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Octane
Octane
Octane
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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 InfoCard 100.003.539 Edit this at Wikidata
EC Number
  • 203-892-1
82412
KEGG
MeSH octane
RTECS number
  • RG8400000
UNII
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
CH3(CH2)6CH3
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
0.007 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)
361.20 J/(K·mol)
−252.1 to −248.5 kJ/mol
−5.53 to −5.33 MJ/mol
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)[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).
☒N verify (what is checkY☒N ?)

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.[5]

Isomers

[edit]

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

[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 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.

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.

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Octane

View on Grokipedia
from Grokipedia
Octane is an with the molecular formula C₈H₁₈, consisting of a chain of eight carbon atoms saturated with hydrogen. It exists as a colorless, volatile at , exhibiting a characteristic gasoline-like and low in due to its nonpolar . As a major component of petroleum-derived fuels, octane plays a central role in internal combustion engines, where its properties influence engine performance and efficiency. The term "octane" also refers to a family of 18 structural isomers, with n-octane (the straight-chain form) serving as the reference for low anti-knock performance in fuel testing, while branched isomers like (isooctane) provide high resistance to premature ignition. The , a standardized measure of a fuel's ability to withstand compression without causing , is defined relative to a scale where isooctane is assigned a value of 100 and n-heptane (a related ) is 0; higher ratings indicate better suitability for high-compression engines, enabling improved power output and fuel economy. Octane is primarily obtained through of crude oil or cracking processes in refineries, and it is blended into to achieve desired octane numbers, often enhanced by additives like (historically) or oxygenates such as in modern formulations. Beyond fuels, octane finds applications as a solvent in industries including paints, adhesives, and chemical , owing to its ability to dissolve organic compounds effectively. Its flammability and low (approximately 125°C for n-octane) necessitate careful handling to prevent hazards, and environmental concerns have driven efforts to reduce its emissions through cleaner standards.

Chemical Identity and Properties

Molecular Structure and Formula

Octane is a saturated belonging to the series, characterized by the molecular formula C8H18C_8H_{18}. This formula indicates a composition of eight carbon atoms and eighteen atoms, with all carbon-carbon bonds being single covalent bonds, making it a paraffin hydrocarbon. Alkanes like octane are also termed paraffins due to their low reactivity, derived from the Latin parum affinis, meaning "little affinity."/03%3A_Organic_Compounds-_Alkanes_and_Their_Stereochemistry/3.05%3A_Properties_of_Alkanes) The molecular weight of octane is 114.23 g/mol, calculated from its atomic composition. Structurally, octane features an eight-carbon chain where the carbons are connected exclusively by single bonds, allowing for either straight-chain or branched configurations. The straight-chain form, known as n-octane, has the condensed structural formula \ceCH3(CH2)6CH3\ce{CH3(CH2)6CH3}. Under the International Union of Pure and Applied Chemistry (IUPAC) , the name "octane" specifically denotes the unbranched , while common usage often employs "n-octane" to distinguish it from branched variants. The term originates from the Latin octo, meaning "eight," highlighting the molecule's eight carbon atoms. While multiple isomeric forms of C8H18C_8H_{18} exist, the foundational structure emphasizes its role as a prototypical .

Physical Characteristics

n-Octane appears as a colorless, volatile with a characteristic gasoline-like . At standard room temperature (20°C), it exists in the state, with a of -56.8°C and a of 125.6°C. Its is 0.703 g/cm³ at 20°C, making it less dense than and prone to floating on aqueous surfaces. n-Octane exhibits low solubility in water, approximately 0.00066 g/L at 20°C, reflecting its nonpolar nature. In contrast, it is miscible with many organic solvents, including , acetone, , and , facilitating its use in non-aqueous environments. Additional optical and vapor properties include a of 1.397 at 20°C and a of 1.33 kPa at the same , indicating moderate volatility under ambient conditions. Thermodynamic characteristics encompass a of 41.5 kJ/mol and a liquid of 254 J/mol·K.
PropertyValueConditionsSource
Density0.703 g/cm³20°CCAMEO Chemicals
Vapor Pressure1.33 kPa20°CPubChem
Refractive Index1.39720°CPubChem
Heat of Vaporization41.5 kJ/mol25°CPubChem
Heat Capacity (liquid)254 J/mol·K25°CNIST WebBook

Chemical Reactivity

As a straight-chain , n-octane exhibits general chemical inertness under standard conditions, showing no reactivity toward aqueous acids, bases, or common oxidizing agents due to the strength of its carbon-hydrogen and carbon-carbon bonds. It is also resistant to , as it does not react with and remains stable in aqueous environments. One of the primary reactions of n-octane is combustion in the presence of oxygen, which proceeds exothermically to form carbon dioxide and water. The balanced equation for the complete combustion of liquid n-octane is: \ceC8H18(l)+12.5O2(g)−>8CO2(g)+9H2O(l)\ce{C8H18 (l) + 12.5 O2 (g) -> 8 CO2 (g) + 9 H2O (l)} This reaction releases a standard enthalpy of combustion of -5470.3 kJ/mol, reflecting the high energy content of the molecule. Under light, n-octane undergoes , a where atoms are replaced by such as , yielding a of chloro-octane isomers. This process involves initiation by homolytic cleavage of the halogen molecule, propagation through radical abstraction and addition steps, and termination by radical recombination, and is characteristic of alkanes due to the relative weakness of C-H bonds compared to other functional groups./Alkanes/Reactivity_of_Alkanes/Halogenation_of_Alkanes) In industrial contexts, n-octane can be transformed through cracking and reforming processes to produce smaller hydrocarbons or higher-octane components. cracking involves high-temperature (typically 500–800°C) to break C-C bonds, generating alkenes, alkanes, and coke as byproducts, while catalytic uses metal catalysts like on alumina at 450–550°C to rearrange the structure into branched or aromatic compounds, enhancing quality. Despite its , n-octane is highly flammable, with a of 13°C and an of °C, indicating ignition risk at relatively low temperatures in the presence of an ignition source.

Isomers

Constitutional Isomers

Constitutional isomers of octane, with the molecular formula C₈H₁₈, are compounds that share the same molecular formula but differ in the connectivity of their carbon atoms, resulting in variations in chain length, branching, and substituent positioning. These structural differences arise from different ways to arrange eight carbon atoms into acyclic skeletons while maintaining the total of 18 atoms. There are exactly 18 constitutional isomers of octane, each representing a unique carbon skeleton. The naming of these isomers follows the International Union of Pure and Applied Chemistry (IUPAC) systematic conventions, where the parent chain is the longest continuous carbon chain, and branches are denoted as alkyl groups (e.g., methyl or ethyl) listed alphabetically with their locant numbers indicating attachment positions. Common names persist for some, such as n-octane for the linear chain and isooctane for the branched 2,2,4-trimethylpentane. The complete list of constitutional isomers, with their IUPAC names and Chemical Abstracts Service (CAS) registry numbers, is presented below:
IUPAC NameCAS Number
Octane111-65-9
2-Methylheptane592-27-8
3-Methylheptane589-81-1
4-Methylheptane589-53-7
2,2-Dimethylhexane590-73-8
2,3-Dimethylhexane584-94-1
2,4-Dimethylhexane589-43-5
2,5-Dimethylhexane592-13-2
3,3-Dimethylhexane563-16-6
3,4-Dimethylhexane583-48-2
3-Ethylhexane619-99-8
2,2,3-Trimethylpentane564-02-3
540-84-1
2,3,3-Trimethylpentane560-21-4
2,3,4-Trimethylpentane565-75-3
3-Ethyl-2-methylpentane609-26-7
3-Ethyl-3-methylpentane1067-08-9
2,2,3,3-Tetramethylbutane594-82-1
Prominent examples include n-octane (straight chain), 2-methylheptane (single methyl branch on a seven-carbon chain), 3-ethylhexane (ethyl branch on a six-carbon chain), and 2,2,4-trimethylpentane (isooctane, with three methyl branches on a five-carbon chain). Isooctane is particularly notable for its extensive branching, which contributes to its high research octane number (RON) of 100, serving as a standard reference fuel for high anti-knock performance. In general, branched constitutional isomers of octane display lower boiling points than the straight-chain n-octane because their more spherical, compact structures reduce molecular surface area, weakening van der Waals intermolecular forces. For example, n-octane has a of 125.6 °C, whereas isooctane boils at 99.2 °C. Some constitutional isomers exhibit due to chiral centers, as explored in the Stereoisomers section.

Stereoisomers

Among the constitutional isomers of octane (C₈H₁₈), five exhibit stereocenters that give rise to . These include four isomers each with a single chiral carbon, producing eight enantiomeric forms (four pairs), and one isomer with two chiral carbons, yielding three stereoisomers (a pair of enantiomers and one ). Branching patterns in these constitutional isomers create the necessary asymmetry for such stereocenters. n-Octane, the straight-chain isomer, lacks chiral centers and is achiral, displaying no optical rotation. Stereoisomers of octane encompass enantiomers, which are nonsuperimposable mirror images that rotate plane-polarized light in opposite directions; diastereomers, which are stereoisomers that are not enantiomers and may have different physical properties; and meso compounds, which are achiral due to an internal plane of symmetry despite containing chiral centers. A representative example with a single chiral center is 3-methylheptane, where the carbon at position 3 is attached to four different substituents (, methyl, ethyl, and pentyl groups), resulting in a pair of enantiomers. For isomers with two chiral centers, 3,4-dimethylhexane features two adjacent chiral carbons at positions 3 and 4; the (3R,4S) configuration forms a due to , while the (3R,4R) and (3S,4S) configurations constitute the enantiomeric pair. In total, the 18 constitutional isomers of octane, when accounting for stereoisomers from those with one or two asymmetric carbons, yield 24 distinct unique compounds. Chiral stereoisomers of octane can be resolved from racemic mixtures via chromatographic separation using chiral stationary phases, which exploit differential interactions between enantiomers and the chiral medium.

Production

Natural Sources

Octane and its isomers occur naturally as components of the paraffin () fraction within crude oil, where the C8 hydrocarbons form a significant portion of the gasoline-range hydrocarbons (typically C5–C10), comprising approximately 5–15% of that fraction depending on the crude's composition. These C8 alkanes, including n-octane and branched variants like , arise from the thermal maturation of organic sediments buried in sedimentary basins. Geologically, octane originates from ancient , primarily planktonic and algal remains, that transforms into during —a low-temperature process (below 50–100°C) involving compaction and early chemical alterations under shallow burial conditions over millions of years. Subsequent catagenesis, occurring at deeper levels (2–4 km) and temperatures of 50–150°C, cracks the into liquid hydrocarbons, including C8 alkanes, through progressive breakdown of complex macromolecules into simpler chains. This stage dominates formation, with octane emerging as part of the generated oil over geological timescales spanning the to eras. The distribution of octane varies by crude oil type: it is more abundant in lighter crudes with high (above 30°), such as those from Middle Eastern fields like Saudi Arabia's Ghawar, where the gasoline-range fraction yields higher proportions of C8 components due to greater prevalence of shorter-chain hydrocarbons. In contrast, heavy crudes ( below 20°), often from Venezuelan or Canadian sources, contain lower concentrations of octane, as they are dominated by longer-chain and more aromatic compounds. Octane is present only in minor amounts in liquids (NGLs), which primarily consist of C2–C5 hydrocarbons extracted from associated gas, with C8 traces limited to heavier condensates. In natural extraction, octane is isolated from crude oil through in refineries, where the or light fraction is collected at boiling temperatures of approximately 98–140°C, encompassing the range for C8 s (n-octane boils at 125.6°C, while isomers like isooctane boil near 99°C). This process separates the volatile C8 components based on differences in a column. As of , global proven crude oil reserves stand at about 1.57 barrels, with octane yields higher in light crudes (API >31.1°) that produce up to 30–40% versus 10–20% in heavy crudes (API <22.3°), influencing overall C8 recovery.

Industrial Synthesis

The primary industrial synthesis of octane isomers begins with refining, where crude oil is processed through catalytic cracking to break down heavier hydrocarbons into lighter fractions, followed by to isolate , a key precursor containing C5-C10 alkanes including octane components. This cracking process, typically using or (FCC) units, converts gas oils into at temperatures around 500-550°C, yielding a of straight-chain and branched octanes essential for high-octane fuels. The fraction, derived from natural deposits, is further refined to enhance branching for improved fuel quality. A critical step in producing high-octane octane isomers, particularly iso-octane (), involves the process, where reacts with olefins in the presence of acid catalysts such as (HF) or (H₂SO₄) at low temperatures (0-40°C) to form branched C8 alkylates. This reaction selectively generates iso-octane and other trimethylpentane isomers, which have octane ratings exceeding 100, making them vital for blending. Alkylation units in refineries operate under controlled conditions to maximize yield and minimize side products like heavy ends. Catalytic reforming complements alkylation by converting lower-boiling alkanes (C6-C8) into branched isomers and aromatics using platinum-based s on alumina supports at approximately 500°C and moderate pressures (10-35 bar) with recirculation. This process promotes , cyclization, and dehydrogenation, increasing the proportion of branched octanes such as 2,2,4- and 2,3,4-trimethylpentanes in the reformate stream. Continuous regeneration mitigates coke deposition, ensuring sustained operation. Global production of C8 fractions from these refining processes supports the gasoline market, with an estimated 100 million metric tons per year in 2025, of which about 70% consists of branched isomers produced via and reforming to meet high-octane demands. Emerging alternatives include bio-octane synthesis from , such as of fusel oils (by-products of production) to yield branched C8 alcohols convertible to hydrocarbons, though this accounts for less than 1% of total output as of 2025 due to scaling challenges.

Applications

Role in Fuels and Octane Rating

Octane plays a pivotal role in gasoline as a key hydrocarbon component, where its isomers contribute to the fuel's anti-knock properties during combustion in spark-ignition engines. Normal heptane (n-heptane), a straight-chain alkane, serves as the reference fuel with an assigned octane number of 0 due to its high propensity for auto-ignition and knocking under compression, while 2,2,4-trimethylpentane (iso-octane), a highly branched isomer, is assigned 100 for its superior resistance to premature detonation. These reference fuels form the basis for evaluating all gasoline blends, as straight-run gasoline from crude oil distillation typically yields low-octane fractions around 70, necessitating refinement to meet engine requirements. The system quantifies a fuel's ability to resist knocking, measured through two primary metrics: the Research Octane Number (RON) and the Motor Octane Number (MON), both determined using standardized Cooperative Fuel Research (CFR) engines developed in the . RON is assessed under mild conditions—low engine speed (600 rpm) and cooler intake air—to simulate light-load operation, while MON uses harsher conditions—higher speed (900 rpm) and preheated air—to mimic high-load scenarios like acceleration. The Anti-Knock Index (AKI), commonly posted at U.S. pumps as (R+M)/2, averages these values to provide a practical indicator of real-world performance, with modern unleaded typically targeting 87–93 AKI for regular to premium grades. Gasoline blending enhances octane by incorporating branched octane isomers, such as iso-octane produced via industrial processes like and , which convert low-octane straight-chain paraffins into higher-rated branched structures. Historically, additives like methyl tert-butyl ether (MTBE) were widely used to boost octane by 2–3 points, but environmental concerns over led to its phase-out in the U.S. around 2006 and gradual bans in many European countries in the early . The system originated in the 1920s through collaboration between the automotive and petroleum industries, formalized by the American Society for Testing and Materials (ASTM) via standards D2699 (RON, introduced 1930s) and D2700 (MON), using the CFR engine to address in emerging high-compression designs. By the mid-20th century, unleaded became standard following the phase-out of , aligning with modern AKI targets of 87–93 to support efficient without additives. As of 2025, the automotive shift toward turbocharged engines for improved and emissions compliance is driving demand for higher-octane fuels (91+ AKI), enabling higher boost pressures without knocking and yielding up to 5–10% better efficiency in downsized engines. Global demand stands at approximately 1.2 billion metric tons annually (about 27 million barrels per day), fueled by this trend in emerging markets and advanced vehicle technologies.

Other Uses

Octane and its isomers, particularly n-octane and iso-octane, find applications as solvents in several industrial sectors due to their non-polar nature and ability to dissolve resins, fats, oils, and other non-polar substances. In the paints and coatings industry, they are used as thinners and components in formulations, providing effective solvency without aromatic content for low-odor products. Similarly, in varnishes, these hydrocarbons aid in dissolving and blending resins to achieve desired viscosity and drying properties. In adhesives and rubber processing, octane isomers serve as solvents in special formulations for bonding plastics and elastomers, such as in the production of elastane fibers like , where they facilitate processing without degrading the base materials. Their selective solvency makes them suitable for rubber compounding and activation, enhancing in elastomer-based products. As chemical intermediates, octane derivatives are employed in the synthesis of and detergents, leveraging processes like oxidation to produce higher-value compounds. N-octane also acts as a in the production of lubricants and related additives through controlled chemical transformations. In settings, n-octane is widely used as a calibration standard in for analyzing hydrocarbons, owing to its high purity and well-defined retention time. This application supports precise quantification in and environmental samples. Niche uses include n-octane as an extraction solvent for purifying organic compounds in pharmaceutical processes, where its non-reactivity preserves sensitive materials.

Health, Safety, and Environmental Impact

Toxicity and Health Effects

Octane, primarily referring to n-octane, poses health risks primarily through and contact, with acute exposure leading to (CNS) depression symptoms such as , , , and vomiting at high vapor concentrations. In animal studies, the median lethal concentration (LC50) for in rats over 4 hours exceeds 24.88 mg/L (approximately 5,300 ppm), indicating relatively low compared to shorter-chain hydrocarbons. contact with octane causes , though it is not highly toxic dermally, with a rabbit LD50 greater than 2,000 mg/kg. Its flammability can exacerbate exposure risks in industrial settings by generating vapors during fires or spills. Chronic exposure to octane may result in prolonged CNS depression and potential , though subchronic studies in rats at concentrations up to 11,640 ppm for 6 hours/day, 5 days/week over 4 weeks showed no significant histopathological changes or behavioral alterations beyond transient . n-octane has not been classified by the International Agency for Research on Cancer (IARC) regarding its carcinogenicity to humans. In March 2025, IARC classified automotive , which contains octane, as (carcinogenic to humans). There is no evidence of from available data, as octane has not been adequately tested for effects on or development. To mitigate health risks, occupational exposure limits have been established: the (OSHA) (PEL) is 500 ppm as an 8-hour time-weighted average (TWA), while the National Institute for Occupational Safety and Health (NIOSH) (REL) is 75 ppm TWA with a 15-minute ceiling of 385 ppm. workers handling octane or octane-containing fuels face higher exposure risks due to prolonged contact in processing environments. Upon , octane is rapidly absorbed through the lungs and primarily excreted unchanged via the lungs, with a in blood of approximately 4 hours based on in similar n-alkanes. Minor occurs in the liver, producing alcohols and carboxylic acids excreted in urine.

Environmental Persistence and Regulations

Octane exhibits moderate environmental persistence, primarily degrading through microbial oxidation in aerobic and environments. Under favorable conditions, its ranges from 1 to 4 weeks, driven by indigenous bacteria that utilize it as a carbon source, leading to mineralization into and . This biodegradability reduces long-term accumulation in most ecosystems, though anaerobic conditions can extend persistence to months. Despite a log Kow of 5.15 indicating potential for partitioning into organic phases, octane shows low in aquatic organisms due to its rapid and . Spills pose acute risks to aquatic life, with evidenced by an LC50 of 11 mg/L for species such as the over 96 hours. As a (VOC), octane emissions from evaporation or incomplete combustion contribute to photochemical smog formation by reacting with nitrogen oxides in the atmosphere to produce . Regulatory frameworks address octane's environmental risks due to its role in petroleum products. Octane is regulated as a (VOC) under the U.S. Clean Air Act, subjecting emissions from industrial sources and fuels to monitoring and control standards. In the , the REACH regulation requires registration of octane due to its production volume, but it is not subject to specific restrictions or authorization. As of 2025, the EU ETS2 begins monitoring emissions from fossil fuels including , with auctioning of allowances starting in 2027 to impose costs on suppliers and incentivize low-carbon alternatives. Mitigation strategies emphasize , where with hydrocarbon-degrading microbes or via nutrient addition accelerates octane breakdown in contaminated sites. International spill responses incorporate the MARPOL Convention (Annex I), which mandates prevention and cleanup of hydrocarbon discharges at sea to protect marine environments. On climate scales, octane yields 3.08 kg of CO₂ per kg, amplifying the transport sector's contribution of approximately 25% to global CO₂ emissions.

References

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