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Saving copy of the {{chembox}} taken from revid 464361478 of page Butane for the Chem/Drugbox validation project (updated: ''). |
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{{Short description|Organic compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Butane|oldid=464361478}} 464361478] of page [[Butane]] with values updated to verified values.}} |
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{{Distinguish|butene|butyne|Bhutan}} |
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{{chembox |
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{{Use dmy dates|date=March 2021}} |
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| verifiedrevid = 408554574 |
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{{Chembox |
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| Name = ''n''-Butane |
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| Watchedfields = changed |
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| ImageFileL1 = Butane-2D-Skeletal.svg |
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| verifiedrevid = 464365466 |
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| ImageSizeL1 = 120px |
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| ImageFileL1 = Butan Lewis.svg |
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| ImageNameL1 = skeletal structure of the butane molecule |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileR1 = Butane-2D-flat.png |
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| ImageSizeL1 = 130px |
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| ImageAltL1 = Skeletal formula of butane with all carbon and hydrogen atoms shown |
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| ImageNameR1 = displayed structure of the butane molecule |
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| ImageFileR1 = Butane simple.svg |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageSizeR1 = 110px |
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| ImageAltR1 = Skeletal formula of butane with all implicit hydrogens shown |
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| ImageFileL2 = Butane-3D-balls.png |
| ImageFileL2 = Butane-3D-balls.png |
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| ImageFileL2_Ref = {{chemboximage|correct|??}} |
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| ImageSizeL2 = 120px |
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| ImageSizeL2 = 130px |
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| ImageNameL2 = ball-and-stick model of the butane molecule |
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| ImageAltL2 = Ball-and-stick model of the butane molecule |
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| ImageFileR2 = Butane-3D-space-filling.png |
| ImageFileR2 = Butane-3D-space-filling.png |
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| ImageFileR2_Ref = {{chemboximage|correct|??}} |
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| ImageSizeR2 = 120px |
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| ImageSizeR2 = 110px |
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| ImageNameR2 = space-filling model of the butane molecule |
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| ImageAltR2 = Space-filling model of the butane molecule |
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| PIN = butane |
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| PIN = Butane<ref name=iupac2013>{{cite book |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) |chapter=General Principles, Rules, and Conventions |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |date=2014 |location=Cambridge |at=P-12.1 |doi=10.1039/9781849733069-00001 |isbn=978-0-85404-182-4 |quote=Similarly, the retained names 'ethane', 'propane', and 'butane' were never replaced by systematic names 'dicarbane', 'tricarbane', and 'tetracarbane' as recommended for analogues of silane, 'disilane'; phosphane, 'triphosphane'; and sulfane, 'tetrasulfane'.}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Tetracarbane (never recommended<ref name=iupac2013 />) |
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| SMILES = CCCC |
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| OtherNames = {{Unbulleted list|Butyl hydride<ref <ref name=PGCH/>|Quartane<ref name=quartane>{{Cite journal|title=I. On the action of trichloride of phosphorus on the salts of the aromatic monamines |author=August Wilhelm Von Hofmann |year=1867 |journal=Proceedings of the Royal Society of London |volume=15 |pages=54–62 |doi=10.1098/rspl.1866.0018 |s2cid=98496840 |url=https://books.google.com/books?id=w1BJAAAAcAAJ&pg=RA1-PA58}}</ref>|R600}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|Section1={{Chembox Identifiers |
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| ChEMBL = 134702 |
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| CASNo = 106-97-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 7843 |
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| ChemSpiderID = 7555 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII = 6LV4FOR43R |
| UNII = 6LV4FOR43R |
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| |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-448-7 |
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| UNNumber = 1011 |
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| KEGG = D03186 |
| KEGG = D03186 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/C4H10/c1-3-4-2/h3-4H2,1-2H3 |
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| MeSHName = butane |
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| InChIKey = IJDNQMDRQITEOD-UHFFFAOYAE |
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| ChEBI = 37808 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 134702 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| RTECS = EJ4200000 |
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| Beilstein = 969129 |
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| Gmelin = 1148 |
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| SMILES = CCCC |
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| StdInChI = 1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 |
| StdInChI = 1S/C4H10/c1-3-4-2/h3-4H2,1-2H3 |
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| |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = IJDNQMDRQITEOD-UHFFFAOYSA-N |
| StdInChIKey = IJDNQMDRQITEOD-UHFFFAOYSA-N |
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| |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 106-97-8 |
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|Section2={{Chembox Properties |
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| PubChem = 7843 |
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| C=4 | H=10 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 37808 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7555 |
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| UNNumber = [[List of UN Numbers 1001 to 1100|1011]]<br />''As [[Liquefied petroleum gas]]: ''[[List of UN Numbers 1001 to 1100|1075]] |
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}} |
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| Section2 = {{Chembox Properties |
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|C=4|H=10 |
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| Appearance = Colorless gas |
| Appearance = Colorless gas |
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| Odor = Gasoline-like or natural gas-like<ref name=PGCH/> |
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| Density = 2.48 kg/m<sup>3</sup>, gas (15 °C, 1 [[Atmosphere (unit)|atm]])<br />600 kg/m<sup>3</sup>, liquid (0 °C, 1 [[Atmosphere (unit)|atm]]) |
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| Density = 2.48 kg/m<sup>3</sup> (at {{convert|15|C}}) |
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| MeltingPtK = 133 to 139 |
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| MeltingPt = −138.4 °C (135.4 K) |
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| BoilingPtK = 272 to 274 |
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| BoilingPt = −0.5 °C (272.6 K) |
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| Solubility = 61 mg/L (at {{convert|20|C}}) |
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}} |
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| LogP = 2.745 |
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| Section7 = {{Chembox Hazards |
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| MagSus = −57.4·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| EUClass = Highly flammable ('''F+''') |
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| VaporPressure = ~170 kPa at 283 K <ref>{{Cite journal|title=Pressure-Volume-Temperature Relations for n-Butane|journal=Industrial & Engineering Chemistry|volume=32|issue=3|pages=358–360|author=W. B. Kay|doi=10.1021/ie50363a016|year=1940}}</ref> |
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| HenryConstant = 11 nmol Pa<sup>−1</sup> kg<sup>−1</sup> |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −126.3–−124.9 kJ/mol |
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| DeltaHc = −2.8781–−2.8769 MJ/mol |
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| HeatCapacity = 98.49 J/(K·mol) |
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}} |
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|Section4={{Chembox Hazards |
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| Hazards_ref = <ref name="chemadvisor">{{cite web|title=Safety Data Sheet, Material Name: N-Butane|url=http://www.chemadvisor.com/Matheson/database/msds/MAT15370000800003.PDF|publisher=Matheson Tri-Gas Incorporated|access-date=11 December 2011|location=USA|date=5 February 2011|url-status=dead|archive-url=https://web.archive.org/web/20111001074639/http://www.chemadvisor.com/Matheson/database/msds/MAT15370000800003.PDF|archive-date=1 October 2011}}</ref> |
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| GHSPictograms = {{GHS flame}} {{GHS gas cylinder}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|220}} |
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| PPhrases = {{P-phrases|210}} |
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| NFPA-H = 1 |
| NFPA-H = 1 |
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| NFPA-F = 4 |
| NFPA-F = 4 |
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| NFPA-R = |
| NFPA-R = 0 |
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| |
| NFPA-S = SA |
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| FlashPtC = −60 |
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| AutoignitionPtC = 405 |
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| ExploLimits = 1.8 – 8.4% <ref> [http://www.chemadvisor.com/Matheson/database/msds/MAT15370000800003.PDF MSDS Butane] </ref> |
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| ExploLimits = 1.8–8.4% |
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}} |
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| PEL = none<ref name=PGCH>{{PGCH|0068}}</ref> |
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| Section8 = {{Chembox Related |
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| IDLH = 1600 ppm<ref name=PGCH/> |
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| Function = [[alkane]]s |
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| REL = TWA 800 ppm (1900 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| OtherFunctn = [[Propane]]; [[Pentane]] |
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}} |
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| OtherCpds = [[Isobutane]]; [[Cyclobutane]] |
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|Section5={{Chembox Related |
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}} |
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| OtherFunction_label = alkanes |
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| OtherFunction = {{Unbulleted list|[[Propane]]|[[Isobutane]]|[[Pentane]]}} |
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| OtherCompounds = [[Perfluorobutane]] |
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}} |
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}} |
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'''Butane''' ({{IPAc-en|ˈ|b|juː|t|eɪ|n}}) is an [[alkane]] with the formula C<sub>4</sub>H<sub>10</sub>. Butane exists as two isomers, ''n''-butane with connectivity {{chem2|CH3CH2CH2CH3}} and iso-butane with the formula {{chem2|(CH3)3CH}}. Both isomers are highly flammable, colorless, easily [[liquefy|liquefied]] [[gas]]es that quickly vaporize at room temperature and pressure. Butanes are a trace components of [[natural gas]]es (NG gases). The other hydrocarbons in NG include [[propane]], [[ethane]], and especially [[methane]], which are more abundant. [[Liquified natural gas]] is a mixture of propane and some butanes.<ref>{{cite book |doi=10.1002/14356007.a17_073.pub2 |chapter=Natural Gas |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2006 |last1=Hammer |first1=Georg |last2=Lübcke |first2=Torsten |last3=Kettner |first3=Roland |last4=Pillarella |first4=Mark R. |last5=Recknagel |first5=Herta |last6=Commichau |first6=Axel |last7=Neumann |first7=Hans-Joachim |last8=Paczynska-Lahme |first8=Barbara |isbn=978-3-527-30385-4 }}</ref> |
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The name butane comes from the root [[IUPAC nomenclature of organic chemistry#Alkanes|but-]] (from [[butyric acid]], named after the Greek word for [[butter]]) and the suffix [[alkanes|-ane]]. |
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== History == |
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The first synthesis of butane was accidentally achieved by British chemist [[Edward Frankland]] in 1849 from [[ethyl iodide]] and [[zinc]], but he had not realized that the [[ethyl radical]] dimerized and misidentified the substance.<ref>{{cite journal |doi=10.1021/om010439f |title=Zinc Alkyls, Edward Frankland, and the Beginnings of Main-Group Organometallic Chemistry |year=2001 |last1=Seyferth |first1=Dietmar |journal=Organometallics |volume=20 |issue=14 |pages=2940–2955 |doi-access=free}}</ref> |
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It was discovered in crude petroleum in 1864 by [[Edmund Ronalds]], who was the first to describe its properties,<ref name="Watts">{{cite book | last1=Watts | first1=H. | last2=Muir | first2=M. M. P. | last3=Morley | first3=H. F. | title=Watts' Dictionary of Chemistry | publisher=Longmans, Green | volume=4 | year=1894 | url=https://books.google.com/books?id=J3kPAQAAIAAJ |page=385}}</ref><ref>{{Cite journal |last=Maybery |first=C. F. |date=1896 |title=On the Composition of the Ohio and Canadian Sulphur Petroleums |journal=Proceedings of the American Academy of Arts and Sciences |volume=31 |pages=1–66 |doi=10.2307/20020618 |jstor=20020618}}</ref> which he named "hydride of [[butyl]]",<ref>{{cite web | url=https://books.google.com/books?id=YyO3j9Yi3nEC&pg=PA54 | title=Journal of the Chemical Society | year=1865 }}</ref> based on the naming for the then-known [[Butyric Acid|butyric acid]], which had been named and described by the French chemist [[Michel Eugène Chevreul]]<ref>Chevreul (1817) [https://books.google.com/books?id=y1E3AAAAYAAJ&pg=PA79 "Extrait d'une lettre de M. Chevreul à MM. les Rédacteurs du Journal de Pharmacie"] (Extract of a letter from Mr. Chevreul to the editors of the Journal of Pharmacy), ''Journal de Pharmacie et des sciences accessoires'', '''3''' : 79–81. On p. 81, he named butyric acid: ''"Ce principe, que j'ai appelé depuis acid butérique, … "'' (This principle [i.e., constituent], which I have since named "butyric acid", … )</ref> 40 years earlier. Other names arose in the 1860s: "butyl hydride",<ref>{{cite web | url=https://books.google.com/books?id=6ss-AAAAcAAJ&pg=PA41 | title=Petroleum and Its Products: An Accoumt of the Properties, Uses, and Commercial Value Etc., of Petroleum, the Methods Employed in Refining it and the Properties, Uses, Etc., of Its Product | last1=Norman Tate | first1=A. | year=1863 }}</ref> "hydride of tetryl"<ref>{{cite web | url=https://books.google.com/books?id=6YvPAAAAMAAJ&pg=PA181 | title=A Dictionary of Chemistry | last1=Watts | first1=Henry | year=1865 }}</ref> and "tetryl hydride",<ref>{{cite web | url=https://books.google.com/books?id=Q7YHAAAAIAAJ&pg=PA277 | title=Elements of chemistry pt. 3 1867 | last1=Miller | first1=William Allen | year=1867 }}</ref> "diethyl" or "ethyl ethylide"<ref>{{cite web | url=https://books.google.com/books?id=b7ktAAAAYAAJ&pg=PA266 | title=Elements of Chemistry: Theoretical and Practical: Organic chemistry | last1=Miller | first1=William Allen | year=1869 }}</ref> and others. [[August Wilhelm von Hofmann]], in his 1866 systemic nomenclature, proposed the name "quartane",<ref name=quartane/> and the modern name was introduced to English from German around 1874.<ref>{{cite web | url=https://books.google.com/books?id=w9MJAAAAMAAJ&pg=PA154 | title=A Manual of the Chemistry of the Carbon Compounds: Or, Organic Chemistry | last1=Schorlemmer | first1=Carl | year=1874 }}</ref> |
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Butane did not have much practical use until the 1910s, when W. Snelling identified butane and propane as components in gasoline. He found that if they were cooled, they could be stored in a volume-reduced liquified state in pressurized containers. In 1911, Snelling's liquified petroleum gas was publicly available, and his process for producing the mixture was patented in 1913.<ref>{{Cite web |url=http://blog.texaspropane.com/history-propane/ | title=The History of Propane | author=Texas Propane | year=2022}}</ref> Butane is one of the most produced industrial chemicals in the 21st century, with around 80-90 billion [[Pound (mass)|lbs]] (40 million US tons, 36 million [[Tonne|metric tons]]) produced by the [[United States]] every year.<ref>{{cite web | url=https://www.epa.gov/chemical-data-reporting/chemical-production-data | title=Chemical Production Data |year=2024 }}</ref> |
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== Density == |
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The density of butane is highly dependent on temperature and pressure in the reservoir.<ref name="Zivenko-2019">{{Cite journal|last=Zivenko|first=Oleksiy|title=LPG Accounting Specificity During ITS Storage and Transportation |date=2019|journal=Measuring Equipment and Metrology|language=en|volume=80|issue=3|pages=21–27|doi=10.23939/istcmtm2019.03.021|s2cid=211776025 |issn=0368-6418|doi-access=free}}</ref> For example, the density of liquid butane is 571.8±1 kg/m<sup>3</sup> (for pressures up to 2 MPa and temperature 27±0.2 °C), while the density of liquid butane is 625.5±0.7 kg/m<sup>3</sup> (for pressures up to 2 MPa and temperature −13±0.2 °C). |
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== Isomers == |
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{| class="wikitable" style="text-align:center" |
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|- |
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| style="background:#def;"|Common name |
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|'''normal butane'''<br />'''unbranched butane'''<br />'''''n''-butane''' |
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|'''[[isobutane]]'''<br />'''''i''-butane''' |
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|- |
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| style="background:#def;"|IUPAC name |
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|'''butane''' |
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|'''methylpropane''' |
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|- |
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| style="background:#def;"|Molecular<br />diagram |
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|[[Image:Butan Lewis.svg|150px]] |
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|[[Image:Isobutane 1.svg|120px]] |
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|- |
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| style="background:#def;"|Skeletal<br />diagram |
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|[[Image:Butane simple.svg|120px]] |
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|[[Image:I-Butane-2D-Skeletal.svg|100px]] |
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|} |
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[[Rotation]] about the central C−C [[Chemical bond|bond]] produces two different [[conformational isomerism|conformations]] (''trans'' and ''gauche'') for ''n''-butane.<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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{{stack| |
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[[File:Spectrum of blue flame - intensity corrected.png|thumb|upright=1.15|Spectrum of the blue flame from a [[butane torch]] showing CH molecular [[Radical (chemistry)|radical]] band emission and C<sub>2</sub> [[Swan band]]s]] |
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}} |
}} |
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When oxygen is plentiful, butane undergoes [[complete combustion]] to form [[carbon dioxide]] and [[water vapor]]; when oxygen is limited, due to [[incomplete combustion]], carbon ([[soot]]) or [[carbon monoxide]] may be formed instead of carbon dioxide. Butane is denser than air. |
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When there is sufficient oxygen: |
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: 2 C<sub>4</sub>H<sub>10</sub> + 13 O<sub>2</sub> → 8 CO<sub>2</sub> + 10 H<sub>2</sub>O |
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When oxygen is limited: |
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: 2 C<sub>4</sub>H<sub>10</sub> + 9 O<sub>2</sub> → 8 CO + 10 H<sub>2</sub>O |
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By weight, butane contains about {{convert|49.5|MJ/kg|kWh/kg MJ/lb Btu/lb|lk=on|abbr=on|sp=us}} or by liquid volume {{convert|29.7|MJ/L|kWh/L MJ/usgal Btu/usgal|abbr=out|lk=in|sp=us}}. |
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The maximum [[adiabatic flame]] temperature of butane with air is {{convert|2243|K}}. |
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''n''-Butane is the feedstock for [[DuPont]]'s catalytic process for the preparation of [[maleic anhydride]]: |
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:2 CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> + 7 O<sub>2</sub> → 2 C<sub>2</sub>H<sub>2</sub>(CO)<sub>2</sub>O + 8 H<sub>2</sub>O |
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''n''-Butane, like all [[Hydrocarbon|hydrocarbons]], undergoes [[free radical]] chlorination providing both 1-chloro- and 2-chlorobutanes, as well as more highly chlorinated derivatives. The relative rates of the chlorinations are partially explained by the differing [[bond dissociation energies]]: 425 and 411 [[joule|kJ]]/[[Mole (unit)|mol]] for the two types of C-H bonds. |
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== Uses == |
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Normal butane can be used for [[gasoline]] blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with [[propane]], and as a feedstock for the manufacture of [[ethylene]] and [[butadiene]], a key ingredient of [[synthetic rubber]]. [[Isobutane]] is primarily used by [[refineries]] to enhance (increase) the [[octane]] number of motor gasoline.<ref>[https://www.sec.gov/Archives/edgar/data/1166036/000104746912001759/a2207469z10-k.htm MarkWest Energy Partners, L.P. Form 10-K]. Sec.gov.</ref><ref>[https://www.sec.gov/Archives/edgar/data/1297067/000119312512089552/d270993d10k.htm Copano Energy, L.L.C. Form 10-K]. Sec.gov. Retrieved on 2012-12-03.</ref><ref>[https://www.sec.gov/Archives/edgar/data/1379661/000138917012000005/form10-k.htm Targa Resources Partners LP Form10-k]. Sec.gov. Retrieved on 2012-12-03.</ref><ref>[https://www.sec.gov/Archives/edgar/data/1179060/000104746912001738/a2207540z10-k.htm Crosstex Energy, L.P. FORM 10-K]. Sec.gov.</ref> |
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For gasoline blending, n-butane is the main component used to manipulate the [[Reid vapor pressure]] (RVP). Since winter fuels require much higher vapor pressure for engines to start, refineries raise the RVP by blending more butane into the fuel.<ref>{{Cite web|last=Maurice Stewart, Ken Arnold|title=Reid Vapour Pressure|url=https://www.sciencedirect.com/topics/engineering/reid-vapour-pressure|url-status=live|website=Science Direct|archive-url=https://web.archive.org/web/20200613130216/https://www.sciencedirect.com/topics/engineering/reid-vapour-pressure |archive-date=13 June 2020 }}</ref> n-Butane has a relatively high [[Octane rating#Research_Octane_Number_(RON)|research octane number]] (RON) and [[Octane rating#Motor_Octane_Number_(MON)|motor octane number]] (MON), which are 93 and 92 respectively.<ref>{{Cite web|last=Jechura|first=John|title=octane rating|url=https://inside.mines.edu/~jjechura/Refining/11_Blending_Optimization.pdf|url-status=live|website=Colorado School of Mines|archive-url=https://web.archive.org/web/20150501041749/http://inside.mines.edu:80/~jjechura/Refining/11_Blending_Optimization.pdf |archive-date=1 May 2015 }}</ref> |
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When blended with [[propane]] and other hydrocarbons, the mixture may be referred to commercially as [[liquefied petroleum gas]] (LPG). It is used as a petrol component, as a feedstock for the production of base [[petrochemicals]] in [[steam cracking]], as fuel for cigarette [[lighter]]s and as a [[propellant]] in [[aerosol spray]]s such as [[deodorant]]s.<ref>[http://eprinc.org/?p=300 A Primer on Gasoline Blending] {{Webarchive|url=https://web.archive.org/web/20130630221725/http://eprinc.org/?p=300 |date=30 June 2013 }}. An EPRINC Briefing Memorandum.</ref> |
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Pure forms of butane, especially isobutane, are used as [[refrigerant]]s and have largely replaced the [[Ozone depletion|ozone-layer-depleting]] [[halomethane]]s in refrigerators, freezers, and air conditioning systems. The operating pressure for butane is lower than operating pressures for halomethanes such as [[Dichlorodifluoromethane|Freon-12]] (R-12). Hence, R-12 systems, such as those in automotive air conditioning systems, when converted to pure butane, will function poorly. Instead, a mixture of isobutane and propane is used to give cooling system performance comparable to R-12.<ref>{{Cite web |title=R600a {{!}} Product Information |url=https://www.agas.com/au/products-services/refrigerants/r600a/ |access-date=2023-12-01 |website=www.agas.com |language=en-AU}}</ref> |
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Butane is also used as lighter fuel for common [[lighter]]s or [[butane torch]]es, and is sold bottled as a fuel for cooking, barbecues and camping stoves. In the 20th century, the [[Braun (company)|Braun]] company of [[Germany]] made a cordless hair styling device product that used butane as its heat source to produce [[steam]].<ref name="braun">{{cite news |title=Braun C 100 TS Styling Iron User Manual Type 3589 |url=http://personalcare.manualsonline.com/manuals/mfg/braun/c_100_ts_1.html |publisher=Inmar-OIQ, LLC |date=n.d.}}</ref> |
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As fuel, butane is often mixed with small amounts of [[mercaptan]]s to give the unburned gas an offensive smell easily detected by the human nose. In this way, butane leaks can easily be identified. While [[hydrogen sulfide]] and mercaptans are toxic, they are present in levels so low that [[suffocation]] and [[fire hazard]] by the butane becomes a concern far before [[toxicity]].<ref name="Gresham 2019">{{cite web | last=Gresham | first=Chip | title=Hydrogen Sulfide Toxicity: Practice Essentials, Pathophysiology, Etiology | website=Medscape Reference | date=16 November 2019 | url=https://emedicine.medscape.com/article/815139 | access-date=22 March 2021 |url-access=registration}}</ref><ref name="Toxicology2013">{{cite book |author1=Committee on Acute Exposure Guideline Levels |author2=Committee on Toxicology |author3=Board on Environmental Studies and Toxicology |author4=Division on Earth and Life Studies |author5=National Research Council |title=2. Methyl Mercaptan Acute Exposure Guideline Levels |via=NCBI Bookshelf |date=26 September 2013 |publisher=National Academies Press (US) |url=https://www.ncbi.nlm.nih.gov/books/NBK201324/ }}</ref> Most commercially available butane also contains some contaminant oil, which can be removed by filtration. If not removed, it will otherwise leave a deposit at the point of ignition and may eventually block the uniform flow of gas.<ref>{{Cite web |title=BHO Mystery Oil |date=2013-08-26 |website=Skunk Pharm Research |url=https://skunkpharmresearch.com/bho-mystery-oil/ |access-date=2019-12-05}}</ref> |
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The butane used as a solvent for fragrance extraction does not contain these contaminants.<ref name="SAGE">{{cite journal |title=Final Report of the Safety Assessment of Isobutane, Isopentane, n-Butane, and Propane |journal=Journal of the American College of Toxicology |publisher=SAGE Publications |volume=1 |issue=4 |year=1982 |issn=0730-0913 |doi=10.3109/10915818209021266 |pages=127–142| s2cid=208503534}}</ref> Butane gas can cause [[Gas explosion|gas explosions]] in poorly ventilated areas if leaks go unnoticed and are ignited by spark or flame.<ref name="chemadvisor"/> Purified butane is used as a solvent in the industrial extraction of cannabis oils. |
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<gallery mode="packed" heights="140"> |
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File:Photo D2.jpg | Butane fuel canisters for use in camping stoves |
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File:The Green Lighter 1 cropped.jpg | Butane lighter, showing liquid butane reservoir |
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File:Aerosol.png | An aerosol spray can, which may be using butane as a propellant |
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File:ButaneGasCylinder WhiteBack.jpg | Butane gas cylinder used for cooking |
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</gallery> |
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== Health effects == |
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[[File:HarmCausedByDrugsTable.svg|thumb|upright=1.35|Table from the 2010 ISCD study ranking various drugs (legal and illegal) based on statements by drug-harm experts. Butane was found to be the 14th overall most dangerous drug.<ref name="Nutt_2010">{{cite journal | vauthors = Nutt DJ, King LA, Phillips LD | title = Drug harms in the UK: a multicriteria decision analysis | journal = Lancet | volume = 376 | issue = 9752 | pages = 1558–1565 | date = November 2010 | pmid = 21036393 | doi = 10.1016/S0140-6736(10)61462-6 | s2cid = 5667719 | citeseerx = 10.1.1.690.1283 }}</ref>]] |
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Inhalation of butane can cause [[euphoria]], [[drowsiness]], [[unconsciousness]], [[asphyxia]], [[cardiac arrhythmia]], fluctuations in blood pressure and temporary memory loss, when abused directly from a highly pressurized container, and can result in death from [[asphyxiation]] and [[ventricular fibrillation]]. Butane enters the blood supply, and within seconds, leads to intoxication.<ref>{{cite web |title=Neurotoxic Effects from Butane Gas |date=19 Dec 2009 |website=thcfarmer.com |url=https://www.thcfarmer.com/community/threads/neurotoxic-effects-from-butane-gas.15291/ |access-date=3 October 2016}}</ref> Butane is the most commonly abused [[volatile]] substance in the UK, and was the cause of 52% of solvent related deaths in 2000.<ref>{{cite web |title=Trends in death Associated with Abuse of Volatile Substances 1971–2004 |vauthors=Field-Smith M, Bland JM, Taylor JC |publisher=Department of Public Health Sciences. London: St George’s Medical School |url=http://www.sgul.ac.uk/dms/AF54AFD9D207A9A41D353717989DC4E0.pdf |display-authors=etal |url-status=dead |archive-url=https://web.archive.org/web/20070327161634/http://www.sgul.ac.uk/dms/AF54AFD9D207A9A41D353717989DC4E0.pdf |archive-date=March 27, 2007}}</ref> By spraying butane directly into the throat, the jet of fluid can cool rapidly to {{convert|−20|C}} by expansion, causing prolonged [[laryngospasm]].<ref name="multiple">{{cite journal |vauthors=Ramsey J, Anderson HR, Bloor K |display-authors=etal |title=An introduction to the practice, prevalence and chemical toxicology of volatile substance abuse |journal=Hum Toxicol |year=1989 |volume=8 |pages=261–269 |doi=10.1177/096032718900800403 |pmid=2777265 |issue=4| s2cid=19617950}}</ref> [[Intoxicative inhalant#Sudden sniffing death syndrome|"Sudden sniffer's death"]] syndrome, first described by Bass in 1970,<ref>{{cite journal |vauthors=Bass M |title=Sudden sniffing death |journal=JAMA |year=1970 |volume=212 |issue=12 |pages=2075–2079 |doi=10.1001/jama.1970.03170250031004 |pmid=5467774}}</ref> is the most common single cause of solvent related deaths, resulting in 55% of known fatal cases.<ref name="multiple"/> |
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== See also == |
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* [[Cyclobutane]] |
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* [[Volatile substance abuse]] |
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* [[Butane (data page)]] |
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* [[Industrial gas]] |
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== References == |
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{{Reflist}} |
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== External links == |
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{{commons}} |
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* [http://www.inchem.org/documents/icsc/icsc/eics0232.htm International Chemical Safety Card 0232] |
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* [https://www.cdc.gov/niosh/npg/npgd0068.html NIOSH Pocket Guide to Chemical Hazards] |
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{{Alkanes}} |
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{{Hydrides by group}} |
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{{E number infobox 930-949}} |
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{{GABAAR PAMs}} |
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{{Authority control}} |
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[[Category:Butane| ]] |
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[[Category:Alkanes]] |
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[[Category:Fuel gas]] |
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[[Category:Refrigerants]] |
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[[Category:GABAA receptor positive allosteric modulators]] |
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[[Category:E-number additives]] |