Caprolactam = CPL
CAS Number: 105-60-2
EC Number: 203-313-2
Chemical formula: C6H11NO
Molar mass: 113.160 g·mol−1
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH.
This colourless solid ,Caprolactam, is a lactam (a cyclic amide) of caproic acid.
Global demand for Caprolactam is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics.
Synthesis and production of Caprolactam:
Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam.
World demand for caprolactam was estimated to reach five million tons per year for 2015.
90% of caprolactam produced is used to make filament and fiber, 10% for plastics, and a small amount is used as a chemical intermediate.
Due to Caprolactams commercial significance, many methods have been developed for the production of caprolactam.
Caprolactam was estimated that 90% of all caprolactam is synthesised from cyclohexanone, which is first converted to its oxime.
Treatment of Caprolactam with acid induces the Beckmann rearrangement to give caprolactam.
The immediate product of the acid-induced rearrangement is the bisulfate salt of caprolactam.
This salt is neutralized with ammonia to release the free lactam and cogenerate ammonium sulfate.
In optimizing the industrial practices, much attention is directed toward minimizing the production of ammonium salts.
The other major industrial route involves formation of the oxime from cyclohexane using nitrosyl chloride, and this method accounts for 10% of world production.
The advantage of this method is that cyclohexane is less expensive than cyclohexanone.
Other paths to caprolactam include the depolymerization of waste Nylon 6, and the reaction of caprolactone with ammonia.
At bench scale, the reaction between cyclohexanone with hydrazoic acid to give caprolactam in the Schmidt reaction has been reported.
Uses of Caprolactam:
Almost all caprolactam produced goes into the manufacture of Nylon 6.
The conversion entails a ring-opening polymerization.
Nylon 6 is widely used in fibers and plastics.
Physical characteristic: White Dust
Chemical formula: C6H11NO
Molecular weight:113,16 g/mol
Caprolactam is one of the chemical products of engineering.
Areas of usage of Caprolactam:
Caprolactam is used in the production of various chemicals.
Caprolactam is used in the production of resin, paint and glue.
Caprolactam is used as an auxiliary activator in the MDF chipboard coating group.
Caprolactam is also used in the leather sector.
In situ anionic polymerization is employed for cast nylon production where conversion from ε-caprolactam to Nylon 6 takes place inside a mold.
In conjunction with endless fiber processing the term thermoplastic resin transfer molding (T-RTM) is often used.
Caprolactam is also used in the synthesis of several pharmaceutical drugs including pentylenetetrazol, meptazinol, and laurocapram.
Physical Description of Caprolactam:
Caprolactam is a clear to milky white-colored solution with a mild, disagreeable odor.
Caprolactam contact may cause slight irritation to skin, eyes, and mucous membranes.
Caprolactam may be mildly toxic by ingestion.
The primary hazard of Caprolactam is the threat to the environment.
Immediate steps should be taken to limit Caprolactams spread to the environment.
As a liquid Caprolactam can easily penetrate the soil and contaminate groundwater and nearby streams.
Caprolactam is used to make other chemicals.
Identifiers of Caprolactam:
CAS Number: 105-60-2
Beilstein Reference: 106934
CHEBI: 28579
ChEMBL: ChEMBL276218
ChemSpider: 7480
ECHA InfoCard: 100.003.013
EC Number: 203-313-2
Gmelin Reference: 101802
KEGG: C06593
PubChem CID: 7768
UNII: 6879X594Z8
CompTox Dashboard (EPA): DTXSID4020240
Caprolactam is used as an auxiliary activator in the MDF chipboard coating group.
KEYWORDS:
105-60-2, 203-313-2, CPL, 1-Aza-2-cycloheptanone, 2-Azacycloheptanone, Capron PK4, Cyclohexanone iso-oxime, Extrom 6N, Hexahydro-2-azepinone, Hexahydro-2H-azepin-2-one (9CI)
Applications of Caprolactam:
ε-Caprolactam can be used as a precursor for the production of nylon-6 by ring-opening polymerization.
Caprolactam is also microwave irradiated with ε caprolactone in the presence of an anionic catalyst to yield poly(ε caprolactam-co-ε-caprolactone).
Properties of Caprolactam:
Chemical formula: C6H11NO
Molar mass: 113.160 g·mol−1
Appearance: White solid
Density: 1.01 g/cm3
Melting point: 69.2 °C (156.6 °F; 342.3 K)
Boiling point: 270.8 °C (519.4 °F; 544.0 K) at 1013.25 hPa
Solubility in water: 866.89 g/L (22 °C)
Vapor pressure: 0.00000008 mmHg (20° C)
Caprolactam (CPL) is the main raw material for making nylon-6 fibers and resin.
Caprolactam is also CPDC’s main product.
We are the sole manufacturer of Caprolactam in Taiwan and one of the top five in the world.
Uses of Caprolactam:
Caprolactam is primarily used in the manufacture of synthetic fibers (especially Nylon 6).
Caprolactam is also used in brush bristles, textile stiffeners, film coatings, synthetic leather, plastics, plasticizers, paint vehicles, cross-linking for polyurethanes, and in the synthesis of lysine.
Caprolactam (CL) is preferred to ω-aminocaproic acid for the manufacture of PA6 because it is easier to make and to purify.
Over the years, many routes for the manufacture of Caprolactam itself have been developed.
Of these routes, the bulk of manufacture is via cyclohexanone and cyclohexanone oxime.
Physical Properties of Caprolactam:
The chemical formula for caprolactam is C6H11ON, and its molecular weight is 113.16 g/mol.
Caprolactam is a white, hygroscopic, crystalline solid or leaflets that are very soluble in water.
Caprolactam has a unique, unpleasant odor; the odor threshold has not been established.
The vapor pressure of caprolactam is 1.9 × 10-3 mm Hg at 25 °C, and its log octanol/water partition coefficient (log Kow) is -0.19.
Product Information of Caprolactam:
CAS number: 105-60-2
EC index number: 613-069-00-2
EC number: 203-313-2
Hill Formula: C₆H₁₁NO
Molar Mass: 113.16 g/mol
HS Code: 2933 71 00
Caprolactam is a crystalline cyclic amide with a melting point of 70 °C.
Caprolactam is soluble in water, most oxygenated and chlorinated solvents, and some hydrocarbons.
Because Caprolactam is the only common caprolactam isomer, the ε is usually dropped.
It derives Caprolactams name from ε-aminocaproic acid, or 6-aminohexanoic acid; in principle, the lactam is formed when the terminal carboxylic acid and amino groups react to form the amide.
The amide formation reaction succeeds only when run in dilute solution; otherwise, aminocaproic acid polymerizes.
The commercial synthesis consists of the acid-catalyzed Beckmann rearrangement of cyclohexanone oxime, which was discovered by Prussian chemist and Nobel Prize winner Otto Wallach way back in 1900.
Numerous articles and patents have been devoted to improving this method ever since.
Wallach didn’t live to see it, but caprolactam turned out to be extremely valuable.
In 1938, Paul Schlack at IG Farben found that heating caprolactam neat to 260 °C causes the ring to open and the terminal functional groups to react to form a long-chain polyamide.
This polymer later became known as “nylon 6”*.
Caprolactam can be formed into high-strength fibers, resins, and films that have dozens of end-use applications ranging from clothing to violin strings to automotive mechanical parts.
*Nylon 6 is similar to—but should not be confused with—nylon 6,6, which is prepared from hexamethylenediamine and adipic acid.
Caprolactam is preferred to ω-aminocaproic acid for the manufacture of nylon 6 because it is easier to make and to purify.
Over the years many routes for the manufacture of caprolactam itself have been developed and major commercial routes are summarised.
Of these routes the bulk of manufacture is via cyclohexanone and cyclohexanone oxime.
Physicochemical Information of Caprolactam:
Boiling point: 270.8 °C (1013 hPa)
Density: 1.020 g/cm3 (75 °C)
Explosion limit: 1.4 - 8 %(V)
Flash point: 152 °C DIN 51758
Ignition temperature: 395 °C DIN 51794
Melting Point: 68 - 71 °C
pH value: 7.0 - 8.5 (333 g/l, H₂O)
Vapor pressure: <0.01 hPa (20 °C)
Bulk density: 500 - 550 kg/m3
Solubility: 4560 g/l
Caprolactam is a crystalline cyclic amide which is water-soluble in nature.
Caprolactam has a melting point of 70°C. Caprolactam is a very important raw material for the production of nylon 6 fibers and resins through the method of ring-opening polymerization.
Cyclohexane and ammonia are the basic raw materials used for the production of caprolactam.
Nylon 6 polymers are used to manufacture high-strength fibers, resins, and films.
And has a wide range of applications from the textile industry to the automotive industry.
The textile industry consumes around 68% of caprolactam for the production of nylon fibers for textile, carpets, and industrial yarns.
And the rest of the caprolactam is used in manufacturing engineering resins and films.
Due to an increase in demand for caprolactam in end-use industries such as textile yarn, industrial yarn, engineering plastics, carpet fibers, and staple fibers; has driven the demand for caprolactam.
Due to this the global demand for this compound is around 5 million tons per year.
And the majority of this compound is used to manufacture nylon filaments and fibers for the clothing industry.
The demand for caprolactam is also increasing in automobile industries for the production of engine covers and gears.
For the production of caprolactam, raw materials like cyclohexane, ammonia, and phenol are used.
And these materials are mainly produced in the US and China region because of the presence of a large number of oil refineries in that region.
The increasing demand for nylon 6 polymers in apparel, sportswear, swimwear, and fashion wear has also increased the demand for caprolactam.
Examples for applications of Caprolactam:
-Molded components
-Carpets
-Packaging films
-Brushes
-Fishing nets
Caprolactam is used in the manufacture of synthetic fibers.
Acute (short-term) exposure to caprolactam may result in irritation and burning of the eyes, nose, throat, and skin in humans.
Headaches, malaise, confusion, and nervous irritation have been observed in workers exposed to caprolactam by inhalation.
Chronic (long-term) exposure of workers to caprolactam has been observed to cause peeling of the hands and some eye, nose, and throat irritation, but no other effects on general health.
EPA has not classified caprolactam for carcinogenicity.
Specifications of Caprolactam:
Density: 1.01
pH: 7 to 8.5
Melting Point: 68°C to 72°C
Boiling Point: 270°C
Flash Point: 152°C (305°F)
Beilstein: 106934
Merck Index: 14,1761
Solubility Information: Soluble in benzene,ethanol,water,chloroform,methanol,tetrahydrofurfuryl alcohol,ether,dimethylformamide,chlorinated hydrocarbons,cyclohexene and petroleum fractions.
Formula Weight: 113.16
Percent Purity: 99%
Chemical Name or Material: epsilon-Caprolactam
About Caprolactam:
Caprolactam is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 000 to < 10 000 000 tonnes per annum.
Caprolactam is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of Caprolactam:
Caprolactam is used in the following products: inks and toners, coating products, fillers, putties, plasters, modelling clay and paper chemicals and dyes.
Other release to the environment of Caprolactam is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Article service life of Caprolactam:
Release to the environment of Caprolactam can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal).
Other release to the environment of Caprolactam is likely to occur from: indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Caprolactam can be found in complex articles, with no release intended: vehicles, machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines) and electrical batteries and accumulators.
Caprolactam can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones), fabrics, textiles and apparel (e.g. clothing, mattress, curtains or carpets, textile toys), leather (e.g. gloves, shoes, purses, furniture) and rubber (e.g. tyres, shoes, toys).
Widespread uses by professional workers of Caprolactam:
Caprolactam is used in the following products: laboratory chemicals.
Caprolactam is used for the manufacture of: plastic products and textile, leather or fur.
Release to the environment of Caprolactam can occur from industrial use: formulation of mixtures.
Other release to the environment of Caprolactam is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Formulation or re-packing of Caprolactam:
Caprolactam is used in the following products: adhesives and sealants, coating products, fillers, putties, plasters, modelling clay, inks and toners, leather treatment products, polymers and textile treatment products and dyes.
Release to the environment of Caprolactam can occur from industrial use: formulation of mixtures and formulation in materials.
Uses at industrial sites of Caprolactam:
Caprolactam is used in the following products: polymers.
Caprolactam has an industrial use resulting in manufacture of another substance (use of intermediates).
Caprolactam is used for the manufacture of: chemicals and plastic products.
Release to the environment of Caprolactam can occur from industrial use: for thermoplastic manufacture, as processing aid, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, in the production of articles and in processing aids at industrial sites.
Manufacture of Caprolactam:
Release to the environment of Caprolactam can occur from industrial use: manufacturing of the substance.
Production of polyamide fibers and resins:
Caprolactam is the main raw material for the production of polyamide fiber and resin. Polyamide fiber, in the United States, is called nylon; in China, is called Chinlon because it was first commercialized in Jinzhou Petrochemical. Chinlon 66 is a polycondensation product of adipic acid and hexamethylene diamine.
Polyamide 6 obtained from the ring-opening polymerization of caprolactam.
At present, the 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 a kind of important chemical raw material with wide range of application fields.
Caprolactam is colorless and odorless transparent liquid with mint and acetone odor.
Caprolactam is slightly soluble in water and soluble in ether, alcohol and other organic solvents.
Caprolactam is mainly used as the intermediates of caprolactam and others diacids and their salts.
Because of Caprolactams strong solubility, low toxicity and relatively low price, it is widely used as solvent and thinner for various paints, paints, inks and resins, polishes and thinners for leather processing, photographic and magnetic recording material and coating solvent, and so on.
At the same time, Caprolactam can also be used for preparation of some downstream derivatives, such as cyclohexanone-formaldehyde resin, peroxy cyclohexanone, o-methyl phenol, antioxidant 4010 and so on.
Phenol is also called phenolic acid, is one of the simplest phenolic organic matter with weak acidity.
Pure phenol is a colorless crystal which exhibits pink color in the air due to being oxidized in a small part.
Caprolactam is toxic, corrosive, being slightly soluble in water at room temperature, easily soluble in alcohol and other organic solvents; when the temperature is higher than 65 ℃, it is miscible with water in any proportion.
Concentrated solution has strong corrosiveness on the skin.
Mistakenly contact with skin can be treated through rinsing with alcohol.
Addition of bromine water into the phenol solution will generate white precipitate immediately (2, 4, 6-Tribromophenol); being capable of having substitution reaction in the benzene ring with halogen, nitric acid, sulfuric acid, etc.; being able to have reaction with ferric chloride so that the solution is turned into a purple color; addition of bromine water into the solution will immediately generate white precipitate (2, 4, 6-Tribrominephenol).
Caprolactam is mainly used in the manufacture of phenolic resin, bisphenol A and caprolactam.
The production of phenolic resin is its biggest use, accounting for more than half of phenol production.
Chemical properties of Caprolactam:
Caprolactam is a white‚ hygroscopic‚ crystalline solid with a characteristic odor.
Most caprolactam is used to make nylon 6‚ which is the starting material for fibers that have many uses in textile manufacture and in the industrial sector.
Polymerization is caprolactam's most important chemical property.
The ring is hydrolyzed at 260 to 270°C.
Liner polymer chains are formed by polycondensation.
Caprolactam also reacts directly by polyaddition with the polymer chains.
These reactions lead to an equilibrium between the polymer and caprolactam that favors a 90% conversion to polymer.
Uses of Caprolactam:
(1) The majority of caprolactam is used in the production of polycaprolactam, of which about 90% is used for the production of synthetic fibers, that is, Kaplon, 10% used as plastic for the manufacture of gears, bearings, pipe, medical equipment and electrical, insulating materials. Also used in coatings, plastics and for the synthesis of lysine in a small amount and so on.
(2) Caprolactam is mainly used for the preparation of caprolactam resin, fiber and leather, also used as pharmaceutical raw materials.
(3) Caprolactam can be used as polymer solvent, for the manufacture of polyamide-based synthetic fiber and the fixing phase of gas chromatography.
Production method of Caprolactam:
In 1943, the I.G. Farben AG Company, through the cyclohexanone-hydroxylamine synthesis (now referred to as the oxime), had first realized the industrial production of caprolactam.
With the development of synthetic fiber industry, there have been successively toluene (ANIA), photo nitrosation (PNC), caprolactone (UCC), cyclohexane nitration and cyclohexanone nitration.
The newly developed ammoxidation of cyclohexanone has attracted much attention because of its simplicity in the production of cyclohexanone oximation without the use of hydroxylamine.
1. Oxime method: first apply the high-purity cyclohexanone and hydroxylamine sulfate for condensation reaction at 80-110 °C to generate cyclohexanone oxime.
The isolated cyclohexanone oxime is converted into crude caprolactam at 80-110°C via Beckmann Rearrangement reaction using sulfuric acid as catalyst, followed by extraction, distillation and crystallization to obtain high purity caprolactam.
The raw material cyclohexanone used in oxime method can be obtained from the hydrogenation of phenol to cyclohexanol, followed by dehydrogenation; alternatively by cyclohexane air oxidation into cyclohexanol and cyclohexanone with the separated cyclohexanol catalytic dehydrogenation generating ring Pentanone.
2. Toluene; toluene, under the effect of the cobalt oxide catalyst, can be subject to oxidation to generate benzoic acid which with liquid hydrogenation using the palladium catalyst on the activated carbon carrier to generate hexahydrobenzoic acid, which, in fuming sulfuric acid, reacts with nitrosyl sulfuric acid to generate caprolactam.
Toluene method, due to that toluene is rich in resources with low production cost, has a certain development prospects.
3. Photo nitrosation method: cyclohexane, under the irradiation of the mercury vapor lamp can have photochemical reaction with chlorinated nitrosyl, further being direct converted into cyclohexanone oxime hydrochloride, which can be further converted into caprolactam by the Beckman rearrangement in the presence of fuming sulfuric acid.
4. Phenol method: phenol, in the presence of nickel catalyst, is subject to hydrogenation to obtain cyclohexanol with purification and dehydrogenation to generate crude cyclohexanone.
Cyclohexanone, after being purified, can react with hydroxylamine to cyclohexanone oxime, followed by Beckmann shift to generate caprolactam.
The sulfuric acid in the reaction product can neutralized with ammonia to generate by-product of thiamine.
Crude caprolactam can be purified by a series of chemical and physical treatments to obtain pure caprolactam.
Description of Caprolactam:
Caprolactam, CH2CH2CH2CH2CH2NHCO, is a solid material composed of white flakes.
Caprolactam is soluble in water and has a specific gravity (in a 70% solution)of 1.05, which is heavier than water.
Caprolactam may also be encountered as a molten material.
Caprolactam is toxic by inhalation, with a TLV of (vapor) 5 ppm in air and (dust) 1 mg/m3 of air.
The primary uses are in the manufacture of synthetic fibers, plastics, film, coatings, and polyurethanes.
Chemical Properties of Caprolactam:
Caprolactum is a white crystalline combustible solid with an unpleasant odor.
The Odor Threshold is 0.3 milligram per cubic meter.
Physical properties of Caprolactam:
Caprolactam is a yellowish solid or white crystals or flakes; amine, spicy aroma.
Caprolactam is soluble in water, chlorinated solvents, petroleum hydrocarbons, cyclohexene, benzene, methanol, ethanol and ether.
Uses of Caprolactam:
manufacture of synthetic fibers of the polyamide type (Perlon); solvent for high mol wt polymers; precursor of nylon-6, q.v.
Uses of Caprolactam:
Caprolactam is used as a monomer in the preparation of synthetic fibers of the polyamide as well as a solvent for high molecular weight polymers.
Caprolactam is also used in coatings and plasticizers.
Further, Caprolactam is used as a cross linking agent for polyurethanes.
In addition to this, Caprolactam is used to prepare nylon-6, which finds application in fibers and plastics.
Preparation of Caprolactam:
About 90% of the caprolactam is produced by the conventional cyclohexanone process.
Cyclohexanone is obtained by catalytic oxidation of cyclohexane with air? or by hydrogenation of phenol and dehydrogenation of the cyclohexanol byproduct.
The conversion of cyclohexanone to cyclohexanone oxime followed by Beckmann rearrangement gives caprolactam.
About 10% of caprolactam is produced by photonitrosation of cyclohexane or by nitrosation of cyclohexanecarboxylic acid in the presence of sulfuric acid.
Definition of Caprolactam:
ChEBI: A member of the class of caprolactams that is azepane substituted by an oxo group at position 2.
Definition of Caprolactam:
A white crystalline substance used in the manufacture of NYLON.
Aroma threshold values:
High strength odor; spicy type; recommend smelling in a 0.01% solution or less
General Description of Caprolactam:
Clear to milky white-colored solution with a mild, disagreeable odor.
Contact may cause slight irritation to skin, eyes, and mucous membranes.
May be mildly toxic by ingestion.
The primary hazard is the threat to the environment.
Immediate steps should be taken to limit its spread to the environment.
As a liquid Caprolactam can easily penetrate the soil and contaminate groundwater and nearby streams. Used to make other chemicals.
Air & Water Reactions of Caprolactam:
Caprolactam is water soluble.
Reactivity Profile of Caprolactam:
Caprolactam is hygroscopic.
Caprolactam can react with strong oxidizing agents and strong bases.
2-Oxohexamethylenimine can also react with chlorinated hydrocarbons and nitro compounds.
A potentially explosive reaction occurs with acetic acid + dinitrogen trioxide.
Hazard:
Toxic by inhalation.
Upper respiratory tract irritant.
Health Hazard:
Inhalation causes coughing or mild irritation.
Contact with hot liquid will burn eyes and skin.
Fire Hazard:
Special Hazards of Combustion Products: Toxic oxides of nitrogen
Safety Profile:
Moderately toxic by ingestion, skin contact, intraperitoneal, and subcutaneous routes. Human systemic effects by inhalation: nose and throat irritation, cough.
Experimental reproductive effects.
A skin and eye irritant.
Potentially explosive reaction with acetic acid + dinitrogen trioxide.
Potential Exposure:
Caprolactam is used in the manufacture of nylon, plastics, bristles, film, coatings, synthetic leather, plasticizers, and paint vehicles; as a crossslinking agent for curing polyurethanes; and in the synthesis of lysine
Carcinogenicity:
Caprolactam was not mutagenic in bacterial assays or in in vivo rodent assays; it did induce chromosomal aberrations and aneuploidy in human lymphocytes in vitro.
Purification Methods:
The lactam is distilled under reduced pressure, recrystallised from acetone or pet ether and redistilled.
Incompatibilities:
Caprolactum decomposes on heating, and on burning producing toxic fumes including nitrogen oxides, ammonia.
Reacts violently with strong oxidizers, producing toxic fumes.
Toxic decomposition above 400C
Waste Disposal:
Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).
Also, Caprolactam may be recovered from Caprolactam still bottoms or nylon waste
Molecular Weight: 113.16
XLogP3: -0.1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 113.084063974
Monoisotopic Mass: 113.084063974
Topological Polar Surface Area: 29.1 Ų
Heavy Atom Count: 8
Formal Charge: 0
Complexity: 90.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count : 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Caprolactam is the raw material for Nylon 6 fiber and Nylon 6 resin.
UBE has achieved world-leading quality and secured stable supply based on our 60 years of experience and the technologies we have developed since starting to manufacture caprolactam in 1956.
Synonym(s): epsilon-Caprolactam, 2-Oxohexamethyleneimine, Aza-2-cycloheptanone
Empirical Formula (Hill Notation): C6H11NO
CAS Number: 105-60-2
Molecular Weight: 113.16
Beilstein: 106934
EC Number: 203-313-2
MDL number: MFCD00006936
PubChem Substance ID: 24892472
NACRES: NA.22
Applications of Caprolactam:
ε-Caprolactam is used as a monomer in the preparation of synthetic fibers of the polyamide as well as a solvent for high molecular weight polymers.
Caprolactam is also used in coatings and plasticizers.
Further, Caprolactam is used as a cross linking agent for polyurethanes.
In addition to this, Caprolactam is used to prepare nylon-6, which finds application in fibers and plastics.
Solubility of Caprolactam:
Soluble in benzene, ethanol, water, chloroform, methanol, tetrahydrofurfuryl alcohol, ether, dimethylformamide, chlorinated hydrocarbons, cyclohexene and petroleum fractions.
Notes about Caprolactam:
Caprolactam is hygroscopic.
Caprolactam is incompatible with strong oxidizing agents and strong bases.
PROPERTIES of Caprolactam:
vapor pressure: <0.01 mmHg ( 20 °C)
Quality Level: 200
assay: 99%
form: crystals
autoignition temp.: 707 °F
expl. lim.: 8 %
bp: 136-138 °C/10 mmHg (lit.)
mp: 68-71 °C (lit.)
SMILES string: O=C1CCCCCN1
InChI: 1S/C6H11NO/c8-6-4-2-1-3-5-7-6/h1-5H2,(H,7,8)
Inchi Key: JBKVHLHDHHXQEQ-UHFFFAOYSA-N
Caprolactam (CPL) is a widely used chemical intermediate for the production of Nylon-6.
However, existing synthetic routes in industry have severe drawbacks.
The development on the synthesis of CPL from 6-aminocapronitrile (ACN), using near- and supercritical water as the solvent, reactant and catalyst, is described in this paper.
The two-step reaction (hydrolysis and cyclization) to produce CPL is combined in a single process, by using a continuous-flow system.
Effects of pressure, temperature, residence time and the concentration of ACN were studied.
The high-temperature high-pressure environment possesses unique properties which result in very efficient catalysis.
The overall CPL yield reaches 90% within a short residence time (<2 min).
Safety of Caprolactam:
Caprolactam is an irritant and is mildly toxic, with an LD50 of 1.1 g/kg (rat, oral).
In 1991, Caprolactam was included on the list of hazardous air pollutants by the U.S. Clean Air Act of 1990.
Caprolactam was subsequently removed from the list in 1996 at the request of the manufacturers.
In water, caprolactam hydrolyzes to aminocaproic acid, which is used medicinally.
As of 2016 caprolactam had the unusual status of being the only chemical in the International Agency for Research on Cancer's lowest hazard category, Group 4: "probably not carcinogenic to humans".
Currently, there is no official permissible exposure limit set for workers handling caprolactam in the United States.
The recommended exposure limit is set at 1 mg/m3 over an eight-hour work shift for caprolactam dusts and vapors.
The short-term exposure limit is set at 3 mg/m3 for caprolactam dusts and vapors.
Preferred IUPAC name:
Azepan-2-one
Regulatory process names:
Caprolactam
caprolactam
e-Caprolactam
ε-caprolactam
ε-caprolactam
Translated names:
azepan-2-on (pl)
e-kaprolaktám (hu)
epsilon-kaprolaktamas (lt)
heksahydro-2H-azepin-2-on (pl)
heksano-6-laktam (pl)
hexahydro-2H-azépin-2-one (fr)
kaprolaktam (pl)
laktam kwasu ω-aminokapronowego (pl)
ε -kaprolaktam (cs)
ε-caprolactam (da)
ε-Caprolactam (de)
ε-caprolactam (nl)
ε-caprolactam (no)
ε-caprolactam (ro)
ε-caprolactama (es)
ε-caprolactama (pt)
ε-caprolactame (fr)
ε-caprolattame (it)
ε-hexahydro-2H-azepin-2-on (sv)
ε-kaprolaktaam (et)
ε-Kaprolaktaami (fi)
ε-kaprolaktam (hr)
ε-kaprolaktam (sv)
ε-kaprolaktams (lv)
ε-kaprolaktám (sk)
ε-καπρολακτάμ (el)
ε-капролактам (bg)
CAS names:
2H-Azepin-2-one, hexahydro-
IUPAC names:
.epsilon.-Caprolactam
2H-Azepin-2-one, hexahydro-
??-caprolactam
azacycloheptan-2-one
Azepan-2-one
azepan-2-one
azepan-2-one OR 2H-azapin-2-one, hexahydro OR Hexahydro-2H-azepin-2-one (9CI)
azepan‐2‐one
Caprolactam
caprolactam
Caprolactam
caprolactam
Caprolactam epsilon
e-caprolactam
e-caprolactam
epsilon caprolactam
EPSILON-CAPROLACTAM
epsilon-Caprolactam
epsilon-caprolactam
epsilon-caprolactam
epsilon-Caprolactam Zone Refined (number of passes:24)
ε-caprolactam
ε-Caprolactam
ε-caprolactam
Trade names:
.epsilon.-Caprolactam
.omega.-Caprolactam
1-Aza-2-cycloheptanone
2-Azacycloheptanone
2-Ketohexamethylenimine
2-Oxohexamethylene-imine n
2-Oxohexamethylenimine
2-Perhydroazepinone
2H-Azepin-2-one, hexahydro- (8CI, 9CI)
6-Amino caproic acid lactam
6-Caprolactam
6-Hexanelactam
Aminocaproic lactam
Caprolactam
caprolactam
Caprolactam, technical grade
Capron
epsilon-Caprolactam
Epsilon-Caprolactam; Caprolactam; 2-Oxohexamethylenimine; 6-Caprolactam
Hexahydro-2-azepinone
Hexahydro-2H-azepin-2-one
Hexahydroxo-2H-azepin-2-one
Hexanoic acid, 6-amino-, cyclic lactam
Kaprolaktam
Nylon 6
nylon 6
Polyamide 6
polyamide 6
Volgamid XX
ε-caprolactam
Other identifiers:
105-60-2
117955-36-9
117955-36-9
168214-28-6
168214-28-6
2953-03-9
2953-03-9
32838-21-4
32838-21-4
32838-23-6
32838-23-6
34876-18-1
34876-18-1
613-069-00-2
Other names:
1-Aza-2-cycloheptanone
2-Azacycloheptanone
ε-Caprolactam
Capron PK4
Cyclohexanone iso-oxime
Extrom 6N
Hexahydro-2-azepinone
Hexahydro-2H-azepin-2-one (9CI)
Hexanolactam
Hexano-6-lactam
Aminocaproic lactam
azepan-2-one
epsilon-Caprolactam
CAPROLACTAM
105-60-2
6-Caprolactam
2-Oxohexamethylenimine
Aminocaproic lactam
2H-Azepin-2-one, hexahydro-
Hexahydro-2H-azepin-2-one
2-Azacycloheptanone
6-Hexanelactam
Hexanolactam
2-Perhydroazepinone
2-Oxohexamethyleneimine
Hexahydro-2-azepinone
1,6-Hexolactam
E-Caprolactam
Hexanone isoxime
Caprolattame
Hexanonisoxim
2-Ketohexamethylenimine
Cyclohexanone iso-oxime
6-Aminocaproic acid lactam
Caprolactam monomer
Epsylon kaprolaktam
2-Ketohexamethyleneimine
1-Aza-2-cycloheptanone
Kaprolaktam
Kapromine
Stilon
hexannic acid
e-Kaprolaktam
Hexamethylenimine, 2-oxo-
6-Aminohexanoic acid cyclic lactam
Extrom 6N
Capron PK4
2H-Azepin-7-one, hexahydro-
Perhydroazepin-2-one
E-caprolactum
gamma-caprolactam
omega-caprolactum
Hexanoic acid, 6-amino-, lactam
.omega.-Caprolactam
NCI-C50646
.epsilon.-Caprolactam
Hexanoic acid, 6-amino-, cyclic lactam
2H-azepin-7-one,hexahydro
Aza-2-cycloheptanone
2H-Azepin-2-one, hexahydro-, homopolymer
cis-Hexahydro-2-azepinone
hexanoic acid-6-amino-,lactam
9012-16-2
CHEBI:28579
2-Azepinone, hexahydro-, (Z)-
Cyclohexanoneisooxime
Hexanoic acid, lactam
DSSTox_CID_240
WLN: T7MVTJ
6879X594Z8
DSSTox_RID_75454
DSSTox_GSID_20240
Hexanoic acid, cyclic lactam
1,6-Hexalactam
HEXANOIC ACID,6-AMINO,LACTAM E-CAPROLACTAM
Caprolattame [French]
e-Kaprolaktam [Czech]
Hexanonisoxim [German]
Epsylon kaprolaktam [Polish]
Caprolactam solution
CAS-105-60-2
CCRIS 119
HSDB 187
hexahydroazepin-2-one
EINECS 203-313-2
MFCD00006936
Caprolactam dust and vapor
NSC 117393
BRN 0106934
caprolactim
Alkamid
Bonamid
Chemlon
Danamid
Kaprolit
Kaprolon
Metamid
Orgamide
Steelon
Akulon
Capron
Grilon
Itamid
Kapron
Stylon
Vidlon
Widlon
Orgamid rmnocd
Durethan bk
Ultramid bmk
6-hexanolactam
AI3-14515
Tarlon xb
Caprolon B
Caprolon V
Kaprolit B
Kaprolon B
Renyl mv
Tarnamid T
hexano-6-lactam
Itamide S
2-Azepanone
Capron B
Ertalon 6sa
Kapron A
Kapron B
Polyamide pk 4
Caprolactam,(S)
Relon P
epsilon caprolactam
UNII-6879X594Z8
Durethan bk 30S
Tarlon X-A
Tarnamid T 2
Ultramid B 3
Ultramid B 4
Ultramid B 5
2-Azepanone #
Durethan bkv 30H
Durethan bkv 55H
Itamide 25
Itamide 35
Miramid H 2
Miramid wm 55
Torayca N 6
epsilon-?Caprolactam
Lactam, aminocaproic
Tarnamid T 27
azacycloheptan-2-one
Capran 77C
Capran 80
Plaskon 8201hs
Plaskon xp 607
Itamide 250
Itamide 250G
Itamide 350
Plaskon 20
Spencer 401
Spencer 601
azacycloheptane-2-one
Sipas 60
Itamid 250
Maranyl F 114
Maranyl F 124
Maranyl F 500
Nylon A1035sf
Plaskon 8202C
Capron gr 8256
Capron gr 8258
Plaskin 8200
Plaskon 8201
Plaskon 8205
Plaskon 8207
Plaskon 8252
Capron 8250
Capron 8252
Capron 8253
Capron 8256
Capron 8257
Nylon cm 1031
Zytel 211
Amilan CM 1001C
Amilan CM 1001G
Amilan CM 1001
Amilan CM 1011
Dull 704
Nylon X 1051
ATM 2(NYLON)
bmse000372
epsilon-Caprolactam, 99%
EC 203-313-2
6-Aminohexanoic acid lactam
hexahydro 2H Azepin 2 one
SCHEMBL19610
hexanoic acid-6-amino-lactam
5-21-06-00444 (Beilstein Handbook Reference)
CHEMBL276218
PK 4
DTXSID4020240
NIOSH/CM3900000
UBE 1022B
NSC4977
NSC-4977
NSC25536
STR02412
ZINC5133576
Tox21_202202
Tox21_300163
c0432
MFCD19226350
NSC-25536
NSC117393
STK378587
AKOS000119969
CM 1001
CM 1011
CM 1031
CM 1041
NSC-117393
epsilon-Caprolactam, analytical standard
NCGC00247913-01
NCGC00247913-02
NCGC00253933-01
NCGC00259751-01
AM802872
DB-003880
DB-032192
CM39000000
FT-0623443
FT-0625676
A23500
C06593
D70254
Q409397
J-510225
F0001-0110
Caprolactam [Wiki]
105-60-2 [RN]
106934 [Beilstein]
203-313-2 [EINECS]
2-Azepanon [German] [ACD/IUPAC Name]
2-Azepanone [ACD/IUPAC Name]
2-Azépanone [French] [ACD/IUPAC Name]
2H-Azepin-2-one, hexahydro- [ACD/Index Name]
2-ketohexamethylenimine
2-Oxohexamethyleneimine
2-Oxohexamethylenimine
2-perhydroazepinone
6-caprolactam
6-Hexanelactam
aminocaproic lactam
Aza-2-cycloheptanone
Azepan-2-on
azepan-2-one
Caprolactam [German]
Caprolactama [Spanish]
Caprolactama [Portuguese]
Caprolactame [French]
Caprolattame [Italian]
e-Caprolactam
Hexahydro-2-azepinone
MFCD00006936 [MDL number]
ε-caprolactam
ε-Caprolactam
ε-カプロラクタム [Japanese]
Капролактам [Russian]
己内酰胺 [Chinese]
&γ;-caprolactam
&ε
1,6-Hexalactam
1,6-hexolactam
169297-53-4 [RN]
1-Aza-2-cycloheptanone
203-313-2MFCD00006936
2-Azacycloheptanone
2H-Azepin-7-one, hexahydro-
2H-azepin-7-one,hexahydro
2-ketohexamethyleneimine
2-ketohexamethyleneimine,cp
5-21-06-00444 [Beilstein]
6-aminocaproic acid lactam
6-Aminocaproic acid lactam, 2-Oxohexamethyleneimine
6-aminohexanoic acid cyclic lactam
6-Aminohexanoic acid lactam
6-Hexanolactam
Akulon
Alkamid
azaperhydroepin-2-one
Bonamid
CaP
Capran 77C
Capran 80
caprolactim
Caprolattame [French]
Caprolon B
Caprolon V
Capron
Capron B
Capron PK4
Chemlon
cis-Hexahydro-2-azepinone
cyclohexanone iso-oxime
Danamid
Durethan BK
Durethan BK 30S
Durethan BKV 30H
Durethan BKV 55H
E-caprolactum
e-Kaprolaktam [Czech]
Epsylon kaprolaktam [Polish]
Ertalon 6SA
Extrom 6N
Grilon
Hexahydro 2H Azepin 2 One
Hexahydro-2H-azepin-2-one
Hexahydro-2H-azepine-2-one
Hexamethylenimine, 2-oxo-
hexannic acid
Hexano-6-lactam
Hexanoic acid, 6-amino-, cyclic lactam
Hexanoic acid, 6-amino-, lactam
hexanoic acid-6-amino-,lactam
hexanolactam
hexanone isoxime
hexanone isozime
Hexanonisoxim [German]
ICC
Itamid
Itamide 250
Kaprolaktam
Kaprolit
Kaprolit B
Kaprolon
Kaprolon B
Kapromine
Kapron
Kapron A
Kapron B
Lactam, Aminocaproic
Maranyl F 114
Maranyl F 124
Maranyl F 500
Metamid
MFCD19226350 [MDL number]
Miramid H 2
Miramid WM 55
Orgamid rmnocd
Orgamide
PA 6
Perhydroazepin-2-one
PK 4
PKA
Plaskon 201
Plaskon XP 607
Relon P
Renyl MV
Spencer 401
Spencer 601
Steelon
STR02412
Stylon
T7MVTJ [WLN]
Tarlon X-A
Tarlon XB
Tarnamid T
Tarnamid T 2
Tarnamid T 27
tert-butyl 4-(2-(benzyloxycarbonyl)ethyl)piperazine-1-carboxylate
Torayca N 6
Ultramid B 3
Ultramid B 4
Ultramid B 5
Ultramid BMK
Vidlon
Widlon
ε-caprolactam
ε-Caprolactam
ω-caprolactum