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Cyclooctane

Cyclooctane is a cycloalkane and saturated cyclic hydrocarbon with the molecular formula C₈H₁₆, consisting of eight carbon atoms arranged in a ring, each bonded to two hydrogen atoms. It appears as a colorless liquid at room temperature, with a melting point of 14.8 °C, a boiling point of 151 °C, a density of 0.834 g/mL at 25 °C, and limited solubility in water (approximately 0.008 g/L).^[1]^[2]^[3] In terms of molecular structure, cyclooctane exhibits multiple conformations due to its medium-sized ring, with the boat-chair (BC) form identified as the lowest-energy and most stable configuration in the gas phase, featuring average C–C bond lengths of 1.540 Å and C–C–C bond angles of 116.8°. This conformational flexibility distinguishes it from smaller cycloalkanes like cyclohexane, which prefer a chair form, and contributes to its unique physical properties compared to linear alkanes of similar molecular weight, such as n-octane.^[4] Cyclooctane finds applications primarily as a chemically inert solvent in organic synthesis and as a synthetic intermediate for producing derivatives like cyclooctanone, which is used in further chemical manufacturing. It is also employed in homogeneous catalysis precursors and pharmaceutical synthesis, leveraging its stability and nonpolar nature. Safety considerations include its flammability, with a flash point of 28 °C, necessitating proper handling in laboratory and industrial settings.^[5]^[2]^[6]

Properties

Physical properties

Cyclooctane has the molecular formula C₈H₁₆ and a molar mass of 112.21 g/mol.^[7] It appears as a colorless liquid at room temperature with a camphoraceous odor.^[8]^[9] The compound exhibits a melting point of 14.7 °C and a boiling point of 151 °C at standard pressure.^[10] Its density is 0.834 g/cm³ at 25 °C, while the refractive index is 1.458 (n²⁰/D).^[8] Cyclooctane is insoluble in water, with a solubility of 7.9 mg/L at 25 °C, but it is miscible with common organic solvents such as ethanol and diethyl ether.^[11]^[3] Additional bulk properties include a kinematic viscosity of 1.996 mm²/s at 40 °C and a surface tension of 30 mN/m at 20 °C.^[12]^[13] Compared to smaller cycloalkanes like cyclohexane, the larger ring size of cyclooctane contributes to its liquidity at ambient conditions despite a slightly higher melting point.^[10]

Property	Value	Conditions	Source
Melting point	14.7 °C	-	PubChem
Boiling point	151 °C	987 hPa	Sigma-Aldrich
Density	0.834 g/cm³	25 °C	Sigma-Aldrich
Refractive index	1.458	20 °C (D line)	Sigma-Aldrich
Water solubility	7.9 mg/L	25 °C	Good Scents Co.
Kinematic viscosity	1.996 mm²/s	40 °C	Sigma-Aldrich
Surface tension	30 mN/m	20 °C	Cheméo

Thermodynamic properties

Cyclooctane exhibits thermodynamic properties indicative of moderate ring strain, with contributions from both angle deviation and torsional interactions in its eight-membered ring. The standard enthalpy of formation in the gas phase is ΔH_f° = -126.1 ± 1.6 kJ/mol at 298 K.^[14] In the liquid phase, this value is -169.4 ± 1.6 kJ/mol at 298 K.^[14] The heat of combustion for liquid cyclooctane is 5265.7 ± 0.9 kJ/mol at 298 K, reflecting the energy released upon complete oxidation to CO₂ and H₂O.^[14] The enthalpy of vaporization is 43.35 ± 0.21 kJ/mol at its boiling point of 422 K.^[14] Cyclooctane's ring strain energy is approximately 39 kJ/mol relative to acyclic alkanes, primarily due to torsional strain from eclipsed C-H bonds and minor angle strain from bond angles averaging near 115°.^[15]^[16] This strain influences phase energetics and contributes to the molecule's overall stability under standard conditions. The molar heat capacity at constant pressure for liquid cyclooctane is C_p = 215 J/mol·K at 298 K.^[14] The standard entropy is S° = 262.0 J/mol·K for the liquid and 366.8 ± 1.3 J/mol·K for the gas phase at 298 K.^[14] These values highlight cyclooctane's relatively high conformational flexibility, where thermodynamic stability favors low-energy boat-chair forms.

Structure and conformations

Molecular structure

Cyclooctane, with the IUPAC name cyclooctane and molecular formula C₈H₁₆, is a saturated cyclic hydrocarbon consisting of eight methylene (–CH₂–) groups linked by single bonds to form a closed ring. Its skeletal formula depicts a simple octagonal ring of carbon atoms, where each carbon is implied to bear two hydrogen atoms, reflecting the general structure of unbranched cycloalkanes.^[1] The molecule features eight sp³-hybridized carbon atoms, each bonded to two adjacent carbons and two hydrogens via sigma bonds. Electron diffraction studies in the gas phase have determined the average C–C bond length to be 1.540 ± 0.001 Å and the average C–H bond length to be 1.112 ± 0.003 Å. These bond lengths are typical for unstrained aliphatic hydrocarbons, indicating minimal bond strain in the connectivity of cyclooctane.^[17] For an eight-membered ring, the ideal C–C–C bond angle based on tetrahedral sp³ hybridization is 109.5°, but the cyclic constraint and resulting puckering lead to an average observed angle of 116.8° ± 0.5°, with H–C–H angles at 108.0° ± 1.0°. This deviation arises from the ring's inability to remain planar, as the large size allows flexibility that distorts the geometry to reduce overall strain. In contrast to smaller rings like cyclopropane, which is forced into a planar configuration with severe angle strain (C–C–C angles of 60°), cyclooctane's greater ring size permits non-planar puckering, avoiding excessive torsional and angle strain.^[17]^[18] This puckered ring structure facilitates the adoption of various conformations, providing pathways to minimize steric interactions among the methylene groups.

Conformational isomers

Cyclooctane exhibits a flexible ring structure that allows for multiple conformational isomers, with the boat-chair (BC) form serving as the global energy minimum at 0 kJ/mol relative energy. This conformation, characterized by C_s symmetry, minimizes angle and torsional strain while avoiding significant steric interactions among the methylene groups. Experimental electron diffraction studies in the gas phase at 59°C confirm the BC as the predominant species, accounting for over 97% of the population, with no evidence of significant contributions from other forms under these conditions.^[17] Local energy minima beyond the BC include the crown (D_{2d} symmetry), approximately 4.9 kJ/mol higher in energy, the twist-boat-chair (TBC), boat-boat (BB), and tub conformations. The crown features alternating up and down bonds in a symmetric arrangement, while the TBC represents a distorted variant within the BC pseudorotation family, with energies only slightly elevated above the BC (around 4.2 kJ/mol in some mappings). The BB and tub forms are higher-energy structures, with the BB estimated at about 12 kJ/mol above the BC, contributing negligibly to the equilibrium population due to increased strain. These relative energies derive from molecular mechanics calculations that align closely with spectroscopic and diffraction data.^[19]^[20] Pseudorotation facilitates interconversions within conformational families, particularly between the BC and TBC, through low-energy pathways with barriers on the order of 5-6 kJ/mol, allowing rapid equilibration at ambient temperatures. For instance, the saddle point connecting BC and TBC lies approximately 5.4 kJ/mol above the BC minimum. Higher barriers govern transitions between families, such as ring inversion in the BC form, estimated at 31 kJ/mol from NMR studies, though pseudorotation within the BC family precludes direct observation of distinct enantiomers. These dynamics underscore cyclooctane's fluxional behavior in both gas and solution phases.^[20]^[19] Computational approaches, including molecular mechanics (e.g., MM3 force field) and density functional theory (DFT), have mapped the full conformational landscape, consistently identifying the BC as the most stable minimum and reproducing experimental geometries from electron diffraction. These methods reveal a complex topology akin to a Klein bottle for the low-energy BC-TBC subspace, with higher-energy paths to crown and BB forms involving multiple transition states. Such simulations provide quantitative validation of the BC stability and barriers, essential for understanding the molecule's thermodynamic favorability.^[19]^[17]

Synthesis

Industrial production

Cyclooctane is primarily produced on an industrial scale through a two-step process starting from 1,3-butadiene. The first step involves the nickel(0)-catalyzed cyclodimerization of butadiene to form 1,5-cyclooctadiene (COD), typically using zero-valent nickel complexes with phosphite ligands under mild conditions of around 80°C and 1 atm pressure. This reaction achieves high selectivity, with yields exceeding 96% for COD and the main byproduct being 4-vinylcyclohexene, which finds use in synthetic rubber production.^[21] The second step entails the catalytic hydrogenation of COD to cyclooctane, commonly employing palladium on carbon (Pd/C) as the catalyst in the presence of hydrogen gas. Industrial conditions for this full hydrogenation typically operate at temperatures of 40–70°C and hydrogen pressures of 0.2–1 MPa (2–10 atm), yielding cyclooctane with purities above 98%.^[22] This process is scalable and integrated into butadiene oligomerization facilities, where COD serves as a key intermediate.^[2] The nickel-catalyzed dimerization route was developed and commercialized in the 1950s, with early implementations by companies including BASF and DuPont as part of broader efforts to valorize butadiene streams from petrochemical sources.^[23] Variants of this process, often run continuously, support annual production capacities in the thousands of tons, emphasizing efficient catalyst recovery and byproduct minimization for economic viability.^[24]

Laboratory synthesis

One common laboratory method for synthesizing cyclooctane involves the catalytic hydrogenation of cyclooctene. Wilkinson's catalyst, chlorotris(triphenylphosphine)rhodium(I), facilitates this transformation under mild conditions, typically at room temperature and atmospheric pressure in solvents like benzene or ethanol, proceeding via oxidative addition of hydrogen, migratory insertion of the alkene, and reductive elimination. Yields are generally high, making it suitable for small-scale preparations. Similarly, 1,5-cyclooctadiene can be fully hydrogenated to cyclooctane using Raney nickel as a heterogeneous catalyst. This process requires elevated temperatures (around 100–150°C) and hydrogen pressures (20–50 atm) in an autoclave, with the nickel promoting stepwise reduction of the diene. The method is robust for laboratory use, achieving yields of 85–95% after filtration to remove the catalyst.^[25]^[26] Ring expansion strategies from cycloheptane derivatives also enable cyclooctane synthesis on a laboratory scale. Treatment of cycloheptanone (derived from cycloheptane oxidation) with diazomethane or trimethylsilyldiazomethane in the presence of a Lewis acid effects a one-carbon homologation, yielding cyclooctanone, which is subsequently reduced using Wolff–Kishner conditions to cyclooctane. Photochemical methods complement this, as seen in the ring expansion of cycloheptene oxide to cis-cyclooct-2-enol, followed by hydrogenation to cyclooctane. These techniques afford yields of 70–90%, ideal for preparing isotopically labeled or substituted variants. Purification of laboratory-synthesized cyclooctane typically involves distillation under reduced pressure to separate it from unreacted starting materials and byproducts, exploiting its boiling point of approximately 148°C at atmospheric pressure (lowered to 50–60°C at 10–20 mmHg). This method routinely achieves purities >98% with overall yields of 80–95% from the crude reaction mixture, often preceded by extraction with nonpolar solvents and drying over molecular sieves.^[27]

Reactions

General reactivity

As a saturated cyclic hydrocarbon, cyclooctane exhibits the typical reactivity of alkanes, primarily undergoing reactions that involve C-H bond cleavage under specific conditions such as high temperature, light, or catalysis.^[2] It is chemically inert under ambient conditions due to the absence of functional groups or unsaturation, showing no reactivity toward dilute acids or bases, which aligns with the general stability of sp³-hybridized C-H and C-C bonds in cycloalkanes.^[28] Free radical halogenation is a key reaction for cyclooctane, proceeding via a chain mechanism initiated by UV light or heat with Cl₂ or Br₂, substituting a hydrogen atom to form halocyclooctanes. Due to the equivalence of all 16 methylene hydrogens in its symmetric structure, monohalogenation yields primarily chlorocyclooctane or bromocyclooctane as the major product, with polyhalogenation minimized by controlling reagent stoichiometry; the boat-chair conformation may slightly enhance radical stability at certain positions compared to smaller rings.^[29] Bromination is more selective than chlorination, favoring secondary hydrogens inherent to the ring, and this reaction is commonly used in synthetic routes to cyclooctene derivatives.^[30] Combustion of cyclooctane is complete under oxygen-rich conditions, yielding carbon dioxide and water: C₈H₁₆ + 12 O₂ → 8 CO₂ + 8 H₂O, with a standard enthalpy of combustion (Δ_c H°) of -5266 kJ/mol for the liquid phase at 298 K.^[31] This exothermic process releases significant energy, reflecting the high carbon and hydrogen content, and is analogous to other C₈ alkanes.^[32] Thermal or catalytic cracking breaks the ring and C-C bonds at high temperatures (450–750°C) and pressures (up to 70 atm), producing smaller alkanes (e.g., methane, ethane) and olefins (e.g., ethylene, propene) as valuable feedstocks for petrochemicals. In catalytic processes using zeolites or metal oxides, the reaction favors branched or linear fragments over intact ring retention, enhancing selectivity for gaseous products.^[33]

Functionalization methods

One notable method for functionalizing cyclooctane involves peroxide-mediated amination using nitroarenes, as reported in a 2009 study. In this metal-free process, cyclooctane reacts with nitrobenzene in the presence of dicumyl peroxide under aqueous conditions at 130°C, yielding N-phenylcyclooctanamine in 82% isolated yield. The reaction proceeds via a radical mechanism initiated by peroxide decomposition, enabling direct C-H amination at the tertiary-like positions influenced by the molecule's flexible ring structure. Photochemical and metal-catalyzed C-H activation techniques have also been applied to introduce aryl groups or deuterium into cyclooctane. In a complementary approach, iridium-based PCP pincer complexes catalyze H/D exchange in cyclooctane using D₂ gas in C₆D₆ solvent at 65°C, resulting in up to 36% deuteration after 5 days, preferentially at methylene positions via reversible C-H activation.^[34] Oxidation of cyclooctane to cyclooctanone represents another key functionalization route, often employing catalytic systems for selectivity. Polyoxometalate catalysts, such as cobalt-substituted tungstates, facilitate the reaction with aqueous H₂O₂ in acetonitrile, producing cyclooctanone, cyclooctanol, and cyclooctyl hydroperoxide. Traditional oxidants like chromic acid have been used historically for alkane oxidations, though modern catalytic methods with H₂O₂ or O₂ are preferred for efficiency and reduced waste.^[35] The general reaction for peroxide-mediated amination can be represented as:

\text{C}_8\text{H}_{16} + \text{PhNO}_2 + (\text{PhC(Me)}_2\text{O})_2 \rightarrow \text{C}_8\text{H}_{15}\text{NPh} + \text{byproducts}

This equation highlights the direct incorporation of the arylamino group, expanding cyclooctane's synthetic utility.

Applications and occurrence

Industrial applications

Cyclooctane serves as a nonpolar solvent in various industrial processes, including polymerizations and extractions, owing to its chemical inertness and high solubility in apolar substances.^[2] Its liquidity at room temperature and boiling point of 150–152°C make it suitable for applications requiring stable saturated cyclic hydrocarbons, such as in the dissolution of resins, oils, and waxes during synthetic organic processes.^[36] In chemical manufacturing, cyclooctane acts as a key intermediate for the production of cyclooctanone through catalytic oxidation, achieving high selectivity (up to 82%) using hydrogen peroxide and polyoxometalate catalysts. Cyclooctanone, in turn, is employed in the synthesis of fragrance and flavor compounds, contributing to the growing demand in the perfumery and food industries.^[37] Additionally, cyclooctane functions as a building block in the manufacture of plastics, fibers, adhesives, and coatings.^[36] Cyclooctane is utilized as a reference standard in industrial research for conformational studies of cyclic hydrocarbons and as a model substrate in catalyst testing, particularly for dehydrogenation reactions to produce cyclooctene.^[38] For instance, iridium-based pincer complexes have demonstrated up to 61 turnovers in the selective dehydrogenation of cyclooctane to cyclooctene, informing catalyst development for hydrogen storage and transfer processes.^[39] In specialty chemicals, cyclooctane serves as a precursor for cyclooctene derivatives, including trans-cyclooctene, which is applied in bioorthogonal chemistry for click reactions in pharmaceutical labeling and imaging.^[40] These applications leverage the ring's strain for efficient, metal-free cycloadditions with tetrazines.^[41]

Natural occurrence and derivatives

Cyclooctane occurs rarely in nature, primarily as trace components in petroleum fractions such as diesel fuel, where it appears in chromatographic analyses alongside other cycloalkanes.^[42] It is also detected in minute quantities, around 0.07%, in certain essential oils like those from lavender, though it does not constitute a major volatile component.^[43] Beyond its direct presence, cyclooctane serves as a core structural motif in various cyclooctanoid natural products, particularly terpenoids, which exhibit diverse biological activities and have inspired synthetic efforts due to their conformational complexity.^[44] These include medium-ring terpenes within bicyclo[6.3.0]undecane frameworks, highlighting cyclooctane's role in bioactive scaffolds found in marine and plant sources.^[45] Key derivatives of cyclooctane include unsaturated analogs like 1,5-cyclooctadiene (COD), which functions as a bidentate ligand in transition metal catalysis, such as in iridium complexes for selective dehydrogenation reactions.^[39] Perdeuterated variants, such as cyclooctane-d₁₆, are employed in nuclear magnetic resonance (NMR) spectroscopy to probe conformational dynamics and isotope effects in the boat-chair form.^[46]

Safety and environmental considerations

Health hazards

Cyclooctane poses significant health risks primarily through aspiration and inhalation routes due to its physical properties as a low-viscosity hydrocarbon liquid. It is classified as an aspiration hazard (H304), where ingestion and subsequent entry into the airways can be fatal, leading to chemical pneumonitis or pulmonary edema; this risk arises from its low viscosity (approximately 2.0 cP at 25 °C) and surface tension (around 30 mN/m), allowing it to penetrate deep into the lungs without triggering protective reflexes.^[47]^[13] Inhalation of cyclooctane vapors can cause irritation to the respiratory tract, particularly at high concentrations, resulting in symptoms such as coughing, shortness of breath, and central nervous system depression. With a flash point of 28 °C, its flammable vapors contribute to potential exposure during handling or spills, exacerbating irritation or narcotic effects like drowsiness, fatigue, and muscle weakness above 1,000 ppm.^[1]^[8]^[48] Acute systemic toxicity is low. Chronic exposure may cause skin irritation (H315) and allergic skin reaction (H317). No evidence supports carcinogenicity, and it remains unclassified by the International Agency for Research on Cancer (IARC).^[47]

Environmental impact

Cyclooctane demonstrates slow biodegradability under aerobic conditions, consistent with observations for saturated hydrocarbons, where microbial breakdown is hindered by the compound's stable cyclic structure. The compound's bioaccumulation potential is moderate, driven by its octanol-water partition coefficient (log Kow) of approximately 4.5, which facilitates uptake in lipid-rich tissues of aquatic organisms but is tempered by metabolic processes in fish and invertebrates. Experimental data suggest bioconcentration factors (BCF) in the range of hundreds to low thousands for similar cycloalkanes, indicating limited but notable accumulation in lower trophic levels.^[1]^[49] It is classified as very toxic to aquatic life with long-lasting effects (Aquatic Acute 1, H400; Aquatic Chronic 1, H410).^[47] In the atmosphere, cyclooctane undergoes degradation primarily through reaction with hydroxyl (OH) radicals, with a rate constant of (1.4 ± 0.2) × 10⁻¹¹ cm³ molecule⁻¹ s⁻¹ at 298 K, leading to an estimated lifetime of several days under typical tropospheric conditions. This process results in minimal contribution to photochemical smog formation, as the oxidation products do not significantly promote ozone generation compared to unsaturated hydrocarbons.^[50] Under the European REACH regulation, cyclooctane is registered with EC number 206-031-8 and classified as a hydrocarbon substance subject to monitoring as a potential environmental pollutant, though no specific bans or restrictions are imposed due to its low production volume and non-persistent organic pollutant status. Industrial emissions represent a primary release pathway, necessitating controls to mitigate localized aquatic and soil contamination.^[47]

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[54]
Chemical Properties of Cyclooctane, 1,2-diethyl-, trans - Cheméo
logPoct/wat : Octanol/Water partition coefficient. McVol : McGowan's characteristic volume (ml/mol). Pc : Critical Pressure (kPa). Inp : ...
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Showing metabocard for Cyclooctane (HMDB0250661)
Sep 11, 2021 · Cyclooctane is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. ...
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Reactions of tropospheric oxidants- Cl, OH and O3 with cyclic ...
Sep 15, 2019 · The results suggest that Cl atom is more effective in the atmospheric degradation of cyclooctane than OH, in the conditions of marine boundary layer.