will pay for remediation is controversial. In one case, the cost to oil companies to clean up the MTBE in wells belonging to the city of Santa Monica, California is estimated to exceed $200 million.

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. It has an ethereous odor. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

N-Methylaniline (NMA) is an aniline derivative. It is an organic compound with the chemical formula C6H5NH(CH3). The substance is a colorless viscous liquid, Samples turn brown when exposed to air. The chemical is insoluble in water. It is used as a latent and coupling solvent and is also used as an intermediate for dyes, agrochemicals and other organic products manufacturing. NMA is toxic and exposure can cause damage to the central nervous system and can also cause liver and kidney failure.

The history of gasoline started around the invention of internal combustion engines suitable for use in transportation applications. The so-called Otto engines were developed in Germany during the last quarter of the 19th century. The fuel for these early engines was a relatively volatile hydrocarbon obtained from coal gas. With a boiling point near 85 °C (185 °F), it was well-suited for early carburetors (evaporators). The development of a "spray nozzle" carburetor enabled the use of less volatile fuels. Further improvements in engine efficiency were attempted at higher compression ratios, but early attempts were blocked by the premature explosion of fuel, known as knocking.

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. 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.
  3. stason.org, Stas Bekman: stas (at). "10.1 The myth of Triptane". stason.org. Retrieved 2024-11-16.