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Octane

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For the gasoline rating system, see octane rating. For other uses, see Octane (disambiguation).
Octane
Skeletal formula of octane
Skeletal formula of octane with all implicit carbons shown, and all explicit hydrogens added
Ball-and-stick model of octane
Space-filling model of octane
Names
IUPAC name
Octane[1]
Identifiers
3D model (JSmol)
3DMet
1696875
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.539 Edit this at Wikidata
EC Number
  • 203-892-1
82412
KEGG
MeSH octane
RTECS number
  • RG8400000
UN number 1262
  • InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3 checkY
    Key: TVMXDCGIABBOFY-UHFFFAOYSA-N checkY
  • CCCCCCCC
Properties
C8H18
Molar mass 114.232 g·mol−1
Appearance Colorless liquid
Odor Gasoline-like[2]
Density 0.703 g cm−3
Melting point −57.1 to −56.6 °C; −70.9 to −69.8 °F; 216.0 to 216.6 K
Boiling point 125.1 to 126.1 °C; 257.1 to 258.9 °F; 398.2 to 399.2 K
0.007 mg dm−3 (at 20 °C)
log P 4.783
Vapor pressure 1.47 kPa (at 20.0 °C)
29 nmol Pa−1 kg−1
Conjugate acid Octonium
-96.63·10−6 cm3/mol
1.398
Viscosity 542 μPa s (at 20 °C)
Thermochemistry
255.68 J K−1 mol−1
361.20 J K−1 mol−1
−252.1–−248.5 kJ mol−1
−5.53–−5.33 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Danger
H225, H304, H315, H336, H410
P210, P261, P273, P301+P310, P331
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 13.0 °C (55.4 °F; 286.1 K)
220.0 °C (428.0 °F; 493.1 K)
Explosive limits 0.96–6.5%
Lethal dose or concentration (LD, LC):
428 mg/kg (mouse, intravenous)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 500 ppm (2350 mg/m3)[2]
REL (Recommended)
 TWA 75 ppm (350 mg/m3) C 385 ppm (1800 mg/m3) [15-minute][2]
IDLH (Immediate danger)
 1000 ppm[2]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

Octane is a component of gasoline (petrol). As with all low-molecular-weight hydrocarbons, octane is volatile and very flammable.

Use of the term in gasoline

"Octane" is colloquially used as a short form of "octane rating" (an index of a fuel's ability to resist engine knock at high compression, which is a characteristic of octane's branched-chain isomers, especially iso-octane), particularly in the expression "high octane."

The octane rating was originally determined by mixing a gasoline made entirely of heptane and 2,2,4-trimethylpentane (a highly branched octane), and assigning anti-knock ratings of 0 for pure heptane and 100 for pure 2,2,4-trimethylpentane. The anti-knock rating of this mixture would be the same as the percentage of 2,2,4-trimethylpentane in the mix. Modern octane ratings of gasoline are given octane ratings equal to those from this original heptane/octane scale. Different isomers of octane can contribute to a higher or lower octane rating. For example, n-octane (the straight chain of 8 carbon atoms with no branching) has a -10 (negative) octane rating, while pure 2,2,4-trimethylpentane (a highly branched octane) has an octane rating of 100.[4][better source needed] Some fuels have an octane rating higher than 100, notably those containing methanol or ethanol.

Metaphorical use

Octane became well known in American popular culture in the mid- and late 1960s, when gasoline companies boasted of "high octane" levels in their gasoline advertisements.

The compound adjective "high-octane", meaning powerful or dynamic, is recorded in a figurative sense from 1944.[5] By the mid-1990s, the phrase was commonly being used as an intensifier and has found a place in modern English vernacular.

Isomers

Octane has 18 structural isomers (24 including stereoisomers):

References

  1. ^ "octane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 6 January 2012.
  2. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0470". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Octane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ eejit's guides – Octane ratings explained
  5. ^ Oxford English Dictionary.
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