Isopentane

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Isopentane
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Template:Longitem 49318
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MeSH isopentane
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UN number 1265
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colorless liquid
Odor Gasoline-like
Density 616 mg mL−1[2]
Melting point Template:Chembox CalcTemperatures
Boiling point Template:Chembox CalcTemperatures
Vapor pressure 76.992 kPa (at 20 °C)
Template:Longitem 7.2 nmol Pa−1 kg−1
UV-vismax) 192 nm
Template:Longitem 1.354
Viscosity 0.214 cP (at 20 °C)
Template:Longitem 164.85 J K−1 mol−1
Template:Longitem 260.41 J K−1 mol−1
Template:Longitem −179.1–−177.3 kJ mol−1
Template:Longitem ~ 3.3 MJ mol−1, 19,664 Btu/lb
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Flash point Template:Chembox CalcTemperatures
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Explosive limits 1.4–8.3%
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Template:Longitem 2-Ethyl-1-butanol

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Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon (an alkane) with five carbon atoms, with formula Template:Chem/link or Template:Chem/link.

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]

History

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]

Nomenclature

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.

Uses

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]

References

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  1. a b Script error: No such module "citation/CS1".
  2. James Wei (1999), Molecular Symmetry, Rotational Entropy, and Elevated Melting Points. Ind. Eng. Chem. Res., volume 38 issue 12, pp. 5019–5027 Script error: No such module "CS1 identifiers".
  3. Georg Hammer, Torsten Lübcke, Roland Kettner, Mark R. Pillarella, Herta Recknagel, Axel Commichau, Hans-Joachim Neumann and Barbara Paczynska-Lahme "Natural Gas" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
  4. a b Ivan F. Avery, L. V. Harvey (1958): Natural-gasoline and Cycling Plants in the United States, Information circular, U.S. Department of the Interior, Bureau of Mines. 12 pages.
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  9. Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
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  11. Byproduct Isopentane also used in some of the LPG plant to run the boiler and generate the power. HS Orka HF Energy Plant IV Script error: No such module "webarchive".
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  16. Sheng Wang, Ying Zhang, Mao-Gang He, Xiong Zheng, and Li-Bin Chen (2014): "Thermal Diffusivity and Speed of Sound of Saturated Pentane from Light Scattering". International Journal of Thermophysics, volume 35, pages 1450–1464. Script error: No such module "CS1 identifiers".

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External links

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