Product
Cyclohexanone
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Cyclohexanone is a colorless clear liquid with an earthy smell; its impure product is pale yellow. It is miscible with several other solvents. Easily soluble in ethanol and ether. The lower limit of exposure is 1.1%, and the upper limit of exposure is 9.4%. Cyclohexanone may be incompatible with oxidizing agents and nitric acid.
Cyclohexanone is mainly used in industry, up to 96%, as a chemical intermediate in the production of nylon 6 and 66. Oxidation or conversion of cyclohexanone produces adipate and caprolactam, two immediate precursors of the respective nylons. Cyclohexanone is also used as a solvent in a variety of products, including paints, varnishes and resins. It has not been found to occur in natural processes.
| chemical properties | Cyclohexanone is a colorless clear liquid with an earthy smell; its impure product is pale yellow. It is miscible with several other solvents. Soluble in ethanol, ether. The lower limit of exposure is 1.1%, and the upper limit of exposure is 9.4%. Cyclohexanone may be incompatible with oxidizing agents and nitric acid. Cyclohexanone is mainly used in industry, up to 96%, as a chemical intermediate in the production of nylon 6 and 66. Oxidation or conversion of cyclohexanone produces adipic acid and caprolactam, two direct precursors to their respective nylons. Cyclohexanone is also used as a solvent in a variety of products, including paints, varnishes and resins. It has not been found to occur in natural processes. |
| application | In the production of nylon intermediates (adipic acid and caprolactam), cyclohexanone is mainly consumed individually or as a mixture. About 4% is consumed in markets other than nylon, such as solvents for paints, dyes and pesticides. Cyclohexanone is also used in the manufacture of pharmaceuticals, films, soaps and coatings. Fibrant is one of the largest producers of cyclohexanone, a raw material used in the production of caprolactam. |
| use | Cyclohexanone is an important chemical raw material and the main intermediate for the manufacture of nylon, caprolactam and adipic acid. It is also an important industrial solvent, for example in paints, especially those containing nitrocellulose, vinyl chloride polymers and their copolymers, or methacrylate polymer paints. It is used as an excellent solvent for organic phosphorus insecticides and other pesticides. Used as a solvent for dyes, a viscous solvent for piston aviation lubricants, and a solvent for grease, wax and rubber. It is also used as a leveling agent for silk dyeing and fading; a degreasing agent for metal polishing; a wood stain; and also used for cyclohexanone stripping, stain removal and spot removal. The condensation reaction between cyclohexanone and cyanoacetic acid produces cyclohexylidene acetic acid, which is eliminated and decarboxylated to obtain cyclohexene acetonitrile, and finally hydrogenated to obtain cyclohexene ethylamine [3399-73-3]. Cyclohexylethylamine is an intermediate for some drugs. |
| Production Method | In the 1940s, the industrial production of cyclohexanone mainly used the hydrogenation of phenol to generate cyclohexanol, and then dehydrogenated to obtain cyclohexanone. In the 1960s, with the development of the petrochemical industry, the cyclohexane oxidation production method gradually occupied a dominant position. In 1967, the one-step hydrogenation method of phenol developed by the Dutch National Mining Company (DSM) was industrialized. The production process of this method is short, the product quality is good, and the yield is high, but phenol and catalyst raw materials are expensive, so most of the industry still adopts the cyclohexane oxidation method. 1. The phenol method uses nickel as a catalyst; first hydrogenates phenol to obtain cyclohexanol, and then uses zinc as a catalyst to dehydrogenate cyclohexanone. 2. The cyclohexane oxidation method uses cyclohexane as the raw material; firstly, the catalyst-free conditions are applied; the cyclohexyl hydroperoxide is oxidized with oxygen-enriched air, and then decomposed into cyclohexanol and cyclohexyl hydroperoxide in the presence of tert-butyl chromate catalyst. Mixtures of ketones, alcohols, and ketones. Further carry out a series of distillation and refining to obtain qualified products. Raw material consumption quota: cyclohexane (99.6%) 1040kg/t. 3. Benzene hydrogenation oxidation method; benzene is hydrogenated (using hydrogen) at 120-180°C in the presence of a nickel catalyst to generate cyclohexane; cyclohexane undergoes oxidation reaction with air at 150-160°C and 0.908MPa to obtain cyclohexane Mixture of hexanol and cyclohexanone. They are separated to obtain the product cyclohexanone. Cyclohexanol is dehydrogenated at 350-400°C in the presence of zinc-calcium catalyst to form cyclohexanone. Raw material consumption quota: benzene (99.5%) 1144kg/t, hydrogen (97.0%) 1108kg/t, caustic soda (42.0%) 230kg/t. |
| describe | Cyclohexanone, a colorless liquid, is a cyclic ketone. It is an important component in the synthesis of many organic compounds. Most of the cyclohexanone synthesized is used as an intermediate in nylon synthesis. Cyclohexanone, used as a polyvinyl chloride (PVC) solvent, caused contact dermatitis in a woman who manufactured PVC liquid treatment bags. Cyclohexanone may not cross-react with cyclohexanone resin. Cyclohexanone-derived resins used in paints and varnishes cause contact dermatitis in painters.  |
| chemical properties | Cyclohexanone is a watery white to slightly yellow liquid with a mint-like or acetone-like odor. The odor threshold in the air is 0.12 - 0.24 ppm. |
| physical properties | Transparent, colorless to light yellow oily liquid with mint-like odor. The experimentally determined threshold concentration for detection and identification of odorants is the same: 480 μg/m 3 (120 ppm v ) (Hellman and Small, 1974). |
| occur | Reported to exist in cistus. |
| use | Industrial solvent for cellulose acetate resin, vinyl resin, rubber, wax; PVC solvent sealant; in the printing industry; coating solvent in the production of audio-visual products |
| use | Cyclohexanone is used as an industrial solvent and paint stripper. It is the precursor of nylon 6,6 as well as nylon 6 and cyclohexanone oxime, which rearranges to produce caprolactam. Additionally, it is used as a chemical reaction medium, adhesive, sealant and agricultural product. |
| use | Cyclohexanone is used in the production of adipic acid, which is used in the manufacture of nylon; in the preparation of cyclohexanone resin; and as a solvent for nitrocellulose, cellulose acetate, resins, fats, waxes, shellac, rubber, and DDT. |
| definition | ChEBI: A cyclic ketone consisting of cyclohexane with a single oxo substituent. |
| synthetic references | Canadian Journal of Chemistry, 62, p. 1031, 1984 DOI: 10.1139/v84-171 Tetrahedron Letters, 25, p. 1031 3309, 1984 DOI: 10.1016/S0040-4039(01)81371-X |
| general instructions | Colorless to light yellow liquid with pleasant odor. Less dense than water. Flash point 111°F. Vapor is heavier than air. Used in the manufacture of nylon, as a medium for chemical reactions, and as a solvent. |
| air and water reaction | Flammable. Dissolved in water. |
| reactive profile | Cyclohexanone forms explosive peroxides with H2O2 and reacts violently with oxidizing substances (nitric acid). |
| health hazard | Inhalation of vapors from hot substances can cause anesthesia. The fluid may cause dermatitis. |
| health hazard | The toxicity of cyclohexanone was found to be low to moderate in the tested species. Exposure to vapors can cause eye and throat irritation. Splashes in the eyes may damage the cornea. Throat irritation may occur in humans exposed to airborne concentrations of 50 ppm for 3-5 minutes. Symptoms of chronic poisoning in animals after inhalation are liver and kidney damage and weight loss. However, its acute toxicity is below 3000 ppm. Symptoms in guinea pigs were lacrimation, salivation, decreased heart rate and anesthesia. Exposure to concentrations of 4000 ppm for 4-6 hours resulted in death in rats and guinea pigs. The compound has low oral toxicity. Ingestion may cause central nervous system narcosis and depression. It can be absorbed through the skin. LD50 value, dermal (rabbit): 1000 mg/kg LD50 value, intraperitoneal (rat): 1130 mg/kg. |
| fire hazard | Highly flammable: Easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may reach source of ignition and flash back. Most vapors are heavier than air. They spread along the ground and collect in low or tight areas (sewers, basements, water tanks). There is a vapor explosion hazard indoors, outdoors or in sewers. Runoff into sewers may create a fire or explosion hazard. Container may explode if heated. Many liquids are lighter than water. |
| Flammability and explosiveness | Flammable |
| chemical reactivity | Reactivity with water: Not relevant; Reactivity with common materials: Not relevant; Stability during transport: Stable; Neutralizer for acids and caustics: Not relevant; Polymerization: Not relevant; Polymerization inhibitors: Not relevant. |
| Contact allergens | Cyclohexanone was used as a polyvinyl chloride solvent to cause contact dermatitis in a woman producing PVC liquid therapy bags. Cyclohexanone may not cross-react with cyclohexanone resins. A cyclohexanone-derived resin used in paints and varnishes causes painters' contact dermatitis |
| Security overview | Suspected carcinogen. Moderately toxic by ingestion, inhalation, subcutaneous, intravenous and intraperitoneal routes. Severe irritation to skin and eyes. Systemic effects of inhalation: olfactory changes, conjunctival irritation, and unspecified respiratory changes. Irritating to human body if inhaled. Mdd's narcotic properties have also been attributed to it. Human mutation data are reported. Experimental reproductive effects. It is a flammable liquid when exposed to heat or flame; it can react violently with oxidizing substances. Slight explosion hazard in vapor form if exposed to flame. Reacts with hydrogen peroxide + nitric acid to form explosive peroxide. When extinguishing fire, use alcohol foam, dry powder or carbon dioxide. When heated and decomposed, acrid and irritating fumes are released. See also ketone and cyclohexane. |
| synthesis | It can be synthesized on a laboratory scale via the oxidation of cyclohexanol. |
| potential contact | May form explosive mixture with air. Contact with oxidizing agents or nitric acid may cause a violent reaction. Do not use brass, copper, bronze or lead fittings. Attacks many coatings and plastic materials. |
| Carcinogenicity | IARC considered that the animal data for cyclohexanone were insufficient to demonstrate carcinogenicity and classified cyclohexanone as not classifiable carcinogenic (IARC Category 3). |
| environmental fate | biology. In the activated sludge inoculation, the COD removal rate reached 96.0%. The average biodegradation rate is 30.0 mg COD/g?h (Pitter, 1976). Photolytic. Atkinson (1985) reported an estimated photooxidation rate constant of 1.56 x 10 -11 cm 3 /molecule·second for the reaction of cyclohexanone and OH radicals in the atmosphere at 298 K. Chemistry/Physics. Cyclohexanone does not hydrolyze because it has no hydrolyzable functional groups. When the inlet water concentration is 1,000 mg/L, the effluent concentration after GAC treatment is 332 mg/L. The adsorption capacity of the carbon used was 134 mg/g carbon (Guisti et al., 1974). Similarly, the GAC adsorption capacities were 36, 6.2, 1.1, and 0.19 mg/g at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, respectively (Dobbs and Cohen, 1980). |
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| 纯化方法 | 将环己酮用MgSO4、CaSO4、Na2SO4或Linde型13X分子筛干燥，然后蒸馏。环己醇和其他可氧化杂质可以用铬酸或稀KMnO4处理除去。通过转化为亚硫酸氢盐加成化合物或缩氨基脲，然后用 Na2CO3 分解和蒸汽蒸馏，可以进行更彻底的纯化。[例如，将等重量的亚硫酸氢盐加合物（从水中结晶）和Na2CO3溶解在热水中，在蒸汽蒸馏后，将馏出物用NaCl饱和，并用Et2O萃取，然后干燥（无水MgSO4或Na2SO4），过滤并在进一步蒸馏之前蒸发溶剂。] 易燃 [Beilstein 7 III 14, 7 IV 15.] |
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