Cyclohexanone (also known as Anone, Ketohexamethylene, Pimelic ketone) is a cyclic aliphatic ketone with the chemical formula C₆H₁₀O (structural formula: (CH₂)₅CO) and a molecular weight of 98.14. It is a clear, colorless to pale yellow liquid at room temperature with a characteristic peppermint or acetone-like irritating odor. As a critical industrial chemical and high-performance solvent, it is primarily produced via catalytic oxidation of cyclohexane or partial hydrogenation of phenol. Featuring a polar carbonyl (C=O) group within a nonpolar six-membered carbon ring, it exhibits exceptional solvency for both polar and nonpolar substances, making it indispensable in nylon production, chemical synthesis, and high-performance coatings industries.
Cyclohexanone is a high-performance industrial ketone solvent and key chemical intermediate with molecular formula C6H10O and CAS No. 108-94-1.
It is widely used in the production of caprolactam, adipic acid, nylon 6, nylon 66, paints, coatings, adhesives, and synthetic resins.
Cyclohexanone is a clear to slightly yellow liquid with excellent solvency and stable chemical performance.
Chemical Properties and Performance Characteristics
Chemical Properties
Stability: Cyclohexanone is chemically stable under normal temperature and pressure but is reactive with strong oxidizing agents (e.g., nitric acid, potassium permanganate), typically oxidizing to adipic acid. It undergoes classic ketone reactions, including condensation, addition, reduction, and halogenation. It is corrosive to certain plastics and coatings but generally non-corrosive to metals. Prolonged storage in air may lead to the formation of trace peroxides, and it is incompatible with strong reducers. It does not undergo polymerization under normal conditions.
Thermal Stability: Its melting point is -47 °C, and its boiling point is 155.6 °C (155.7 °C at 760 mmHg). It is a liquid at ambient temperature with moderate volatility. It remains stable at processing temperatures below its boiling point; however, high temperatures or contact with catalysts may cause decomposition. Its relatively high boiling point makes it a valuable high-boiling-point solvent, suitable for applications requiring slow evaporation to ensure film formation.
Toxicity and Irritation: Cyclohexanone is moderately toxic and a severe irritant. Inhalation of its vapors irritates the respiratory tract, eyes, and skin, which may cause headache, dizziness, nausea, and central nervous system depression. High concentrations of vapors can be anesthetic and may cause pulmonary edema. Oral ingestion is harmful and can lead to gastrointestinal discomfort and damage to liver and kidney functions. Prolonged skin contact causes defatting, dryness, itching, and may lead to dermatitis. It is classified as a Group 3 carcinogen (not classifiable as to its carcinogenicity to humans) by IARC, and the occupational exposure limit is TLV-TWA 25 ppm (100 mg/m³, skin) according to ACGIH.
Combustibility: Cyclohexanone is a flammable liquid. Its closed-cup flash point is approximately 44 °C (43-46.7 °C depending on specifications), and its autoignition temperature is 420 °C. Its vapors form explosive mixtures with air within the range of 1.1%–9.4% by volume. Vapors are heavier than air (vapor density 3.38 vs air = 1) and can travel to ignition sources, posing fire and explosion risks in poorly ventilated areas, so it must be stored away from open flames and high-temperature heat sources. Its combustion products are carbon monoxide and carbon dioxide.
Performance Characteristics
Physical Appearance: It is a colorless to pale yellow, mobile liquid with a characteristic peppermint/acetone-like irritating odor. Pure material is clear; industrial grades may exhibit a pale yellow hue due to minor impurities. It is free of suspended matter and remains stable in appearance under normal storage conditions, with no obvious color change unless contaminated.
Solubility: It is slightly soluble in water (150 g/L at 10 °C, ~50 g/L at 30 °C) and miscible with almost all common organic solvents, including alcohols, ethers, ketones, esters, benzene, and chlorinated hydrocarbons. This dual solubility makes it an excellent mutual solvent for water-oil systems and a powerful coupling solvent, widely used in formulations that require compatibility between polar and nonpolar components. It can effectively dissolve various resins, waxes, oils, and organic compounds.
Physical Parameters: Its density is 0.9478 g/cm³ (20 °C, ~0.95 g/cm³ at 20 °C), vapor pressure is 0.7 kPa (20 °C, 1.33 kPa at 38.7 °C), refractive index is 1.4507 (20 °C, 1.453), and viscosity is 2.2 mPa·s (25 °C). Its moderate evaporation rate balances coating flow and drying, making it particularly suitable for applications where a slow-evaporating solvent is needed to ensure proper film formation and improve product performance.
Solvency: Due to its polar carbonyl group and nonpolar six-membered carbon ring, cyclohexanone exhibits strong solvency for a wide range of substances, including nitrocellulose, acrylics, epoxies, polyurethanes, vinyl resins, and other film-forming polymers. This property makes it a key solvent in coatings, inks, and adhesives, as it can effectively dissolve and disperse various raw materials, improving product quality and application performance.
Technical Data Sheet (Cyclohexanone, CAS 108-94-1)
Applications
Cyclohexanone (CAS 108-94-1) is a high-priority industrial chemical, serving as both a primary chemical intermediate and a high-performance solvent across numerous key industries, valued for its excellent solvency, moderate volatility, and high reactivity. Its main applications are as follows:
Nylon & Synthetic Fiber Production
The primary and most critical application (≈95% of global demand) is as the foundational precursor for Nylon manufacturing. It is oxidized to produce adipic acid (a monomer for Nylon 6,6) and converted to cyclohexanone oxime, which undergoes Beckmann rearrangement to form caprolactam (the monomer for Nylon 6). These are the essential building blocks for polyamide fibers and engineering plastics, widely used in textiles, automotive parts, and electronic components.
Coatings & Inks Industry
It is a premier industrial solvent for paints, varnishes, lacquers, and printing inks. It exhibits superior dissolving power for nitrocellulose, acrylics, epoxies, polyurethanes, vinyl resins, and other film-forming polymers. It improves flow, leveling, gloss, and adhesion of coating films, making it ideal for wood finishes, automotive coatings, metal primers, and high-quality gravure/flexographic inks. Its moderate evaporation rate helps reduce film defects and improve product quality.
Adhesives & Polymers
It is used as a solvent and processing aid in the production of hot-melt and solvent-based adhesives, synthetic rubber, and polymer solutions. It aids in polymer processing, adjusts viscosity, improves open time (the time available to bond materials after application), and enhances bond strength, making it suitable for a wide range of bonding applications in construction, packaging, and industrial manufacturing. It also acts as a chain transfer agent or regulator in some polymer polymerization reactions to control polymer molecular weight and performance.
Pharmaceuticals, Agrochemicals & Fine Chemicals
In the pharmaceutical industry, it serves as an extraction and synthesis solvent in the production of antibiotics, hormones, vitamins, and analgesics (e.g., ibuprofen intermediates). In the agrochemical field, it is used as an intermediate for synthesizing herbicides and insecticides, and as an auxiliary agent to improve pesticide adhesion and permeability. It is also a versatile intermediate in organic synthesis, used in the production of spices, dyes, and other fine chemicals. Additionally, it is used as an extractant for the separation and purification of rare metals such as uranium, thorium, cobalt, and titanium.
Other Fields
Cyclohexanone is used for industrial cleaning and degreasing, particularly for removing oil, wax, and resin residues from metal surfaces, precision instruments, and electronic components (e.g., PCB photoresist stripping). It is also a leather finishing agent, a textile processing assistant (to improve fiber softness and dye uptake), and a polishing agent. In laboratories, it is a common solvent for extraction, chromatography, and organic synthesis experiments. It can also be used as an additive in lithium battery electrolytes to optimize battery performance and cycle life.
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