Caprolactam
epsilon-Caprolactam
CAS: 105-60-2
Molecular Formula: C6H11NO
Caprolactam - Names and Identifiers
| Name | epsilon-Caprolactam |
| Synonyms | CPL EPSILON-CAP Caprolactam CAPROLACTAM azepan-2-one E-CAPROLACTAM ε-Caprolactam 6-hexanelactam 1,6-hexanolactam epsilum-Caprolactam EPSILON-CAPROLACTAM EPSILUM-CAPROLACTAM epsilon-Caprolactam perhydroazepin-2-one CYCLOHEXANONEISOOXIME 2-Oxohexamethylenimine 2-Oxohexamethyleneimine HEXAHYDRO-2H-AZEPIN-2-ONE Hexahydro-2H-azepine-2-one |
| CAS | 105-60-2 |
| EINECS | 203-313-2 |
| InChI | InChI=1/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8) |
Caprolactam - Physico-chemical Properties
| Molecular Formula | C6H11NO |
| Molar Mass | 113.16 |
| Density | 1.01 |
| Melting Point | 68-71°C(lit.) |
| Boling Point | 136-138°C10mm Hg(lit.) |
| Flash Point | 152 °C |
| JECFA Number | 1594 |
| Water Solubility | 4560 g/L (20 ºC) |
| Solubility | H2O: 0.1g/mL, clear, colorless |
| Vapor Presure | <0.01 mm Hg ( 20 °C) |
| Appearance | White crystalline solid |
| Specific Gravity | 1.042 (20/4℃) |
| Color | White |
| Exposure Limit | ACGIH: TWA 5 mg/m3NIOSH: TWA 1 mg/m3; TWA 0.22 ppm; STEL 3 mg/m3; STEL 0.66 ppm |
| Merck | 14,1761 |
| BRN | 106934 |
| pKa | 16.61±0.20(Predicted) |
| PH | 7.0-8.5 (333g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 1.4-8%(V) |
| Refractive Index | 1.4935 |
| Physical and Chemical Properties | White flakes or melts. |
| Use | Mainly used for the preparation of caprolactam resin, fiber and artificial leather, also used as pharmaceutical raw materials |
Caprolactam - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/22 - Harmful by inhalation and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S2 - Keep out of the reach of children. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 1 |
| RTECS | CM3675000 |
| TSCA | Yes |
| HS Code | 29337100 |
| Toxicity | LD50 orally in rats: 2.14 g/kg (Smyth) |
Caprolactam - Upstream Downstream Industry
| Raw Materials | sulfur dioxide Sulfuric acid Ammonia Cyclohexanone Hydrogen Ammonia |
| Downstream Products | Hexamethyleneimine |
Caprolactam - Nature
Open Data Verified Data
white flakes or melts. Soluble in water, solvent, petroleum hydrocarbons, cyclohexene, benzene, methanol, ethyl chloride, ether. Melting Point: 69~71 °c. Boiling point of 268.5 deg C (101. 3kPa). 70% relative density of aqueous solution 1.05. Refractive index 4935. The heat of fusion was 121.8J/g. The viscosity was 9mPa · s at 78 ℃ with the heat of evaporation of 487. 2J/G0. The vapor pressure was 100. 9Pa at 399 ℃ and 180. 3kPa at 268.5 ℃ and 6. 665kPa0 at 101 ℃
.Last Update：2024-01-02 23:10:35
Caprolactam - Preparation Method
Open Data Verified Data
- cyclohexane oxidation of benzene by hydrogenation reaction of cyclohexane, the oxidation of cyclohexanone and cyclohexanol mixture, separation of cyclohexanol by catalytic dehydrogenation of cyclohexanone. Cyclohexanone and hydroxylamine oximation reaction, the resulting cyclohexanone oxime, by Beckmann rearrangement to generate caprolactam, sulfuric acid in the reaction product with ammonia neutralization separation of ammonium sulfate, crude caprolactam and trichloroethylene extraction, after purification steps such as vacuum distillation and recrystallization, pure caprolactam is obtained.
- cyclohexanone oxime hydrochloride is generated from cyclohexane and nitrosyl chloride by light irradiation of high-pressure mercury with thallium iodide, and then shifted by Beckmann to form a sulfuric acid solution of caprolactam, after neutralization with ammonia, extraction and rectification, caprolactam is obtained.
- phenol method phenol is hydrogenated in the presence of a nickel catalyst to obtain cyclohexanol, which is purified and then dehydrogenated to obtain crude cyclohexanone. Cyclohexanone is purified and reacted with hydroxylamine to obtain cyclohexanone oxime, which is then shifted by Beckmann to form caprolactam. Sulfuric acid in the reaction product is neutralized with ammonia to obtain thiamine as a by-product. The crude caprolactam was treated with a series of chemical and physical treatments to obtain pure caprolactam.
Last Update：2022-01-01 10:39:08
Caprolactam - Use
Open Data Verified Data
This product is mainly used to prepare caprolactam resin, caprolactam fiber and artificial leather, etc., also used as medical raw materials.
Last Update：2022-01-01 10:39:07
Caprolactam - Safety
Open Data Verified Data
This product is toxic. Long-term inhalation can cause chronic poisoning, such as neurasthenia, dizziness, Head Pain, nosebleeds and respiratory tract inflammation. Have a corrosive effect on the skin, to avoid direct contact. Mice inhaled LC50 450mg/m3. The maximum allowable concentration in air is 10 mg/m3. The production site should be forced ventilation. Operators should wear labor protection equipment.
The use of plastic bags, heat sealing seal, coat nylon woven bag or kraft paper bag, each 25kg. Storage in a dry and clean warehouse, fire, moisture, heat, sun protection. The shelf life was three months.
Last Update：2022-01-01 10:39:09
Caprolactam - Reference Information
| FEMA | 4235 | 1,6-HEXALACTAM |
| LogP | 0.12 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 39, Sup 7, 71) 1999 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| production of polyamide fiber and resin | caprolactam is the main raw material for the production of polyamide fiber and resin. polyamide fiber is called nylon in the United States and nylon in China. Because it was first commercialized by Jinzhou Petrochemical, it is called nylon. Nylon 66 is a polycondensation product of adipic acid and hexamethylene diamine. Nylon 6 is a ring-opening polymerization of caprolactam. At present, the domestic master of caprolactam production technology is mainly Sinopec Baling Petrochemical Design Institute and Yueyang Petrochemical Design Institute. Cyclohexanone and phenol are the main raw materials for the production of caprolactam: Cyclohexanone is an important chemical raw material with a wide range of applications. It has a colorless, odorless and transparent liquid with mint and acetone odor, and is slightly soluble in water. It can be dissolved in various organic solvents such as ether and alcohol. It is mainly used as an intermediate between caprolactam and adipic acid and its salts. Due to its strong dissolving ability, low toxicity and relatively low price, it is widely used as a solvent and diluent for various coatings, paints, inks and resins, polishing agents and diluents for leather processing, and solvents for coating photosensitive and magnetic recording materials. At the same time, some downstream derivatives can be prepared, such as cyclohexanone-formaldehyde resin, peroxycyclohexanone, o-methylphenol, antioxidant 4010, etc. phenol, also called carbolic acid, is one of the simplest phenolic organic matter, with weak acidity, pure phenol is colorless crystal, in the air will be a small part of the oxidation and pink. Toxic, corrosive, slightly soluble in water at room temperature, soluble in organic solutions such as alcohol; When the temperature is higher than 65 ℃, it can be miscible with water in any proportion. The concentrated solution is highly corrosive to the skin and is accidentally stained with alcohol. Bromine water is added dropwise to the phenol solution, and there will be a white precipitate (tribromophenol) immediately; it can be replaced with halogen, nitric acid, sulfuric acid, etc. on this ring; it can react with ferric chloride to make the solution purple, and the solution drops Bromine water immediately has a white precipitate (tribromophenol). Mainly used in the manufacture of phenolic resin, bisphenol A and caprolactam. Among them, the production of phenolic resin is its biggest use, accounting for more than half of the phenol production. |
| use | caprolactam is mostly used to produce polycaprolactam, the latter is about 90% used to produce synthetic fibers, namely caprone, 10% used as plastic, used to make gears, bearings, pipes, medical equipment, electrical and insulating materials, etc. It is also used in coatings, plastics and a small amount of lysine synthesis. It is mainly used to make caprolactam resin, fiber and artificial leather, etc., and is also used as pharmaceutical raw material high molecular polymer solvent to make polyamide type synthetic fiber and gas chromatography stationary liquid. |
| production method | In 1943, German Farben Company first realized the industrial production of caprolactam through cyclohexanone-hydroxylamine synthesis (now referred to as oxime method). With the development of synthetic fiber industry, toluene method (ANIA method), light nitrification method (PNC method), caprolactone method (UCC method), cyclohexane nitrification method and cyclohexanone nitrification method have appeared successively. The newly developed cyclohexanone ammonification oxidation method has attracted people's attention because hydroxylamine is not needed for cyclohexanone oxime in the production process and the process is simple. 1. Oxime method First, cyclohexanone with high purity and hydroxylamine sulfate are condensed at 80-110 ℃ to produce cyclohexanone oxime. The separated cyclohexanone oxime was converted into crude caprolactam by Beckman rearrangement at 80-110 ℃ with fuming sulfuric acid as catalyst. The crude caprolactam was prepared by extraction, distillation, crystallization and other processes. Cyclohexanone, the raw material of the oxime method, can be obtained by hydrogenation of phenol to obtain cyclohexanol, and then dehydrogenation; or cyclohexane is oxidized by air to produce cyclohexanol and cyclohexanone, and the catalytic dehydrogenation of the separated cyclohexanol also produces cyclohexanone. 2. Toluene process toluene is oxidized to generate benzoic acid under the action of cobalt salt catalyst. Benzoic acid is hydrogenated in liquid phase with palladium catalyst on activated carbon carrier to generate hexahydrobenzoic acid. In fuming sulfuric acid, hexahydrobenzoic acid reacts with nitrosyl sulfuric acid to generate caprolactam. Toluene method has certain development prospects due to its abundant toluene resources and low generation cost. 3. Photonitrification cyclohexane under the irradiation of mercury vapor lamp photochemical reaction with chloronitrolyl, directly converted into cyclohexanone oxime hydrochloride, cyclohexanone oxime hydrochloride in the presence of fuming sulfuric acid, through Beckman rearrangement into caprolactam. 4. Phenol phenol is hydrogenated in the presence of nickel catalyst to obtain cyclohexanol, and dehydrogenated to obtain crude cyclohexanone after purification. After cyclohexanone is purified, it reacts with hydroxylamine to obtain cyclohexanone oxime, which is then shifted by Beckman to generate caprolactam. The sulfuric acid in the reaction product is neutralized with ammonia to obtain by-product thiamine. Crude caprolactam is treated with a series of chemical and physical treatments to obtain pure caprolactam. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 1210 mg/kg; Oral-mouse LD50: 930 mg/kg |
| stimulation data | skin-rabbit 500 mg/24 hours mild; Eye-rabbit 20 mg/24 hours moderate |
| Explosive hazard characteristics | Reaction explosion with acetic acid and nitrogen trioxide mixture |
| flammability hazard characteristics | thermal decomposition discharges toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse low temperature ventilation and drying |
| fire extinguishing agent | water, carbon dioxide, foam, dry powder |
| occupational standard | TWA 1 mg/m3; STEL 3 mg/m3 (dust, steam) |
| auto-ignition temperature | 707 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Raw Materials for Caprolactam
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