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CYCLOHEXANONE

CAS NUMBER: 108-94-1

EC NUMBER: 203-631-1

MOLECULAR FORMULA: C6H10(=O)

MOLECULAR WEIGHT: 98.14

Cyclohexanone is a cyclic ketone with a minty odor. 
Cyclohexanone is reported to be present in volatile flavor fraction of kiwi fruit pulp and acerola fruit.
Cyclohexanone appears as a colorless to pale yellow liquid with a pleasant odor. Less dense than water. 

Flash point 111°F. Vapors heavier than air. 
Used to make nylon, as a chemical reaction medium, and as a solvent.
Cyclohexanone is a cyclic ketone that consists of Cyclohexanone bearing a single oxo substituent. 

Cyclohexanone has a role as a human xenobiotic metabolite.
Cyclohexanone (also known as oxoCyclohexanone, pimelic ketone, ketohexamethylene, cyclohexyl ketone or ketoCyclohexanone) is a six-carbon cyclic molecule with a ketone functional group. 
Cyclohexanone is a colorless, oily liquid with an acetone-like smell.

Cyclohexanone is the organic compound with the formula (CH2)5CO. 
The molecule consists of six-carbon cyclic molecule with a ketone functional group. 
This colorless oil has an odor reminiscent of that of acetone. Over time, samples of cyclohexanone assume a yellow color. 

Cyclohexanone is slightly soluble in water and miscible with common organic solvents. 
Billions of kilograms are produced annually, mainly as a precursor to nylon.
Cyclohexanone, a colorless liquid is a cyclic ketone. 

Cyclohexanone is an important building block for the synthesis of a variety of organic compounds. 
Majority of the cyclohexanone synthesized is utilized as an intermediate in the synthesis of nylon. 
One of the methods reported for its synthesis is by the palladium catalyzed hydrogenation of phenol. 
The kinetics of the oxidation reaction of cyclohexanone has been studied in a fused silica jet stirred reactor. 
The Meerwein–Ponndorf–Verley reduction of cyclohexanone has been reported.

Cyclohexanone also known as OxoCyclohexanone, pimelic ketone, cyclohexyl ketone, and CYC is a clear oily liquid that has a colourless to light yellow tinge, a pungent odour and has the molecular formula C6H10O, CAS:108-94-1. 
Cyclohexanone has a specific gravity of 0.945 and a flash point of 46 °C. 

Cyclohexanone is slightly soluble in water and is completely miscible with common solvents.  
Cyclohexanone occurs naturally in crude oils and is also produced synthetically, in large quantities, as it is a key intermediate in the production of nylon.

Cyclohexanone is mostly captively consumed, either isolated or as a mixture, in the production of nylon intermediates (adipic acid and Caprolactam). 
Around 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.

Cyclohexanone is produced from either phenol or Cyclohexanone. 
Fibrant masters technologies that use any of these feedstocks 
Cyclohexanone has developed a unique technology portfolio to secure a reliable and high quality raw material supply to its Caprolactam units.

Cyclohexanone (also known as oxoCyclohexanone, pimelic ketone, cyclohexyl ketone, and CYC) is a clear oily liquid that has a colourless to light yellow tinge and a pungent odour. 

Cyclohexanone is a sixcarbon cyclic molecule belonging to the class of cyclic ketones (organic compounds) with the formula C6H10O.
Cyclohexanone is slightly soluble in water, completely miscible with common solvents and reacts with oxidants such as nitric acid. 
Cyclohexanone occurs naturally in crude oils and is also produced synthetically, in large quantities, as it is a key intermediate in the production of nylon.

Cyclohexanone is an alicyclic hydrocarbon containing a ring of six carbon atoms; The cyclic form of hexane, used as a raw material in the production of nylon.
Cyclohexanone has a role as a non-polar solvent. 
Cyclohexanone is a cycloalkane and a volatile organic compound.

Cyclohexanone appears as a clear colorless liquid with a petroleum-like odor. 
Cyclohexanone is used in making nylon, as a solvent, as a paint remover and in making other chemicals. 
Flash point -4°F. Density 6.5 lb/gal (less than water) and insoluble in water. 
Vapors heavier than air.

Cyclohexanone is a cycloalkane with the molecular formula C6H12. Cyclohexanone is non-polar. 
Cyclohexanone is a colorless, flammable liquid with a distinctive detergent-like odor reminiscent of (sometimes used in) cleaning products.

Cyclohexanone is mainly used for the industrial production of adipic acid and caprolactam, the precursors of nylon.
Cyclohexanone (also known as CYX, hexamethylene, hexahydrobenzene, hexanaphthene, and benzenehexahydride) is a colorless, volatile and flammable liquid with the formula C6H12.

Cyclohexanone has a slight odor and is insoluble in water, but soluble in alcohol, ether, acetone, benzene, and ligroin.
Cyclohexanone occurs naturally in crude oil, volcanic gases, and cigarette smoke.
Cyclohexanone  is an organic compound, belonging to the aliphatic amine class. 

Cyclohexanone is a colorless liquid, although, like many amines, samples are often colored due to contaminants. 
Cyclohexanone has a fishy odor and is miscible with water. 
Like other amines, Cyclohexanone is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.

Cyclohexanone is a useful intermediate in the production of many other organic compounds.
Cyclohexanone  is used as an intermediate in synthesis of other organic compounds. 
Cyclohexanone is the precursor to sulfenamide-based reagents used as accelerators for vulcanization. 

Cyclohexanone is a building block for pharmaceuticals (e.g., mucolytics, analgesics, and bronchodilators). 
The amine itself is an effective corrosion inhibitor. Some sweeteners are derived from this amine, notably cyclamate. 
The herbicide hexazinone and the anesthetic hexylcaine are derived from Cyclohexanone.
Cyclohexanone is corrosive. 

Cyclohexanone  is listed as an extremely hazardous substance as defined by Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. 
Cyclohexanone has been used as a flushing aid in the printing ink industry.

Cyclohexanone  appears as a clear colorless to yellow liquid with an odor of ammonia. 
Flash point 90°F. Irritates the eyes and respiratory system. 
Skin contact may cause burns. Less dense than water.
Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

Cyclohexanone  is a primary aliphatic amine consisting of Cyclohexanone carrying an amino substituent. 
Cyclohexanone has a role as a human xenobiotic metabolite and a mouse metabolite. 
Cyclohexanone is a conjugate base of a cyclohexylammonium.
On distillation with water, Cyclohexanone  forms azeotropic mixt, boiling @ 96.4 °C @ 760 mm Hg; reacts with excess ammonia and zinc chloride @ 350 °C to produce alpha-picoline.

Cyclohexanone  showed dose dependent kinetics after administration of single oral doses of 35, 200, or 500 mg/kg in rats, with a reduction in plasma clearance from 37 to 24 ml/min/kg, an increase in apparent half-life from 11.8 to 12 hr, and an increased area under the testicular concentration vs time curve. 

The steady state plasma clearance was 33 ml/min/kg. 
The concentrations of Cyclohexanone in the plasma and testes of rats showed a nonlinear relationship to dietary intake. 
Elevated concentrations were found at intake greater than 200 mg/kg/day.Generally, Cyclohexanone , is readily absorbed & rapidly excreted from the body. 

After admin to rats, Cyclohexanone  appears in body tissues with the highest concn in the lungs, spleen, liver, adrenals, heart, GI tract & kidneys.After oral admin (0.2 g/kg) to rabbits, Cyclohexanone  gave rise to unchanged Cyclohexanone  & N-hydroxyCyclohexanone  in the urine. 
When C14-labeled Cyclohexanone  was admin, 68% of the radioactivity was recovered in the urine after 60 hr. 

A small amount (0.5%) was eliminated in the breath & 45% of the admin dose was shown to be excreted in the urine as unconjugated Cyclohexanone , 0.2% as N-hydroxyCyclohexanone  in conjugated form, & 2.5% as cyclohexanone oxime. The authors postulated the latter metabolite to be an artifact formed form the glucuronide of N-hydroxyCyclohexanone  during the hydrolysis procedure.

All of these species convert cyclamate to Cyclohexanone , via the action of gastrointestinal microflora on unabsorbed cyclamate. 
The metabolism of Cyclohexanone  to other products differs somewhat in humans and other species, although most Cyclohexanone  is rapidly excreted unchanged in the urine. In rats, it is metabolized mainly by hydroxylation of the Cyclohexanone ring; in humans, it is metabolized by deamination; and in guinea pigs and rabbits, it is metabolized by ring hydroxylation and deamination.

Concentrations of Cyclohexanone  in plasma (ug/ml) after 3 weeks feeding were 0.20; after 7 weeks 0.18; and after 13 weeks, 4.51 + or - 2.94. 
Concentrations of the chemical in testes (ug/g wet weight) varied from 6.81 + or - 5.21 at 3 weeks to 4.51 + or - 2.94 at 13 weeks.
Wistar and DA rats were fed Cyclohexanone  (as the hydrochloride) at constant intake of 400 mg/kg/day for 13 weeks. 

The metabolism of (14)C-labeled Cyclohexanone  administered as a single oral dose (8 uCi per rat) was similar for both strains of rat, with no consistent effect due to age or prolonged feeding with Cyclohexanone. 
However, there was reduced elimination of (14)C in the treated Wistar and DA rats compared to that in the controls during the first 6 hr after dosing; the difference was statistically significant at 3 weeks in both strains and at 13 weeks in the DA strain. 

The major metabolites produced were 3- and 4-aminocyclohexanols; at 13 weeks the total metabolism was 17% to 18% for the Wistar rats, 4% to 6% in the DA rats. 
After 13 weeks, testicular atrophy was demonstrated in both strains of rat fed Cyclohexanone ; DA rats appeared more sensitive to testicular toxicity than the Wistar rats. 
Concentrations of Cyclohexanone  and its metabolites in plasma and in testicular tissue were higher in Wistar rats than in DA rats.

Cyclohexanone  showed dose dependent kinetics after administration of single oral doses of 35, 200 or 500 mg/kg in mice, with a reduction in plasma clearance from 61 to 53 ml/min/kg, an increase in apparent half-life from 1.4 to 3.5 hr, and an increased area under the testicular concentration vs time curve. During chronic dietary administration the concentrations of Cyclohexanone  in the plasma and testes showed little diurna variation. 
The steady state plasma clearance was 65 ml/min/kg. 

The concentrations of Cyclohexanone  in the plasma and testes of the mice showed a linear relationship to dietary intake, even at the highest intake, about 900 mg/kg/day.Prepared by catalytic hydrogenation of aniline at elevated temp and pressures. Fractionation of crude reaction product yields Cyclohexanone , unchanged aniline, and high-boiling residue containing n-phenylCyclohexanone  (cyclohexylaniline) and diCyclohexanone .

Used as a polyvinyl chloride (PVC) solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. 
Cyclohexanone probably does not cross react with cyclohexanone resin. 

Cyclohexanone derived resin used in paints and varnishes caused contact dermatitis in painters.
A colorless liquid alkane that is commonly used as a solvent and in the production of hexanedioic acid (adipic acid) for the manufacture of nylon. 
Cyclohexanone, itself, is manufactured by the reformation of longer chain hydrocarbons present in crude-oil fractions. 

Cyclohexanone is also interesting from a structural point of view, existing as a ‘puckered’ six-membered ring, having all bonds between carbon atoms at 109.9° (the tetrahedral angle). 
The molecule undergoes rapid interconversion between two ‘chair-like’ conformation, which are energetically equivalent, passing through a ‘boat-like’ structure of higher energy. It is commonly represented by a hexagon.

Cyclohexanone is fractionated from crude oil and may be released wherever petroleum products are refined, stored, and used. 
Cyclohexanone is prepared synthetically from benzene, by hydrocracking of cyclopentane, or from toluene by simultaneous dealkylation and double bond hydrogenation.

USES:

The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon. 
About half of the world's supply is converted to adipic acid, one of two precursors for nylon. 
For this application, the KA oil (see above) is oxidized with nitric acid. 
The other half of the cyclohexanone supply is converted to cyclohexanone oxime.

Cyclohexanone is an important industrial chemical as it is a chemical intermediate used in the production of specific target molecules.  
In fact, the consumption of cyclohexanone is linked almost entirely to the nylon industry with derivatives of it used to produce adipic acid and caprolactam, which are precursors for nylon 6. 
Other cyclohexanone derivatives are used for the synthesis of pharmaceuticals, dyes, herbicides, pesticides, plasticizers and rubber chemicals.

Cyclohexanone has many industrial uses, primarily as an industrial chemical and chemical intermediate in the production of specific target molecules.
In fact, the consumption of cyclohexanone is linked almost entirely to the nylon industry with derivatives oxidised to produce adipic acid and caprolactam, which are precursors for nylon 6. Up to 70% of the world’s caprolactam is produced via cyclohexanone.

Other cyclohexanone derivatives are used for the synthesis of pharmaceuticals, dyes, herbicides, pesticides, plasticisers, and rubber chemicals. 
Additional industry uses of cyclohexanone include as an adhesive, fuel, paint and coating additive and laboratory chemical.

Cyclohexanone is used as a solvent for lacquers, paints, resins, degreasers, spot removers, polymers, copolymers, waxes, crude rubber, cellulose acetate, the manufacturing of herbicides and anihistamines.

Cyclohexanone is used predominantly in the nylon industry, where about 90% is consumed in the industrial production of adipic acid and caprolactam, which are themselves used to produce nylon6 and nylon6.6.
The remaining 10% is used both as a solvent and plasticizer for paints, resins, varnish and oil.

Cyclohexanone is also used as an intermediate in the manufacture of other industrial chemicals such as Cyclohexanone, cyclohexanone, and nitrocyclohexanone.
Cyclohexanone is a water-white to slightly yellow liquid with a peppermint-like or acetone-like odor. 
The Odor Threshold is 0.12 0.24 ppm in air.

Industrial solvent for cellulose acetate resins, vinyl resins, rubber, and waxes; solventsealer for polyvinyl chloride; in printing industry; coating solvent in audio and videotape production

Cyclohexanone is a petroleum product obtainedby distilling C4- 400°F boiling rangenaphthas, followed by fractionation andsuperfractionation; also formed by catalytichydrogenation of benzene. 
Cyclohexanone is usedextensively as a solvent for lacquers andresins, as a paint and varnish remover, andin the manufacture of adipic acid, benzene,cyclohexanol, and cyclohexanone.

USAGE AREAS:

-Cyclohexanone is used in the production of chemical substances.

-Cyclohexanone is used in the sectors of paint and varnish.

-Cyclohexanone is used as a cleaner.

-Cyclohexanone is used as a solvent.

-Cyclohexanone is used in the sector of agricultural pesticide.

 

APPLICATION:

Cyclohexanone is the raw material for the production of caprolactam and adipic acid; used as the solvents and diluent agents of paints, inks, synthetic resins and synthetic rubber; also used as leather degreasing agent.
Used as organic solvent;
Raw materials and solvents of synthetic resin and synthetic fiber;
Cyclohexanone is an important chemical raw material, being the major intermediates of making nylon, caprolactam and adipic acid. 

Cyclohexanone is also an important industrial solvent, for example, for paints, especially for those containing nitrocellulose, vinyl chloride polymers and their copolymers or methacrylate polymer paints. Used as an excellent solvent for pesticides such as organophosphate insecticide. 

Cyclohexanone is used as a solvent for dyes, viscous solvents for piston aviation lubricants, solvents for greases, waxes and rubbers. 
Also used as leveling agent for dyeing and fading silk; degreasing agents for polishing metal; wood coloring paint; also used for cyclohexanone stripping, decontamination and spot removal. 

Cyclohexanone and cyanoacetic acid can have condensation reaction to generate cyclohexylidene acetic acid, and then followed by elimination and decarboxylation to get cyclohexene acetonitrile, and finally giving cyclohexene ethylamine by hydrogenation. 

Cyclohexene ethylamine is a intermediate for some drugs.
The solvents for fibers, resins, rubbers, paraffins, shellac and DDT; for organic synthesis; it can dissolve many of the complexes formed by the elements and organic reagents; bismuth determination; extract rare metal such as uranium, thorium, cobalt and titanium.

-Cyclohexanone is used as an additive in agricultural pesticides.
-Cyclohexanone is used in the plastic industry.

-Cyclohexanone is used in the adhesive industry.
-Cyclohexanone is used in the paint and varnish industry.
-Cyclohexanone is a toxic chemical material. Not inhalation, contact with skin should be avoided.

PROPERTIES:


-Cyclohexanone is used as an additive in agricultural pesticides.
-Cyclohexanone is used in the plastic industry.
-Cyclohexanone is used in the adhesive industry.

-Cyclohexanone is used in the paint and varnish industry.
-Cyclohexanone is a colorless, clear and liquid chemical substance.
-Cyclohexanone is a chemical material with its own characteristic odor.
-Cyclohexanone has ketone dissolving properties.

-biological source: synthetic

-Agency/Method: meets purity specifications of JECFA

-vapor density: 3.4 (vs air)

-vapor pressure: 3.4 mmHg ( 20 °C)

-assay: 99.8%

-form: liquid

-autoignition temp.: 788 °F

-expl. lim.: 1.1 %, 100 °F 9.4 %

-refractive index: n20/D 1.450 (lit.)

CHEMICAL PROPERTIES:

Cyclohexanone is a colorless, clear liquid with soil smell; its impure product appears as light yellow color. 
Cyclohexanone is miscible with several other solvents. easily soluble in ethanol and ether. 
The lower exposure limit is 1.1% and the upper exposure limit is 9.4%. 
Cyclohexanone may be incompatible with oxidizers and nitric acid.

Cyclohexanone is a primarily used in industry, up to 96%, as a chemical intermediate in the production of nylons 6 and 66. 
Oxidation or conversion of cyclohexanone yields adipic acid and caprolactam, two of the immediate precursors to the respective nylons. 
Cyclohexanone can also be used as a solvent in a variety of products, including paints, lacquers, and resins. 
Cyclohexanone has not been found to occur in natural processes.

PHYSICAL PROPERTIES:

Clear, colorless to pale yellow, oily liquid with a peppermint-like odor. 

PRODUCTION:

Production of cyclohexanone is based on the hydrogenation of benzene or by the oxidation of Cyclohexanone, in air, and typically in the presence of cobalt crystals.


STORAGE:

Cyclohexanone can be transported in drums and/or tank trucks. 
Cyclohexanone should be stored in a cool, dry, well-ventilated area that is free from the risk of ignition. 
For transportation purposes, it falls into packing group III and hazard class III and it is an Irritant and is highly flammable. 
Cyclohexanone has a specific gravity of 0.945 and a flashpoint of 46 °C (closed cup).


SYNONYM:

Ketohexamethylene
Pimelic ketone
Sextone
Cyclohexyl ketone
Nadone
Anone
Anon
Cyclohexanon
Hytrol O
Hexanon
ketoCyclohexanone
oxoCyclohexanone
Pimelin ketone
Cykloheksanon
Cicloesanone
Cyclohexanone, homopolymer

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