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Cyclopentane

Cyclopentane is a saturated hydrocarbon and cycloalkane with the molecular formula C₅H₁₀, consisting of a five-membered ring of carbon atoms where each carbon is bonded to two hydrogen atoms, forming a puckered envelope conformation in its most stable form.^[1] It appears as a clear, colorless liquid at room temperature, with a molecular weight of 70.13 g/mol, a melting point of -93.4 °C, a boiling point of 49.2 °C, and a density of 0.7457 g/cm³ at 20 °C.^[1] Cyclopentane is insoluble in water (solubility approximately 156 mg/L) but miscible with organic solvents such as ethanol, ether, acetone, and benzene, reflecting its nonpolar nature.^[1] Produced industrially through the cracking of petroleum fractions or as a byproduct in aromatic hydrocarbon processing, it serves primarily as a blowing agent in the manufacture of polyurethane foams for insulation, replacing chlorofluorocarbons due to its low ozone-depletion potential.^[1] Additional applications include its use as a solvent in paints and wax extraction, a component in motor fuels, and a precursor in the synthesis of pharmaceuticals and insecticides.^[1] Safety concerns arise from its high flammability (flash point -37 °C) and potential to cause central nervous system depression, eye and skin irritation, and respiratory issues upon exposure, while it is also harmful to aquatic life with long-lasting effects.^[1]

Properties

Physical properties

Cyclopentane has the molecular formula C₅H₁₀ and a molecular weight of 70.13 g/mol.^[1] It appears as a clear, colorless liquid with a petroleum-like odor.^[1] The compound exhibits a boiling point of 49.2 °C and a melting point of -93.4 °C.^[1] Its density is 0.7457 g/cm³ at 20 °C.^[1] Cyclopentane has a refractive index of 1.4065 at 20 °C.^[1] Cyclopentane is insoluble in water, with a solubility of 0.0156 g/100 mL (156 mg/L) at 25 °C, but it is miscible with organic solvents such as ethanol, ethyl ether, acetone, benzene, and carbon tetrachloride.^[1] The flash point is -37 °C.^[1] Its vapor pressure is approximately 318 mmHg at 25 °C, and the heat of vaporization is 28.5 kJ/mol.^[1]

Property	Value	Conditions	Source
Boiling point	49.2 °C	1 atm	PubChem
Melting point	-93.4 °C	-	PubChem
Density	0.7457 g/cm³	20 °C	PubChem
Refractive index	1.4065	20 °C (n_D)	PubChem
Water solubility	0.0156 g/100 mL	25 °C	PubChem
Flash point	-37 °C	-	PubChem
Vapor pressure	318 mmHg	25 °C	PubChem
Heat of vaporization	28.5 kJ/mol	25 °C	PubChem

Chemical properties

Cyclopentane is classified as a non-polar, saturated hydrocarbon consisting solely of carbon-carbon and carbon-hydrogen sigma bonds, with no functional groups, resulting in low chemical reactivity under standard conditions.^[1] Its stability arises from these strong sigma bonds, providing resistance to oxidation except in the presence of strong oxidizing agents like halogens; however, it is highly flammable, with an autoignition temperature of 361 °C.^[1]^[2] The molecule exhibits a ring strain energy of approximately 6.5 kcal/mol, which is lower than that of cyclobutane (26.3 kcal/mol) but higher than that of the unstrained cyclohexane (0 kcal/mol).^[3] This moderate strain contributes to its relative stability compared to smaller rings but influences reactivity in strain-relief processes. Typical reactions of cyclopentane include free radical halogenation, such as chlorination in the presence of light or heat to yield chlorocyclopentane, and catalytic dehydrogenation to produce cyclopentadiene.^[4] The standard combustion reaction of cyclopentane is highly exothermic:

\ce{C5H10 + 7.5 O2 -> 5 CO2 + 5 H2O} \quad \Delta H = -787 \, \text{kcal/mol}

This value is derived from experimental calorimetry data.^[5] Infrared spectroscopy of cyclopentane shows characteristic C-H stretching vibrations for alkanes around 2950 cm⁻¹, along with other peaks in the 1000–1500 cm⁻¹ region associated with C-H bending modes.^[6] The ¹H NMR spectrum features a signal at approximately 1.6 ppm for the ten equivalent methylene protons, appearing as a broad singlet due to rapid puckering.^[7]

Synthesis and production

Industrial production

Cyclopentane is primarily produced industrially through fractional distillation of light petroleum naphtha fractions boiling between 30 and 100 °C, in which it typically comprises 1-5% of the mixture.^[8] This process isolates cyclopentane from other C5 hydrocarbons present in crude oil-derived naphtha, sourced mainly from refinery crackers.^[9] The naphtha is first obtained as a co-product during crude oil refining, and subsequent distillation under controlled conditions yields a cyclopentane-rich stream that is further purified to achieve commercial grades of 95% or higher purity.^[10] Another significant industrial method is the hydrogenation of cyclopentadiene, often obtained from petroleum cracking byproducts. This involves catalytic hydrogenation using catalysts such as palladium or nickel under moderate pressure (1-10 atm) and temperature (50-150 °C), achieving high yields of cyclopentane suitable for blowing agent applications.^[11] An alternative industrial route involves the catalytic reforming of n-pentane, where the linear hydrocarbon is converted to cyclopentane using dual-stage catalytic processes, followed by fractional distillation to obtain up to 90-95% purity.^[12] This method enhances yields by rearranging the carbon skeleton under hydrogenating conditions with metal catalysts like platinum or palladium.^[13] Global production of cyclopentane is estimated at approximately 217,000 metric tons annually as of 2024, with major production in Asia-Pacific, North America, and Europe, driven by large-scale refining and chemical manufacturing facilities.^[14]^[15] Purification often employs vacuum distillation to separate cyclopentane from close-boiling isomers such as methylcyclobutane, minimizing energy inputs through reduced pressure operations that lower boiling points and prevent thermal decomposition.^[16] Additional steps may include adsorption or extractive distillation for high-purity grades required in applications like foam blowing agents.^[17]

Laboratory synthesis

One common laboratory method for preparing cyclopentane involves the reduction of cyclopentanone using the Wolff-Kishner reaction, which converts the carbonyl group to a methylene group under basic conditions. In this procedure, cyclopentanone is treated with hydrazine hydrate to form the hydrazone intermediate, followed by heating with potassium hydroxide in a high-boiling solvent such as diethylene glycol at 180–200°C for several hours, yielding cyclopentane in 80–90% efficiency.^[18] An alternative reduction employs the Clemmensen method, where cyclopentanone is refluxed with zinc amalgam (Zn/Hg) and concentrated hydrochloric acid for 4–6 hours, also achieving yields above 80% while being suitable for acid-tolerant substrates.^[19] Hydrogenation of cyclopentadiene provides another straightforward route to cyclopentane in laboratory settings, involving catalytic addition of two equivalents of hydrogen. Typically, cyclopentadiene is dissolved in ethanol or methanol and hydrogenated over 5–10% Pd/C catalyst at room temperature under 1–3 atm of H₂ pressure, with stirring for 2–4 hours to ensure complete conversion to the saturated product in yields exceeding 95%.^[20] This method benefits from mild conditions and readily available starting materials, though excess hydrogen or slightly elevated pressure may be used to favor full saturation over partial reduction to cyclopentene. A classical intramolecular cyclization approach, analogous to early hydrocarbon syntheses, utilizes 1,5-dibromopentane treated with sodium metal in refluxing ethanol, promoting double dehalogenation and coupling to form the five-membered ring. This historical method, developed in the late 19th century, proceeds by generating organosodium intermediates that cyclize, followed by quenching with water, affording cyclopentane in modest yields of 20–40% after distillation, though modern variants with lithium amalgam improve efficiency to around 50%.^[21] For a contemporary synthetic strategy, ring-closing olefin metathesis of 1,6-heptadiene using Grubbs' second-generation ruthenium catalyst generates cyclopentene, which is subsequently hydrogenated to cyclopentane. The metathesis step occurs in dichloromethane at room temperature with 1–5 mol% catalyst loading for 1–2 hours, yielding cyclopentene in 70–90%, followed by Pd/C-catalyzed hydrogenation under conditions similar to those above to obtain cyclopentane in overall yields of 60–80%.^[22] Purification of cyclopentane from these reactions generally involves fractional distillation under an inert atmosphere (e.g., nitrogen) at atmospheric pressure (boiling point 49°C) to prevent trace oxidation, ensuring >99% purity.^[23]

Natural occurrence

In petroleum

Cyclopentane occurs naturally as a component of crude oil, forming part of the cycloalkane (naphthene) fraction within petroleum deposits. Typical concentrations in crude oil range from trace amounts to about 0.05% by weight, as reported in compositional analyses of various global crudes.^[24] In specific samples, such as those from Ponca, Nebraska, and Santa Barbara, California, cyclopentane has been quantified at 500 mg/L and 460 mg/L, respectively, corresponding to roughly 0.05% and 0.046% by weight given standard crude oil densities of approximately 0.85–0.9 g/mL.^[1] These levels are higher in naphthenic crudes from regions like California fields, where total cycloalkane content can reach up to 60% of the hydrocarbon fraction, though cyclopentane itself remains a minor constituent within that group.^[25] The formation of cyclopentane in petroleum arises during the catagenetic stage of organic matter evolution in sedimentary basins, spanning millions of years under increasing temperature and pressure. It results primarily from the thermoradical cyclization of olefins generated by cracking of n-alkanes and fatty acids, followed by cationic isomerization on clay minerals, rather than direct cracking of polycyclic compounds.^[26] This process occurs at depths of several kilometers, where kerogen transforms into liquid hydrocarbons, incorporating cyclopentane through ring-forming rearrangements and bond cleavages. Cyclopentane co-occurs with other low-molecular-weight cycloalkanes, notably cyclohexane and their alkyl-substituted homologs, which together dominate the single-ring naphthene series in most crude oils.^[27] Concentrations of these light cycloalkanes generally increase with the thermal maturity of the source rock, as progressive cracking generates more volatile components; this correlates inversely with oil density and positively with API gravity, leading to elevated levels in lighter, more mature oils.^[25] Extracting cyclopentane from petroleum reservoirs presents challenges due to its high volatility (boiling point of 49 °C), which causes significant losses to the gas phase during drilling, venting, and initial production phases.^[1] Accurate detection in reservoir fluids relies on advanced analytical techniques like gas chromatography-mass spectrometry (GC-MS), which separates and identifies cyclopentane amid complex hydrocarbon mixtures.^[27] For instance, in lighter crudes like those from Saudi Arabian fields, where total light hydrocarbons are more abundant, cyclopentane contributes to the volatile fraction but requires careful sampling to avoid evaporation artifacts.^[25]

In biological systems

Cyclopentane plays a limited and trace role in biological systems, primarily appearing as a structural moiety in certain microbial lipids rather than as a free molecule. In bacteria, particularly soil-dwelling species, cyclopentane forms one of the five rings in the pentacyclic hopane skeleton of hopanoids, which are essential membrane-stabilizing lipids analogous to cholesterol in eukaryotes. For instance, bacteriohopanetetrol, a polyhydroxylated hopanoid produced by diverse bacteria including those in soil environments, incorporates a cyclopentane ring fused to four cyclohexane rings, contributing to membrane rigidity under varying environmental stresses. These hopanoids are biosynthesized via squalene cyclization by squalene-hopene cyclases, with the cyclopentane ring emerging from the final carbocation rearrangement step.^[28]^[29]^[30] Trace amounts of free cyclopentane have been detected in plant essential oils through gas chromatography-mass spectrometry (GC-MS) analysis, often as a minor volatile component derived from terpenoid degradation or biosynthetic pathways. In coniferous species such as Metasequoia glyptostroboides, cyclopentane constitutes up to 15% of the leaf essential oil profile, alongside monoterpenes like β-myrcene, suggesting its origin from incomplete cyclization of precursor hydrocarbons in resinous tissues. Similar detections in pine-like resins indicate low-level presence, potentially from oxidative breakdown of larger cyclic terpenes during essential oil extraction.^[31] Cyclopentane exhibits no significant role in human metabolism, though upon exposure, it undergoes limited biotransformation to cycloalkanol conjugates, which are excreted primarily via urine with partial unchanged elimination through respiration. Its low solubility and rapid volatility limit endogenous accumulation or physiological function in mammals. In geobiology, hopanoids containing the cyclopentane ring serve as robust biomarkers for ancient bacterial activity, preserved in sediments to trace microbial communities in paleo-environments due to their high thermal stability.^[1] Biosynthesis of cyclopentane derivatives in biological systems is rare and typically involves terpene synthases acting on C10-C15 isoprenoid precursors. In certain fungi, di/sesterterpene synthases catalyze the cyclization of geranyl pyrophosphate (GPP) or extended analogs like geranylfarnesyl pyrophosphate (GFPP) through carbocation-initiated folding, yielding polycyclic products with embedded cyclopentane rings; these enzymes are widespread across fungal genomes and produce bioactive metabolites like ophiobolins. This pathway highlights cyclopentane's niche in fungal secondary metabolism, distinct from more common linear terpenoid elongation.^[32] In environmental contexts tied to biological activity, cyclopentane is emitted at low parts-per-billion (ppb) levels from biomass burning and volcanic gases, often as a pyrolysis product of microbial or plant-derived organics. During biomass combustion, such as crop residue fires, emission factors reach approximately 0.002 g/kg of fuel, reflecting thermal cracking of cyclopentane-containing lipids in vegetation. Volcanic gas analyses via GC-MS detect cyclopentane at concentrations around 0.03 ppmv in fumarole emissions from El Chichón, Mexico, likely from subsurface microbial degradation or geothermal alteration of organic matter.^[33]^[34]

Applications

Solvent uses

Cyclopentane serves as a non-polar solvent in various polymerization processes, particularly in the solution polymerization of styrene-butadiene rubber (SBR). Its low polarity facilitates the dissolution of monomers like styrene and butadiene, while its volatility allows for efficient recovery post-reaction, enabling continuous production in industrial reactors. For instance, in the Versalis S-SBR process, cyclopentane is employed alongside n-hexane as a dry solvent, loaded continuously with initiators and reactants to produce high-performance rubbers for tire manufacturing.^[35] In extraction applications, cyclopentane acts as a selective solvent for hydrocarbons, particularly in oil refining operations such as the non-aqueous extraction of bitumen from oil sands. Studies have demonstrated its effectiveness in the non-aqueous extraction of bitumen from oil sands due to its ability to dissolve heavy hydrocarbons while precipitating asphaltenes.^[36] Additionally, in pharmaceutical manufacturing, cyclopentane is utilized for isolating active compounds through extraction and dissolution steps, leveraging its compatibility with organic materials and limited water solubility.^[37] One key advantage of cyclopentane as a solvent is its high solvency for resins, waxes, and fats, making it suitable for applications in paints, adhesives, and shoe manufacturing where it dissolves non-polar substances effectively. Its evaporation rate is comparable to that of n-pentane (boiling point of 49.3°C versus 36.1°C), providing similar volatility for quick drying without excessive residue, yet it exhibits lower toxicity than benzene, lacking the carcinogenic risks associated with aromatic solvents. These properties stem from its cycloalkane structure, which offers balanced polarity and thermal stability.^[1]

Fuel and chemical feedstock

Cyclopentane serves as a component in certain specialty fuels, including aviation gasoline (avgas), where it is blended to enhance octane performance in high-performance formulations. Its motor octane number (MON) of approximately 85 and research octane number (RON) of 101-103 allow it to contribute to fuels requiring resistance to knocking.^[38] Early patents describe its use in combination with isooctane to produce aviation superfuels with octane ratings exceeding 95, highlighting its role in legacy high-octane avgas compositions before widespread leaded fuel dominance.^[38] As a chemical feedstock, cyclopentane undergoes dehydrogenation to produce cyclopentadiene, a key diene in Diels-Alder reactions for synthesizing resins and adhesives. This process typically involves catalytic dehydrogenation at elevated temperatures around 500-600 °C, often with oxidative conditions to improve selectivity and yield. Cyclopentadiene derived from cyclopentane is polymerized into dicyclopentadiene, which serves as a monomer for hydrocarbon resins used in hot-melt adhesives, tire compounds, and coatings.^[39]^[40] The retro-Diels-Alder reversibility of these products enables applications in self-healing materials and recyclable polymers.^[41] In combustion applications, cyclopentane exhibits an energy density of approximately 46 MJ/kg (higher heating value), comparable to other cycloalkanes, making it suitable for blending in fuels where volumetric efficiency is critical. Its lower heating value is similarly high at around 44.6 MJ/kg, supporting efficient energy release in internal combustion engines. As a non-aromatic hydrocarbon, cyclopentane burns cleanly with minimal soot formation, attributed to its cyclic structure that favors complete oxidation over incomplete pyrolysis pathways leading to polycyclic aromatic hydrocarbons.^[42]^[43] This low sooting tendency positions it as a potential additive for reducing particulate emissions in advanced fuel blends.^[43] Cyclopentane is also converted to derivatives like cyclopentanol through air oxidation processes, typically using catalysts such as supported gold or metal oxides under mild conditions to achieve high selectivity. Cyclopentanol serves as an intermediate for producing cyclopentanone, which acts as a precursor in the synthesis of specialty chemicals, including potential nylon analogs and other polyamides.^[44]^[45] Although traditional nylons derive from C6 precursors like caprolactam, cyclopentane-based routes enable bio-derived or alternative polyamide production via ring-opening polymerization of cyclopentanone oxime derivatives.^[46] This allocation reflects its versatility beyond blowing agents, supporting the expansion of resin and polymer sectors.

Other industrial roles

Cyclopentane is widely utilized as a physical blowing agent in the manufacture of rigid polyurethane foams for thermal insulation applications, such as in refrigerators, freezers, and building panels. This role emerged as a direct replacement for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs), which were phased out under the Montreal Protocol due to their ozone-depleting properties; cyclopentane offers zero ozone depletion potential and a global warming potential of less than 10, enabling efficient foam expansion through its vapor pressure at low temperatures without contributing significantly to climate change.^[47] Its high insulation efficiency allows for thinner foam layers while maintaining superior thermal performance, reducing energy consumption in insulated products.^[48] In analytical laboratories, high-purity cyclopentane serves as a reference standard for gas chromatography (GC) calibration, particularly in the analysis of hydrocarbons and volatile organic compounds. It provides a consistent retention time under standard GC conditions, aiding in the identification and quantification of similar aliphatic compounds by establishing baseline elution profiles on non-polar columns.^[49] This application leverages cyclopentane's well-characterized chromatographic behavior, as documented in retention index databases, ensuring accurate method validation in environmental and petrochemical testing.^[50] Within the electronics sector, cyclopentane derivatives such as multiply-alkylated cyclopentane (MAC) are applied as high-performance lubricants in semiconductor fabrication, providing low volatility and excellent thermal stability for precision machinery components. These lubricants reduce friction in vacuum environments during wafer processing, enhancing equipment reliability without residue formation.^[51] Additionally, cyclopentane is blended with other hydrocarbons like isopentane or isobutane for use as a blowing agent in polyurethane foam insulation for refrigeration systems, supporting low global warming potential designs in domestic and commercial appliances.^[52] In terms of market allocation, the blowing agent segment, including foam production and related specialty insulation applications, accounts for approximately 62-70% of global cyclopentane consumption, underscoring its prominence in sustainable manufacturing.^[53] The remaining production supports niche chemical syntheses and analytical uses, with ongoing growth driven by demand for eco-friendly alternatives in insulation technologies.^[15]

Molecular structure

Bonding and geometry

Cyclopentane consists of five carbon atoms, each sp3 hybridized, connected in a ring with ten hydrogen atoms attached. This hybridization results in a tetrahedral local geometry around each carbon, but the cyclic structure leads to a non-planar, puckered envelope conformation to minimize overall strain. In this arrangement, four carbon atoms are nearly coplanar, while the fifth is displaced out of the plane by approximately 0.4 Å, allowing for a balance between angle and torsional strain.^[54] Experimental bond lengths in cyclopentane, determined by electron diffraction, show an average C-C distance of 1.54 Å, while C-H bonds are approximately 1.09 Å, consistent with typical sp3-hybridized alkanes. The C-C-C bond angles average around 105°-108°, deviating slightly from the ideal tetrahedral angle of 109.5° and introducing modest angle strain. This deviation is less severe than in smaller rings like cyclopropane or cyclobutane, contributing to cyclopentane's relative stability among cycloalkanes.^[55]^[56] The electronic structure of cyclopentane features a sigma bonding framework composed entirely of sp3 hybrid orbitals, with no pi bonds due to the saturated nature of the molecule. The highest occupied molecular orbital (HOMO) is a sigma orbital, and the lowest unoccupied molecular orbital (LUMO) is an antibonding sigma* orbital, resulting in a large HOMO-LUMO energy gap that underscores the molecule's chemical inertness and stability. In the solid state, X-ray crystallography reveals similar puckered conformations within the crystal lattice, though intermolecular interactions in phases like Phase III at low temperatures (e.g., 93 K) slightly influence the overall packing without significantly altering intramolecular bond parameters.^[57]^[58] Compared to acyclic n-pentane, which exhibits fully staggered conformations with no angle strain and ideal 109.5° bond angles, the closure of the ring in cyclopentane introduces angle strain from the compressed C-C-C angles but partially relieves torsional strain through puckering, reducing eclipsing interactions that would be present in a planar cyclic form. This trade-off results in a total ring strain of about 6.5 kcal/mol for cyclopentane, primarily torsional in origin.^[56]^[59]

Conformational isomers

Cyclopentane displays dynamic conformational flexibility, primarily adopting an envelope conformation where four carbon atoms lie in a plane and the fifth is displaced out-of-plane by approximately 0.4 Å. This arrangement facilitates pseudorotation, a low-barrier process involving sequential transitions between envelope (C_s symmetry) and twist (C_2 symmetry) forms, allowing the out-of-plane carbon to migrate around the ring without breaking bonds.^[60] The concept of pseudorotation in cyclopentane was first analyzed in the 1940s by Kilpatrick, Pitzer, and Spitzer, who modeled the ring puckering modes as a vibrational coordinate that enables rapid interconversion of equivalent puckered structures, reducing torsional strain from eclipsed C-C bonds.^[61] The energy barrier for pseudorotation is notably low, ranging from 0.1 to 0.3 kcal/mol, which permits averaging of conformations on the NMR timescale at room temperature, resulting in equivalent signals for all methylene protons. Puckering significantly alleviates torsional strain compared to a hypothetical planar form; while planar cyclopentane would incur substantial torsional strain estimated at around 10 kcal/mol due to fully eclipsed bonds, the actual puckered conformation lowers the total ring strain to approximately 6.5 kcal/mol.^[54] Density functional theory calculations, such as those performed at the B3LYP/6-31G* level, accurately predict the vibrational frequencies associated with the puckering mode, confirming the low barrier and dynamic nature of the envelope-to-twist transitions with puckering amplitudes near 0.45 Å.^[62]

Safety and regulation

Health hazards

Cyclopentane exposure primarily occurs through inhalation due to its high volatility, which can lead to acute effects such as dizziness, lightheadedness, headache, drowsiness, and nausea at high concentrations.^[63] In animal studies, the acute inhalation LC50 in rats exceeds 25.3 mg/L (approximately 8,800 ppm) over 4 hours, indicating relatively low acute toxicity via this route.^[64] Skin contact with the liquid form causes mild irritation, including defatting and potential dryness or cracking upon prolonged exposure, though it is not severely corrosive.^[65] Chronic exposure to cyclopentane, like other aliphatic hydrocarbons, may pose risks of neurotoxicity, particularly through repeated aspiration leading to central nervous system depression or cumulative effects on cognitive function, though specific long-term human data are limited.^[63] There is no evidence of carcinogenicity for cyclopentane, and it has not been classified as a human carcinogen by the International Agency for Research on Cancer (IARC).^[64] As a highly flammable liquid, cyclopentane presents significant health risks from fire and explosion, with explosive limits in air ranging from 1.1% to 8.7% by volume; ignition sources must be avoided through proper ventilation, grounding of equipment, and static electricity control to prevent inhalation of combustion products or traumatic injury.^[66] Occupational exposure is regulated with a NIOSH recommended exposure limit (REL) of 600 ppm as a 10-hour time-weighted average (TWA) and an ACGIH threshold limit value (TLV) of 1000 ppm as an 8-hour TWA (as of 2024); OSHA has not established a specific PEL but references similar hydrocarbon limits.^[66]^[1] For ingestion, first aid protocols emphasize not inducing vomiting to avoid aspiration pneumonia, a potentially fatal complication from hydrocarbon entry into the lungs; immediate medical attention is required.^[1] Exposure incidents involving cyclopentane in industrial settings like refineries are rare, typically resulting from leaks or spills, with reported symptoms such as respiratory irritation and dizziness resolving after removal from the source and supportive care.^[67]

Environmental impact

Cyclopentane enters the environment primarily through industrial emissions during its production, use as a blowing agent in polyurethane foams, and as a solvent or fuel additive, with the majority of releases occurring to the atmosphere due to its high volatility.^[1] Vehicular exhaust and manufacturing processes contribute trace amounts, typically at concentrations below 0.5% by weight in emissions.^[1] Once released to water or soil, cyclopentane rapidly volatilizes, with an estimated Henry's law constant of 0.21 atm·m³/mol at 25°C, facilitating quick partitioning to air and limiting long-term aqueous persistence.^[1] This volatility reduces its accumulation in environmental compartments but can contribute to volatile organic compound (VOC) levels in the troposphere, potentially influencing local air quality and photochemical reactions.^[68] Biodegradation of cyclopentane is minimal under aerobic conditions, with studies showing 0% degradation in 28-day ready biodegradability tests using the OECD 301F manometric respirometry method.^[69] Microorganisms isolated from soil exhibit negligible breakdown, indicating that microbial degradation is not a significant fate process in terrestrial or aquatic systems.^[1] Anaerobic conditions show marginal evidence of isomer-specific degradation for related alicyclic hydrocarbons, but cyclopentane itself demonstrates low susceptibility.^[70] Its octanol-water partition coefficient (log Kow) of 3.00 suggests moderate potential for bioaccumulation, though estimated bioconcentration factors (BCF) remain below 100, classifying it as not highly bioaccumulative.^[1] Cyclopentane exhibits acute toxicity to aquatic organisms, classified under the EU CLP regulation as harmful to aquatic life with long-lasting effects (H412).^[71] Key ecotoxicity endpoints include an LC50 of 29.3 mg/L for fish (96-hour exposure, species unspecified), an EC50 of 2.3–10.5 mg/L for Daphnia magna (48-hour static test, range from multiple studies), and an EC50 of 3.4 mg/L for green algae (96-hour growth inhibition).^[72]^[64]^[1] These values indicate moderate hazard levels, with chronic effects inferred from limited biodegradation and persistence in sediment. No significant terrestrial ecotoxicity data are available, but its volatility suggests low risk to soil organisms beyond initial exposure.^[73] In applications such as rigid polyurethane foam production for appliances and insulation, cyclopentane serves as an environmentally preferable alternative to hydrochlorofluorocarbons (HCFCs) and hydrofluorocarbons (HFCs), offering zero ozone depletion potential (ODP) and a global warming potential (GWP) of approximately 11 over 100 years (IPCC estimate)—far lower than HFC-245fa's GWP of 1,030 (as of AR6, 2021).^[74]^[75] This substitution has reduced equivalent CO2 emissions in manufacturing by up to 90% in some processes, supporting global efforts to phase out high-GWP blowing agents under the Montreal Protocol and Kigali Amendment (as of 2025).^[75] However, incomplete capture during foam production can lead to unintended VOC releases, necessitating engineering controls to minimize atmospheric emissions.^[76] Overall, while cyclopentane poses localized aquatic risks if released untreated, its profile favors reduced climate impact compared to prior alternatives.^[74]

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The Clemmensen Reduction can effect a similar conversion under strongly acidic conditions, and is useful if the starting material is base-labile. Mechanism of ...<|separator|>
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Clemmensen Reduction of Ketones/Aldehydes to Alkanes
Description: Addition of zinc amalgam, Zn(Hg) and acid to a ketone results in an alkane. This is called the Clemmensen reduction.
[23]
Method of preparing cyclopentane by continuous hydrogenation of ...
The molar ratio between cyclopentadiene and hydrogen is 1 to (3-4), and the reaction system has pressure of 0.9-1.8MPa and temperature of 44-72 deg.c. The ...
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Process for the preparation of cyclic alkanes - Google Patents
Cyclobutane was finally prepared using 1,4-dibromobutane and sodium in refluxing toluene at a 7% yield, J. Cason and R. L. Way, J. Org. Chem., 14, 31 (1949) and ...Missing: Freund 1882
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Tandem Ring-Opening/Ring-Closing Metathesis Polymerization
Jul 11, 2013 · Monomer structure plays a role since 1,9-decadiene produces mol. wts. typical of ADMET chem., whereas 1,5-hexadiene produces only oligomers.Introduction · Results and Discussions · Supporting Information · References
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Preparation of Alkanes and Cycloalkanes, Chemistry tutorial
Rating 4.9 (37,128) (i) When 1, 5-dihalogen derivatives of alkanes are treated by sodium or zinc, the analogous cycloalkane is formed, for example 1, 5-dibromopentane would shape ...
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https://www.sciencedirect.com/topics/earth-and-planetary-sciences/cycloalkane
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CRUDE OIL - Occupational Exposures in Petroleum Refining - NCBI
The cycloalkane composition in crude oil worldwide typically varies from 30% to 60% (see also Table 3). The predominant monocycloalkanes in crude oil are in the ...
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The origin of light cycloalkanes in petroleum - ScienceDirect.com
It has been suggested that the light cycloalkanes in petroleum are generated through the thermal decomposition of heavier polycyclic natural products, ...Missing: diagenetic cyclization
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Cycloalkane - an overview | ScienceDirect Topics
The most abundant cycloalkanes in oil are the single-ring cyclopentane (C5H10) and cyclohexane (C6H12), and their alkylated (from C1 to C14) homologs (alkyl ...
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Origin and Geochemical Implications of Hopanoids in Saline ...
Nov 4, 2021 · Hopanoids are pentacyclic triterpenoid lipids and are important for bacterial membrane stability and functioning. These pentacyclic ...
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Hopanoids as functional analogues of cholesterol in bacterial ... - NIH
We find that hopanoids determine bacterial outer membrane order in a manner analogous to sterol ordering in the eukaryotic plasma membrane.<|separator|>
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Hopanoid lipid - microbewiki
May 11, 2018 · Hopanoid lipids, with a basic hopane skeleton structure (Figure 4), contain four cyclohexanes and one cyclopentane, all of which connecting ...
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Chemical composition, antibacterial and antioxidant activities of leaf ...
The GC-MS analysis revealed 49 compounds representing 94.62% of the total oil containing 2-butaneone (30.6%), cyclopentane (15.1%), beta-myrcene (13.29 ...
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Cyclopentane-forming di/sesterterpene synthases - ResearchGate
Terpene synthases are remarkable enzymes that catalyze some of the most complex transformations in natural product biosynthesis. [1] [2] [3] The type I of these ...
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Emission Factors for Crop Residue and Prescribed Fires in the ...
Sep 2, 2023 · Cyclopentane, C5H10, WAS, 0.002 (0.002), 26, 0.003 (0.003) ... Emission of trace gases and aerosols from biomass burning – An updated assessment.
[37]
(PDF) Gas Chromatographic–Mass Spectrometric Analysis of ...
Aug 7, 2025 · ... Cyclopentane 3.0 0.9902 5. Cyclopentene 1.5 0.9922 5. Furan 5.6 0.9950 ... Volcanic gas emissions are strictly related to a specific stage of ...
[38]
[PDF] S -S B R - Versalis - Eni
Dry solvent (n-hexane or cyclopentane), styrene, initiator, butadiene and other reactants are continuously loaded to the polymerization reactor train or ...
[39]
Performance of Solvent Mixtures for Non-aqueous Extraction of ...
Mar 10, 2015 · They concluded that cyclopentane was the best solvent and obtained a bitumen recovery of 90% using their extraction protocol.
[40]
US2407716A - Superfuel - Google Patents
Cyclopentane may be blended with isooctane to form aviation super fuels in 75 and an octane number above 95 C. F. YR.R. 2. An Iaviation super fuel whichY ...Missing: avgas formulations
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WO/2022/138746 METHOD FOR PRODUCING CYCLOPENTADIENE
A method for producing cyclopentadiene according to one aspect of the present disclosure includes a dehydrogenation step for obtaining cyclopentadiene by ...
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Design of a “green” one-step catalytic production of ε-caprolactam ...
Here we describe a viable laboratory-scale, single-step, solvent-free process of producing ε-caprolactam using a family of designed bifunctional, heterogeneous ...
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[PDF] Properties of Bicyclic and Multicyclic Hydrocarbons as Bio
Apr 22, 2021 · methylcyclopentane, which is indeed promising, owing to its reported heat of combustion (HHV. – higher heating value) of 46.8 MJ/kg.21,22 ...
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Sooting Tendency of a Series of Kerosene Surrogates and Blends ...
The present work aims at analyzing the sooting tendency of 32 additives considered as potential alternative transportation fuels.
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Preparation method for cyclopentanol and cyclopentanone by ...
The method comprises the following steps: (1) continuously introducing the cyclopentane, a catalyst and oxygen-contained gas into an oxidation reactor and ...
[46]
Method for preparing cyclopentanol and cyclopentanone by using ...
According to the method, cyclopentane is taken as a reactant, oxygen is taken as an oxidant, and a supported gold catalyst is used for catalytic oxidation of ...
[47]
Beyond Nylon 6: Polyamides via Ring Opening Polymerization ... - NIH
Employing a benzoylated caprolactam activator or acid-catalysed cationic ring opening polymerization are also ineffective in preparing high-molecular weight ...
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Cyclopentane Market Size, Industry Share Forecast & Trends Report
Wide use of cyclopentane in solvent and reagent applications is expected to drive the market. Pressing need for cyclopentane in thermal energy storage ...
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[PDF] Transitioning to Low-GWP Alternatives in Building/Construction Foams
A variety of climate-friendly blowing agents have been or are being developed for use in building/construction foam applications to replace CFCs, HCFCs, and ...
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Physical blowing agents: role of pentane quality in insulation
Aug 2, 2023 · Due to its physical properties, Cyclopentane enables very high insulation performance at low insulating foam layer thicknesses. Furthermore, ...
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https://www.sciencedirect.com/science/article/abs/pii/S0008622313007860
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https://www.epa.gov/sites/default/files/2016-12/documents/transitioning_to_low-gwp_alternatives_in_domestic_refrigeration.pdf
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Fabrication and tribological properties of a multiply-alkylated ...
A composite thin film composed of multiply-alkylated cyclopentane (MAC) and reduced graphene oxide (rGO) is prepared on a silicon substrate.
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[PDF] Transition to Low-GWP Alternatives in Domestic Refrigeration
Cyclopentane Blends. • Cyclopentane, cyclopentane/isopentane, and cyclopentane/ isobutane blends are the most globally used blowing agents in domestic ...
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Cyclopentane Market Size & Trends Analysis Report, 2030
The global cyclopentane market size was estimated at USD 358.5 million in 2021 and is anticipated to reach USD 675.7 million by 2030, growing at a CAGR of 7.3% ...
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Carbon—Carbon Bond Distances. The Electron Diffraction ...
Carbon—Carbon Bond Distances. The Electron Diffraction Investigation of Ethane, Propane, Isobutane, Neopentane, Cyclopropane, Cyclopentane, Cyclohexane ...
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Cycloalkanes and strain - Oregon State University
Cyclopentane Total strain: 6.5 kcal/mol 1.3 kcal/mol per CH · Jmol._Canvas2D (Jmol) "Cyclopentane"[x]. C-C: 1.538-1.560 Å C-C-C: 104.2, 105.8° C-C-H: 110.1°
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Ch 3 : Cycloalkanes - University of Calgary
Cycloalkanes are ring structures with only C-C and C-H bonds. The C atoms are sp3 hybridized, and they are 'puckered' except for cyclopropane.
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Solid Phases of Cyclopentane: Combined Experimental and ...
In this paper we aim to elucidate the structural and dynamical properties of the different phases of this compound, using X-ray single-crystal, X-ray powder, ...
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https://doi.org/10.1021/ja01202a069
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[PDF] Pseudorotation of Cyclopentane - Semantic Scholar
DFT/B3LYP does not reach the accuracy of the MBPT(2)/cc-pVTZ description of cyclopentane; however, calculated conformational parameters are reasonable so that ...
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[PDF] Cyclopentane - Santa Cruz Biotechnology
Cyclopentane: " reacts violently with strong oxidisers, nitrogen tetraoxide " may generate electrostatic charges, due to low conductivity, following flow or ...Missing: metabolism | Show results with:metabolism
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[PDF] Cyclopentane - Chevron Phillips Chemical
Cyclopentane Aspiration toxicity : May be fatal if swallowed and enters airways.
[65]
CYCLOPENTANE - CAMEO Chemicals - NOAA
Cyclopentane is a clear, colorless, flammable liquid with a petroleum-like odor, less dense than water, and insoluble in water. It is highly flammable.Missing: metabolism | Show results with:metabolism
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NIOSH Pocket Guide to Chemical Hazards - Cyclopentane - CDC
Flash Point. -35°F. Upper Explosive Limit. 8.7%. Lower Explosive Limit. 1.1%. Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F ...
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[PDF] CYCLOPENTANE CAS Number - NJ.gov
* Exposure can cause you to feel dizzy, lightheaded, and to pass out. Very high levels can cause coma. * Cyclopentane is a FLAMMABLE LIQUID and a FIRE. HAZARD.
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Identifying New Persistent and Bioaccumulative Organics Among ...
Feb 17, 2010 · A database of 22000 chemicals is developed to select about 600 persistent and bioaccumulative chemicals that are potential new contaminants.
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[PDF] SAFETY DATA SHEET cyclopentane - Balchem
Decomposition temperature. No data available. Auto-ignition temperature. 361 °C ; 1013 hPa. Explosive properties. No chemical group associated with explosive ...
[70]
Anaerobic biodegradation of alicyclic constituents of gasoline and ...
There was also marginal evidence for the biodegradation of. 1,1-dimethylcyclopentane, but the other isomers identi- fied in our incubations were essentially ...<|separator|>
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Cyclopentane - Substance Information - ECHA
This substance is used in the following products: polymers, adhesives and sealants, coating products, fuels, heat transfer fluids, perfumes and fragrances, ...
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[PDF] CYCLOPENTANE - Climalife UK
Highly flammable liquid and vapour. May be fatal if swallowed and enters airways. May cause drowsiness or dizziness. Harmful to aquatic life with long lasting ...
[73]
[PDF] Material Safety Data
- Cyclopentane : EC50 3.415 mg/L/96h Aquatic algae(Green algae). 2 ... - Cyclopentane : LC50 4.659 mg/L/48h Aquatic invertebrates(Daphnia magna).
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Registration Dossier - ECHA
### Summary of Ecotoxicological Data for Cyclopentane from Registration Dossier
[75]
Reducing Greenhouse Gas Emissions at GE's Refrigerator ...
Jan 11, 2011 · GE uses cyclopentane, a new insulation material with a lower GWP (10) than R134a (1300) and R245fa (950), to reduce emissions.Missing: blend | Show results with:blend
[76]
The effect of blowing agent choice on energy use and global ...
The most common replacements with zero ozone depletion potential have been c-pentane and mixtures of c-pentane with other hydrocarbons, along with some HFCs, ...
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[PDF] Natural Foam Blowing Agents - Green Cooling Initiative
Contrary to CFCs and HCFCs, pentanes used as polyurethane blowing agents have no environmental impact. ... In terms of the potential economic impact of ...