Names | |
---|---|
Preferred IUPAC name 2-Methylbutane [1] | |
Other names Isopentane | |
Identifiers | |
3D model (JSmol) | |
1730723 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.039 |
EC Number |
|
49318 | |
MeSH | isopentane |
PubChem CID | |
RTECS number |
|
UNII | |
UN number | 1265 |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C5H12 | |
Molar mass | 72.151 g·mol−1 |
Appearance | Colorless liquid |
Odor | Gasoline-like |
Density | 616 mg mL−1 [2] |
Melting point | −161 to −159 °C; −258 to −254 °F; 112 to 114 K |
Boiling point | 27.8 to 28.2 °C; 81.9 to 82.7 °F; 300.9 to 301.3 K |
Vapor pressure | 76.992 kPa (at 20 °C) |
Henry's law constant (kH) | 7.2 nmol Pa−1 kg−1 |
UV-vis (λmax) | 192 nm |
Refractive index (nD) | 1.354 |
Viscosity | 0.214 cP (at 20 °C) |
Thermochemistry | |
Heat capacity (C) | 164.85 J K−1 mol−1 |
Std molar entropy (S⦵298) | 260.41 J K−1 mol−1 |
Std enthalpy of formation (ΔfH⦵298) | −179.1–−177.3 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) | ~ 3.3 MJ mol−1, 19,664 Btu/lb |
Hazards | |
GHS labelling: | |
Danger | |
H224, H301, H302, H305, H336, H411 | |
P210, P261, P273, P301+P310, P331 | |
NFPA 704 (fire diamond) | |
Flash point | −51 °C (−60 °F; 222 K) |
420 °C (788 °F; 693 K) | |
Explosive limits | 1.4–8.3% |
Related compounds | |
Related alkanes | |
Related compounds | 2-Ethyl-1-butanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon (an alkane) with five carbon atoms, with formula C
5H
12 or CH(CH
3)
2(C
2H
5).
Isopentane is a volatile and flammable liquid. It is one of three structural isomers with the molecular formula C5H12, the others being pentane (n-pentane) and neopentane (2,2-dimethylpropane).
Isopentane is commonly used in conjunction with liquid nitrogen to achieve a liquid bath temperature of −160 °C. Natural gas typically contains 1% or less isopentane, [3] but it is a significant component of natural gasoline. [4]
Although the mixture of pentanes was first isolated from the destructive distillation (pyrolysis) products of the boghead coal by Charles Greville Williams in 1862. [5] In 1864–1865 two chemists tried to extract same hydrocarbons from the Pennsylvanian oil. Carl Schorlemmer noted "that a mere trace of the liquid boiled below 30°C", [6] but the first to properly separate isomers (and thus discover isopentane) was American chemist Cyrus Warren (1824–1891) slightly later, who measured the boiling point of the more volatile one at 30°C. [7]
The traditional name isopentane, attested in English as early as 1875, [8] was still retained in the 1993 IUPAC recommendations, [9] [10] but is no longer recommended according to the 2013 recommendations. [1] The preferred IUPAC name is the systematic name 2-methylbutane. An isopentyl group is a subset of the generic pentyl group. It has the chemical structure -CH3CH2CH(CH3)2.
Isopentane is used in a closed loop in geothermal power production to drive turbines. [11]
Isopentane is used, in conjunction with dry ice or liquid nitrogen, to freeze tissues for cryosectioning in histology. [12]
Isopentane is a major component (sometimes 30% or more) of natural gasoline, an analog of common petroleum-derived gasoline that is condensed from natural gas. [4] Its share in commercial car fuel is highly variable: 19–45% in 1990s Sweden, [13] 4–31% in 1990s US [14] and 3.6–11% in the US in 2011. [15] It has a substantially higher octane rating (RON 93.7) than n-pentane (61.7), and therefore there is interest in conversion from the latter. [16]
In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.
In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.
Hexane or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14.
Isobutane, also known as i-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colorless, odorless gas. It is the simplest alkane with a tertiary carbon atom. Isobutane is used as a precursor molecule in the petrochemical industry, for example in the synthesis of isooctane.
In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.
Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.
Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.
Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure.
m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.
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.
Silanes are saturated chemical compounds with the empirical formula SixHy. They are hydrosilanes, a class of compounds that includes compounds with Si−H and other Si−X bonds. All contain tetrahedral silicon and terminal hydrides. They only have Si−H and Si−Si single bonds. The bond lengths are 146.0 pm for a Si−H bond and 233 pm for a Si−Si bond. The structures of the silanes are analogues of the alkanes, starting with silane, SiH4, the analogue of methane, continuing with disilane Si2H6, the analogue of ethane, etc. They are mainly of theoretical or academic interest.
Natural gasoline is a liquid hydrocarbon mixture condensed from natural gas, similar to common gasoline (petrol) derived from petroleum.
The Penex process is a continuous catalytic process used in the refining of crude oil. It isomerizes light naphtha (C5/C6) into higher-octane, branched C5/C6 molecules. It also reduces the concentration of benzene in the gasoline pool. It was first used commercially in 1958. Ideally, the isomerization catalyst converts normal pentane (nC5) to isopentane (iC5) and normal hexane (nC6) to 2,2- and 2,3-dimethylbutane. The thermodynamic equilibrium is more favorable at low temperature.
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.
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.
Butane is an alkane with the formula C4H10. Butane exists as two isomers, n-butane with connectivity CH3CH2CH2CH3 and iso-butane with the formula (CH3)3CH. Both isomers are highly flammable, colorless, easily liquefied gases that quickly vaporize at room temperature and pressure. Butanes are a trace components of natural gases (NG gases). The other hydrocarbons in NG include propane, ethane, and especially methane, which are more abundant. Liquefied petroleum gas is a mixture of propane and some butanes.
Methylcyclopentane is an organic compound with the chemical formula CH3C5H9. It is a colourless, flammable liquid with a faint odor. It is a component of the naphthene fraction of petroleum usually obtained as a mixture with cyclohexane. It is mainly converted in naphthene reformers to benzene.
In chemical nomenclature, a descriptor is a notational prefix placed before the systematic substance name, which describes the configuration or the stereochemistry of the molecule. Some of the listed descriptors should not be used in publications, as they no longer accurately correspond with the recommendations of the IUPAC. Stereodescriptors are often used in combination with locants to clearly identify a chemical structure unambiguously.
The names 'isobutane', 'isopentane' and 'neopentane' are no longer recommended.