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Octane

From Wikipedia, the free encyclopedia
Hydrocarbon compound with the formula C8H18
Not to be confused withoctene oroctyne.
For the gasoline rating system, seeOctane rating. For other uses, seeOctane (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
Systematic IUPAC name
Octane[1]
Other names
n-Octane
Identifiers
3D model (JSmol)
1696875
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.003.539Edit this at Wikidata
EC Number
  • 203-892-1
82412
KEGG
MeSHoctane
RTECS number
  • RG8400000
UNII
UN number1262
  • InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3 checkY
    Key: TVMXDCGIABBOFY-UHFFFAOYSA-N checkY
  • CCCCCCCC
Properties
CH3(CH2)6CH3
Molar mass114.232 g·mol−1
AppearanceColourless liquid
OdorGasoline-like[2]
Density0.703 g/cm3
Melting point−57.1 to −56.6 °C; −70.9 to −69.8 °F; 216.0 to 216.6 K
Boiling point125.1 to 126.1 °C; 257.1 to 258.9 °F; 398.2 to 399.2 K
0.007 mg/dm3 (at 20 °C)
logP4.783
Vapor pressure1.47 kPa (at 20.0 °C)
29 nmol/(Pa·kg)
Conjugate acidOctonium
−96.63·10−6 cm3/mol
1.398
Viscosity
  • 0.509 mPa·s (25 °C)[3]
  • 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
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225,H304,H315,H336,H410
P210,P261,P273,P301+P310,P331
NFPA 704 (fire diamond)
Flash point13.0 °C (55.4 °F; 286.1 K)
220.0 °C (428.0 °F; 493.1 K)
Explosive limits0.96 – 6.5%
Lethal dose or concentration (LD, LC):
428 mg/kg (mouse, intravenous)[4]
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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Octane is ahydrocarbon and also analkane with thechemical formula C8H18, and the condensed structural formula CH3(CH2)6CH3. Octane has manystructural isomers that differ by the location of branching in thecarbon chain. One of these isomers,2,2,4-trimethylpentane (commonly called iso-octane), is used as one of the standard values in theoctane rating scale.

Octane is a component ofgasoline and petroleum. Understandard temperature and pressure, octane is an odorless, colorless liquid. Like other short-chained alkanes with a low molecular weight, it isvolatile, flammable, and toxic. Octane is 1.2 to 2 times more toxic thanheptane.[5]

Isomers

[edit]

N-octane has 23constitutional isomers. 8 of these isomers have onestereocenter; 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 chiralenantiomers.(meso)-3,4-Dimethylhexane (bottom) has a superimposable mirror image, so it is an achiralmeso compound.

Achiral Isomers:

Chiral Isomers:

Production and use

[edit]

In petrochemistry, octanes are not typically differentiated or purified as specific compounds. Octanes are components of particular boiling fractions.[6]

A common route to such fractions is thealkylation reaction between iso-butane and 1-butene, which forms iso-octane.[7]

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 isomer2,3,3-Trimethylpentane has an octane rating exceeding 100.

References

[edit]
  1. ^"octane - Compound Summary".PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved6 January 2012.
  2. ^abcdNIOSH Pocket Guide to Chemical Hazards."#0470".National Institute for Occupational Safety and Health (NIOSH).
  3. ^Dymond, J. H.; Oye, H. A. (1994). "Viscosity of Selected Liquidn-Alkanes".Journal of Physical and Chemical Reference Data.23 (1):41–53.Bibcode:1994JPCRD..23...41D.doi:10.1063/1.555943.ISSN 0047-2689.
  4. ^"Octane".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health (NIOSH).
  5. ^"1988 OSHA PEL Project - Octane | NIOSH | CDC".www.cdc.gov. 2020-02-27. Retrieved2024-04-19.
  6. ^"Fractionation".www.appliedcontrol.com. Retrieved2024-04-19.
  7. ^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.

External links

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