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Isopentane

Isopentane, also known as 2-methylbutane, is a branched-chain alkane hydrocarbon with the molecular formula C₅H₁₂ and one of three structural isomers of pentane, alongside n-pentane and neopentane.^[1] Its branched structure consists of a butane chain substituted by a methyl group at the second carbon position, resulting in a colorless, volatile liquid with a gasoline-like odor at standard temperature and pressure.^[1] Key physical properties include a boiling point of 27.8 °C, a melting point of -159.9 °C, a density of 0.62 g/cm³ at 20 °C, and high flammability with a flash point of -51 °C.^[1] Chemically, it is insoluble in water but miscible with organic solvents like alcohol and ether, and it undergoes typical alkane reactions such as combustion and halogenation.^[1] Isopentane is widely utilized as a refrigerant, a solvent in chemical manufacturing, a blowing agent for expanded polystyrene foams, and an additive in gasoline to improve octane ratings.^[1] Due to its extreme volatility and flammability, it poses significant safety risks, including aspiration hazards and the formation of explosive vapor-air mixtures, necessitating careful handling in industrial applications.^[1]

Structure and Nomenclature

Molecular Structure

Isopentane, chemically known as 2-methylbutane, is a branched-chain alkane with the molecular formula C₅H₁₂. The carbon skeleton features a primary chain of four carbons, where carbon 1 (CH₃) is attached to carbon 2 (CH), which in turn connects to carbon 3 (CH₂) and a branching methyl group (carbon 5, CH₃), and carbon 3 links to the terminal carbon 4 (CH₃). This arrangement gives carbon 2 a tertiary character, bonded to three carbons and one hydrogen, while the other carbons exhibit primary or secondary bonding typical of alkanes. All five carbon atoms in isopentane adopt sp³ hybridization, leading to tetrahedral local geometries with bond angles approximating the ideal value of 109.5°. Due to the branching at carbon 2, specific C-C-C bond angles deviate slightly from this ideal; for instance, angles around the branched carbon measure about 110.8° to 111.7°, reflecting minor distortions from steric crowding. C-C bond lengths average 1.53 Å across the molecule, with computed values such as 1.5361 Å for bonds from the branched carbon to adjacent methyl groups and 1.5452 Å for the C2-C3 linkage. These parameters underscore the molecule's saturated, single-bonded nature without significant bond strain beyond standard alkane values.^[2]^[3] Conformational flexibility in isopentane arises primarily from rotation about the C2-C3 single bond, which can be analyzed using Newman projections viewed along this axis. In these projections, the front carbon (C2) displays two identical methyl groups and a hydrogen substituent, while the rear carbon (C3) shows two hydrogens and a methyl group. The energy minima occur in staggered arrangements: the most stable is the anti conformation, where the rear methyl group is positioned opposite the hydrogen on C2 (dihedral angle ≈180°), minimizing steric repulsion between the branching methyls and the chain. Gauche conformations, with dihedral angles of ≈60° and 300° (where the rear methyl is adjacent to one of the front methyls), represent local minima but are destabilized by gauche interactions, raising their energy by roughly 0.9 kcal/mol relative to the anti form. The torsional barriers between these minima, corresponding to eclipsed transition states, reach up to several kcal/mol, favoring the anti conformer as the predominant species at room temperature.^[4]^[5] Compared to straight-chain n-pentane, isopentane's branched architecture yields a more globular shape, enhancing steric hindrance near the branch point and altering rotational energetics by introducing additional methyl-methyl interactions not present in the linear isomer.

Naming Conventions

Isopentane, an isomer of the molecular formula C₅H₁₂, is systematically named 2-methylbutane under IUPAC nomenclature rules for alkanes. This name identifies butane as the parent chain—a continuous four-carbon alkane—with a single methyl substituent attached to the second carbon atom in the chain, ensuring the lowest possible locant for the branch.^[1]^[6] Common names for this compound include isopentane, where the "iso-" prefix denotes the branched structure relative to the straight-chain form, and the simplified methylbutane. These trivial names originated in early organic chemistry practices for distinguishing structural variants.^[1]^[6] The nomenclature for branched alkanes like isopentane evolved in early 20th-century organic chemistry, transitioning from ad hoc common names to the standardized IUPAC system established by the International Union of Pure and Applied Chemistry (IUPAC). Initial IUPAC recommendations for organic nomenclature date to 1892, with refinements in the 1910s and 1920s that formalized rules for parent chains and substituents, replacing inconsistent historical designations used in petroleum and synthetic chemistry contexts./02:_Fundamental_of_Organic_Structures/2.02:_Nomenclature_of_Alkanes)^[7] This compound is distinguished from other C₅H₁₂ isomers, such as n-pentane—the unbranched, straight-chain pentane—and neopentane, a highly branched form systematically named 2,2-dimethylpropane with a quaternary central carbon.^[1]

Physical Properties

Thermodynamic Properties

Isopentane, or 2-methylbutane, exhibits characteristic phase transition temperatures that reflect its branched alkane structure. Its boiling point is 27.8 °C at standard atmospheric pressure, while the melting point is -159.9 °C. The critical point occurs at 187.2 °C and 3.38 MPa, marking the conditions beyond which distinct liquid and gas phases cease to exist.^[1]^[8] At 20 °C, the density of liquid isopentane is 0.620 g/cm³. Its vapor pressure reaches approximately 100 kPa at the boiling point of 27.8 °C. Heat capacities vary by phase: for the liquid phase at 298 K, it is 164.5 J/mol·K, and for the ideal gas phase at 298 K, it is 119.2 J/mol·K. These values indicate moderate energy storage capacity compared to linear alkanes.^[1]^[9]^[10] Isopentane demonstrates low solubility in water, approximately 48 mg/L at 25 °C, due to its nonpolar nature. In contrast, it is miscible with many organic solvents, such as ethanol and diethyl ether, facilitating its use in solvent applications.^[1] Standard thermodynamic data for the gas phase at 298 K include an enthalpy of formation of -154.1 kJ/mol, a Gibbs free energy of formation of -15 kJ/mol, and a standard molar entropy of 344 J/mol·K. For the liquid phase, the standard molar entropy is 260 J/mol·K. These parameters underscore isopentane's relative stability and entropy-driven phase behavior.^[9]^[10]^[11]

Spectroscopic Data

The infrared (IR) spectrum of isopentane exhibits characteristic absorption bands typical of branched alkanes, with prominent peaks at approximately 2960 cm⁻¹ corresponding to the asymmetric C-H stretching vibration in methyl groups and 1465 cm⁻¹ attributed to the C-H bending deformation.^[12] The branching in isopentane leads to an absence of strong absorptions associated with linear CH₂ sequences, such as intensified bands around 2920 cm⁻¹ for symmetric CH₂ stretches, distinguishing it from n-pentane.^[1] These features confirm the molecular structure through the reduced symmetry and prevalence of tertiary and methyl environments.^[12] In nuclear magnetic resonance (NMR) spectroscopy, the ¹H NMR spectrum of isopentane in CDCl₃ solvent displays distinct signals reflecting its four proton environments: a doublet at ~0.9 ppm (6H, two equivalent methyl groups attached to the branched carbon), a triplet at ~0.9 ppm (3H, terminal methyl group), a multiplet at ~1.3 ppm (2H, methylene protons), and a multiplet at ~1.5 ppm (1H, methine proton).^[1]^[13] The ¹³C NMR spectrum reveals four distinct carbon signals due to the symmetry in the branched structure, with the two methyl carbons at the branch point being equivalent; chemical shifts typically range from ~12 ppm (terminal methyl carbon) to ~32 ppm (methylene and methine carbons), providing unequivocal evidence of the carbon environments.^[14] These shifts are influenced by the structural branching, which slightly alters the deshielding effects compared to linear isomers.^[1] Mass spectrometry of isopentane under electron ionization shows a molecular ion peak at m/z 72 (C₅H₁₂⁺), with major fragmentation resulting in peaks at m/z 57 from loss of a methyl radical (forming the stable tert-butyl-like C₄H₉⁺ ion) and m/z 43 from further loss of ethylene (C₃H₇⁺).^[15] Additional prominent fragments include m/z 41 and 29, arising from sequential cleavages at the branched carbon, which favor carbocation stability and distinguish isopentane from straight-chain pentane spectra.^[16] Ultraviolet-visible (UV-Vis) spectroscopy of isopentane reveals negligible absorption above 200 nm, with the λ_max occurring at approximately 192 nm due to the absence of conjugated π systems or chromophores, limiting utility to vacuum UV regions for structural analysis. This weak end-absorption is characteristic of saturated hydrocarbons, confirming the purely aliphatic nature without electronic transitions in the accessible UV range.^[1]

Chemical Properties

Reactivity Profile

Isopentane, like other alkanes, is highly stable and inert under standard conditions, showing no reactivity with water, acids, bases, or common materials at room temperature.^[17] It remains unreactive toward mild oxidizing agents in the absence of ignition sources, though contact with strong oxidizers can lead to fire or explosion hazards.^[1] The absence of polar functional groups renders isopentane resistant to electrophilic or nucleophilic attacks, limiting its participation in ionic reactions without activation.^[1] The primary chemical transformation of isopentane involves combustion, where it undergoes complete oxidation to carbon dioxide and water. The balanced equation for this reaction is

\mathrm{C_5H_{12}(l) + 8\, O_2(g) \to 5\, CO_2(g) + 6\, H_2O(l)},

with a standard enthalpy change of \Delta H^\circ = -3505 \pm 1 \, \mathrm{kJ/mol} at 298 K. This exothermic process releases significant energy, making isopentane a valuable fuel component, and produces no other products under ideal conditions with sufficient oxygen. Isopentane also participates in free radical halogenation reactions, typically initiated by light or heat, where selectivity favors the tertiary carbon at position 2 due to the stability of the resulting radical. For bromination, this leads to 2-bromo-2-methylbutane as the predominant product, with over 99% yield at that site owing to the high relative reactivity of tertiary hydrogens (1600:82:1 for 3°:2°:1°)./Alkanes/Reactivity_of_Alkanes/Free_Radical_Halogenation_of_Alkanes) In chlorination, the tertiary position still shows preference (relative reactivity 5:3.8:1 for 3°:2°:1° per hydrogen), yielding 2-chloro-2-methylbutane as a major component alongside secondary and primary substitution products.^[18] The branching in isopentane enhances reactivity at this tertiary site compared to n-pentane, which lacks such a position./Alkanes/Reactivity_of_Alkanes/Free_Radical_Halogenation_of_Alkanes)

Isomer Relations

Isopentane, or 2-methylbutane, is one of three constitutional isomers of pentane (C₅H₁₂), alongside n-pentane, which features a straight chain of five carbon atoms, and neopentane, which has a central carbon atom bonded to four methyl groups. These structural differences lead to distinct physical properties, particularly in boiling points: n-pentane boils at 36.1 °C, isopentane at 27.8 °C, and neopentane at 9.5 °C.^[19]^[1]^[20] The observed trend arises from increasing branching, which decreases molecular surface area and thus weakens London dispersion forces (van der Waals interactions), resulting in lower boiling points for more branched isomers.^[21] Chemically, the isomers exhibit reactivity differences primarily in free radical substitution reactions, such as halogenation. Isopentane contains a tertiary hydrogen atom at the branch point, which forms a more stable tertiary radical intermediate, making it approximately 5 times more reactive than the secondary hydrogens predominant in n-pentane (which has no tertiary hydrogens). Neopentane, lacking both secondary and tertiary hydrogens (only primary ones), is the least reactive toward such substitutions.^[22] These variations highlight how branching influences radical stability and reaction selectivity. The structural isomerism also affects thermodynamic stability, as evidenced by differences in heats of combustion. For the gaseous state at standard conditions, n-pentane releases -3537 kJ/mol, while neopentane releases -3514 kJ/mol; isopentane falls in between at approximately -3530 kJ/mol. These values indicate that branched isomers are more stable due to reduced steric strain and optimized bond angles, requiring less energy release to reach the same combustion products (CO₂ and H₂O).^[23]^[24]^[25]

Production and Occurrence

Natural Sources

Isopentane occurs naturally as a significant component of petroleum and natural gas deposits, particularly within the naphtha fractions of light crude oils. In natural gas, it forms part of the C5+ condensates known as natural gasoline, comprising a major portion of these lighter hydrocarbon mixtures extracted from gas fields. These occurrences stem from the thermal maturation processes in sedimentary basins, contributing to the volatility and composition of unrefined fossil fuels. In biological systems, isopentane is emitted as a volatile organic compound (VOC) from various plants, including bay-leaved willows, aspens, balsam poplars, European oaks, European larches, and European firs.^[1] Such emissions contribute to biogenic VOC fluxes that influence air quality and tropospheric chemistry. Geologically, isopentane forms through the pyrolysis of kerogen in sedimentary rocks, a process occurring over millions of years under increasing temperature and pressure in source rock formations. This thermal cracking of organic matter yields light alkanes like isopentane, with ratios of branched to straight-chain isomers increasing as maturation progresses, mirroring observations in laboratory simulations of geological conditions.^[26]

Industrial Production Methods

Isopentane is primarily produced through fractional distillation of crude oil or natural gas liquids, where it is separated from the pentane-rich C5 fraction boiling in the range of approximately 20–40°C.^[1] This process involves heating the feedstock to vaporize lighter components and condensing fractions in a distillation column, yielding isopentane alongside n-pentane and other isomers from petroleum sources.^[27] In large-scale refineries, this method accounts for the majority of commercial isopentane, with the C5 cut further refined to isolate branched isomers based on their distinct boiling points, such as 27.8°C for isopentane. As of 2025, production has increased due to expanded natural gas liquids from shale formations in regions like the United States.^[28] An additional synthetic route involves the isomerization of n-pentane to isopentane using bifunctional catalysts, typically platinum supported on alumina (Pt/Al₂O₃) or sulfated zirconia-alumina composites, under hydrogen atmosphere.^[29] The reaction occurs at temperatures of 200–250°C and pressures around 2 MPa, with a hydrogen-to-hydrocarbon molar ratio of 4:1, promoting skeletal rearrangement while minimizing cracking side reactions.^[29] This hydroisomerization process enhances the branched isomer content in refinery streams, achieving selectivities up to 80% for isopentane in optimized conditions, and is integrated into light naphtha processing units.^[30] Isopentane also arises as a byproduct in alkylation units during the reaction of isobutane with C4–C5 olefins, such as propylene or amylenes, in the presence of sulfuric acid or hydrofluoric acid catalysts.^[31] Hydrogen transfer reactions in these media convert olefins like isopentene to isopentane, particularly when processing amylene feeds, contributing to overall C5 production in gasoline blending operations.^[31] This method supplements primary distillation and isomerization, with isopentane yields varying based on olefin composition but typically comprising 5–10% of the alkylate stream.^[32] Purification of crude isopentane streams from these processes relies on multi-stage distillation to achieve >99% purity, often employing deisopentanizers to separate it from n-pentane and hexanes.^[33] In large-scale plants, energy inputs for distillation average 1–2 GJ per ton of product, with advanced heat-integrated designs reducing consumption by up to 30% through coupled rectification and adsorption.^[34] Overall yields from refinery C5 feeds exceed 90% recovery of high-purity isopentane, supporting its use in specialized applications.^[35]

Applications

Fuel and Energy Uses

Isopentane is widely used as a blending component in gasoline to enhance its octane rating and reduce engine knocking. Its research octane number (RON) is approximately 92, which contributes to the overall anti-knock properties when incorporated into fuel formulations.^[36] Typically blended at levels of 6-10% by weight in conventional gasoline, isopentane helps produce high-octane fuels suitable for modern spark-ignition engines.^[37] This addition is particularly valuable in reformulated gasolines, where it improves volatility without significantly increasing vapor pressure.^[1] The low boiling point of isopentane (27.8°C) makes it effective for aiding cold starts in spark-ignition engines, such as those in aviation, by providing rapid vaporization to facilitate ignition under low-temperature conditions.^[1] In aviation fuels, its volatility supports quick engine priming during startup procedures. Isopentane has a research octane number (RON) of approximately 92.^[36] Isopentane exhibits a high calorific value of approximately 45.2 MJ/kg, enabling efficient energy release during combustion in spark-ignition engines.^[1] When blended into gasoline, it supports high combustion efficiency, contributing to better fuel economy and power output while maintaining compatibility with existing engine designs. Its thermodynamic properties, such as high volatility, further enhance mixture formation and burn completeness in these applications.^[38]

Industrial and Commercial Roles

Isopentane serves as a key blowing agent in the production of expanded polystyrene (EPS) and extruded polystyrene (XPS) foams, as well as rigid polyurethane foams, primarily due to its low boiling point of approximately 27.8°C, which facilitates the expansion of polymer matrices during manufacturing to create lightweight insulating materials for construction and packaging applications.^[39]^[40] In these processes, isopentane is often blended with other pentane isomers to optimize foam density and thermal performance, enabling the production of energy-efficient insulation boards used in building envelopes.^[41] Its volatility allows for efficient gas release without leaving residues, contributing to the material's closed-cell structure that enhances moisture resistance and longevity.^[42] As a hydrocarbon refrigerant designated R-601a, isopentane is employed in specialized low-global-warming-potential (GWP) systems, particularly in industrial heat pumps and organic Rankine cycles where it supports high-temperature operations up to 160°C under low pressure, offering an environmentally friendly alternative to synthetic fluorocarbons.^[43]^[44] This natural refrigerant exhibits zero ozone depletion potential and a minimal GWP, making it suitable for applications in process cooling and heating in chemical and food industries, though its flammability requires enhanced safety measures in equipment design.^[1] Leveraging its non-polar nature and low polarity, isopentane functions as an effective solvent in extraction processes for non-polar substances, including essential oils from plants, natural resins, and active pharmaceutical ingredients, where it selectively dissolves target compounds while being easily recoverable through distillation.^[45] In the pharmaceutical sector, it is used for purifying lipid-based drugs and extracting botanical derivatives, benefiting from its high solvency power for hydrocarbons and organics without reacting with sensitive molecules.^[46] Its immiscibility with water further aids in phase separation during extractions, improving yield efficiency in industrial-scale operations for cosmetics and fine chemicals.^[1] Isopentane is utilized as an aerosol propellant in formulations for personal care products, paints, and insecticides, where its rapid vaporization provides fine mist dispersion and serves as a non-ozone-depleting substitute for phased-out chlorofluorocarbons (CFCs).^[47] Often blended with other hydrocarbons like isobutane, it ensures consistent pressure release in spray cans, enabling targeted application in surface coatings and pest control without compromising product stability.^[48] This role highlights its versatility in consumer goods manufacturing, where it contributes to the shift toward sustainable propellant systems with reduced environmental footprint.

Safety, Health, and Environmental Aspects

Toxicity and Health Risks

Isopentane primarily poses health risks through inhalation due to its high volatility, leading to acute narcotic effects such as dizziness, headache, and central nervous system depression at concentrations exceeding 1% (10,000 ppm).^[49] High-level exposure can cause respiratory irritation, including coughing and shortness of breath, and may result in unconsciousness or death; the LC50 for inhalation in rats exceeds 25.3 mg/L (approximately 8,500 ppm) over 4 hours, indicating relatively low acute toxicity compared to more hazardous hydrocarbons.^[1]^[50] Direct contact with isopentane can act as a mild irritant to the skin and eyes, potentially causing redness, dryness, or temporary discomfort, though significant systemic absorption through the skin is minimal due to its rapid evaporation.^[49] Prolonged or repeated skin exposure may lead to defatting and cracking, but it is not classified as a severe corrosive or sensitizer.^[1] Ingestion of isopentane exhibits low acute toxicity, with an oral LD50 greater than 5,000 mg/kg in rats, but it carries a significant aspiration hazard that can result in chemical pneumonia if swallowed and inhaled into the lungs.^[51] Symptoms from ingestion may include nausea and vomiting, necessitating immediate medical attention to prevent respiratory complications.^[1] Chronic exposure to isopentane vapors is associated with ongoing central nervous system depression and potential irritation of the respiratory tract, possibly contributing to bronchitis-like symptoms such as persistent coughing and phlegm production.^[49] Limited evidence suggests possible effects on the liver and heart with long-term occupational contact, though comprehensive studies on carcinogenicity or reproductive toxicity are lacking.^[49] To mitigate risks, occupational exposure limits include an OSHA permissible exposure limit (PEL) of 1,000 ppm as an 8-hour time-weighted average, with NIOSH recommending a lower REL of 120 ppm (10-hour TWA) and a 15-minute ceiling of 610 ppm.^[52] First aid measures emphasize moving affected individuals to fresh air for inhalation exposure, flushing skin or eyes with water for contact, and seeking medical evaluation for ingestion to address aspiration risks.^[49]

Environmental and Regulatory Considerations

Isopentane, as a volatile organic compound (VOC), undergoes rapid atmospheric degradation primarily through gas-phase reaction with hydroxyl (OH) radicals, with a rate constant of 3.60 × 10⁻¹² cm³ molecule⁻¹ s⁻¹ at 25 °C, resulting in an estimated atmospheric lifetime of approximately 4 days under typical tropospheric conditions.^[53] This reaction initiates a chain of oxidation processes involving peroxy and alkoxy radicals, ultimately producing photolysis products such as formaldehyde and carbonyl compounds that contribute to photochemical smog formation. Isopentane's high photochemical ozone creation potential (POCP), valued at 41 relative to ethene (POCP = 100), underscores its role in tropospheric ozone production, particularly in urban environments with elevated NOx levels.^[54] In environmental media, isopentane exhibits ready biodegradability by soil and water microorganisms. Screening tests indicate 71.43% degradation over 28 days in aqueous systems using activated sludge inoculum, with a half-life of about 2.4 days observed in seawater mixtures containing isopentane.^[55] This microbial breakdown, primarily via aerobic processes, confirms its non-persistence in soil and aquatic compartments, where volatilization may compete but does not dominate fate.^[53] Isopentane is regulated under major chemical control frameworks due to its VOC properties and use in fuels and solvents. In the United States, it is listed as an active substance on the Toxic Substances Control Act (TSCA) Inventory and subject to VOC emission limits under EPA regulations, including 40 CFR Part 60 Subpart VV for equipment leaks in synthetic organic chemical manufacturing and 40 CFR Part 80 for Reid vapor pressure controls in gasoline formulations to curb evaporative emissions.^[1] In the European Union, isopentane is registered under REACH (Registration number 01-2119475602-38), requiring safety data assessments for environmental releases, with additional controls on VOC emissions under the Industrial Emissions Directive to mitigate air quality impacts.^[56] Regarding climate impacts, isopentane has a low 100-year global warming potential (GWP) of approximately 3, reflecting its short atmospheric lifetime and minimal direct radiative forcing compared to long-lived greenhouse gases.^[44] However, its elevated ozone formation potential amplifies indirect contributions to radiative forcing through tropospheric ozone, a potent greenhouse gas.^[57]

Historical Development

Discovery and Early Research

Isopentane, a branched isomer of pentane with the molecular formula C₅H₁₂, was first identified during the mid-19th century amid efforts to characterize hydrocarbons from natural sources like petroleum and coal derivatives. The initial isolation of the pentane fraction occurred in 1862 when German-born chemist Carl Schorlemmer, working at Owens College in Manchester, separated normal pentane (n-pentane) from the pyrolysis products of Wigan cannel coal through fractional distillation; he described a volatile liquid boiling around 36°C.^[58] The theoretical foundation for recognizing isopentane as a branched-chain alkane emerged from advancements in structural organic chemistry during the same era. Russian chemist Alexander Butlerov, in his 1861 formulation of the chemical structure theory, predicted the possibility of isomeric hydrocarbons with the same molecular formula but different atomic arrangements, laying the groundwork for understanding C₅H₁₂ variants beyond the straight-chain form. Building on this, Vladimir Markovnikov, in his 1865 master's thesis On the Isomerism of Organic Compounds, applied these principles to alkanes, theorizing branched structures for pentane-like molecules and emphasizing how carbon valency enables such diversity in saturated hydrocarbons; his work directly influenced the classification of C₅ isomers isolated from petroleum.^[59] By the early 20th century, further structural elucidation of isopentane relied on classical analytical techniques to differentiate it definitively from n-pentane. Through precise fractional distillation under reduced pressure and combustion analysis—yielding consistent C:H ratios of 5:12—researchers in the 1910s and 1920s, including William F. Seyer and colleagues, confirmed isopentane's branched 2-methylbutane skeleton via synthesis from isobutyl derivatives, with its lower boiling point (27.8°C) and density (0.620 g/cm³) serving as key physical markers; these methods, refined in industrial laboratories, highlighted isopentane's greater volatility and solubility compared to the linear isomer. Initial spectroscopic confirmation arrived in the 1930s with the advent of infrared (IR) spectroscopy, where early near-infrared studies at the National Bureau of Standards revealed distinct absorption patterns for isopentane compared to n-pentane, particularly tertiary absorptions around 8,150 cm⁻¹, enabling unambiguous identification of its branched structure; this technique marked a shift from empirical separation to molecular-level verification.^[60]

Commercial Evolution

Following World War I, the expansion of petroleum refining in the United States and Europe significantly increased the availability of light hydrocarbons like isopentane, derived from natural gas liquids and crude oil fractions. By the 1920s and 1930s, isopentane's high research octane number (approximately 92) made it a valuable component in aviation gasoline blends, where it helped mitigate engine knocking in early aircraft engines during the interwar period.^[61] During the 1940s, amid World War II demands, isopentane was incorporated into high-octane fuels for military aviation, contributing to blends that supported boosted engine performance in Allied aircraft, with production scaling up through enhanced distillation and fractionation techniques in refineries.^[62] In the 1950s, advancements in catalytic isomerization technologies revolutionized isopentane production for fuel applications. UOP's Penex process, commercialized around 1958, enabled efficient conversion of normal pentanes to isopentane and other branched isomers in light naphtha streams, boosting octane ratings for reformulated gasoline without lead additives. Exxon (then Humble Oil) and Shell concurrently developed proprietary isomerization units, with Shell's processes integrating platinum-based catalysts to produce high-purity isopentane for blending into premium fuels, aligning with post-war automotive growth and stricter emission standards. These innovations increased isopentane yields by up to 80% in refinery operations, solidifying its role in high-octane gasoline production through the 1960s and 1970s.^[63]^[64] The 1980s marked a pivotal shift for isopentane toward non-fuel applications, driven by the 1987 Montreal Protocol's mandate to phase out chlorofluorocarbons (CFCs) due to ozone depletion. Isopentane, with zero ozone-depleting potential, emerged as a key hydrocarbon blowing agent in polyurethane foam production, replacing CFC-11 in rigid insulation foams for appliances and construction. By the 1990s and into the 2000s, as hydrochlorofluorocarbons (HCFCs) like HCFC-141b faced phase-out under protocol amendments (complete in developed countries by 2010), isopentane adoption surged, particularly in Europe and North America, where it was blended with cyclopentane for improved foam stability and thermal efficiency. Global production for this sector grew substantially, with isopentane comprising over 50% of blowing agents in expanded polystyrene by the early 2000s.^[65]^[66] Post-2010 trends reflect growing emphasis on sustainability, with bio-based isopentane production gaining traction amid green regulations like the EU's F-Gas Regulation and the U.S. AIM Act, which prioritize low-global-warming-potential (GWP) substances (isopentane GWP ≈ 0). Fermentation processes using renewable feedstocks such as ethanol have supported development of bio-isopentane, as demonstrated by initiatives from companies like INEOS, which announced plans as of 2023 for commercial viability by 2026 to reduce reliance on fossil-derived sources. Concurrently, isopentane's use in refrigerants has expanded in low-GWP blends for commercial cooling systems, supported by EPA approvals under SNAP rules that favor hydrocarbons over high-GWP HFCs, enhancing its market in eco-friendly heat transfer applications.^[67]^[68]^[41]

References

[1]
Isopentane | C5H12 | CID 6556 - PubChem - NIH
Isopentane is an alkane that is butane substituted by a methyl group at position 2. It has a role as a refrigerant.
[2]
[PDF] Sebuah Kajian Pustaka:
LENGTH AND BOND ANGLE OF CHEMICAL TREES OF. PENTANE ISOMERS. Kailas S. Ahire ... In pentane bond length of C1-C2 and C1-C5 are 1.5327 Å which is maximum ...
[3]
[PDF] chapter-2-alkanes.pdf
Recall that the geometry around C-H single bonds is tetrahedral and that the bond angle is 109.50, as shown for pentane below. Also remember that we can have ...
[4]
Study of the torsional potential energies of 2-methylpropane, n ...
Jul 15, 2007 · For this calculation, the torsional angle scans between −180° and 180°, in 10° intervals, and all other bond lengths and angles are optimized in ...
[5]
Conformational analysis of 2-methylbutane - ACS Publications
... Study of the torsional potential energies of 2-methylpropane, n-butane, and 2-methylbutane with high-level ab initio calculations. Journal of Molecular ...
[6]
Butane, 2-methyl-
### Summary of 2-Methylbutane (Isopentane) Properties
[7]
[PDF] Principles of Chemical Nomenclature - IUPAC
The first version of this book was written in the conviction that although precise and accurate nomenclature is a vital aspect of professional training.
[8]
ISOPENTANE - CAMEO Chemicals - NOAA
Isopentane is a watery, colorless liquid with a gasoline-like odor, that floats on water, and is highly flammable. It is insoluble in water.
[9]
Butane, 2-methyl- - the NIST WebBook
Gas phase thermochemistry data ; ΔcH° · -3528.6 ± 0.63, kJ/mol, Cm, Knowlton and Rossini, 1939 ; ΔcH° · -3527.6 ± 3.5, kJ/mol, Ccb, Roth and Pahlke, 1936 ...
[10]
Standard enthalpy of formation, Gibbs energy of formation, entropy ...
The standard enthalpy of formation, Gibbs energy of formation, entropy and molar heat capacity are tabulated for more than hundred organic substances.
[11]
isopentane
Standard molar entropy S0 (298.15 K, J/(mol·K)):. 260.4 (l). Molar heat capacity at constant pressure Cp (298.15 K, J/(mol·K)):. 164.8 (l). References: CRC ...
[12]
Butane, 2-methyl- - the NIST WebBook
isopentane. ISOPENTANE. State, GAS (100 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg). Instrument, DOW KBr FOREPRISM-GRATING. Instrument parameters, GRATING CHANGED ...
[13]
C-13 nmr spectrum of 2-methylbutane analysis of chemical shifts ...
Oct 7, 2025 · The carbon-13 NMR spectra a provides direct evidence of 4 different 13C carbon atom environments in the 2-methylbutane molecule from 4 different ...
[14]
Butane, 2-methyl- - the NIST WebBook
Butane, 2-methyl- · Formula: C5H · Molecular weight: 72.1488 · IUPAC Standard InChI: InChI=1S/C5H12/c1-4-5(2)3/h5H,4H2,1-3H3 Copy · IUPAC Standard InChIKey: ...
[15]
mass spectrum of 2-methylbutane fragmentation pattern of m/z m/e ...
The pattern ratios for m/z 39 to 43 are similar for pentane and 2-methylbutane, but m/z 42 and 43 ions are almost absent from the 2,2-dimethylpropane spectrum.
[16]
[PDF] ISOPENTANE - CAMEO Chemicals
SOLUBILITY IN WATER. Temperature. (degrees F). Pounds per 100 pounds of water. I. N. S. O. L. U. B. L. E. 9.25. SATURATED VAPOR PRESSURE. Temperature. (degrees ...
[17]
[PDF] Reactions of Alkanes: Radical Chain Halogenation
2-Methylbutane. Four products: Chlorinate at one of the two methyl groups. 6H 27%. Chlorinate at the unique methyl group. 3H 14%. Chlorinate at methylene. 2H 36 ...
[18]
Pentane | C5H12 | CID 8003 - PubChem - NIH
Pentane is a straight chain alkane consisting of 5 carbon atoms. It has a role as a non-polar solvent and a refrigerant. It is a volatile organic compound and ...Missing: angle | Show results with:angle
[19]
Neopentane | C5H12 | CID 10041 - PubChem - NIH
Neopentane is a hydrocarbon and one of three isomers of pentane. Pentanes are components of some fuels, such as gasoline, and are also used as specialty ...
[20]
Boiling & Melting Points - MSU chemistry
Notice that the boiling points of the unbranched alkanes (pentane through decane) increase rather smoothly with molecular weight, but the melting points of ...
[21]
Chapter 7 - Alkanes and Halogenated Hydrocarbons - Chemistry
... hydrogen atoms, can help stabilize the formation of the carbon radical. Thus, in the halogenation reaction tertiary carbons will be the most reactive ...
[22]
Pentane - the NIST WebBook
Constant pressure heat capacity of gas ; 127.84 ± 0.26, 323.15 ; 135.90 ± 0.27, 348.15 ; 143.95 ± 0.29, 373.15 ; 151.92 ± 0.30, 398.15 ; 159.67 ± 0.32, 423.15.
[23]
Chemical Properties of Neopentane (CAS 463-82-1) - Cheméo
Neopentane (C5H12) has a molecular weight of 72.15, boiling point of 282.15-283.00 K, and gas enthalpy of combustion of -3514.10 kJ/mol.
[24]
GAV
As branching increases from 1 to 3, the heats of formation become more negative (stable) and heats of combustion decrease. Each isomer can be characterized by ...
[25]
Light Naphtha - an overview | ScienceDirect Topics
It typically constitutes 15-30 % of crude oil by weight. Light naphtha is the fraction boiling between 30 and 90°C and consists of molecules with five to six ...
[26]
Natural Gasoline and Isopentane - OPIS, A Dow Jones Company
A mixture of hydrocarbons, mostly pentanes and heavier, extracted from natural gas, that meets vapor pressure, end-point, and other specifications for natural ...
[27]
Biogenic isoprene in subtropical urban settings and implications for ...
In forest and rural atmospheres, the primary source of isoprene is plants. Nevertheless, isoprene has both biogenic and anthropogenic sources in urban areas ( ...
[28]
Showing metabocard for Isopentane (HMDB0253668)
Sep 11, 2021 · Isopentane is possibly neutral. Isopentane is a potentially toxic compound. The main metabolite is 2-pentanol, followed by 3-pentanol, and 2- ...Missing: metabolism | Show results with:metabolism
[29]
Petroleum Hydrocarbons: Generation from Fatty Acid - Science
Without water the ratio of isobutane or isopentane to normal butane or normal pentane is much higher than with water. Besides C21 and lower n-alkanes, n-alkanes ...
[30]
Isopentane Production Cost Analysis From Crude Oil
Fractional distillation helps in separating the required compound (here, isopentane) from the crude oil mixture, and then purified to yield isopentane as ...
[31]
Effect of Al Content on the Isomerization Performance of Solid ...
The isopentane yield reached 64.3% at a temperature of 238 °C, a reaction pressure of 2.0 MPa, a space velocity of 1.0 h − 1 and a H2/n-pentane molar ratio of ...
[32]
Hydroisomerization of n-pentane over hybrid catalysts containing a ...
Isomerization of n-pentane to iso-pentane was studied on a series of ZSM-5 zeolite catalysts under hydrogen and nitrogen atmosphere.
[33]
[PDF] The economic benefit for propylene and amylene alkylation is ...
In both sulfuric acid and HF alkylation, introduction of amylene feeds will increase production of isopentane through hydrogen transfer reactions (although at ...
[34]
[PDF] Ionic Liquid Alkylation - White Paper - Honeywell UOP
No hydrogen transfer reaction. Productions of propane and isopentane from the olefin feed during the alkylation step are nearly zero. Also, isobutane ...
[35]
Method of separating isopentane-pentane-hexane fraction
Invention relates to a method of separating an isopentane-pentane-hexane fraction during an isomerisation process, consisting of a first fractionation column ...
[36]
A coupled technology to produce high-purity normal and isomeric ...
The coupled technology is adsorption after rectification technology, which is better than the traditional one in product purity and energy consumption. The ...Missing: isopentane yield
[37]
An economical approach to produce iso-pentane component for ...
An economical rectification approach to produce iso-pentane component from hydrocracking light naphtha for aviation gasoline fuels is proposed in this ...
[38]
[PDF] Ignition of Isomers of Pentane: An Experimental and Kinetic ... - OSTI
With its high research octane number (RON = 92.3), isopentane is the least reactive among the three isomers. The igrution delay times in the NTC zone are the ...
[39]
Table E-1.b, Major Hydrocarbon Components of Gasoline - NCBI
Gasoline Weight Percent Range, Gasoline Weight Percent Mean. C6 Aromatics ... Isopentane, 6.07–10.17, 6.22. 2-Methylpentane, 2.91–3.85, 3.35. 3-Methylpentane ...
[40]
[PDF] Refinery Feedstocks & Products Properties & Specifications
Other Crude Oil Assays – Light Crudes. 30. Property. Bakken. WTI. API Gravity. 41 ... Light Naphtha. 55. 175. 1.7. 5.6. Ethane. -127.49. -258.73 -127.49. 0.02.
[41]
Why Use Pentane as a Blowing Agent in Foam Production? - Trecora
Pentane is attractive as a blowing agent for foam production because it is comparatively inexpensive. It is also readily available.
[42]
Blowing agents - Isopentane |Cyclo pentane - Arpadis
Blowing agent plays a fundamental role in the production of polystyrene (PS), polyurethane (PU) and polyisocyanurate (PIR) insulations foam.
[43]
Isopentane Market Size, Share, Trends, Analysis by 2032
Isopentane is commonly used as a blowing agent in the production of polyurethane foams, which helps create a lightweight and insulating material.
[44]
Physical blowing agents: role of pentane quality in insulation
Aug 2, 2023 · Pentanes are particularly suitable as physical blowing agents for the production of insulating materials, such as PU, PIR, EPS or XPS foams.
[45]
Isopentane (R601a) Refrigerant Supplier - AGT International
Isopentane (R601a) is supplied as a liquid under its own vapour pressure in cylinders and in T11 ISO containers for international transport as well as road ...
[46]
Isopentane (R601a) Heat Pump - Budzar Industries
Isopentane (R601a) is an ideal natural refrigerant for processes that require high temperatures, while maintaining a low pressure. With separate cooling and ...
[47]
Isopentane - Equilex
... organic solvent widely used in industrial applications. Thanks to its excellent miscibility with water and many organic solvents, it is ideal for use in ...
[48]
Isopentane Prices, Trends, Index, News, Monitor and Demand
In the pharmaceutical industry, isopentane serves as a solvent for the extraction of various compounds. It is also utilized in the cosmetics industry as a ...
[49]
Isopentane - Cosmetics Info
Butane, Isobutane, Propane and Isopentane are volatile substances derived from petroleum and natural gas. These ingredients are used in cosmetics and personal ...
[50]
NovaSpray™ isopentane/isobutane (75/25) - Climalife
With a constant quality, it meets all the requirements of a propellant. This very specific blend of liquid and liquefied gas has been formulated by Climalife to ...
[51]
[PDF] Hazardous Substance Fact Sheet - NJ.gov
Isopentane is a flammable liquid that can irritate skin, eyes, nose, throat, and lungs. It may cause coughing, wheezing, and may affect the liver and heart.
[52]
[PDF] SAFETY DATA SHEET - Airgas
Avoid contact with eyes, skin and clothing. Empty containers retain product ... LC50 Inhalation Gas. Rat. 10000 ppm. 7 hours. LD50 Oral. Rat. 930 mg/kg.
[53]
[PDF] Isopentane - Megaloid
LD50 (oral) >5000mg/kg (rat). LD50 (skin) no data available – very high volatility makes testing difficult, perhaps impossible. LC50 (inhalation) >20,000 ...
[54]
https://archive.ipcc.ch/pdf/special-reports/sroc/Tables/t0211.pdf
[55]
https://pubchem.ncbi.nlm.nih.gov/compound/Isopentane#section=Environmental-Biodegradation
[56]
[PDF] Table 2.11. Propensity of VOCs to form tropospheric ozone accor
conditions, and the Photochemical Ozone Creation Potential (POCP) for multi ... Isopentane. 1.67. 41. Ethylene. 9.07. 100. Propylene. 11.57. 112. Dimethylether.
[57]
https://www.researchgate.net/publication/225115300_Smog_chamber_studies_of_ozone_formation_potentials_for_isopentane
[58]
https://acs.digitellinc.com/p/s/carl-schorlemmers-research-and-the-rise-and-development-of-organic-chemistry-575094
[59]
Smog chamber studies of ozone formation potentials for isopentane
Aug 7, 2025 · The photolysis of HONO is responsible for the initiation of isopentane in photochemical reactions. The reaction rate constant for NO2 → HONO was ...
[60]
Carl Schorlemmer's research and the “Rise and Development of ...
His studied the whole series of alkanes up to octane and isolated for the first time n-pentane, n-heptane, and diisopropyl. By halogenation of hydrocarbons and ...
[61]
C5-C6 Fractions Isomerization - SIE NEFTEHIM, LLC
This phenomenon was first explained by A.M. Butlerov. The first monograph “About organic compounds isomery” by V.V. Markovnikov was published in 1865.
[62]
[PDF] Spectral differentiation of pure hydrocarbons
of the spectra of various isomers. In isopentane (Fig. 7) the second- ary absorption has dropped very appreciably from that found in n-pentane and tertiary ...
[63]
[PDF] Aviation Fuels - Chevron
In the 1940s, the turbine engine emerged as the answer to the quest for still more power. In a replay of avgas development, kerosine – the fuel used in the.
[64]
High-Octane Victory – How New Super Fuels Powered the Allied Air ...
Jan 9, 2024 · Newer high-octane formulations also gave British and American warplanes an edge over German and Japanese fighters in air combat.
[65]
UOP PENEX™ PROCESS | McGraw-Hill Education
The history of light straight-run (LSR) naphtha (a mostly C5–C6 fraction) isomerization is intertwined with the developments discussed in the Introduction to ...
[66]
[PDF] Gasoline Upgrading: Reforming, Isomerization, & Alkylation
• Produce isooctane. • Liquid acid catalyst. Products. ▫ Gasoline blend stocks of improved octane and/or volatility. 4. EIA, Jan. 1, 2019 database, published ...
[67]
Blowing Agent - an overview | ScienceDirect Topics
A targeted worldwide complete phase-out of CFCs was soon among the amendments to the Montreal protocol approved unanimously by 93 nations at a 1987 meeting in ...
[68]
[PDF] Polyurethane Foam Without Ozone Depleting Substances ...
Flexible integral foam has been developed, using isopentane as a blowing agent. This development has been encouraged by the Danish phasing-out strategy ...<|separator|>
[69]
Isopentane Market Size | Global Report [2033]
With environmental regulations tightening on traditional refrigerants, isopentane's non-ozone-depleting properties make it a preferred substitute ...Isopentane Market Trends · Isopentane Market Dynamics · Isopentane Market...
[70]
Isopentane Market Size, Production, Price, Market Share, Import Vs ...
September 2023 – INEOS declared a new initiative to produce bio-based isopentane in Belgium by 2026 under its “Project Green Hydrocarbons,” a move aligned with ...