Octane

Last updated
Octane
Octane-2D-Skeletal.svg
OctaneFull.png
Octane 3D ball.png
N-octane-spaceFilling.png
Names
Systematic IUPAC name
Octane [1]
Other names
n-Octane
Identifiers
3D model (JSmol)
3DMet
1696875
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.539 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-892-1
82412
KEGG
MeSH octane
PubChem CID
RTECS number
  • RG8400000
UNII
UN number 1262
  • InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3 Yes check.svgY
    Key: TVMXDCGIABBOFY-UHFFFAOYSA-N Yes check.svgY
  • CCCCCCCC
Properties
CH3(CH2)6CH3
Molar mass 114.232 g·mol−1
AppearanceColourless 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
0.007 mg/dm3 (at 20 °C)
log P 4.783
Vapor pressure 1.47 kPa (at 20.0 °C)
29 nmol/(Pa·kg)
Conjugate acid Octonium
−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)
Std molar
entropy
(S298)
361.20 J/(K·mol)
−252.1 to −248.5 kJ/mol
−5.53 to −5.33 MJ/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H225, H304, H315, H336, H410
P210, P261, P273, P301+P310, P331
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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) [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 their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 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.

Contents

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. For examples, as a neurotoxin with narcotic effects, n-octane is almost twice times as toxic as n-heptane. [5]

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. Octane stereo isomers 10 3 4 dimethylhexane.svg
(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 se

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 the alkylation reaction between iso-butane and 1-butene, which forms iso-octane. [7]

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

Metabolism

Octanes are not produced biologically.

N-octane is the octane isomer that has the longest carbon skeleton. Unlike its constitutional isomers, it has a very low knock resistance. N-octane.jpg
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. Iso-octane.jpg
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. 2,3,3-Trimethylpentane (view 2).jpg
The octane isomer 2,3,3-Trimethylpentane has an octane rating exceeding 100.

Related Research Articles

<span class="mw-page-title-main">Alkane</span> Type of saturated hydrocarbon compound

In organic chemistry, an alkane, or paraffin, is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula CnH2n+2. The alkanes range in complexity from the simplest case of methane, where n = 1, to arbitrarily large and complex molecules, like pentacontane or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane.

<span class="mw-page-title-main">Gasoline</span> Liquid fuel, also called petrol, derived from petroleum

Gasoline or petrol is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When formulated as a fuel for engines, gasoline is chemically composed of organic compounds derived from the fractional distillation of petroleum and later chemically enhanced with gasoline additives. It is a high-volume profitable product produced in crude oil refineries.

<span class="mw-page-title-main">Heptane</span> Chemical compound

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without undergoing pre-ignition. The higher the octane number, the more compression the fuel can withstand before detonating. Octane rating does not relate directly to the power output or the energy content of the fuel per unit mass or volume, but simply indicates gasoline's resistance to detonating under pressure without a spark.

<span class="mw-page-title-main">Liquid fuel</span> Liquids that can be used to create energy

Liquid fuels are combustible or energy-generating molecules that can be harnessed to create mechanical energy, usually producing kinetic energy; they also must take the shape of their container. It is the fumes of liquid fuels that are flammable instead of the fluid. Most liquid fuels in widespread use are derived from fossil fuels; however, there are several types, such as hydrogen fuel, ethanol, and biodiesel, which are also categorized as a liquid fuel. Many liquid fuels play a primary role in transportation and the economy.

<span class="mw-page-title-main">E85</span> Fuel blend of 85% ethanol and 15% another hydrocarbon

E85 is an abbreviation typically referring to an ethanol fuel blend of 85% ethanol fuel and 15% gasoline or other hydrocarbon by volume.

<span class="mw-page-title-main">2,2,4-Trimethylpentane</span> Chemical compound

2,2,4-Trimethylpentane, also known as isooctane or iso-octane, is an organic compound with the formula (CH3)3CCH2CH(CH3)2. It is one of several isomers of octane (C8H18). This particular isomer is the standard 100 point on the octane rating scale (the zero point is n-heptane). It is an important component of gasoline, frequently used in relatively large proportions (around 10%) to increase the knock resistance of fuel.

<span class="mw-page-title-main">Alcohol fuel</span> Alcohols used as fuel for internal combustion engines

Various alcohols are used as fuel for internal combustion engines. The first four aliphatic alcohols are of interest as fuels because they can be synthesized chemically or biologically, and they have characteristics which allow them to be used in internal combustion engines. The general chemical formula for alcohol fuel is CnH2n+1OH.

<span class="mw-page-title-main">2-Methylheptane</span> Chemical compound

2-Methylheptane is a colourless liquid, chemical compound which is part of the branched alkane family and is isomeric to octane Where a methyl group has been added to the second carbon in heptane. Its structural formula is (CH3)2CH(CH2)4CH3.

Octane is an alkane with the chemical formula C8H18.

An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuel's octane rating by raising the temperature and pressure at which auto-ignition occurs. The mixture known as gasoline or petrol, when used in high compression internal combustion engines, has a tendency to knock and/or to ignite early before the correctly timed spark occurs.

Natural gasoline is a liquid hydrocarbon mixture condensed from natural gas, similar to common gasoline (petrol) derived from petroleum.

<span class="mw-page-title-main">Triptane</span> Chemical compound

Triptane, or 2,2,3-trimethylbutane, is an organic chemical compound with the molecular formula C7H16 or (H3C-)3C-C(-CH3)2H. It is therefore an alkane, specifically the most compact and heavily branched of the heptane isomers, the only one with a butane (C4) backbone.

<span class="mw-page-title-main">2,3,3-Trimethylpentane</span> Chemical compound

2,3,3-Trimethylpentane is a chemical compound in the family of hydrocarbons which has a formula of C8H18. It is an isomer of octane. It has a role as a human metabolite, a bacterial metabolite and a mammalian metabolite. It is an alkane and a volatile organic compound.

The molecular formula C8H18 (molar mass: 114.23 g/mol) may refer to:

<span class="mw-page-title-main">2,3-Dimethylpentane</span> Chemical compound

2,3-Dimethylpentane is an organic compound of carbon and hydrogen with formula C
7
H
16
, more precisely CH
3
CH(CH
3
)
CH(CH
3
)
CH
2
CH
3
: a molecule of pentane with methyl groups –CH
3
replacing hydrogen atoms on carbon atoms 2 and 3. It is an alkane, a fully saturated hydrocarbon; specifically, one of the isomers of heptane.

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. 1 2 3 4 NIOSH 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 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.
  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. Retrieved 2024-04-19.
  6. "Fractionation". www.appliedcontrol.com. Retrieved 2024-04-19.
  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.