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Latest revision as of 13:57, 9 April 2024 edit undoAumur (talk | contribs)2 editsm neopentane (2,2-dimethylpropane)Tag: Visual edit |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443885058 |
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| Watchedfields = changed |
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| Name = Isopentane |
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| verifiedrevid = 464398176 |
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| ImageFile = 2-methylbutane-2D-skeletal.svg |
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| ImageFile = Isopentane-2D-skeletal.svg |
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| ImageSize = 140px |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = Isopentane |
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| ImageSize = 100 |
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| ImageFile1 = Isopentane-3D-balls.png |
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| ImageName = Skeletal formula of isopentane |
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| ImageSize1 = 140px |
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| ImageName1 = Isopentane |
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| ImageFile1 = Isopentane.PNG |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| IUPACName = 2-Methylbutane |
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| ImageSize1 = 160 |
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| OtherNames = Methylbutane |
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| ImageName1 = Skeletal formula of isopentane with all implicit carbons shown, and all explicit hydrogens added |
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| Section1 = {{Chembox Identifiers |
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| ImageFile2 = Isopentane-3D-balls.png |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ChEBI = 30362 |
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| SMILES = CC(C)CC |
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| ImageSize2 = 100 |
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| ImageName2 = Ball and stick model of isopentane |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = 2-Methylbutane<ref name="IUPAC2013_652">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 652 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The names ‘isobutane’, ‘isopentane’ and ‘neopentane’ are no longer recommended.}}</ref> |
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| OtherNames = Isopentane |
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|Section1={{Chembox Identifiers |
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| CASNo = 78-78-4 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 6556 |
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| ChemSpiderID = 6308 |
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| ChemSpiderID = 6308 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = ZH67814I0O |
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| UNII = ZH67814I0O |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3 |
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| EINECS = 201-142-8 |
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| InChIKey = QWTDNUCVQCZILF-UHFFFAOYAE |
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| UNNumber = 1265 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| MeSHName = isopentane |
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| ChEBI = 30362 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| RTECS = EK4430000 |
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| Beilstein = 1730723 |
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| Gmelin = 49318 |
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| SMILES = CCC(C)C |
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| StdInChI = 1S/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3 |
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| StdInChI = 1S/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QWTDNUCVQCZILF-UHFFFAOYSA-N |
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| StdInChIKey = QWTDNUCVQCZILF-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 78-78-4 |
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}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section2={{Chembox Properties |
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| RTECS = EK4430000 |
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| C=5 | H=12 |
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}} |
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| Appearance = Colorless liquid |
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| Section2 = {{Chembox Properties |
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| Odor = Gasoline-like |
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| Formula = C<sub>5</sub>H<sub>12</sub> |
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| Density = 616 mg mL<sup>−1</sup><ref name="Wei">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}}</ref> |
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| MolarMass = 72.15 g/mol |
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| BoilingPtK = 300.9 to 301.3 |
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| Appearance = colorless liquid |
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| MeltingPtK = 112 to 114 |
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| Density = 0.616 g/ml, liquid<ref name="Wei"/> |
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| VaporPressure = 76.992 kPa (at 20 °C) |
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| Solubility = Immiscible |
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| HenryConstant = 7.2 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| MeltingPt = −159.9 °C (113.3 K)<ref name="Wei"/> |
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| LambdaMax = 192 nm |
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| BoilingPt = 27.7 °C (300.9 K)<ref name="Wei"> |
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| RefractIndex = 1.354 |
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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}} |
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| Viscosity = 0.214 cP (at 20 °C) |
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</ref> |
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}} |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = −179 kJ/mol |
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| DeltaHf = −179.1–−177.3 kJ mol<sup>−1</sup> |
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| DeltaHc = −3504 kJ/mol |
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| DeltaHc = ~ 3.3 MJ mol<sup>−1</sup>, 19,664 Btu/lb |
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| Entropy = 260.7 J·K<sup>−1</sup>·mol<sup>−1</sup> |
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| Entropy = 260.41 J K<sup>−1</sup> mol<sup>−1</sup> |
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| HeatCapacity = 164.85 J K<sup>−1</sup> mol<sup>−1</sup> |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section5={{Chembox Hazards |
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| ExternalMSDS = |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}} |
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| EUClass = Highly flammable ('''F+''')<br />Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''') |
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| GHSSignalWord = '''DANGER''' |
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| NFPA-H = 1 |
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| HPhrases = {{H-phrases|224|301|302|305|336|411}} |
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| NFPA-F = 4 |
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| PPhrases = {{P-phrases|210|261|273|301+310|331}} |
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| NFPA-R = |
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| NFPA-H = 1 |
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| RPhrases = {{R12}}, {{R51/53}}, {{R65}},<br />{{R66}}, {{R67}} |
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| NFPA-F = 4 |
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| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S29}},<br />{{S33}}, {{S61}}, {{S62}} |
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| NFPA-R = 0 |
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| FlashPt = <−51 °C |
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| FlashPtC = −51 |
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| Autoignition = 420 °C |
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| AutoignitionPtC = 420 |
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| ExploLimits = 1.4–7.6% |
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| ExploLimits = 1.4–8.3% |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section6={{Chembox Related |
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| Function = ] |
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| OtherFunction_label = alkanes |
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| OtherFunctn = ]<br />]<br />] |
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| OtherFunction = {{Unbulleted list|]|]|]|]}} |
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| OtherCpds = ]<br />] |
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| OtherCompounds = ] |
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}} |
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}} |
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'''Isopentane''', also called '''methylbutane''' or '''2-methylbutane''', is a branched-chain saturated ] (an ]) with five ] atoms, with formula {{chem|C|5|H|12}} or {{chem|CH(CH|3|)|2|(C|2|H|5|)}}. |
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Isopentane is a ] and ] liquid. It is one of three ] with the ] C<sub>5</sub>H<sub>12</sub>, the others being ] (''n''-pentane) and ] (2,2-dimethylpropane). |
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'''Isopentane''', ]], also called '''methylbutane''' or '''2-methylbutane''', is a branched-chain ] with five ] atoms. Isopentane is an extremely ] and extremely ] liquid at room ] and ]. The ] is just a few degrees above room temperature and isopentane will readily boil and evaporate away on a warm day. Isopentane is commonly used in conjunction with ] to achieve a liquid bath temperature of -160 °C. |
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Isopentane is commonly used in conjunction with ] to achieve a liquid bath temperature of −160 °C. ] typically contains 1% or less isopentane,<ref>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}}</ref> but it is a significant component of ].<ref name=aver1958>Ivan F. Avery, L. V. Harvey (1958): '''', Information circular, U.S. Department of the Interior, Bureau of Mines. 12 pages.</ref> |
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An '''isopentyl''' group is a subset of the generic pentyl group. It has the chemical structure -CH<sub>3</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>. |
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==Nomenclature== |
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==Nomenclature== |
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Isopentane is the name recommended by the ] (IUPAC) in its ''1993 Recommendations for the Nomenclature of Organic Chemistry''.<ref>{{cite book | author=Panico, R.; & Powell, W. H. (Eds.) | title=A Guide to IUPAC Nomenclature of Organic Compounds 1993 | location=Oxford | publisher=Blackwell Science | year=1994 | isbn = 0-632-03488-2 | url = http://www.acdlabs.com/iupac/nomenclature/93/r93_679.htm}}</ref> It is one of only four acyclic hydrocarbons to retain its pre-IUPAC name. |
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The traditional name isopentane was still retained in the 1993 ] recommendations,<ref></ref><ref name="panico">{{cite book | editor=Panico, R. | editor2= Powell, W. H. | name-list-style= amp | title=A Guide to IUPAC Nomenclature of Organic Compounds 1993 | location=Oxford | publisher=Blackwell Science | year=1994 | isbn=0-632-03488-2}} |
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An isopentyl group is a subset of the generic pentyl group. It has the chemical structure -CH<sub>3</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>. |
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</ref> but is no longer recommended according to the 2013 recommendations.<ref name="IUPAC2013_652"/> 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 -CH<sub>3</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub>. |
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==Isomers== |
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Isopentane is one of three ] with the ] C<sub>5</sub>H<sub>12</sub>, the others being ] (''n''-pentane) and dimethyl propane (]). |
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==Uses== |
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==Uses== |
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Isopentane is used in a closed loop in geothermal power production to drive turbines.<ref>Byproduct Isopentane also used in some of the LPG plant to run the boiler and generate the power. |
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Isopentane is one of the ingredients in both ]® and ]®.<ref></ref> |
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{{Webarchive|url=https://web.archive.org/web/20141018154915/http://hsorka.is/english/HSProduction/Svartsengi/OrkuverIV.aspx |date=2014-10-18 }}</ref> |
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Isopentane is used, in conjunction with ] or liquid nitrogen, to freeze ] for ]ing in ]. |
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<ref>{{Cite web|url=http://www.uab.edu/research/administration/offices/ARP/ComparativePathology/Pathology/Histopathology/TissueSubmission/Pages/Freezing-Tissues-for-Cryosectioning.aspx|title = Animal Resources Program - the Office of the Vice President for Research | UAB}}</ref> |
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Isopentane is a major component (sometimes 30% or more) of natural gasoline, an analog of common ]-derived ] that is condensed from natural gas.<ref name=aver1958/> It has a substantially higher ] (RON 93.7) than ''n''-pentane (61.7), and therefore there is interest in conversion from the latter.<ref name=wang2014>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}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Reflist}} |
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==External links== |
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==External links== |
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* (online version of the "''Blue Book''") |
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* (online version of the "''Blue Book''") |
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{{alkanes}} |
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{{Alkanes}} |
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{{Authority control}} |
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