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Cyclohexanone

Cyclohexanone is an organic compound with the molecular formula C₆H₁₀O, consisting of a six-membered carbon ring with a ketone functional group, appearing as a colorless to pale yellow liquid with a peppermint-like odor.^[1] It has a molecular weight of 98.14 g/mol, a melting point of -47 °C, a boiling point of 155.6 °C, a density of 0.9478 g/mL at 20 °C, and is soluble in water (approximately 8.6 g/100 mL at 20 °C) as well as miscible with most organic solvents.^[1] Cyclohexanone is primarily produced on an industrial scale through the catalytic oxidation of cyclohexane, which yields a mixture of cyclohexanol and cyclohexanone, followed by separation and purification steps such as distillation or dehydrogenation of the alcohol component.^[2] Alternatively, it can be synthesized via the hydrogenation of phenol, though this route is less common.^[3] The compound serves as a key chemical intermediate, with over 95% of global production directed toward the manufacture of nylon precursors: specifically, conversion to caprolactam for nylon-6 and to adipic acid for nylon-6,6 via oxidation and further processing.^[1] Remaining applications include its use as a versatile solvent in the formulation of paints, lacquers, resins, inks, and adhesives, as well as in the production of pharmaceuticals, pesticides, and plasticizers.^[2]^[1] Cyclohexanone is classified as a flammable liquid (flash point 44 °C) and poses health risks including irritation to the eyes, skin, and respiratory tract, with potential for central nervous system depression upon inhalation or ingestion; it is harmful if swallowed or inhaled and requires careful handling in industrial settings.^[1] The International Agency for Research on Cancer (IARC) has not classified it as carcinogenic to humans (Group 3).^[1]

Properties

Physical properties

Cyclohexanone is an organic compound with the molecular formula C₆H₁₀O, consisting of a six-membered carbocyclic ring with a ketone functional group.^[4] It appears as a colorless to pale yellow oily liquid possessing a peppermint- or acetone-like odor.^[4] Key physical properties of cyclohexanone are summarized in the following table:

Property	Value	Conditions
Molar mass	98.14 g/mol	-
Melting point	-47 °C	-
Boiling point	155 °C	101.3 kPa
Density	0.947 g/cm³	20 °C
Refractive index	1.4507	20 °C
Vapor pressure	5 mmHg	25 °C

^[4]^[5] Cyclohexanone exhibits slight solubility in water, approximately 8.6 g/100 mL at 20 °C, while being miscible with common organic solvents including ethanol, diethyl ether, and acetone.^[5]^[4] Thermodynamic properties include a heat of vaporization of 45.1 kJ/mol and a liquid heat capacity of 177 J/mol·K at 27 °C.^[6]^[7] Cyclohexanone occurs in trace amounts in cigarette smoke^[8] and serves as a urinary metabolite in humans following exposure to xenobiotics.^[9]

Chemical properties

Cyclohexanone features a carbonyl group (C=O) where the carbon atom is sp² hybridized, forming a planar structure with the surrounding atoms and exhibiting characteristic bond lengths of approximately 1.21 Å for the C=O bond and 1.50 Å for the adjacent C-C bonds.^[10] This configuration contributes to a significant dipole moment of about 2.9 D, arising from the polarity of the C=O bond.^[11] The alpha-hydrogens in cyclohexanone are moderately acidic, with a pKa value ≈ 18-20, which facilitates enolization through deprotonation to form resonance-stabilized enolate ions.^[12] The carbonyl oxygen is weakly basic, capable of coordinating with Lewis acids but not exhibiting strong proton affinity.^[1] In infrared spectroscopy, cyclohexanone displays a characteristic C=O stretching absorption at 1715 cm⁻¹, indicative of the unconjugated ketone functionality.^[13] Proton NMR spectroscopy reveals the alpha-methylene protons at approximately 2.3 ppm, shifted downfield due to deshielding by the carbonyl, while the other ring methylene protons appear between 1.6 and 2.0 ppm.^[14] In ¹³C NMR, the carbonyl carbon resonates at around 208 ppm, reflecting its electron-deficient nature.^[15] Cyclohexanone exhibits thermal stability up to temperatures exceeding 300 °C before significant decomposition occurs, though it is susceptible to polymerization under acidic conditions via self-condensation mechanisms.^[16] As a typical ketone, cyclohexanone undergoes nucleophilic addition reactions at the electrophilic carbonyl carbon and alpha-deprotonation under basic conditions to generate enolates for further reactivity.^[1] It also absorbs ultraviolet light at approximately 280 nm due to the forbidden n→π* electronic transition involving the carbonyl oxygen's non-bonding electrons.^[17]

History and synthesis

Discovery

Cyclohexanone was first identified in 1888 by German chemist Edmund Drechsel during experiments involving the electrolysis of phenol dissolved in a slightly acidified aqueous solution using alternating current.^[18] Among the mixture of products formed, Drechsel isolated a new compound, which he named "hydrophenoketone" based on its presumed origin from phenol.^[19] He proposed that the substance arose through a sequence of hydrogenation and oxidation steps during the electrolytic process.^[19] Early characterization efforts by Drechsel confirmed the compound's ketonic functionality when it reacted with hydroxylamine to yield an oxime derivative, a standard test for carbonyl groups at the time.^[19] This reaction, along with elemental analysis and boiling point determination, supported its identification as a simple aliphatic ketone.^[19] The structural formula, recognized as a six-carbon ring with a ketone group (C₆H₁₀O), was established in the late 19th century through comparative studies with known cyclic compounds and degradation reactions.^[19] In the pre-20th century era, cyclohexanone appeared sporadically as a byproduct in various organic synthesis experiments, such as distillations or oxidations involving cyclic hydrocarbons, but its scarcity from these low-yield sources limited any practical applications.^[19] Researchers primarily viewed it as a curiosity in the expanding field of alicyclic chemistry rather than a compound of immediate utility.^[19]

Laboratory synthesis

In laboratory settings, cyclohexanone is commonly synthesized through the oxidation of cyclohexanol, a secondary alcohol, using chromic acid as the Jones reagent, prepared from chromium trioxide (CrO₃) dissolved in aqueous sulfuric acid and acetone. This method selectively converts the alcohol to the ketone under mild conditions, typically at room temperature, with the reaction proceeding via chromate ester formation followed by elimination of water. Yields for this oxidation are typically around 90%, making it a reliable approach for small-scale preparations. The balanced equation for the process is:

\ce{C6H11OH + [O] -> C6H10O + H2O}

An alternative oxidation employs pyridinium chlorochromate (PCC) in dichloromethane as the reagent, which offers the advantage of avoiding over-oxidation and is particularly suitable for anhydrous conditions. PCC, formed from pyridine, hydrochloric acid, and chromium trioxide, oxidizes secondary alcohols to ketones with high selectivity and minimal side products, achieving yields of approximately 80-90%. This method is often preferred in research labs for its compatibility with acid-sensitive substrates.^[20] For milder conditions, cyclohexanol can be oxidized using sodium hypochlorite (NaOCl) in acetic acid, known as the Chapman-Stevens oxidation, where household bleach serves as a convenient source of the oxidant. The acetic acid generates hypochlorous acid in situ, which facilitates the transformation at ambient temperature without requiring heavy metal catalysts, yielding 84-89% of cyclohexanone. This approach is valued in educational and green chemistry contexts for its accessibility and reduced toxicity. A direct synthesis from cyclohexane involves photochemical oxidation with air using sensitizers like methylene blue to generate reactive oxygen species, though this method is less practical due to low yields, often below 10%, and requires irradiation setups. It proceeds via radical intermediates but is mainly exploratory rather than routine.^[21] Regardless of the method, the crude cyclohexanone is purified by distillation under reduced pressure to separate it from unreacted alcohol, water, and byproducts, taking advantage of its boiling point of approximately 155°C at atmospheric pressure to minimize thermal decomposition.

Industrial production

The dominant industrial method for producing cyclohexanone involves the catalytic oxidation of cyclohexane with air to form a mixture of cyclohexanol and cyclohexanone known as KA oil, followed by dehydrogenation of the mixture to yield primarily cyclohexanone.^[2] This two-step process accounts for the majority of global production due to its economic viability and integration with nylon precursor manufacturing. In the first step, cyclohexane is oxidized in the liquid phase at 140–160 °C and 10–15 bar pressure using homogeneous catalysts such as cobalt(II) or manganese naphthenates, achieving a cyclohexane conversion of approximately 5–10% per pass with a selectivity of about 80–85% to KA oil.^[22] The reaction proceeds via a free-radical autoxidation mechanism, producing KA oil with a typical cyclohexanol-to-cyclohexanone ratio of 4:1. The KA oil is then subjected to catalytic dehydrogenation, often using zinc oxide or palladium-based catalysts at 250–300 °C, converting the cyclohexanol component to cyclohexanone while recycling unreacted cyclohexane.^[2] An alternative route is the direct hydrogenation of phenol to cyclohexanone, which is employed in regions with abundant phenol supply from cumene processes.^[23] This liquid-phase reaction uses palladium or nickel catalysts supported on carbon or alumina, conducted at 120–150 °C and 1–10 bar hydrogen pressure, with high selectivity (>95%) to cyclohexanone under optimized conditions. The balanced equation for this transformation is:

\mathrm{C_6H_5OH + 2 H_2 \rightarrow C_6H_{10}O}

This method offers advantages in terms of lower oxidation byproducts but is less common globally due to higher hydrogen consumption and phenol feedstock costs compared to the KA oil route. Emerging processes aim to improve sustainability and integration by starting from benzene. One such approach, developed by ExxonMobil, involves hydroalkylation of benzene to cyclohexylbenzene using a bifunctional catalyst (e.g., ruthenium on zeolite), followed by air oxidation to the hydroperoxide and acid-catalyzed cleavage to co-produce phenol and cyclohexanone.^[24] This route has seen pilot-scale demonstrations and potential commercial implementations in the 2020s, offering higher atom efficiency and reduced waste compared to traditional methods. Global production of cyclohexanone is estimated at approximately 3.7 million metric tons per year as of 2022, with projections for steady growth driven by nylon demand; major producing regions include China (over 50% share), the United States, and Western Europe.^[25] Leading producers such as BASF, Fibrant, and Asahi Kasei have focused on energy efficiency enhancements through integrated KA oil processing, including heat recovery and catalyst recycling, reducing overall energy intensity by up to 20% in modern facilities.^[2]

Uses and reactions

Industrial applications

Cyclohexanone serves as a key intermediate in the industrial production of nylon polymers, accounting for approximately 85% of its global consumption as of 2023 in the synthesis of adipic acid and caprolactam.^[26] In the manufacture of nylon 6,6, cyclohexanone—typically as part of a mixture known as KA oil (cyclohexanone and cyclohexanol)—is oxidized to adipic acid using nitric acid as the oxidant. This process generates adipic acid, which is then polymerized with hexamethylenediamine to form nylon 6,6, widely used in textiles, automotive parts, and engineering plastics.^[2] For nylon 6 production, cyclohexanone is converted to cyclohexanone oxime by reaction with hydroxylamine, followed by the Beckmann rearrangement to yield caprolactam, the monomer for nylon 6. Approximately 90% of caprolactam worldwide is produced via this cyclohexanone-based route as of 2023. Global cyclohexanone consumption for these nylon applications reached about 3.3 million metric tons in 2023, driven by demand in the automotive and textile sectors.^[25] Beyond nylon precursors, approximately 10% of cyclohexanone production is utilized as a solvent in the formulation of paints, inks, resins, and adhesives, owing to its ability to dissolve cellulose ethers, vinyl polymers, and other resins effectively.^[26] It also finds minor applications as an intermediate in the synthesis of herbicides and in the production of cyclohexanone-formaldehyde resins, which are employed in coatings and printing inks.^[27]

Other reactions

Cyclohexanone reacts with hydroxylamine (NH₂OH) to form cyclohexanone oxime, a key intermediate in various synthetic transformations.^[28] This condensation typically occurs under mildly acidic or neutral conditions, proceeding via nucleophilic addition of the hydroxylamine nitrogen to the carbonyl carbon, followed by dehydration. The resulting oxime serves as a precursor for the Beckmann rearrangement, where treatment with an acid catalyst, such as sulfuric acid or phosphorus pentachloride, induces migration of the anti-alkyl group to the nitrogen, yielding ε-caprolactam.^[29] The stereospecificity of this rearrangement stems from the anti migration aptitude, where the group trans to the hydroxyl moiety preferentially migrates, ensuring high selectivity in the formation of the amide product.^[30] Similarly, cyclohexanone undergoes condensation with hydrazine to form the corresponding hydrazone, which is a crucial step in the Wolff-Kishner reduction for deoxygenation to cyclohexane.^[31] Reduction of the carbonyl to a secondary alcohol yields cyclohexanol, achievable through mild hydride transfer using sodium borohydride (NaBH₄) in protic solvents like methanol or ethanol, often at room temperature with high yields exceeding 90%.^[32] Catalytic hydrogenation over metal catalysts, such as palladium or nickel on carbon, also efficiently converts cyclohexanone to cyclohexanol under moderate hydrogen pressure, achieving complete selectivity to the alcohol.^[33] For complete deoxygenation to the methylene group, forming cyclohexane, the Clemmensen reduction employs zinc amalgam in concentrated hydrochloric acid under refluxing conditions, effectively cleaving the C=O bond in acidic media.^[34] Alternatively, the Wolff-Kishner reduction utilizes the hydrazone intermediate treated with a strong base like potassium hydroxide at elevated temperatures, proceeding via a carbanion mechanism to afford the hydrocarbon in good yields.^[35] Alpha-functionalization of cyclohexanone begins with deprotonation at the alpha position using strong bases like lithium diisopropylamide (LDA) at low temperatures to generate the kinetic enolate, which can then be alkylated with primary alkyl halides to introduce substituents selectively at the alpha carbon.^[36] This enolate alkylation is widely used in synthesis due to its regioselectivity and compatibility with unsymmetrical ketones. In the haloform reaction, treatment of cyclohexanone with halogens (e.g., iodine or bromine) in aqueous base leads to oxidative cleavage, albeit less efficiently than for methyl ketones, ultimately forming adipic acid as the dicarboxylic product through ring opening.^[37] The Baeyer-Villiger oxidation transforms cyclohexanone into ε-caprolactone using peracids such as meta-chloroperoxybenzoic acid (mCPBA) in dichloromethane, inserting an oxygen atom adjacent to the carbonyl.^[38] In this symmetrical case, the reaction proceeds smoothly with the secondary alkyl groups exhibiting equivalent migratory aptitude, but in general, regioselectivity favors migration of the more substituted group, placing the oxygen on the less substituted side of the original ketone.^[39] Photochemical reactions of cyclohexanone include the Paterno-Büchi [2+2] cycloaddition, where UV irradiation of the ketone in the presence of aldehydes or alkenes generates spirocyclic oxetanes through excitation of the carbonyl to its triplet state, followed by addition to the π-bond of the partner.^[40] This reaction highlights the synthetic utility of cyclohexanone in constructing strained four-membered rings for natural product synthesis.^[41]

Illicit use

Cyclohexanone serves as a key precursor in the illicit production of phencyclidine (PCP), a Schedule II controlled substance classified as a dissociative anesthetic. In clandestine syntheses, cyclohexanone is converted to 1-piperidinocyclohexanecarbonitrile through reaction with piperidine and cyanide, followed by a Grignard reaction with phenylmagnesium bromide to yield PCP.^[42] This route has been documented in forensic analyses of seized laboratory materials since the 1970s, when PCP emerged as a street drug.^[43] Cyclohexanone is also employed as an intermediate in the synthesis of ketamine, another dissociative anesthetic, through processes involving bromination of derived cyclohexanone compounds and subsequent cyclization with o-chlorobenzonitrile or related reagents.^[44] These methods exploit cyclohexanone's availability as an industrial solvent and reagent, facilitating small-scale operations in hidden laboratories.^[45] In the United States, cyclohexanone falls under DEA monitoring as a chemical associated with PCP production and is included on the agency's Special Surveillance List to track potential diversions from legitimate commerce.^[46] Clandestine labs producing PCP or ketamine often rely on diverted industrial supplies, with detection complicated by cyclohexanone's volatile solvent properties, which produce a distinctive minty odor that operators may attempt to mask during production.^[47] Under the 1988 United Nations Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances, precursors like those used in PCP and ketamine synthesis are subject to international monitoring, though cyclohexanone itself is not listed in Tables I or II; the International Narcotics Control Board (INCB) reports occasional seizures linked to its diversion for illicit drug manufacture.^[45] For instance, in 2014, U.S. authorities seized 20 liters associated with PCP labs, indicating limited but persistent diversion from industrial sources estimated at less than 1% of global production in the 2010s.^[45]

Safety and environmental impact

Health hazards

Cyclohexanone primarily enters the human body through inhalation in occupational environments, where it is commonly used as a solvent, though skin absorption and ingestion are also possible routes of exposure. Acute exposure causes irritation to the eyes, skin, and respiratory tract, often manifesting as redness, burning sensations, and coughing upon contact or inhalation. Inhalation of vapors can lead to central nervous system effects such as dizziness, nausea, headache, and fatigue, with higher concentrations potentially causing unconsciousness or narcosis. Animal studies indicate moderate acute toxicity, with an oral LD₅₀ of 1,620 mg/kg in rats, a dermal LD₅₀ of 1,100 mg/kg in rabbits, and an inhalation LC₅₀ of 8,000 ppm (4 hours) in rats.^[5]^[48]^[49] Prolonged or repeated exposure to cyclohexanone is associated with potential neurotoxic effects such as headache and dizziness, as well as liver and kidney damage observed in animal studies at elevated doses. The International Agency for Research on Cancer (IARC) classifies cyclohexanone as Group 3, not classifiable as to its carcinogenicity to humans, with no clear evidence of carcinogenic potential in available data. Regarding reproductive toxicity, high-dose animal exposures have shown maternal and fetal toxicity without significant malformations, suggesting possible risks at extreme levels but limited human data. Occupational exposure is regulated to minimize these risks, with the American Conference of Governmental Industrial Hygienists (ACGIH) recommending a threshold limit value (TLV) of 20 ppm as an 8-hour time-weighted average and 50 ppm short-term exposure limit, with skin notation due to absorption concerns.^[48]^[50]^[51] For immediate management of exposure, first aid measures include flushing affected eyes with copious amounts of water for at least 15 minutes while holding eyelids open, and removing contaminated clothing followed by thorough skin washing; in cases of inhalation, move the individual to fresh air with adequate ventilation to disperse vapors and seek medical attention if symptoms persist.^[48]

Environmental considerations

Cyclohexanone is readily biodegradable in aquatic environments, achieving 83-96% degradation within 28 days according to OECD 301F manometric respirometry tests using activated sludge inoculum.^[52] This rapid biodegradation, combined with its half-life in water of approximately 3.1 days due to volatilization and low soil adsorption (log Koc = 1.82), indicates low persistence in soil and water systems.^[53] In air, it degrades primarily through reaction with photochemically produced hydroxyl radicals, with an estimated half-life of 1-2 days, and supplementary direct photolysis contributing a half-life of about 4.3 days.^[1] Bioaccumulation potential is minimal, as evidenced by its low octanol-water partition coefficient (log Kow = 0.81), which suggests negligible uptake in aquatic organisms.^[53] Aquatic toxicity of cyclohexanone is moderate, with 96-hour LC50 values for fish species such as fathead minnow (Pimephales promelas) ranging from 527 to 732 mg/L and golden orfe (Leuciscus idus) at 536-752 mg/L.^[53] For invertebrates, the 24-hour EC50 for Daphnia magna exceeds 800 mg/L, while algal growth inhibition (EC50 for Desmodesmus subspicatus) is reported above 100 mg/L in 72-hour tests, confirming it does not pose high risk to primary producers at environmentally relevant concentrations. These profiles support its classification as not toxic (T) under REACH criteria. As a volatile organic compound (VOC), cyclohexanone contributes to photochemical smog formation through reactions in the troposphere that generate ground-level ozone precursors.^[1] Its emissions are regulated under U.S. EPA VOC control rules for ozone non-attainment areas, requiring capture and control in industrial processes to limit atmospheric releases.^[54] Waste management for cyclohexanone involves absorption of spills using inert materials like vermiculite or sand, followed by containment and disposal as hazardous waste.^[48] Wastewater containing the compound is typically treated via biological processes in activated sludge systems, leveraging its ready biodegradability, or by incineration in facilities equipped with afterburners and scrubbers to ensure complete mineralization.^[55] Under the EU REACH regulation, cyclohexanone undergoes monitoring for potential persistent, bioaccumulative, and toxic (PBT) properties, but assessments conclude it meets none of these criteria due to its rapid degradation, low bioaccumulation, and moderate ecotoxicity.^[56] Global industrial releases, primarily from production and use in nylon manufacturing, are estimated in the range of thousands of tons annually and are subject to environmental reporting to mitigate broader ecological impacts.^[57]

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**Summary for Cyclohexanone:**
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This review will focus on the technical advantages and weaknesses of current tests concerning the technical setup, the inoculum characterization, and its ...
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Volatile Organic Compound Exemptions | US EPA
Jun 13, 2025 · Those VOC, determined to have low photochemical reactivity by approved test methods, may be excluded from the VOC definition for certain regulatory purposes.
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The 'Hazard classification and labelling' section shows the hazards of a substance based on the standardised system of statements and pictograms established ...Missing: acute LD50 LC50<|control11|><|separator|>