Octane
Octane
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Octane
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

View Wikipedia Article

For the gasoline rating system, see octane rating. For other uses, see Octane (disambiguation). Octane Names IUPAC name Octane[1] Identifiers CAS Number
  • 111-65-9 Y
3D model (JSmol)
  • Interactive image
3DMet B00281 Beilstein Reference 1696875 ChEBI
  • CHEBI:17590 N
ChEMBL
  • ChEMBL134886 Y
ChemSpider
  • 349 Y
DrugBank
  • DB02440 N
ECHA InfoCard 100.003.539 EC Number 203-892-1 Gmelin Reference 82412 KEGG
  • C01387 Y
MeSH octane PubChem CID
  • 356
RTECS number RG8400000 UN number 1262 InChI SMILES Properties Chemical formula C8H18 Molar mass 7002114232000000000♠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 Solubility in water 0.007 mg dm−3 (at 20 °C) log P 4.783 Vapor pressure 1.47 kPa (at 20.0 °C) Henry's law
constant (kH) 29 nmol Pa−1 kg−1 Conjugate acid Octonium Magnetic susceptibility (χ) -96.63·10−6 cm3/mol Refractive index (nD) 1.398 Viscosity 542 μPa s (at 20 °C) Thermochemistry Heat capacity (C) 255.68 J K−1 mol−1 Std molar
entropy (So298) 361.20 J K−1 mol−1 Std enthalpy of
formation (ΔfHo298) −252.1–−248.5 kJ mol−1 Std enthalpy of
combustion (ΔcHo298) −5.53–−5.33 MJ mol−1 Hazards GHS pictograms GHS signal word DANGER GHS hazard statements H225, H304, H315, H336, H410 GHS precautionary statements P210, P261, P273, P301+310, P331 NFPA 704 3 1 0 Flash point 13.0 °C (55.4 °F; 286.1 K) Autoignition
temperature 220.0 °C (428.0 °F; 493.1 K) Explosive limits 0.96–6.5% Lethal dose or concentration (LD, LC): LDLo (lowest published) 428 mg/kg (mouse, intravenous)[3] US health exposure limits (NIOSH): PEL (Permissible) TWA 500 ppm (2350 mg/m3)[2] REL (Recommended) TWA 75 ppm (350 mg/m3) C 385 ppm (1800 mg/m3) [2] IDLH (Immediate danger) 1000 ppm[2] Related compounds Related alkanes
  • Heptane
  • Nonane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is YN ?) Infobox references

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.

Contents
  • 1 Use of the term in gasoline
  • 2 Metaphorical use
  • 3 Isomers
  • 4 References
  • 5 External links
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):

  • Octane (n-octane)
  • 2-Methylheptane
  • 3-Methylheptane (2 enantiomers)
  • 4-Methylheptane
  • 3-Ethylhexane
  • 2,2-Dimethylhexane
  • 2,3-Dimethylhexane (2 enantiomers)
  • 2,4-Dimethylhexane (2 enantiomers)
  • 2,5-Dimethylhexane
  • 3,3-Dimethylhexane
  • 3,4-Dimethylhexane (2 enantiomers + 1 meso compound)
  • 3-Ethyl-2-methylpentane
  • 3-Ethyl-3-methylpentane
  • 2,2,3-Trimethylpentane (2 enantiomers)
  • 2,2,4-Trimethylpentane (isooctane)
  • 2,3,3-Trimethylpentane
  • 2,3,4-Trimethylpentane
  • 2,2,3,3-Tetramethylbutane
References
  1. ^ "octane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 6 January 2012..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
  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 and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ eejit's guides – Octane ratings explained
  5. ^ Oxford English Dictionary.
External links
  • International Chemical Safety Card 0933
  • NIOSH Pocket Guide to Chemical Hazards. "#0470". National Institute for Occupational Safety and Health (NIOSH).
  • Dr. Duke's Phytochemical and Ethnobotanical Databases, Octane, http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?OCTANE
  • v
  • t
  • e
Alkanes
  • Methane (CH
    4)
  • Ethane (C
    2H
    6)
  • Propane (C
    3H
    8)
  • Butane (C
    4H
    10)
  • Pentane (C
    5H
    12)
  • Hexane (C
    6H
    14)
  • Heptane (C
    7H
    16)
  • Octane (C
    8H
    18)
  • Nonane (C
    9H
    20)
  • Decane (C
    10H
    22)
  • Undecane (C
    11H
    24)
  • Dodecane (C
    12H
    26)
  • Tridecane (C
    13H
    28)
  • Tetradecane (C
    14H
    30)
  • Pentadecane (C
    15H
    32)
  • Hexadecane / Cetane (C
    16H
    34)
  • Heptadecane (C
    17H
    36)
  • Octadecane (C
    18H
    38)
  • Nonadecane (C
    19H
    40)
  • Icosane (C
    20H
    42)
  • Heneicosane (C
    21H
    44)
  • Tetracosane (C
    24H
    50)
  • Nonacosane (C
    29H
    60)
  • Hentriacontane (C
    31H
    64)
  • Higher alkanes
  • List of alkanes
  • v
  • t
  • e
Binary compounds of hydrogenAlkali metal hydrides
  • LiH
  • NaH
  • KH
  • RbH
  • CsH

Lithium hydride, LiH
ionic metal hydride


Beryllium hydride
Left (gas phase): BeH2
covalent metal hydride
Right: (BeH2)n (solid phase)
polymeric metal hydride


Borane and diborane
Left: BH3 (special conditions), covalent metalloid hydride
Right: B2H6 (standard conditions), dimeric metalloid hydride


Methane, CH4
covalent nonmetal hydride


Ammonia, NH3
covalent nonmetal hydride


Water, H2O
covalent nonmetal hydride


Hydrogen fluoride, HF
covalent nonmetal hydrideAlkaline earth hydridesMonohydrides
  • BeH
  • MgH
  • CaH
  • SrH
  • BaH
Dihydrides
  • BeH2
  • MgH2
  • CaH2
  • SrH2
  • BaH2
Group 13 hydridesBoranes
  • BH3
  • B2H6
  • B2H2
  • B2H4
  • B4H10
  • B5H9
  • B5H11
  • B6H10
  • B6H12
  • B10H14
  • B18H22
Alanes
  • AlH3
  • Al2H6
Gallanes
  • GaH3
  • Ga2H6
Indiganes
  • InH3
  • In2H6
Thallanes
  • TlH3
  • Tl2H6
Group 14 hydridesLinear alkanes
  • CH4
  • C2H6
  • C3H8
  • C4H10
  • C5H12
  • C6H14
  • C7H16
  • C8H18
  • C9H20
  • C10H22
  • more...
Linear alkenes
  • C2H4
  • C3H6
  • C4H8
  • C5H10
  • C6H12
  • C7H14
  • C8H16
  • C9H18
  • C10H20
  • more...
Linear alkynes
  • C2H2
  • C3H4
  • C4H6
  • C5H8
  • C6H10
  • C7H12
  • C8H14
  • C9H16
  • C10H18
  • more...
Silanes
  • SiH4
  • Si2H6
  • Si3H8
  • Si4H10
  • Si5H12
  • Si6H14
  • Si7H16
  • Si8H18
  • Si9H20
  • Si10H22
  • more...
Silenes
  • Si2H4
Silynes
  • Si2H2
  • SiH
Germanes
  • GeH4
  • Ge2H6
  • Ge3H8
  • Ge4H10
  • Ge5H12
Stannanes
  • SnH4
  • Sn2H6
Plumbanes
  • PbH4
  • CH
  • CH2
  • CH3
  • C2H
  • Cycloalkanes
  • Cycloalkenes
  • Annulenes
  • Many more
Pnictogen hydridesAzanes
  • NH3
  • N2H4
  • N3H5
  • N4H6
  • N5H7
  • N6H8
  • N7H9
  • N8H10
  • N9H11
  • N10H12
  • more...
  • Azenes
    • N2H2
    • N3H3
    • N4H4
    Phosphanes
    • PH3
    • P2H4
    • P3H5
    • P4H6
    • P5H7
    • P6H8
    • P7H9
    • P8H10
    • P9H11
    • P10H12
    • more...
    Phosphenes
    • P2H2
    • P3H3
    • P4H4
    Arsanes
    • AsH3
    • As2H4
    Stibanes
    • SbH3
    Bismuthanes
    • BiH3
    • HN3
    • NH
      • radical
    Hydrogen chalcogenidesPolyoxidanes
  • H2O
  • H2O2
  • H2O3
  • H2O4
  • H2O5
  • H2O6
  • H2O7
  • H2O8
  • H2O9
  • H2O10
  • more...
  • Polysulfanes
    • H2S
    • H2S2
    • H2S3
    • H2S4
    • H2S5
    • H2S6
    • H2S7
    • H2S8
    • H2S9
    • H2S10
    • more...
    Selanes
    • H2Se
    • H2Se2
    Tellanes
    • H2Te
    • H2Te2
    Polanes
    • PoH2
    • HO
    • HO2
    • HO3
    • H2O+–O–
    • H2S=S
    • (HS)2S+–S–
    • HS
    • HDO
    • D2O
    • T2O
    Hydrogen halides
  • HF
  • HCl
  • HBr
  • HI
  • HAt
  • Transition metal hydrides
    • ScH2
    • YH2
    • YH3
    • TiH2
    • ZrH2
    • HfH2
    • VH
    • VH2
    • NbH
    • NbH2
    • TaH
    • CrH
    • CrH2
    • CrHx
    • NiH
    • PdHx (x < 1)
    • FeH
    • FeH2
    • FeH5
    • CuH
    • ZnH2
    • CdH2
    • HgH2
    Lanthanide hydrides
    • LaH2
    • LaH3
    • LaH10
    • CeH2
    • CeH3
    • PrH2
    • PrH3
    • NdH2
    • NdH3
    • SmH2
    • SmH3
    • EuH2
    • GdH2
    • GdH3
    • TbH2
    • TbH3
    • DyH2
    • DyH3
    • HoH2
    • HoH3
    • ErH2
    • ErH3
    • TmH2
    • TmH3
    • YbH2
    • YbH2.5
    • LuH2
    • LuH3
    Actinide hydrides
    • AcH2
    • ThH2
    • Th4H15
    • PaH3
    • UH3
    • NpH2
    • NpH3
    • PuH2
    • PuH3
    • AmH2
    • AmH3
    • CmH2


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