Cyclohexanone
Cyclohexanone is an organic compound with the formula (CH2)5CO and it is a precursor to nylon.
Cyclohexanone is a cyclic ketone that consists of cyclohexane bearing a single oxo substituent
Cyclohexanone is also known as oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone or ketocyclohexane and it is a six-carbon cyclic molecule with a ketone functional group.
Preferred IUPAC name: Cyclohexanone
EC / List no.: 203-631-1
CAS no.: 108-94-1
Mol. formula: C6H10O
Chemical formula: C6H10O
Molar mass: 98.15 g/mol
Appearance: Colorless liquid
Odor: peppermint or acetone-like
Density: 0.9478 g/mL, liquid
Melting point: −47 °C (−53 °F; 226 K)[6]
Boiling point: 155.65 °C (312.17 °F; 428.80 K)
Solubility in water: 8.6 g/100 mL (20 °C)
Solubility in all organic solvents: Miscible
log P: 0.81
Vapor pressure: 5 mmHg (20°C
Magnetic susceptibility (χ): -62.04·10−6 cm3/mol
Refractive index (nD): 1.447
Viscosity: 2.02 cP at 25 °C[5]
Synonyms: oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
Cyclohexanone (also known as oxocyclohexane, pimelic ketone, cyclohexyl ketone, and CYC) is a clear oily liquid that has a colourless to light yellow tinge and a pungent odour. It is a sixcarbon cyclic molecule belonging to the class of cyclic ketones (organic compounds) with the formula C6H10O.
It is slightly soluble in water, completely miscible with common solvents and reacts with oxidants such as nitric acid. It 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's molecule consists of six-carbon cyclic molecule with a ketone functional group.
Cyclohexanone is colorless oily liquid and it has an odor reminiscent of acetone.
Over time, samples of cyclohexanone assume a pale yellow color.
Cyclohexanone is slightly soluble in water and miscible with common organic solvents.
Industrial Uses of Cyclohexanone:
Cyclohexanone is used predominantly (about 95% ) for the synthesis of raw materials used in the production of nylon.
The remainder is used as a chemical intermediate in other processes, as an additive or as a high-boiling, slow-drying solvent.
Cyclohexanone is used as a solvent in insecticides, wood stains, paint and varnish removers, spot removers, cellulosics, and natural and synthetic resins and lacquers.
Additive uses of Cyclohexanone include detergents, degreasing of metals, mould release agent for paints or varnishes, levelling agent in dyeing and delustering silk, and lube oil additive, especially for aircraft piston-type engines.
Cyclohexanone is also used as a monomer in the synthesis of cyclohexanone resins, polyvinyl chloride and its copolymers, and methacrylate ester polymers
The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6.
Cyclohexanone is used in the manufacture of precursors to Nylon 6,6 (like adipic acid) and Nylon 6.
About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6.
The other half of the cyclohexanone supply is converted to cyclohexanone oxime.
In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6
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.
Consumer uses of Cyclohexanone:
Cyclohexanone is found in various consumer products including in adhesives, paints, automotive, cleaning and furnishing care products, electronics, and photo chemicals.
Laboratory reactions of Cyclohexanone:
In addition to the large scale reactions conducted in service of the polymer industry, many reactions have been developed for cyclohexanone.
In the presence of light, Cyclohexanone undergoes alpha-chlorination to give 2-chlorocyclohexanone.
Cyclohexanone forms a trimethylsilylenol ether upon treatment with trimethylsilylchloride in the presence of base.
Cyclohexanone also forms an enamine with pyrrolidine.
Illicit use of Cyclohexanone:
Cyclohexanone has been used in the illicit production of phencyclidine and its analogs and as such is often subject to additional checks before purchase.
Production of Cyclohexanone:
Cyclohexanone is produced commercially in several major ways.
One widely used process yields cyclohexanol and cyclohexanone by the catalytic oxidation of cyclohexane.
The cyclohexanol/cyclohexanone product mixture, also called KA oil, is further reacted to produce adipic acid and hexamethylene diamine, intermediates in the manufacture of nylon 66.
Pure cyclohexanone can be produced in high yields by this process either by distillation or by catalytic dehydrogenation of the cyclohexanol.
Another important and very efficient process is based on the hydrogenation of phenol.
The cyclohexanone produced is further reacted to produce cyclohexanone oxime, an intermediate which then can undergo a Beckmann rearrangement to yield caprolactam, the important intermediate for nylon 6.
Cyclohexanone production and consumption are determined by the demand for raw materials for nylon.
Other uses of Cyclohexanone are minor and have little effect on overall production.
Production of cyclohexanone is based on the hydrogenation of benzene or by the oxidation of cyclohexane, in air, and typically in the presence of cobalt crystals.
Substance names and other identifiers
Regulatory process names
Anon
Anone
Cicloesanone
Cyclohexanon
Cyclohexanone
CYCLOHEXANONE
Cyclohexanone
cyclohexanone
Cyclohexyl ketone
Cykloheksanon
Hexanon
Hytrol O
Ketohexamethylene
Nadone
Pimelic ketone
Pimelin ketone
Sextone
Translated names
cicloesanone (it)
cicloexanona (pt)
ciclohexanona (es)
ciclohexanona (ro)
cikloheksanon (hr)
cikloheksanon (sl)
cikloheksanonas (lt)
cikloheksanons (lv)
ciklohexanon (hu)
cyclohexanon (da)
Cyclohexanon (de)
cyclohexanon (nl)
cyclohexanone (fr)
cykloheksanon (no)
cykloheksanon (pl)
cyklohexanon (cs)
cyklohexanon (sv)
cyklohexanón (sk)
Sykloheksanoni (fi)
Tsükloheksanoon (et)
κυκλοεξανόν (el)
цилкохексанон (bg)
CAS names: Cyclohexanone
Other IUPAC names
Cicloesanone
Cyclo hexanone
Cyclo hexanone
Cyclohexan
Cyclohexanon
Cyclohexanon
CYCLOHEXANONE
Cyclohexanone
cyclohexanone
Cyclohexanone
cyclohexanone
Cyclohexyl ketone
Trade names
Anon
Anon, pure
Anone
Cyclohexanon
Cyclohexanone
cyclohexanone
Cyclohexanone (7CI, 8CI, 9CI)
Cyclohexylketon
Cyklohexanone
Hexanon
Hytrol
Ketohexamethylen
Nadone
Oxocyclohexan
P2K KA
Pimelic ketone
Pimelin ketone
Pimelinketon
Sexton
YD-019CX40
ZX-219P40
CYCLOHEXANONE
108-94-1
Ketohexamethylene
Pimelic ketone
Sextone
Nadone
Anon
Anone
Cyclohexanon
Hexanon
Hytrol O
ketocyclohexane
oxocyclohexane
Pimelin ketone
Cykloheksanon
Cicloesanone
Cyclohexanone, homopolymer
Hytrolo
Cyclic ketone
NCI-C55005
RCRA waste number U057
Cyclohexanon [Dutch]
Caswell No. 270
Cicloesanone [Italian]
Cykloheksanon [Polish]
NSC 5711
CCRIS 5897
UNII-5QOR3YM052
MFCD00001625
9003-41-2
CHEMBL18850
5QOR3YM052
CHEBI:17854
NSC-5711
DSSTox_CID_359
DSSTox_RID_75537
DSSTox_GSID_20359
CYH
CAS-108-94-1
HSDB 186
EINECS 203-631-1
UN1915
RCRA waste no. U057
EPA Pesticide Chemical Code 025902
CYCLOHEXANONE POLYMER
cylcohexanone
cylohexanone
cyclo-hexanone
2-cyclohexanone
4-cyclohexanone
AI3-00041
Cyclohexanone,(S)
Cyclohexanon(dutch)
Cyclohexanone ACS grade
BDBM6
Cyclohexanone homopolymer
Cyclohexanone, 99.8%
WLN: L6VTJ
CYCLOHEXANONE [MI]
bmse000405
EC 203-631-1
CYCLOHEXANONE [FHFI]
CYCLOHEXANONE [HSDB]
CYCLOHEXANONE [IARC]
CYCLOHEXANONE [INCI]
MLS002152896
BIDD:ER0292
Cyclohexanone, LR, >=99%
DTXSID6020359
Cyclohexanone (Industrial Grade)
Cyclohexanone, p.a., 99.0%
Cyclohexanone, AR, >=99.5%
NSC5711
Cyclohexanone, analytical standard
HMS3039C04
Cyclohexanone - Reagent Grade ACS
ZINC4528575
Tox21_202121
Tox21_302750
s6236
STL183287
AKOS000119815
DB02060
UN 1915
Cyclohexanone, ACS reagent, >=99.0%
Cyclohexanone, ReagentPlus(R), 99.8%
NCGC00091786-01
NCGC00091786-02
NCGC00256489-01
NCGC00259670-01
9075-99-4
SMR001224507
Cyclohexanone 5000 microg/mL in Methanol
Cyclohexanone, puriss., >=99.5% (GC)
Cyclohexanone, SAJ first grade, >=98.0%
DB-059799
Cyclohexanone, Selectophore(TM), >=99.5%
FT-0624193
FT-0699543
Cyclohexanone [UN1915] [Flammable liquid]
Cyclohexanone, JIS special grade, >=99.0%
Cyclohexanone, Vetec(TM) reagent grade, 98%
EN300-19567
C00414
Cyclohexanone, puriss. p.a., >=99.5% (GC)
Q409178
J-520160
F0001-0185
