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    Isopentane

    Topic: Chemistry

     From Handwiki - Reading time: 3 min
    Isopentane
    Skeletal formula of isopentane
    Skeletal formula of isopentane with all implicit carbons shown, and all explicit hydrogens added
    Ball and stick model of isopentane
    Names
    Preferred IUPAC name
    2-Methylbutane[1]
    Other names
    Isopentane
    Identifiers
    3D model (JSmol)
    1730723
    ChEBI
    ChemSpider
    EC Number
    • 201-142-8
    49318
    MeSH isopentane
    RTECS number
    • EK4430000
    UNII
    UN number 1265
    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)
    7.2 nmol Pa−1 kg−1
    UV-vis (λmax) 192 nm
    1.354
    Viscosity 0.214 cP (at 20 °C)
    Thermochemistry
    164.85 J K−1 mol−1
    260.41 J K−1 mol−1
    −179.1–−177.3 kJ mol−1
    ~ 3.3 MJ mol−1, 19,664 Btu/lb
    Hazards
    GHS pictograms GHS02: Flammable GHS07: Harmful GHS08: Health hazard GHS09: Environmental hazard
    GHS Signal word DANGER
    H224, H301, H302, H305, H336, H411
    P210, P261, P273, P301+310, P331
    NFPA 704 (fire diamond)
    Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
    4
    1
    0
    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).
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    Infobox references
    Tracking categories (test):

    Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon (an alkane) with five carbon atoms, with formula C5H12 or CH(CH3)2(C2H5).

    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 (dimethyl propane).

    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]

    Nomenclature

    The traditional name isopentane was still retained in the 1993 IUPAC recommendations,[5][6] 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.[7]

    Isopentane is used, in conjunction with dry ice or liquid nitrogen, to freeze tissues for cryosectioning in histology. [8]

    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] 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.[9]

    References

    1. ↑ 1.0 1.1 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 652. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. "The names ‘isobutane’, ‘isopentane’ and ‘neopentane’ are no longer recommended." 
    2. ↑ James Wei (1999), Molecular Symmetry, Rotational Entropy, and Elevated Melting Points. Ind. Eng. Chem. Res., volume 38 issue 12, pp. 5019–5027 doi:10.1021/ie990588m
    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. doi:10.1002/14356007.a17_073.pub2
    4. ↑ 4.0 4.1 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.
    5. ↑ Table 19(a) Acyclic and monocyclic hydrocarbons. Parent hydrocarbons
    6. ↑ Panico, R., ed (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2. 
    7. ↑ Byproduct Isopentane also used in some of the LPG plant to run the boiler and generate the power. HS Orka HF Energy Plant IV
    8. ↑ "Animal Resources Program - the Office of the Vice President for Research | UAB". http://www.uab.edu/research/administration/offices/ARP/ComparativePathology/Pathology/Histopathology/TissueSubmission/Pages/Freezing-Tissues-for-Cryosectioning.aspx. 
    9. ↑ 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. doi:10.1007/s10765-014-1718-x

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