| Revision as of 11:41, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 459576885 of page Pentane for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 20:24, 2 November 2024 edit 5.178.188.143 (talk) →ReactionsTag: Visual edit |
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{{short description|Alkane with 5 carbon atoms}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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|Watchedfields = changed |
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|verifiedrevid = 464198186 |
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| Watchedfields = changed |
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|ImageFile = Pentane-2D-Skeletal.svg |
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| verifiedrevid = 417777580 |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| Name = ''n''-Pentane |
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|ImageSize = 160 |
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| ImageFile = Pentane-2D-Skeletal.svg |
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|ImageAlt = Skeletal formula of pentane |
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| ImageSize = 200px |
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|ImageFile1 = Structure of n-Pentan.svg |
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| ImageName = Skeletal formula |
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|ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageFile2 = n-Pentan.png |
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|ImageSize1 = 160 |
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| ImageSize2 = 200px |
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|ImageAlt1 = Skeletal formula of pentane with all explicit hydrogens added |
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| ImageName2 = Structural formula |
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| ImageFile3 = Pentane-3D-space-filling.png |
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|ImageFileL2 = Pentane-3D-balls.png |
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|ImageFileL2_Ref = {{chemboximage|correct|??}} |
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| ImageSize3 = 180px |
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|ImageSizeL2 = 120 |
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| ImageName3 = Space-filling model |
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|ImageAltL2 = Pentane 3D ball.png |
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| IUPACName = pentane |
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|ImageFileR2 = Pentane-3D-space-filling.png |
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| OtherNames = ''n''-pentane<br />amyl hydride<br />Skellysolve A |
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|ImageFileR2_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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|ImageSizeR2 = 120 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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|ImageAltR2 = Pentane 3D spacefill.png |
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| DrugBank = DB03119 |
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|PIN = Pentane<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |page=59 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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|OtherNames = Quintane;<ref>{{cite journal|title=I. On the action of trichloride of phosphorus on the salts of the aromatic monamines|first=August Wilhelm Von|last=Hofmann|date=1 January 1867|journal=Proceedings of the Royal Society of London|volume=15|pages=54–62|doi=10.1098/rspl.1866.0018|s2cid=98496840}}</ref> Refrigerant-4-13-0 |
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| UNII = 4FEX897A91 |
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|Section1 = {{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 37830 |
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|CASNo = 109-66-0 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = CCCCC |
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|PubChem = 8003 |
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| InChI = 1/C5H12/c1-3-5-4-2/h3-5H2,1-2H3 |
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|ChemSpiderID = 7712 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL = 16102 |
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|UNII = 4FEX897A91 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChI = 1S/C5H12/c1-3-5-4-2/h3-5H2,1-2H3 |
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|EINECS = 203-692-4 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|UNNumber = 1265 |
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| StdInChIKey = OFBQJSOFQDEBGM-UHFFFAOYSA-N |
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|DrugBank = DB03119 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| CASNo = 109-66-0 |
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| PubChem = 8003 |
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|MeSHName = pentane |
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|ChEBI = 37830 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID = 7712 |
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| RTECS = RZ9450000 |
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|ChEMBL = 16102 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|RTECS = RZ9450000 |
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|Beilstein = 969132 |
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|Gmelin = 1766 |
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|SMILES = CCCCC |
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|StdInChI = 1S/C5H12/c1-3-5-4-2/h3-5H2,1-2H3 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = OFBQJSOFQDEBGM-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2 = {{Chembox Properties |
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|Properties_ref = <ref name="GESTIS">{{GESTIS|ZVG=10040|CAS=109-66-0|Name=n-Pentane|Date=19 April 2011}}</ref> |
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| Formula = C<sub>5</sub>H<sub>12</sub> |
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|C=5 | H=12 |
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| MolarMass = 72.15 g/mol |
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| Appearance = Colourless liquid |
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|Appearance = Colourless liquid |
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|Odor = Gasoline-like<ref name=PGCH/> |
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| Density = 0.626 g/mL, liquid |
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|Density = 0.626 g/mL; 0.6262 g/mL (20 °C) |
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| Solubility = 0.04 g/L (20 °C)<ref name="GESTIS">{{GESTIS|ZVG=10040|CAS=109-66-0|Name=n-Pentane|Date=19 April 2011}}</ref> |
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|MeltingPtK = 142.7 to 144.1 |
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| MeltingPt = −129.8 °C (143 K) |
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|BoilingPtK = 309.0 to 309.4 |
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| BoilingPt = 36.1 °C (308 K) |
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|Solubility = 40 mg/L (20 °C) |
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| pKa = ~45<!-- approximating as an alkane--> |
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|LogP = 3.255 |
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| Viscosity = 0.240 ] at 20 °C |
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|VaporPressure = 57.90 kPa (20.0 °C) |
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|HenryConstant = 7.8 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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|pKa = ~45 |
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|pKb = ~59 |
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|LambdaMax = 200 nm |
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|RefractIndex = 1.358 |
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|Viscosity = 0.240 mPa·s (at 20 °C) |
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|MagSus = -63.05·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3 = {{Chembox Thermochemistry |
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|DeltaHf = −174.1–−172.9 kJ mol<sup>−1</sup> |
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| MolShape = |
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|DeltaHc = −3.5095–−3.5085 MJ mol<sup>−1</sup> |
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|Entropy = 263.47 J K<sup>−1</sup> mol<sup>−1</sup> |
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|HeatCapacity = 167.19 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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|Section4 = {{Chembox Hazards |
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|GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}} |
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| MainHazards = Highly flammable ('''F+''')<br>Harmful ('''Xn''')<br>Dangerous for the environment ('''N''') |
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|GHSSignalWord = '''DANGER''' |
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| NFPA-H = 1 |
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|HPhrases = {{H-phrases|225|304|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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| FlashPt = – 49 °C |
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|NFPA-F = 4 |
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| Autoignition = 260 °C |
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|NFPA-R = 0 |
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| RSPhrases = ]: {{R12}}, {{R51/53}}, {{R65}},<br />{{R66}}, {{R67}}<br />]: {{S2}}, {{S9}}, {{S16}},<br />{{S29}}, {{S33}}, {{S61}}, {{S62}} |
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|FlashPtC = −49.0 |
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|AutoignitionPtC = 260.0 |
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|ExploLimits = 1.5–7.8%<ref name=PGCH/> |
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|LD50 = {{Unbulleted list|3 g kg<sup>−1</sup> <small>(dermal, rabbit)</small>|5 g kg<sup>−1</sup> <small>(oral, mouse)</small>}} |
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|IDLH = 1500 ppm<ref name=PGCH>{{PGCH|0486}}</ref> |
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|REL = TWA 120 ppm (350 mg/m<sup>3</sup>) C 610 ppm (1800 mg/m<sup>3</sup>) <ref name=PGCH/> |
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|PEL = TWA 1000 ppm (2950 mg/m<sup>3</sup>)<ref name=PGCH/> |
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|LC50 = 130,000 mg/m<sup>3</sup> (mouse, 30 min)<br/>128,200 ppm (mouse, 37 min)<br/>325,000 mg/m<sup>3</sup> (mouse, 2 hr)<ref>{{IDLH|109660|n-Pentane}}</ref> |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section5 = {{Chembox Related |
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|OtherFunction_label = alkanes |
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| Function = ]s |
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| OtherFunctn = ], ],<br />], ] |
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|OtherFunction = {{Unbulleted list|]|]|]}} |
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| OtherCpds = ]}} |
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}} |
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}} |
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}} |
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'''Pentane''' is an ] with the ] C<sub>5</sub>H<sub>12</sub>—that is, an ] with five ] atoms. The term may refer to any of three ], or to a mixture of them: in the ] nomenclature, however, '''pentane''' means exclusively the ''n''-pentane isomer, in which case ] refers to a mixture of them; the other two are called ] (methylbutane) and ] (dimethylpropane). ] is not an isomer of pentane because it has only 10 ] atoms where pentane has 12. |
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Pentanes are components of some fuels and are employed as specialty ]s in the ]. Their properties are very similar to those of ]s and ]s. |
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==Isomers== |
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{{main|C5H12}} |
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{| class="wikitable" style="text-align:left" |
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| bgcolor="#ddeeff" |Common name |
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|'''normal ]'''<br/>'''unbranched pentane'''<br/>'''''n''-pentane''' |
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|''']''' |
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|''']''' |
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| bgcolor="#ddeeff" |IUPAC name |
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|'''pentane''' |
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|'''2-methylbutane''' |
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|'''2,2-dimethylpropane''' |
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| bgcolor="#ddeeff" |] |
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|] |
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|] |
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|] |
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|] |
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|] |
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|] |
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|- |
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| bgcolor="#ddeeff" |] (°C)<ref name="Wei2">{{cite journal | doi = 10.1021/ie990588m| title = Molecular Symmetry, Rotational Entropy, and Elevated Melting Points| date = 1999| last1 = Wei| first1 = James| journal = Industrial & Engineering Chemistry Research| volume = 38| issue = 12| pages = 5019–5027}}</ref> |
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| −129.8 |
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| −159.9 |
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| −16.6 |
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| bgcolor="#ddeeff" |] (°C)<ref name="Wei2"/> |
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| 36.0 |
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| 27.7 |
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| 9.5 |
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| bgcolor="#ddeeff" |]<br/>(0 °C,kg/m<sup>3</sup>)<ref name="Wei2"/> |
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| 621 |
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| 616 |
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| 586 |
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==Industrial uses== |
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Pentanes are some of the primary ]s used in the production of ] and other foams. Usually, a mixture of n-, i-, and increasingly cyclopentane is used for this purpose. |
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Acid-catalyzed isomerization gives isopentane, which is used in producing high-octane fuels.<ref name=Ullmanns>{{cite encyclopedia |author=Karl Griesbaum |author2=Arno Behr |author3=Dieter Biedenkapp |author4=Heinz-Werner Voges |author5=Dorothea Garbe |author6=Christian Paetz |author7=Gerd Collin |author8=Dieter Mayer |author9=Hartmut Höke |chapter=Hydrocarbons|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a13_227|isbn=978-3-527-30673-2}}</ref> |
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Because of their low ]s, low cost, and relative safety, pentanes are used as a ] in ] stations and ]s. It is also used in some blended ]s. |
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Pentanes are solvents in many ordinary products, e.g. in some ]s.<ref name=Milne>{{cite book|editor-last=Milne|editor-first=G. W. A.|title=Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties|date=2005|publisher=John Wiley & Sons, Inc|location=Hoboken, New Jersey|isbn=978-0-471-73518-2|page=477}}</ref> |
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==Laboratory use== |
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Pentanes are relatively inexpensive and are the most ] liquid alkanes at room temperature, so they are often used in the laboratory as ]s that can be conveniently and rapidly evaporated. However, because of their ]ity and lack of ], they dissolve only nonpolar and alkyl-rich compounds. Pentanes are ] with most common nonpolar solvents such as ]s, ]s, and ]s. |
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They are often used in ]. |
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==Physical properties== |
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The ]s of the pentane isomers range from about 9 to 36 °C. As is the case for other alkanes, the more thickly branched isomers tend to have lower boiling points. |
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The same tends to be true for the ]s of alkane isomers, and that of isopentane is 30 °C lower than that of ''n''-pentane. However, the melting point of ], the most heavily branched of the three, is 100 °C ''higher'' than that of isopentane. The anomalously high melting point of neopentane has been attributed to the ] ] packing more closely in solid form; this explanation is contradicted by the fact that neopentane has a lower density than the other two isomers,<ref name="Wei">{{cite journal | last=Wei | first=James | title=Molecular Symmetry, Rotational Entropy, and Elevated Melting Points | journal=Industrial & Engineering Chemistry Research | publisher=American Chemical Society (ACS) | volume=38 | issue=12 | year=1999 | issn=0888-5885 | doi=10.1021/ie990588m | pages=5019–5027}}</ref> and the high melting point is actually caused by neopentane's significantly lower ]. |
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The branched ]s are more stable (have lower ] and ]) than n-pentane. The difference is 1.8 ]/] for isopentane, and 5 kcal/mol for neopentane.<ref>From the values listed at ].</ref><ref name="Good 1970 pp. 237–244">{{cite journal | last=Good | first=W.D | title=The enthalpies of combustion and formation of the isomeric pentanes | journal=The Journal of Chemical Thermodynamics | publisher=Elsevier BV | volume=2 | issue=2 | year=1970 | issn=0021-9614 | doi=10.1016/0021-9614(70)90088-1 | pages=237–244}}</ref> |
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] about two central single C-C ] of ''n''-pentane produces four different ].<ref name=Balabin_2009>{{cite journal |journal=J. Phys. Chem. A |volume = 113 |issue = 6 |pages = 1012–9 |doi=10.1021/jp809639s |title=Enthalpy Difference between Conformations of Normal Alkanes: Raman Spectroscopy Study of n-Pentane and n-Butane |year=2009 |author=Roman M. Balabin |pmid=19152252|bibcode = 2009JPCA..113.1012B |author-link = Roman Balabin }}</ref> |
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==Reactions== |
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Like other ], pentanes are largely unreactive at standard room temperature and conditions - however, with sufficient ] (e.g., an open flame), they readily ] to form ] and water: |
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:C<sub>5</sub>H<sub>12</sub> + 8 O<sub>2</sub> → 5 CO<sub>2</sub> + 6 H<sub>2</sub>O + heat/energy |
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Like other ], pentanes undergo ] ]: |
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:C<sub>5</sub>H<sub>12</sub> + Cl<sub>2</sub> → C<sub>5</sub>H<sub>11</sub>Cl + HCl |
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Without zeolite catalysts, such reactions are unselective, so with ''n''-pentane, the result is a mixture of the 1-, 2-, and 3-chloropentanes, as well as more highly chlorinated derivatives. Other radical ]s can also occur. |
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==Production and occurrence== |
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Pentane is produced by ] of ] and purified by ] (successive distillations).<ref name="PubChem">{{Cite web|title=Pentane|url=https://pubchem.ncbi.nlm.nih.gov/compound/Pentane|access-date=2023-06-29|website=PubChem}}</ref> |
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It occurs in alcoholic beverages and in ].<ref name="PubChem" /> It is a component of exhaled breath for some individuals. A degradation product of unsaturated fatty acids, its presence is associated with some diseases and cancers.<ref>{{cite journal|doi=10.1016/S0378-4347(99)00127-9|pmid=10410929|title=Variation in volatile organic compounds in the breath of normal humans|journal=Journal of Chromatography B: Biomedical Sciences and Applications|volume=729|issue=1–2|pages=75–88|year=1999|last1=Phillips|first1=Michael|last2=Herrera|first2=Jolanta|last3=Krishnan|first3=Sunithi|last4=Zain|first4=Mooena|last5=Greenberg|first5=Joel|last6=Cataneo|first6=Renee N.}}</ref> |
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==References== |
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{{Reflist}} |
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==External links== |
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* at ILO.org |
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* at CDC.gov |
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* at Ars-grin.gov |
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{{Alkanes}} |
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{{Hydrides by group}} |
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] |
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] |