CAS no.: 105-60-2
Mol. formula: C6H11NO
Caprolactam
APPLICATIONS
Caprolactam is primarily used in the manufacture of synthetic fibers (especially Nylon 6).
Furthermore, Caprolactam is also used in brushbristles, textile stiffeners, film coatings, synthetic leather, plastics, plasticizers, paint vehicles, cross-linking for polyurethanes, and in the synthesis of lysine.
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 inhumans.
Some uses of Caprolactam:
Manufacture synthetic fibers of the polyamide type (Perlon); solvent for high mol wt polymers
Manufacture of synthetic fibers (especially nylon 6), plastics, bristles, film, coatings, synthetic leather, plasticizers and paintvehicles, cross-linking agent for polyurethanes, synthesis of amino acid lysine.
Almost all Caprolactam produced goes into the manufacture of Nylon 6.
The conversion entails a ring-opening polymerization.
In situanionic polymerization is employed for cast nylon production where conversion from Caprolactam to Nylon 6 takesplace inside a mold.
Epsilon-Caprolactam is a member of the class of Caprolactams that is azepane substituted by an oxo group at position 2.
Caprolactam has a role as a human blood serum metabolite.
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.
Caprolactam is a clear to milky white-colored solution with a mild, disagreeable odor.
Contact with Caprolactam may cause slight irritation to skin, eyes, and mucous membranes.
Caprolactam 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 it can easily penetrate the soil and contaminate groundwater and nearby streams.
Caprolactam is used to make other chemicals.
Because of its strong solubility, low toxicity and relatively low price, Caprolactam is widely used as solvent and thinner for various 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-formal dehyderesin, peroxy cyclohexanone, o-methyl phenol, antioxidant 4010 and so on.
Caprolactam is also called phenolic acid, is one of the simplest phenolic organic matter with weak acidity.
Furthermore, Caprolactam 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 of Caprolactam has strong corrosiveness on the skin.
Mistakenly contact with skin can be treated through rinsing with alcohol.
Addition of bromine water into the Caprolactam 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.
Caprolactam is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, atindustrial sites and in manufacturing.
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.
The advantage of this method is that cyclohexane is less expensive than cCaprolactam.
The immediate product of the acid-induced rearrangement is the bisulfate salt of Caprolactam.
Caprolactam 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 Caprolactam.
Caprolactam is used in the following products:
Inks and toners
Coating products
Fillers
Putties
Plasters
Modelling clay, 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.
Uses of Caprolactam:
Chemical is found in imported inks and applied to paper.
Dyes
Fabric, textile, and leather products not covered elsewhere
Floor coverings
Paper products
Fillers
Intermediates
Surface active agents
All other basic organic chemical manufacturing
Machinery manufacturing
Organic fiber manufacturing
Paper manufacturing
Plastic material and resin manufacturing
Plastics product manufacturing
Printing and related support activities
Textiles, apparel, and leather manufacturing
Caprolactam is an organic compound, this colourless solid is a lactam or a cyclic amide of caproic acid.
Approximately 4.5 billion kilograms are produced annually.
Caprolactam is the precursor to Nylon 6, a widely used synthetic polymer.
Firstly, Caprolactam was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of Caprolactam.
Given the commercial significance of Nylon-6, many methods have been developed for the production of Caprolactam:
Most of the Caprolactam is synthesised from cyclohexanone, which is first converted to its oxime.
Treatment of this oximewith acid induces the Beckmann rearrangement to give Caprolactam.
Caprolactam is used for industrial production of solid and liquid formulations, as an intermediate, as a monomer for themanufacture of polyamide, polymers, thermoplastics as a monomer for resins, a monomer for thermosetting resins, as aplasticizer for the polyamide, as an agent for leather tanning, processing, impregnation, a component of paints, varnishes andcoatings, as a laboratory reagent, as a component of paints, varnishes and coatings in consumer use.
Further, Caprolactam is an essential chemical used in the manufacture of nylon 6 synthetic fibers.
Nylon 6 fibers are used in the production of commercial and residential carpet, pharmaceutical and engineering plastics, andautomobile plastics parts and housings.
Caprolactam is a high production volume (HPV) chemical produced at over one million pounds annually and is listed by theUnited Nations Environmental Program.
Workplace exposures to Caprolactam during its manufacture, and when used as a chemical intermediate for production ofother chemicals, are expected to be minimal because exposures to Caprolactam dust are controlled with process enclosures,local exhaust ventilation, general dilution ventilation, and use of personal protective equipment.
Workplace exposure limits have been established for use in worksite safety programs.
Caprolactam is a solid, occurring as white flakes or crystals that will readily absorb moisture from the air.
Caprolactam is irritating to the eyes, skin, and respiratory tract.
Repeated or prolonged contact may cause inflammation ofthe skin (e.g. a rash).
Breathing Caprolactam vapors and/or dust may irritate the membranes of the nose and throat, and it may cause reversiblesymptoms such as nausea, vomiting, dizziness and headache at high concentrations.
Caprolactam is slightly toxic in theunlikely event it’s swallowed.
Release to the environment of Caprolactam can occur from industrial use: industrial abrasion processing with low releaserate (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), outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic constructionand building materials), indoor use and outdoor use as reactive substance.
Caprolactam can be found in complex articles, with no release intended: vehicles, machinery, mechanical appliances andelectrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines) and electrical batteries andaccumulators.
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) and rubber (e.g. tyres, shoes, toys).
Widespread uses by professional workers:
Caprolactam is used in the following products: laboratory chemicals.
Caprolactam is used for the manufacture of: textile, leather or fur and plastic products.
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) and outdoor use.
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.
Caprolactam 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 andYueyang Petrochemical Design Institute.
Cyclohexanone and phenol are the main raw materials for the production of Caprolactam:
Caprolactam is a kind of important chemical raw material with wide range of application fields.
Furthermore, 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.
Nylon 6 is produced by ring-opening polymerization of Caprolactam.
More than 98% of the Caprolactam is produced using cyclohexanone as an intermediate.
Cyclohexanone is obtained either by hydrogenation of phenol, or by catalytic and non-catalytic oxidation of cyclohexane withair or by hydration of cyclohexene to cyclohexanol followed by dehydrogenation.
The most common cyclohexanone production process is promoted by oxidation of cyclohexane in the presence of catalyticmetal salts to obtain a reaction mixture known as KA-oil, which contains cyclohexanone, cyclohexanol and other impurities.
Cyclohexanone, after being purified from KA-oil, reacts with hydroxylamine (usually added as hydroxylamine sulphate) toproduce cyclohexanone oxime .
In this reaction, the sulphuric acid formed is neutralized using ammonia and ammonium sulphate is obtained as by-product.
To avoid the formation of ammonium sulphate, the ammoximation of cyclohexanone has been recently proposed.
In the ammoximation of cyclohexanone, aqueous H2O2 and ammonia react with cyclohexanone by means of solidtitanosilicate as a catalyst (known as TS-1).
After oximation, the Beckmann rearrangement (BR) of cyclohexanone oxime in oleum media produces -Caprolactam.However, besides Caprolactam, other by-products are formed in the Beckmann rearrangement process.
Caprolactam is rapidly metabolized and eliminated from the body.
Furthermore, Caprolactam does not interfere with the ability to successfully reproduce or cause adverse effects to a developing childduring pregnancy.
The cancer risk for Caprolactam is low.
The potential for Caprolactam to be toxic to aquatic organisms is low.
Caprolactam has minimal potential to accumulate in the bodies of humans or animals.
Moreover, Caprolactam is readily biodegradable and will not persist in the environment.
Some Spesific Uses of Caprolactam:
(1) The majority of Caprolactam is used in the production of Polycaprolactam, of which about 90% is used for the production ofsynthetic fibers, that is, Kaplon, 10% used as plastic for the manufacture of gears, bearings, pipe, medical equipment andelectrical, 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 rawmaterials.
(3) Caprolactam can be used as polymer solvent, for the manufacture of polyamide-based synthetic fiber and the fixing phaseof gas chromatography:
Manufacture of synthetic fibers of the polyamide type (Perlon); solvent for high mol wt polymers; precursor of nylon-6, q.v.
Monomer for manufacture of polyCaprolactam (Nylon 6) used in carpets, textiles, clothing, and tires
Caprolactam may be released to the environment during its manufacture and use in the preparation of resins and plastics.
Further, Caprolactam has been detected in surface water, groundwater and drinking-water.
Caprolactam can be used as a precursor for the production of nylon-6 by ring-opening polymerization.
Caprolactam is also microwave irradiated with caprolactone in the presence of an anionic catalyst to yield poly(Caprolactam-co-ε-caprolactone).
Caprolactam is one of the most widely used chemical intermediates.
However, almost all of its annual production is consumed as the monomer for nylon 6 fibers and plastics.
Caprolactam is a white, hygroscopic, crystalline solid at room temperature.
Caprolactam production technology is based on the key intermediate cyclohexanone, which is usually produced by theoxidation of cyclohexane, but can also be produced from phenol.
A disadvantage of current processes is the large amounts of ammonium sulfate produced.
Producers are working on new processes to allow for a significant reduction in this by-product.
Caprolactam has a low level of toxicity.
Nylon carpets and rugs are now being recycled, and the nylon 6 fiber used can be depolymerized back to Caprolactam.
Uses other than fibers are in nylon resins for engineering plastics and automotive applications.
Caprolactam is used in the following products: adhesives and sealants, coating products, fillers, putties, plasters, modellingclay, 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 inmaterials.
Uses at industrial sites:
Caprolactam is used in the following products: polymers.
More to that, 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 an intermediatestep in further manufacturing of another substance (use of intermediates), as processing aid and in the production ofarticles.
Caprolactam is primarily used in the manufacture of synthetic fibers (especially Nylon 6).
In addition, 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 is also used in production of :
Brush bristles,
Textile stiffeners,
Film coatings,
Synthetic leather,
Plastics and plasticizers,
Paint vehicles,
Cross-linking for polyurethanes,
Lysine (synthesis).
Other applications of Caprolactam:
Manufacturing of plastics
Manufacturing of fibres
Textile industry
Plastic- and Rubberpolymers
Chemical synthesis
Chemical Industry
DESCRIPTION
Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH.
Caprolactam is a lactam (a cyclic amide) of caproic acid.
Global demand for tCaprolactam is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics.
Caprolactam is a clear to milky white-colored solution with a mild, disagreeable odor.
Contact may cause slight irritation to skin, eyes, and mucous membranes.
Caprolactam 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.
Caprolactam is used to make other chemicals.
Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the productof 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 chemicalintermediate.
Caprolactam, CH2CH2CH2CH2CH2NHCO, is a solid material composed of white flakes.
Further, 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.
Moreover, 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.
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 anddehydrogenation 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 inthe presence of sulfuric acid.
Caprolactam is a crystalline cyclic amide with a melting point of 70 °C.
More to that, Caprolactam is soluble in water, most oxygenated and chlorinated solvents, and some hydrocarbons.
E-Caprolactam is the only common Caprolactam isomer.
Due to its 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 this oxime 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.
The amide formation reaction succeeds only when run in dilute solution; otherwise, aminocaproic acid polymerizes (which is a good thing).
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.
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 manufactureand 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.
SYNONYMS
AMINOCAPROIC LACTAM
2-KETOHEPTAMETHYLENEIMINE
2-KETOHEXAMETHYLENEIMINE
2-KETOHEXAMETHYLENIMINE
2-OXOHEXAMETHYLENEIMINE
2-OXOHEXAMETHYLENIMINE
1,6-HEXOLACTAM
ε-Caprolactam Zone Refined (number of passes:24)
1,6-hexanolactam
.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
CYCLOHEXANONEISOOXIME
E-Caprolactam
Caprolactam
CPL
HEXAHYDRO-2H-AZEPIN-2-ONE
EPSILUM-Caprolactam
EPSILON-CAP
EPSILON-Caprolactam
AZA-2-CYCLOHEPTANONE
6-HEXANOLACTAM
6-Caprolactam
6-AMINOCAPROIC ACID LACTAM
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
Caprolactam,99%
Hexahydro-2H-azepine-2-one~2-Oxohexamethyleneimine
perhydroazepin-2-one
Capron B
Capron gr 8256
Capron gr 8258
Capron pk4
capronpk4
Chemlon
CM 1001
CM 1011
CM 1031
CM 1041
cyclohexanoneiso-oxime[qr]
Caprolactam (NYLON FIBRE GRADE)
6-Aminocaproic lactam
EPSILON-Caprolactam, 99+%
EPSILON-Caprolactam 99%
1,6-Caprolactam
Nylon 6 monomer
epsilon-Caprolactam, 99.5%
1,6-hexolactam[qr]
1-Aza-2-cycloheptanone
2-Azacycloheptanone
6-Aminohexanoic acid lactam
6-amino-hexanoicacicycliclactam
6-amino-hexanoicacicycliclactam[qr]
6-aminohexanoicacidcycliclactam
6-amino-hexanoicacilactam
6-amino-hexanoicacilactam[qr]
6-caprolactan[qr]
6-Hexanelactam
Danamid
Dull 704
Durethan bk
Durethan bk 30S
Durethan bkv 30H
