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Names | |||
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Preferred IUPAC name 2,2,3-Trimethylbutane [1] | |||
Identifiers | |||
3D model (JSmol) | |||
1730756 | |||
ChemSpider | |||
ECHA InfoCard | 100.006.680 | ||
EC Number |
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PubChem CID | |||
UNII | |||
UN number | 1206 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
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 (kH) | 4.1 nmol Pa−1 kg−1 | ||
-88.36·10−6 cm3/mol | |||
Refractive index (nD) | 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 (ΔfH⦵298) | −238.0 – −235.8 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −4.80449 – −4.80349 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
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Danger | |||
H225, H302, H305, H315, H336, H400 | |||
P210, P261, P273, P301+P310, P331 | |||
NFPA 704 (fire diamond) | |||
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]
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.
Hexane or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14.
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.
Octane is a hydrocarbon and also an alkane with the chemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has many structural isomers that differ by the location of branching in the carbon chain. One of these isomers, 2,2,4-trimethylpentane (commonly called iso-octane), is used as one of the standard values in the octane rating scale.
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.
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 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.
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.
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).
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.
1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.
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.
Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor.
3-Methylpentane is a branched alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the third carbon atom in a pentane chain. It is of similar structure to the isomeric 2-methylpentane, which has the methyl group located on the second carbon of the pentane chain.
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.
2-Methylpentane, trivially known as isohexane, is a branched-chain alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the second carbon atom in a pentane chain.
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.
2,2-Dimethylpentane is one of the isomers of heptane. It is also called neoheptane as it contains the (CH3)3C grouping. It has the most extreme properties of the isomers of heptane.