Octane: Difference between revisions

{{two other uses||the gasoline rating system|octane rating}}

{{chembox

| Reference=<ref>[http://cheric.org/kdb/kdb/hcprop/showprop.php?cmpid=8 Chemical and physical properties table]</ref><ref>[http://physchem.ox.ac.uk/MSDS/OC/octane.html Material Safety Data Sheet for Octane]</ref>

| verifiedrevid = 396509741

| Name = Octane

| ImageFile = Octane-2D-Skeletal.svg

| ImageSize = 240px

| ImageName = Skeletal formula

| ImageFile1 = Octane-3D-balls-B.png

| ImageSize1 = 240px

| ImageName1 = Ball-and-stick model

| IUPACName = Octane

| OtherNames = ''n''-Octane

| Section1 = {{Chembox Identifiers

| SMILES = CCCCCCCC

| KEGG = C01387

| InChI = 1/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3

| ChEMBL = 134886

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = TVMXDCGIABBOFY-UHFFFAOYSA-N

| CASNo = 111-65-9

| RTECS = RG8400000

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 356

}}

| Section2 = {{Chembox Properties

| C=8|H=18

| Appearance = Colorless liquid

| Density = 0.703 g/mL

| Solubility = Immiscible

| MeltingPtC = −57

| BoilingPtC = 125.52

| Viscosity = 0.542 [[Poise|cP]] at 20 °C

}}

| Section4 = {{Chembox Thermochemistry

| DeltaHf = −250 kJ/mol

| DeltaHc = −5074.2 kJ/mol

}}

| Section7 = {{Chembox Hazards

| EUClass = Flammable ('''F''')<br />Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''')

| RPhrases = {{R11}} {{R38}} {{R50/53}} {{R65}} {{R67}}

| SPhrases = {{S2}} {{S9}} {{S16}} {{S29}} {{S33}} {{S60}} {{S61}} {{S62}}

| FlashPt = 13 °C

| Autoignition = 220 °C

}}

| Section8 = {{Chembox Related

| Function = [[alkane]]s

| OtherFunctn = [[Heptane]]<br />[[2,2,4-Trimethylpentane]]}}

'''Octane''' is a [[hydrocarbon]] and an [[alkane]] with the [[chemical formula]] C₈H₁₈, and the condensed structural formula CH₃(CH₂)₆CH₃. Octane has many [[structural isomer]]s that differ by the amount and location of branching in the carbon chain. One of these isomers, [[2,2,4-Trimethylpentane|2,2,4-trimethylpentane]] (isooctane) is used as one of the standard values in the [[octane rating]] scale.

As with all low-molecular weight hydrocarbons, octane and its isomers are very flammable. It is a component of [[gasoline]] (petrol).

== Metaphorical use ==

Octane became well-known in American popular culture in the mid- and late-sixties, when [[gasoline]] companies boasted of "high octane" levels in their gasoline in advertisements. These commercials refer to the [[octane rating]], which is a measure for the [[Engine knocking|anti-knocking]] properties of gasoline. The octane rating is not directly related to the amount of octane contained in the gasoline.

These commercials disappeared by the time of the [[1973 Oil Crisis]], which spared gasoline companies the need to compete via advertising. "Octane" was rarely cited in non-technical contexts over the next two decades.

The compound adjective "high-octane" was apparently first used in its figurative sense (i.e. without reference to gasoline) in a book review of [[Michael Crichton]]'s novel ''[[Jurassic Park]]'' (1990), which appeared in the newspaper New York ''[[Newsday]]''.{{Citation needed|date=January 2010}} The review, by Gregory Feeley, called the novel "intellectually provocative, high-octane entertainment," and was quoted the following year in the front matter of the novel's paperback edition, which sold more than 15 million copies in the United States. By the mid-nineties, the phrase was commonly being used as an intensifier and has apparently found a place in modern English vernacular.

Octane has 18 structural isomers (24 including [[stereoisomer]]s):

* Octane (''n''-octane)

* [[3-Methylheptane]] (2 [[enantiomers]])

* [[2,3-Dimethylhexane]] (2 enantiomers)

* [[2,4-Dimethylhexane]] (2 enantiomers)

* [[3,4-Dimethylhexane]] (2 enantiomers + 1 [[meso compound]])

* [[2,2,3-Trimethylpentane]] (2 enantiomers)

* [[2,2,4-Trimethylpentane]] (isooctane)

== References ==

{{reflist}}

== External links ==

* [http://ars-grin.gov/cgi-bin/duke/chemical.pl?OCTANE Phytochemical database entry]

{{alkanes}}

[[ar:أوكتان]]

[[bs:Oktan]]

[[ca:Octà]]

[[cs:Oktan]]

[[da:Octan]]

[[de:Octane (Chemie)]]

[[es:Octano]]

[[eo:Oktano]]

[[fr:Octane]]

[[ko:옥테인]]

[[hi:ऑक्टेन]]

[[it:Ottano]]

[[ku:Oktan]]

[[lv:Oktāns]]

[[hu:Oktán]]

[[nl:Octaan]]

[[ja:オクタン]]

[[no:Oktan]]

[[pms:Otan]]

[[pl:Oktan]]

[[pt:Octano]]

[[ru:Октан]]

[[simple:Octane]]

[[sr:Октан]]

[[fi:Oktaani (kemia)]]

[[sv:Oktan]]

[[tl:Oktano]]

[[ta:ஆக்டேன்]]

[[tr:Oktan]]

[[uk:Октан]]

[[vi:Octan]]

[[zh:辛烷]]