| Identification | More | [Name]
Cyclohexanone | [CAS]
108-94-1 | [Synonyms]
AKOS BBS-00004296
ANONE
CYCLOHEXANONE
FEMA 3909
HEXANONE
KETOCYCLOHEXANE
KETOHEXAMETHYLENE
PIMELIC KETONE
Anon
caswellno270
Cicloesanone
Cykloheksanon
cykloheksanon(polish)
epapesticidechemicalcode025902
Hexanon
Hytrol O
hytrolo
Nadone
NCI-C55005
Oxocyclohexane | [EINECS(EC#)]
203-631-1 | [Molecular Formula]
C6H10O | [MDL Number]
MFCD00001625 | [Molecular Weight]
98.14 | [MOL File]
108-94-1.mol |
| Chemical Properties | Back Directory | [Appearance]
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. | [Melting point ]
-47 °C | [Boiling point ]
155 °C(lit.)
| [density ]
0.947 g/mL at 25 °C(lit.)
| [vapor density ]
3.4 (vs air)
| [vapor pressure ]
3.4 mm Hg ( 20 °C)
| [FEMA ]
3909 | [refractive index ]
n20/D 1.450(lit.)
| [Fp ]
116 °F
| [storage temp. ]
Flammables area | [solubility ]
90g/l | [form ]
Liquid | [pka]
17(at 25℃) | [color ]
APHA: ≤10 | [Odor]
Like peppermint and acetone. | [PH]
7 (70g/l, H2O, 20℃) | [Relative polarity]
0.281 | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [explosive limit]
1.1%, 100°F | [Odor Type]
minty | [Water Solubility ]
150 g/L (10 ºC) | [JECFA Number]
1100 | [Merck ]
14,2726 | [BRN ]
385735 | [Henry's Law Constant]
1.2 x 10-5 atm?m3/mol at 25 °C (Hawthorne et al., 1985)
6.92 x 10-5 atm?m3/mol at 60.00 °C, 10.7 at 70.00 °C, 16.4 at 80.00 °C (headspace-GC, Hovorka et al., 2002) | [Dielectric constant]
18.2（20℃） | [Exposure limits]
TLV-TWA 100 mg/m3 (25 ppm) (ACGIH);
IDLH 5000 ppm (NIOSH). | [Contact allergens]
Used as a polyvinyl chloride solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross-react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters | [LogP]
0.86 at 25℃ | [CAS DataBase Reference]
108-94-1(CAS DataBase Reference) | [IARC]
3 (Vol. 47, 71) 1999 | [NIST Chemistry Reference]
Cyclohexanone(108-94-1) | [EPA Substance Registry System]
108-94-1(EPA Substance) |
| Hazard Information | Back Directory | [Definition]
ChEBI: A cyclic ketone that consists of cyclohexane bearing a single oxo substituent. | [General Description]
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. | [Reactivity Profile]
CYCLOHEXANONE(108-94-1) forms an explosive peroxide with H2O2, and reacts vigorously with oxidizing materials (nitric acid). | [Air & Water Reactions]
Flammable. Soluble in water. | [Health Hazard]
Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis. | [Potential Exposure]
May form explosive mixture with air.
Contact with oxidizing agents or nitric acid may cause a
violent reaction. Do not use brass, copper, bronze, or lead
fittings. Attacks many coatings and plastic materials. | [Fire Hazard]
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
Medical attention immediately. If this chemical contacts
the skin, remove contaminated clothing and wash immedi-
ately with soap and water. Seek medical attention immedi-
ately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precau-
tions, including resuscitation mask) if breathing has stopped
and CPR if heart action has stopped. Transfer promptly to a
medical facility. When this chemical has been swallowed,
get medical attention. Give large quantities of water and
induce vomiting. Do not make an unconscious person
vomit. | [Shipping]
UN1915 Cyclohexanone, Hazard Class: 3;
Labels: 3-Flammable liquid. | [Incompatibilities]
May form explosive mixture with air.
Contact with oxidizing agents or nitric acid may cause a
violent reaction. Do not use brass, copper, bronze, or lead
fittings. Attacks many coatings and plastic materials. | [Description]
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. A cyclohexanone-derived resin used in paints
and varnishes caused contact dermatitis in painters.
| [Waste Disposal]
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. | [Physical properties]
Clear, colorless to pale yellow, oily liquid with a peppermint-like odor. Experimentally
determined detection and recognition odor threshold concentrations were identical: 480 μg/m3
(120 ppmv) (Hellman and Small, 1974). | [Occurrence]
Reported present in Cistus labdaniferus. | [Uses]
Cyclohexanone is used in the productionof adipic acid for making nylon; in thepreparation of cyclohexanone resins; and asa solvent for nitrocellulose, cellulose acetate,resins, fats, waxes, shellac, rubber, and DDT.. | [Uses]
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 | [Synthesis Reference(s)]
Canadian Journal of Chemistry, 62, p. 1031, 1984 DOI: 10.1139/v84-171
Tetrahedron Letters, 25, p. 3309, 1984 DOI: 10.1016/S0040-4039(01)81371-X | [Flammability and Explosibility]
Flammable | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Synthesis]
It may be synthesized on a laboratory scale by the oxidation of cyclohexanol. | [Carcinogenicity]
IARC considers the animal data for cyclohexanone as
inadequate evidence of carcinogenicity and listed cyclohexanone
as not classifiable for carcinogenicity (IARC
Category 3). | [Environmental Fate]
Biological. In activated sludge inoculum, 96.0% COD removal was achieved. The average rate
of biodegradation was 30.0 mg COD/g?h (Pitter, 1976).
Photolytic. Atkinson (1985) reported an estimated photooxidation rate constant of 1.56 x 10-11
cm3/molecule?sec for the reaction of cyclohexanone and OH radicals in the atmosphere at 298 K.
Chemical/Physical. Cyclohexanone will not hydrolyze because it has no hydrolyzable
functional group.
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in effluent
concentration of 332 mg/L. The adsorbability of the carbon used was 134 mg/g carbon (Guisti et
al., 1974). Similarly, at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption
capacities were 36, 6.2, 1.1, and 0.19 mg/g, respectively (Dobbs and Cohen, 1980). | [storage]
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with Cyclohexanone you should be trainedon its proper handling and storage. Before entering confinedspace where this chemical may be present, check to make sure that an explosive concentration does not exist.Cyclohexanone must be stored to avoid contact with oxidizers (such as perchlorates, peroxides, chlorates, nitrates, andpermanganates), since violent reactions occur. Store intightly closed containers in a cool well-ventilated area awayfrom heat, sparks, and flames. Metal containers involvingthe transfer of this chemical should be grounded andbonded. Where possible, automatically pump liquid fromdrums or other storage containers to process containers.Drums must be equipped with self-closing valves, pressurevacuum bungs, and flame arresters. Use only nonsparkingtools and equipment, especially when opening and closingcontainers of this chemical. Sources of ignition, such assmoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could createa potential fire or explosion hazard. Wherever this chemicalis used, handled, manufactured, or stored, use explosionproof electrical equipment and fittings.Cyclohexanone requires a “FLAMMABLELIQUID” label. It falls in Hazard Class 3 and PackingGroup II | [Purification Methods]
Dry cyclohexanone with MgSO4,CaSO4, Na2SO4 or Linde type 13X molecular sieves, then distil it. Cyclohexanol and other oxidisable impurities can be removed by treatment with chromic acid or dilute KMnO4. More thorough purification is possible by conversion to the bisulfite addition compound, or the semicarbazone, followed by decomposition with Na2CO3 and steam distillation. [For example, equal weights of the bisulfite adduct (crystallised from water) and Na2CO3 are dissolved in hot water and, after steam distillation, the distillate is saturated with NaCl and extracted with Et2O which is then dried (anhydrous MgSO4 or Na2SO4), filtered and the solvent evaporated prior to further distillation.] FLAMMABLE [Beilstein 7 III 14, 7 IV 15.] |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable.
R20:Harmful by inhalation. | [Safety Statements ]
S25:Avoid contact with eyes . | [RIDADR ]
UN 1915 3/PG 3
| [WGK Germany ]
1
| [RTECS ]
GW1050000
| [Autoignition Temperature]
788 °F | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29142200 | [Safety Profile]
Suspected carcinogen.
Moderately toxic by ingestion, inhalation,
subcutaneous, intravenous, and
intraperitoneal routes. A skin and severe eye
irritant. Human systemic effects by
inhalation: changes in the sense of smell,
conjunctiva irritation, and unspecified
respiratory system changes. Human irritant
by inhalation. Mdd narcotic properties have
also been ascribed to it. Human mutation
data reported. Experimental reproductive
effects. Flammable liquid when exposed to
heat or flame; can react vigorously with
oxidizing materials. Slight explosion hazard
in its vapor form, when exposed to flame.Reaction with hydrogen peroxide + nitric
acid forms an explosive peroxide. To fight
fire, use alcohol foam, dry chemical, or COa.
When heated to decomposition it emits
acrid smoke and irritating fumes. See also
KETONES and CYCLOHEXANE. | [Hazardous Substances Data]
108-94-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 1.62 ml/kg (Smyth) | [IDLA]
700 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->Benzene-->Hydrogen peroxide-->Hydrogen-->Water-->Cyclohexane-->PETROLEUM ETHER-->Cyclohexanol-->heavy benzol-->2-Hexanone-->tert-Butyl chromate | [Preparation Products]
Tramadol hydrochloride-->Ondansetron-->Venlafaxine hydrochloride-->(1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine-->Deflazacort-->1-Ethynyl-1-cyclohexanol-->Venlafaxine-->1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE-->(R)-2-AMINO-6-METHYLHEPTANE, 98% E.E., 95-->Ethyl 2-oxocyclohexanecarboxylate-->Carbosulfan-->3-AMINO-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE-->Clethodim-->3-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER-->2-ETHYLCYCLOHEXANONE-->Pramipexole-->2-(HYDROXYMETHYL)CYCLOHEXANONE-->2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE-->N-Methylcyclohexylamine-->5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]-PYRIMIDIN-4-ONE-->Acid Orange 33-->Methoxydienone-->1-(aminomethyl)cyclohexan-1-ol-->Sulfamethazine-->ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE-->Cycloheptanone-->1,2-Cyclohexanedione-->2-(1-CYCLOHEXENYL)CYCLOHEXANONE-->ε-Caprolactone-->1-Hydroperoxycyclohexyl-1-hydroxycyclohexyl peroxide-->1-NITROMETHYLCYCLOHEXANOL-->Cyclohexanone peroxide-->Polyurethane varnish-->adhesive No.1 for shrink packaging-->(1-HYDROXY-CYCLOHEXYL)-ACETONITRILE-->N,N-Dimethylcyclohexylamine-->1-AMINOMETHYL-1-CYCLOHEXANOL HYDROCHLORIDE-->1-(1-PIPERIDINO)CYCLOHEXENE-->Porcelain-like coating-->2-Chlorocyclohexanone |
| Questions And Answer | Back Directory | [Chemical properties]
Cyclohexanone is a colorless, clear liquid with soil smell; its impure product appears as light yellow color. It 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. It has not been found to occur in natural processes.
| [Application]
It 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. It 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. It 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 [3399-73-3]. 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.
| [Production method]
In the 1940s, the industrial production of cyclohexanone mainly applied hydrogenation of phenol to generate cyclohexanol, followed by dehydrogenation to give cyclohexanone. In the 1960s, with the development of petrochemical industry, the cyclohexane oxidation production method gradually dominated. In 1967, the one step method of phenol hydrogenation, developed by the Netherlands National Mining Company (DSM) was industrialized. This method has short production process, good product quality and high yield, but the raw materials of phenol and catalyst are expensive, so the majority of the industry still adopts the cyclohexane oxidation method.
1. Phenol method takes nickel as a catalyst; first apply hydrogenation of phenol to give cyclohexanol, followed by dehydrogenation to give cyclohexanone using zinc as the catalyst for zinc.
2. Cyclohexane oxidation method uses cyclohexane as the raw material; first apply non-catalyst condition; use oxygen-rich air for oxidation to give cyclohexyl hydroperoxide, followed by decomposition into the mixture of cyclohexanol, cyclohexanone, alcohol and ketone in the presence of tert-butyl chromate catalyst; further apply a series of distillation refinement to get qualified products. Raw material consumption quota: cyclohexane (99.6%) 1040kg / t.
3. Benzene hydrogenation oxidation method; benzene subjects to hydrogenation (with hydrogen) at 120-180 ℃ in the presence of nickel catalyst to generate cyclohexane; cyclohexane has oxidation reaction with air at 150-160 ℃, 0.908MPa to obtain the mixture of cyclohexanol and cyclohexanone; separate them to obtain the cyclohexanone product. Cyclohexanol is dehydrogenated at 350-400 ° C in the presence of a zinc-calcium catalyst to produce cyclohexanone. Raw material consumption quotas: benzene (99.5%) 1144kg / t, hydrogen (97.0%) 1108kg / t, caustic soda (42.0%) 230kg / t.
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