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Cyclohexanol

Cyclohexanol is a colorless, viscous liquid organic compound classified as a secondary alcohol, with the molecular formula C₆H₁₂O and a structure consisting of a six-carbon cyclohexane ring substituted by a single hydroxyl (-OH) group.^[1] It has a mild odor reminiscent of camphor and exists as a low-melting solid (melting point approximately 25 °C) or liquid just above room temperature, making it versatile for industrial applications.^[1] Key physical properties include a boiling point of 161 °C, a density of 0.962 g/mL at 20 °C, and limited solubility in water (about 4 g/100 mL at 20–30 °C), though it is miscible with common organic solvents such as ethanol, ether, and acetone.^[1] Chemically, it is flammable with a flash point around 63–68 °C and can react vigorously with strong oxidizers, while in the environment, it degrades via hydroxyl radical reactions in air (half-life ~22 hours) and is biodegradable under aerobic conditions.^[1] Cyclohexanol is primarily produced industrially through the hydrogenation of phenol, the partial oxidation of cyclohexane, or the acid-catalyzed hydration of cyclohexene, with the cyclohexane oxidation route being prominent due to its integration with nylon manufacturing processes.^[1] It serves as a crucial intermediate in the synthesis of adipic acid and caprolactam, the monomers for nylon-6,6 and nylon-6 polymers, respectively, accounting for a significant portion of global production.^[1] Additional uses include acting as a solvent for lacquers, varnishes, and resins; a stabilizer in soaps and detergents; and a component in germicides, plastics, and rubber additives.^[1] From a safety perspective, cyclohexanol is an irritant to the skin, eyes, and respiratory tract, and it poses hazards if inhaled or ingested, with occupational exposure limits set at 50 ppm (TLV) for an 8-hour workday; it is handled under controlled conditions in industrial settings to mitigate risks.^[1]

Structure and Properties

Structure

Cyclohexanol has the molecular formula C_6H_{12}O and consists of a six-membered cyclohexane ring with a single hydroxyl group attached to one carbon atom, typically depicted in its preferred chair conformation with the OH group in the equatorial position.^[1]^[2] The preferred IUPAC name is cyclohexanol, with common synonyms including hexahydrophenol and cyclohexyl alcohol.^[1] It is identified by the CAS Registry Number 108-93-0, the InChI key HPXRVTGHNJAIIH-UHFFFAOYSA-N, and the EC number 203-630-6.^[1]^[2] In solution or the gas phase, cyclohexanol predominantly adopts the chair conformation of the cyclohexane ring, where the hydroxyl substituent occupies the equatorial position to minimize 1,3-diaxial steric interactions with axial hydrogens; the axial conformer is higher in energy by approximately 0.87 kcal/mol, as quantified by the conformational free energy (A-value) for the OH group.^[3]^[4] This equatorial preference is primarily steric in origin, though intramolecular hydrogen bonding between the OH group and the ring is negligible in the isolated molecule, with intermolecular hydrogen bonding becoming significant in condensed phases.^[5]^[6] In the solid state, cyclohexanol displays polymorphism with at least two crystalline forms: a low-temperature ordered phase (form II) that crystallizes in a tetragonal structure (space group P\bar{4}2_1c), and a high-temperature plastic crystal phase (phase I) with a face-centered cubic lattice where molecules exhibit orientational disorder and enhanced rotational mobility.^[7] The transition from the plastic phase I to form II occurs around 265 K, highlighting the role of hydrogen bonding in stabilizing the ordered low-temperature structure.

Physical Properties

Cyclohexanol is a colorless, viscous liquid at room temperature, exhibiting a camphor-like odor.^[8] It is hygroscopic, readily absorbing moisture from the air, which contributes to its handling characteristics.^[8] The compound has a molar mass of 100.16 g/mol.^[8] Under standard conditions, cyclohexanol has a density of 0.947 g/mL at 20°C.^[8] Its melting point is 23°C, allowing it to exist as a low-melting solid or liquid depending on slight temperature variations, while the boiling point is 161.84°C at 1 atm.^[8] The viscosity is approximately 4.6 mPa·s at 25°C, reflecting its somewhat syrupy consistency.^[8] Cyclohexanol shows limited solubility in water, with about 4 g dissolving in 100 mL at 20°C, but it is miscible with common organic solvents such as ethanol, diethyl ether, and benzene.^[9]^[8] The refractive index is 1.4641 (n<sup>20</sup><sub>D</sub>) at 20°C.^[8] Additional thermodynamic properties include a flash point of 68°C (154°F) and a vapor pressure of 0.657 mmHg at 25°C, indicating moderate volatility.^[8]

Synthesis and Production

Industrial Production

The primary industrial production method for cyclohexanol is the partial oxidation of cyclohexane with air or oxygen in the liquid phase, catalyzed by soluble cobalt or manganese salts such as cobalt naphthenate or manganese acetate, at temperatures of 125–165 °C and pressures of 8–15 bar. This autoxidation process proceeds via a free-radical mechanism, yielding a crude mixture known as KA oil, which contains approximately 85–90% cyclohexane, 4–6% cyclohexanol, 3–5% cyclohexanone, and minor byproducts like cyclohexyl hydroperoxide. The KA oil is then subjected to distillation to separate and purify the cyclohexanol and cyclohexanone components. The simplified reaction equation is:

\text{C}_6\text{H}_{12} + \frac{1}{2}\text{O}_2 \rightarrow \text{C}_6\text{H}_{11}\text{OH}

This method accounts for the majority of global production due to the availability of cheap cyclohexane feedstock derived from benzene.^[10] Another major route is the acid-catalyzed direct hydration of cyclohexene, employing solid acid catalysts such as zeolite or resin-based sulfonic acids in a water-cyclohexene mixture at 80–150 °C and 20–50 bar, achieving conversions of 10–20% per pass due to thermodynamic equilibrium limitations favoring the alkene. The process involves Markovnikov addition, with the carbocation intermediate leading to the secondary alcohol; unreacted cyclohexene is recycled. This method, pioneered by Asahi Kasei, contributes a smaller share (around 5–10% globally) but offers high selectivity (>95%) and is integrated with propylene oxide production via chlorohydrin processes that generate cyclohexene as a byproduct. The reaction equation is:

\text{C}_6\text{H}_{10} + \text{H}_2\text{O} \rightarrow \text{C}_6\text{H}_{11}\text{OH}

^[11] An alternative route involves the catalytic hydrogenation of phenol, typically using nickel or palladium catalysts supported on carriers like silica or alumina. This process can produce cyclohexanone as the primary product with high selectivity (>95%), but direct production of cyclohexanol is achieved under adjusted conditions with catalysts like Ru or Ni at high pressures (up to 200 bar) and temperatures of 150–250 °C. It is employed in regions with integrated phenol production facilities, such as from cumene oxidation byproducts. The reaction equation for cyclohexanol is:

\text{C}_6\text{H}_5\text{OH} + 3\text{H}_2 \rightarrow \text{C}_6\text{H}_{11}\text{OH}

While less common than the oxidation route for cyclohexanol specifically, it offers advantages where phenol is abundant.^[12] Global cyclohexanol production is integrated with cyclohexanone output, with KA oil capacity exceeding 8 million metric tons annually as of 2024, of which cyclohexanol comprises roughly 3.5–4.5 million tons; key producers include Shell Chemicals, ExxonMobil Chemical, INEOS, Asahi Kasei, and BASF, primarily in Asia-Pacific and Europe. Recent advancements focus on greener processes, including bio-based feedstocks like lignocellulosic biomass-derived phenols for hydrogenation and heterogeneous catalysts (e.g., supported metal oxides) to enhance efficiency and reduce waste in oxidation steps. The cyclohexanol market was valued at approximately USD 1.5 billion in 2023 and is projected to reach USD 2.4 billion by 2031, growing at a CAGR of 5%.^[13]

Laboratory Synthesis

One common laboratory method for synthesizing cyclohexanol involves the reduction of cyclohexanone using sodium borohydride (NaBH₄) as the reducing agent in protic solvents such as methanol or ethanol. This reaction is typically conducted under mild conditions, with the ketone dissolved in the solvent at an initial concentration of approximately 0.25 M, followed by portionwise addition of NaBH₄ (about 0.41 molar equivalents) at room temperature or 0°C to control exothermicity, and stirring for 10–30 minutes until completion, as monitored by thin-layer chromatography. The simplified reaction equation is:

\text{C}_6\text{H}_{10}\text{O} + \text{NaBH}_4 \rightarrow \text{C}_6\text{H}_{11}\text{OH} + \text{byproducts}

After quenching with water or dilute acid, the product is extracted with diethyl ether, dried, and isolated, often yielding cyclohexanol in high purity after purification, though specific yields for this substrate vary around 80–95% based on analogous ketone reductions.^[14] Another bench-scale approach is the catalytic hydrogenation of cyclohexanone using hydrogen gas (H₂) in the presence of heterogeneous catalysts like Raney nickel or platinum on carbon (Pt/C). These reactions occur under mild conditions, typically at 25–50°C and atmospheric or slightly elevated pressure (1–5 atm) in solvents such as ethanol or acetic acid, with catalyst loadings of 1–5 wt% relative to the substrate, proceeding to near-quantitative conversion over 1–4 hours. Raney nickel is particularly favored in laboratory settings for its activity and ease of handling, though Pt/C offers higher selectivity for the alcohol product.^[15] An alternative, though rarely employed in laboratories due to low yields (typically <50%) and side reactions like polymerization from the carbocation intermediate, is the acid-catalyzed hydration of cyclohexene with sulfuric acid. In this procedure, cyclohexene is added to 60–70% H₂SO₄ and stirred vigorously at room temperature for 1 hour, followed by dilution with water, distillation to remove unreacted alkene, and extraction of the product with diethyl ether; the reaction follows Markovnikov addition but is limited by equilibrium.^[16] Regardless of the synthesis route, cyclohexanol is commonly purified by distillation under reduced pressure (e.g., 10–20 mmHg) to lower the boiling point to 60–70°C and prevent thermal decomposition, achieving purities exceeding 95% after a single pass in a simple distillation setup.^[17]^[18]

Chemical Reactions

Oxidation and Reduction

Cyclohexanol undergoes oxidation to cyclohexanone, a key carbonyl compound, primarily through the action of chromium-based reagents. The Jones oxidation, utilizing chromic acid generated from chromium trioxide in aqueous sulfuric acid and acetone, efficiently converts this secondary alcohol to the corresponding ketone by forming a chromate ester intermediate that decomposes to eliminate water. This method, introduced by Bowden, Heilbron, Jones, and Weedon in 1946, provides high yields under mild conditions and is widely used in laboratory settings. The reaction can be represented as:

\ce{C6H11OH ->[CrO3, H2SO4, acetone] C6H10O + H2O}

A milder alternative is pyridinium chlorochromate (PCC), prepared from pyridine, hydrochloric acid, and chromium trioxide, which selectively oxidizes secondary alcohols to ketones in aprotic solvents like dichloromethane, avoiding over-oxidation issues common with aqueous media. Developed by Corey and Suggs in 1975, PCC offers precise control for sensitive substrates and has become a staple in synthetic organic chemistry. Further oxidation of cyclohexanol, typically via the intermediate cyclohexanone, yields adipic acid through ring cleavage and multiple dehydrogenations. Nitric acid serves as a traditional oxidant in this process, promoting oxidative cleavage under heating to produce the dicarboxylic acid in good yields, as detailed in classical organic syntheses. The overall stoichiometry from cyclohexanol is:

\ce{C6H11OH + 4[O] ->[HNO3] HOOC(CH2)4COOH + H2O}

^[19] Catalytic aerobic oxidation with molecular oxygen and transition metal catalysts, such as cobalt-manganese systems, represents a more sustainable approach, reducing reliance on stoichiometric oxidants and minimizing waste. This cyclohexanone intermediate plays a pivotal role in nylon-6,6 production upon its conversion to adipic acid.^[20] Direct reduction of cyclohexanol to cyclohexane is uncommon due to the strength of the C-O bond, but it can be achieved via a two-step dehydration-hydrogenation sequence. Acid-catalyzed dehydration first forms cyclohexene by elimination of water, followed by hydrogenation using hydrogen gas and metal catalysts like rhodium or platinum. For substituted cyclohexanols, such reduction sequences can produce cis or trans isomers in the resulting cyclohexane derivatives, influenced by the original substituent stereochemistry and catalyst selectivity; however, unsubstituted cyclohexanol yields only the symmetric cyclohexane without stereoisomeric complications.

Esterification and Other Transformations

Cyclohexanol, as a secondary alcohol, readily undergoes esterification reactions with carboxylic acids or their anhydrides in the presence of acid catalysts such as sulfuric acid to produce cyclohexyl esters. This equilibrium reaction involves the nucleophilic attack of the alcohol oxygen on the protonated carbonyl group of the carboxylic acid, leading to the formation of water as a byproduct. The general equation for this Fischer esterification is:

\ce{C6H11OH + RCOOH ⇌[H2SO4] C6H11OCOR + H2O}

where R represents an alkyl or aryl group. For instance, reaction with acetic acid yields cyclohexyl acetate, a common solvent and flavoring agent. These cyclohexyl esters, including butyl cyclohexyl phthalate, serve as effective plasticizers in polymers like polyvinyl chloride due to their compatibility and low volatility.^[21] Another key transformation is the dehydration of cyclohexanol to form cyclohexene, an elimination reaction that removes the hydroxyl group and a hydrogen from an adjacent carbon. This is typically accomplished using concentrated sulfuric acid at elevated temperatures (160–180 °C) or phosphorus pentoxide as a dehydrating agent, proceeding via a carbocation intermediate in an E1 mechanism. The reaction equation is:

\ce{C6H11OH ->[conc. H2SO4][\Delta] C6H10 + H2O}

This process is widely used in laboratory syntheses to prepare alkenes from secondary alcohols, with high yields achievable under controlled conditions to minimize side products like dienes.^[22]^[23] Cyclohexanol can also participate in ether formation through the Williamson synthesis, a nucleophilic substitution where the deprotonated alkoxide ion acts as a nucleophile. The alcohol is first converted to its alkoxide using a strong base such as sodium hydride (NaH) or sodium amide (NaNH₂), followed by reaction with a primary alkyl halide (R–X) in an SN2 manner to yield the unsymmetrical ether C₆H₁₁OR. This method is preferred for secondary alkoxides like cyclohexoxide to avoid elimination side reactions, and examples include the synthesis of cyclohexyl ethyl ether from ethyl bromide. The overall process highlights the versatility of alkoxides in building C–O–C linkages.^[24]/18%3A_Ethers_and_Epoxides_Thiols_and_Sulfides/18.02%3A_Preparing_Ethers) Halogenation of cyclohexanol provides a route to alkyl halides, specifically chlorocyclohexane, via reaction with hydrochloric acid (HCl) catalyzed by zinc chloride (ZnCl₂). ZnCl₂ acts as a Lewis acid to enhance the leaving group ability of the protonated hydroxyl, facilitating an SN1 mechanism involving a secondary carbocation intermediate that is then captured by chloride ion. The equation is:

\ce{C6H11OH + HCl ->[ZnCl2] C6H11Cl + H2O}

This transformation is efficient for secondary alcohols, often conducted at room temperature or with mild heating, and is a standard laboratory method for preparing chlorocyclohexane as a synthetic intermediate.Complete_and_Semesters_I_and_II/Map%3A_Organic_Chemistry(Wade)/14%3A_Reactions_of_Alcohols/14.01%3A_Reactions_of_Alcohols_with_Hydrohalic_Acids)^[25]

Applications

Industrial Applications

Cyclohexanol serves as a key precursor in the polymer industry, primarily through its oxidation to adipic acid, which is essential for producing nylon-6,6. This process involves the conversion of cyclohexanol (often as part of KA oil, a mixture with cyclohexanone) via nitric acid oxidation, yielding adipic acid that reacts with hexamethylenediamine to form the polyamide. Additionally, cyclohexanol contributes to caprolactam production for nylon-6 by first dehydrogenating to cyclohexanone, followed by oximation and Beckmann rearrangement. Global annual consumption of cyclohexanol for these polymer applications is several million tons, underscoring its economic significance in textiles, automotive parts, and engineering plastics.^[26]^[27]^[28] In the production of plasticizers, cyclohexanol undergoes esterification with phthalic anhydride to form dicyclohexyl phthalate (DCHP) or with adipic acid to yield dicyclohexyl adipate, both used to enhance flexibility and stabilization in polyvinyl chloride (PVC) formulations. These esters improve the durability of PVC in applications such as flooring, cables, and coatings, where they act as non-migrating plasticizers due to their high molecular weight and compatibility. This sector accounts for a notable portion of cyclohexanol's industrial demand, supporting the global PVC market's growth.^[29] Cyclohexanol functions as a versatile solvent in the coatings industry, dissolving alkyd, phenolic, and cellulosic resins for use in paints, varnishes, and lacquers, where it aids in viscosity control and film formation. It also serves as a homogenizer and stabilizer in soap and detergent emulsions, ensuring uniform blending of surfactants and oils during formulation. In synthetic rubber processing, cyclohexanol acts as a solvent for rubber solutions and an intermediate in adipate-based extenders that improve elasticity. For textile processing, it dissolves dyes and facilitates even application on fibers, enhancing color fastness. Leading producers as of 2025, including BASF, Asahi Kasei, and Invista, dominate these applications through integrated supply chains and innovation in sustainable production methods.^[30]^[31]^[32]^[33]

Other Applications

Cyclohexanol serves as a key intermediate in the pharmaceutical industry for synthesizing analgesics, such as tramadol, a cyclohexanol derivative that acts as a mu-opioid agonist for managing moderate to severe pain.^[34] Derivatives like 4-isopropylcyclohexanol have demonstrated potential analgesic effects by inhibiting TRP channels and ANO1, offering a basis for novel pain relief agents.^[35] Additionally, cyclohexanol contributes to the production of antiseptic formulations, including medicated soaps and disinfectants where it enhances stability and antimicrobial properties.^[36] In the fragrance and flavor sectors, cyclohexanol imparts a camphor-like odor, making it suitable for use in perfumes and as a mimic for essential oils in aromatic compositions.^[1] Its subtle camphoreous profile allows occasional incorporation as a masking agent or base note in sophisticated fragrance blends.^[37] Cyclohexanol functions as a stabilizer in fuels, particularly in hydrous ethanol-gasoline blends, where it improves phase stability and reduces separation issues.^[38] It also serves as an additive in lubricants to enhance performance, though at lower volumes compared to its fuel applications.^[39] In cosmetics and cleaning agents, cyclohexanol acts as an emulsifier and stabilizer, aiding in the formulation of stable emulsions for soaps, detergents, and personal care products.^[36] As of 2025, bio-based cyclohexanol, produced from renewable feedstocks like lignin-derived precursors, is gaining traction as a sustainable solvent in green chemistry processes, including extraction and waste management applications that prioritize reduced environmental impact.^[40] This shift supports broader adoption in eco-friendly chemical syntheses, leveraging industrial production scalability for niche sustainability initiatives.

Safety and Environmental Considerations

Health and Toxicity

Cyclohexanol exhibits moderate acute toxicity through various exposure routes. The oral LD50 in rats is 2060 mg/kg, indicating low to moderate toxicity upon ingestion.^[1] Dermal exposure shows moderate acute toxicity, with an LD50 of 501–794 mg/kg in rabbits. Inhalation toxicity is also moderate, with an LC50 greater than 6.5 mg/L over 1 hour in rats.^[1] Upon contact, cyclohexanol acts as a skin and eye irritant, causing redness, dryness, cracking, and pain due to its defatting action on tissues, which can lead to dermatitis with prolonged exposure.^[1] Inhalation of vapors irritates the respiratory tract, potentially resulting in coughing, sore throat, and in severe cases, pulmonary edema; its narcotic properties at high concentrations may induce dizziness, drowsiness, and central nervous system depression.^[1] Its relatively high vapor pressure contributes to inhalation risks in poorly ventilated areas.^[1] Chronic exposure to cyclohexanol may cause liver and kidney damage, as observed in animal studies involving repeated high doses.^[1] Limited data exist on carcinogenicity, and it is not classified as a human carcinogen by major agencies such as IARC or NTP, though older studies suggest possible co-carcinogenic effects in specific contexts.^[1] As a combustible liquid, cyclohexanol has a flash point of 68°C and forms explosive mixtures with air in the range of 1.2–12.2% by volume, posing fire and explosion hazards that exacerbate health risks during handling.^[1]^[41] Occupational exposure limits include an OSHA PEL of 50 ppm (200 mg/m³) as an 8-hour time-weighted average (TWA) and a NIOSH recommended exposure limit (REL) of 50 ppm (200 mg/m³) TWA with skin notation; the NIOSH IDLH is 400 ppm.^[42] Personal protective equipment (PPE) recommendations include chemical-resistant gloves, eye protection, and respirators with organic vapor cartridges for concentrations up to 400 ppm.^[1] First aid measures involve moving affected individuals to fresh air for inhalation exposure, rinsing skin or eyes with water for at least 15 minutes for contact, and seeking immediate medical attention for ingestion, avoiding induced vomiting.^[1]

Environmental Impact and Regulations

Cyclohexanol is released into the environment primarily during its industrial production, with U.S. Toxic Release Inventory (TRI) data indicating total releases of approximately 3.9 million pounds in 1999, predominantly to air and surface water bodies.^[43] Updated estimates reflect lower release volumes due to enhanced production efficiencies and waste management practices; for example, total releases were approximately 1.2 million pounds in 2022, with most on-site.^[44] Specific recent TRI figures show continued monitoring of on-site and off-site disposals.^[44] In the environment, cyclohexanol exhibits moderate biodegradability, with OECD 301C tests demonstrating 94-99% degradation within 28 days under aerobic conditions using activated sludge inoculum, classifying it as readily biodegradable. Its low octanol-water partition coefficient (log Kow = 1.23) indicates limited bioaccumulation potential in aquatic organisms, as values below 3 typically suggest negligible biomagnification risk.^[1] Due to its moderate water solubility and low soil adsorption (estimated Koc = 11), cyclohexanol has the potential to contaminate groundwater if released to soil or water.^[1] Ecotoxicity assessments reveal moderate impacts on aquatic life, with 96-hour LC50 values for fish such as fathead minnows (Pimephales promelas) ranging from 631 to 704 mg/L, indicating harmful effects at elevated concentrations primarily through biochemical oxygen demand that can deplete dissolved oxygen in water bodies.^[45] Cyclohexanol is listed as an active substance on the U.S. Toxic Substances Control Act (TSCA) inventory, requiring reporting for manufacturing, processing, and import activities exceeding certain thresholds.^[1] In the European Union, it is registered under the REACH regulation (EC 1907/2006), mandating safety data submissions and risk assessments for environmental exposures.^[46] It remains subject to monitoring as a volatile organic compound (VOC) contributor to air emissions under TSCA and other regulations.^[47]

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Mar 1, 2025 · With a substantial increase in global demand in recent years, cyclohexanones command an annual market of approximately 6.6 million tons ...Missing: capacity | Show results with:capacity
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Cyclohexanol - IDLH | NIOSH - CDC
The chosen IDLH, therefore, has been estimated from the rabbit oral LD50 of 2.2 to 2.6 g/kg [Treon et al. 1943 cited in Browning 1965].Missing: dermal LD50
[44]
[PDF] Cyclohexanol - OEHHA
Oct 1, 2001 · Cyclohexanol was added to the Proposition 65 list of chemicals known to the state to cause reproductive toxicity under the authoritative bodies ...
[45]
Toxics Release Inventory (TRI) Program | US EPA
Oct 1, 2025 · The Toxics Release Inventory tracks the management of certain toxic chemicals that may pose a threat to human health and the environment.TRI Toolbox · Reporting for TRI Facilities · What is the Toxics · TRI Data in ActionMissing: cyclohexanol | Show results with:cyclohexanol
[46]
[PDF] 108-93-0.pdf - Fragrance Material Safety Assessment Center
Feb 8, 2021 · Data on cyclohexanol provide a calculated margin of exposure (MOE) >100 for the repeated dose toxicity and reproductive toxicity endpoints. Data ...Missing: releases | Show results with:releases
[47]
Substance Information - ECHA
### Summary of 1,2-Ethanedisulfonic Acid (EC 203-732-0, CAS 110-04-3)
[48]
EPA to Provide Extension for Reporting of Health and Safety Data ...
Jun 5, 2025 · The rule announced today will extend the reporting deadlines for all 16 chemicals to May 22, 2026. This extension will provide EPA additional ...