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Octane
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{{Short description|Hydrocarbon compound with the formula C8H18}} {{Distinguish|octene|octyne}} {{for-multi|the gasoline rating system|Octane rating|other uses}} {{Chembox | ImageFile = Octane-2D-Skeletal.svg | ImageClass = skin-invert-image | ImageFile1 = OctaneFull.png | ImageClass1 = skin-invert-image | ImageFile2 = Octane 3D ball.png | ImageClass2 = bg-transparent | ImageFile3 = N-octane-spaceFilling.png | ImageClass3 = bg-transparent | ImageAlt = Skeletal formula of octane | ImageFile_Ref = {{chemboximage|correct|??}} | ImageAlt1 = Skeletal formula of octane with all implicit carbons shown, and all explicit hydrogens added | ImageFile1_Ref = {{chemboximage|correct|??}} | ImageAlt2 = Ball-and-stick model of octane | ImageFile2_Ref = {{chemboximage|correct|??}} | ImageSize3 = 160 | ImageAlt3 = Space-filling model of octane | ImageFile3_Ref = {{chemboximage|correct|??}} | OtherNames = ''n''-Octane | SystematicName = Octane<ref>{{Cite web|title=octane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=356&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=6 January 2012|location=USA|date=16 September 2004|at=Identification and Related Records}}</ref> | Section1 = {{Chembox Identifiers | CASNo = 111-65-9 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = X1RV0B2FJV | PubChem = 356 | ChemSpiderID = 349 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 203-892-1 | UNNumber = 1262 | DrugBank = DB02440 | DrugBank_Ref = {{drugbankcite|changed|drugbank}} | KEGG = C01387 | KEGG_Ref = {{keggcite|correct|kegg}} | MeSHName = octane | ChEBI = 17590 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEMBL = 134886 | ChEMBL_Ref = {{ebicite|correct|EBI}} | RTECS = RG8400000 | Beilstein = 1696875 | Gmelin = 82412 | 3DMet = B00281 | SMILES = CCCCCCCC | StdInChI = 1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = TVMXDCGIABBOFY-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} | Section2 = {{Chembox Properties | Formula = {{chem2|CH3(CH2)6CH3}} | C=8|H=18 | Appearance = Colourless liquid | Odor = Gasoline-like<ref name=PGCH/> | Density = 0.703 g/cm<sup>3</sup> | MeltingPtK = 216.0 to 216.6 | BoilingPtK = 398.2 to 399.2 | Solubility = 0.007 mg/dm<sup>3</sup> (at 20 °C) | LogP = 4.783 | VaporPressure = 1.47 kPa (at 20.0 °C) | HenryConstant = 29 nmol/(Pa·kg) | RefractIndex = 1.398 | Viscosity = {{plainlist| * 0.509 mPa·s (25 °C)<ref name="Dymond1994">{{cite journal|last1=Dymond|first1=J. H.|last2=Oye|first2=H. A.|title=Viscosity of Selected Liquid ''n''-Alkanes|journal=Journal of Physical and Chemical Reference Data|volume=23|issue=1|year=1994|pages=41–53|issn=0047-2689|doi=10.1063/1.555943|bibcode=1994JPCRD..23...41D}}</ref> * 0.542 mPa·s (20 °C)}} | MagSus = −96.63·10<sup>−6</sup> cm<sup>3</sup>/mol | ConjugateAcid = [[Octonium]] }} | Section3 = {{Chembox Thermochemistry | DeltaHf = −252.1 to −248.5 kJ/mol | DeltaHc = −5.53 to −5.33 MJ/mol | Entropy = 361.20 J/(K·mol) | HeatCapacity = 255.68 J/(K·mol) }} | Section4 = {{Chembox Hazards | GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}} | GHSSignalWord = '''DANGER''' | NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 0 | HPhrases = {{H-phrases|225|304|315|336|410}} | PPhrases = {{P-phrases|210|261|273|301+310|331}} | FlashPtC = 13.0 | AutoignitionPtC = 220.0 | ExploLimits = 0.96 – 6.5% | IDLH = 1000 ppm<ref name=PGCH>{{PGCH|0470}}</ref> | REL = TWA 75 ppm (350 mg/m<sup>3</sup>) C 385 ppm (1800 mg/m<sup>3</sup>) [15-minute]<ref name=PGCH/> | PEL = TWA 500 ppm (2350 mg/m<sup>3</sup>)<ref name=PGCH/> | LDLo = 428 mg/kg (mouse, intravenous)<ref>{{IDLH|111659|Octane}}</ref> }} | Section5 = {{Chembox Related | OtherFunction_label = alkanes | OtherFunction = {{Unbulleted list|[[Methane]]|[[Ethane]]|[[Propane]]|[[Butane]]|[[Pentane]]|[[Hexane]]|[[Heptane]]|}} }} | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 411133144 }} '''Octane''' is a [[hydrocarbon]] and also an [[alkane]] with the [[chemical formula]] C<sub>8</sub>H<sub>18</sub>, and the condensed structural formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>CH<sub>3</sub>. Octane has many [[structural isomer]]s that differ by the location of branching in the [[carbon chain]]. One of these isomers, [[2,2,4-Trimethylpentane|2,2,4-trimethylpentane]] (commonly called iso-octane), is used as one of the standard values in the [[octane rating]] scale. Octane is a component of [[gasoline]] and petroleum. Under [[standard temperature and pressure]], octane is an odorless, colorless liquid. Like other short-chained alkanes with a low molecular weight, it is [[Volatility (chemistry)|volatile]], flammable, and toxic. Octane is 1.2 to 2 times more toxic than [[heptane]].<ref>{{Cite web |date=2020-02-27 |title=1988 OSHA PEL Project - Octane {{!}} NIOSH {{!}} CDC |url=https://www.cdc.gov/niosh/pel88/111-65.html |access-date=2024-04-19 |website=www.cdc.gov }}</ref> ==Isomers== N-octane has 23 [[Structural isomers|constitutional isomers]]. 8 of these isomers have one [[stereocenter]]; 3 of them have two stereocenters. [[File:Octane_stereo_isomers_10_3_4_dimethylhexane.svg|thumb|437x437px|[[3,4-Dimethylhexane|(3''S'',4''S'')-3,4-Dimethylhexane]] (top left) and [[3,4-Dimethylhexane|(3''R'',4''R'')-3,4-Dimethylhexane]] (top right) are non-superimposable mirror images, so they are chiral [[enantiomer]]s. [[3,4-Dimethylhexane|(''meso'')-3,4-Dimethylhexane]] (bottom) has a superimposable mirror image, so it is an achiral [[meso compound]].]] '''Achiral isomers:''' * [[2-Methylheptane]] * [[4-Methylheptane]] * [[3-Ethylhexane]] * [[2,2-Dimethylhexane]] * [[2,5-Dimethylhexane]] * [[3,4-Dimethylhexane|(''meso'')-3,4-Dimethylhexane]] * [[3,3-Dimethylhexane]] * [[3-Ethyl-2-methylpentane]] * [[3-Ethyl-3-methylpentane]] * [[2,2,4-Trimethylpentane]] (i.e. iso-octane) * [[2,3,3-Trimethylpentane]] * [[2,3,4-Trimethylpentane]] * [[2,2,3,3-Tetramethylbutane]] '''Chiral isomers:''' * [[3-Methylheptane|(3''R'')-3-Methylheptane]] * [[3-Methylheptane|(3''S'')-3-Methylheptane]] * [[2,3-Dimethylhexane|(3''R'')-2,3-Dimethylhexane]] * [[2,3-Dimethylhexane|(3''S'')-2,3-Dimethylhexane]] * [[2,4-Dimethylhexane|(4''R'')-2,4-Dimethylhexane]] * [[2,4-Dimethylhexane|(4''S'')-2,4-Dimethylhexane]] * [[3,4-Dimethylhexane|(3''R'',4''R'')-3,4-Dimethylhexane]] * [[3,4-Dimethylhexane|(3''S'',4''S'')-3,4-Dimethylhexane]] * [[2,2,3-Trimethylpentane|(3''R'')-2,2,3-Trimethylpentane]] * [[2,2,3-Trimethylpentane|(3''S'')-2,2,3-Trimethylpentane]] == Production and use == In petrochemistry, octanes are not typically differentiated or purified as specific compounds. Octanes are components of particular boiling fractions.<ref>{{Cite web |title=Fractionation |url=https://www.appliedcontrol.com/industries/midstream-oil-and-gas/natural-gas-processing/fractionation/ |access-date=2024-04-19 |website=www.appliedcontrol.com }}</ref> A common route to such fractions is the [[Alkylation|alkylation reaction]] between iso-butane and 1-butene, which forms iso-octane.<ref>{{Cite journal |last=Ross |first=Julian |date=January 1986 |title=Ullmann's Encyclopedia of industrial chemistry |url=http://dx.doi.org/10.1016/s0166-9834(00)82943-7 |journal=Applied Catalysis |volume=27 |issue=2 |pages=403–404 |doi=10.1016/s0166-9834(00)82943-7 |issn=0166-9834|url-access=subscription }}</ref> Octane is commonly used as a solvent in paints and adhesives. {| class="wikitable sortable mw-collapsible" |[[File:N-octane.jpg|none|thumb|338x338px|''N-octane'' is the octane isomer that has the longest carbon skeleton. Unlike its constitutional isomers, it has a very low knock resistance.]] |[[File:Iso-octane.jpg|none|thumb|271x271px|The octane isomer, ''iso-octane'', is used as one of the standards for octane ratings. It has a rating of 100 by definition.]] |[[File:2,3,3-Trimethylpentane_(view_2).jpg|none|thumb|224x224px|The octane isomer ''2,3,3-Trimethylpentane'' has an octane rating exceeding 100.]] |} ==References== <references /> ==External links== * {{ICSC|0933|09}} * {{PGCH|0470}} * Dr. Duke's Phytochemical and Ethnobotanical Databases, Octane, [https://archive.today/20121213000953/http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?OCTANE] {{Alkanes}} {{Hydrides by group}} [[Category:Alkanes]] [[Category:Hydrocarbons]]
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