Octane

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Octane
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Names
Systematic IUPAC name
Octane[1]
Other names
n-Octane
Identifiers
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3D model (JSmol)
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1696875
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EC Number Page Template:Plainlist/styles.css has no content.
82412
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MeSH octane
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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 Colourless liquid
Odor Gasoline-like[2]
Density 0.703 g/cm3
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
0.07 mg / 100 g (at 298 K)[3]
log P 4.783
Vapor pressure 1.47 kPa (at 20.0 °C)
29 nmol/(Pa·kg)
−96.63·10−6 cm3/mol
1.398
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  • 0.509 mPa·s (25 °C)[4]
  • 0.542 mPa·s (20 °C)
Thermochemistry
255.68 J/(K·mol)
361.20 J/(K·mol)
−252.1 to −248.5 kJ/mol
−5.53 to −5.33 MJ/mol
Hazards
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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)[5]
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
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Octane is a hydrocarbon and also an alkane with the chemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has many structural isomers that differ by the location of branching in the carbon chain. One of these isomers, 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 volatile, flammable, and toxic. Octane is 1.2 to 2 times more toxic than heptane.[6]

Isomers

N-octane has 23 constitutional isomers. 8 of these isomers have one stereocenter; 3 of them have two stereocenters.

(3S,4S)-3,4-Dimethylhexane (top left) and (3R,4R)-3,4-Dimethylhexane (top right) are non-superimposable mirror images, so they are chiral enantiomers. (meso)-3,4-Dimethylhexane (bottom) has a superimposable mirror image, so it is an achiral meso compound.

Achiral isomers:

Chiral isomers:

Production and use

In petrochemistry, octanes are not typically differentiated or purified as specific compounds. Octanes are components of particular boiling fractions.[7]

A common route to such fractions is the alkylation reaction between iso-butane and 1-butene, which forms iso-octane.[8]

Octane is commonly used as a solvent in paints and adhesives.

N-octane is the octane isomer that has the longest carbon skeleton. Unlike its constitutional isomers, it has a very low knock resistance.
The octane isomer, iso-octane, is used as one of the standards for octane ratings. It has a rating of 100 by definition.
The octane isomer 2,3,3-Trimethylpentane has an octane rating exceeding 100.

See also

  • Octane rating, measure of a fuel's ability to withstand compression in an internal combustion engine without causing engine knocking

References

  1. ^ Page Module:Citation/CS1/styles.css has no content."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 Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0470". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Page Module:Citation/CS1/styles.css has no content."IUPAC-NIST Solubilities Database". Srdata.nist.gov. Retrieved May 27, 2026.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Dymond, J. H.; Oye, H. A. (1994). "Viscosity of Selected Liquid n-Alkanes". Journal of Physical and Chemical Reference Data. 23 (1): 41–53. Bibcode:1994JPCRD..23...41D. doi:10.1063/1.555943. ISSN 0047-2689.
  5. ^ Page Module:Citation/CS1/styles.css has no content."Octane". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  6. ^ Page Module:Citation/CS1/styles.css has no content."1988 OSHA PEL Project - Octane | NIOSH | CDC". Cdc.gov. 2020-02-27. Retrieved 2024-04-19.
  7. ^ Page Module:Citation/CS1/styles.css has no content."Fractionation". Appliedcontrol.com. Retrieved 2024-04-19.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Ross, Julian (January 1986). "Ullmann's Encyclopedia of industrial chemistry". Applied Catalysis. 27 (2): 403–404. doi:10.1016/s0166-9834(00)82943-7. ISSN 0166-9834.

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