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Cyclohexanone

Chemical properties Application Production method
Cyclohexanone
Cyclohexanone structure
CAS No.
108-94-1
Chemical Name:
Cyclohexanone
Synonyms
Anon;ANONE;Nadone;Hexanon;hytrolo;Sextone;NSC 5711;Hytrol O;HEXANONE;FEMA 3909
CBNumber:
CB8347660
Molecular Formula:
C6H10O
Formula Weight:
98.14
MOL File:
108-94-1.mol

Cyclohexanone Properties

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)
refractive index 
n20/D 1.450(lit.)
FEMA 
3909 | CYCLOHEXANONE
Flash point:
116 °F
storage temp. 
Flammables area
solubility 
90g/l
pka
17(at 25℃)
form 
Liquid
color 
APHA: ≤10
Relative polarity
0.281
PH
7 (70g/l, H2O, 20℃)
Odor
Like peppermint and acetone.
explosive limit
1.1%, 100°F
Water Solubility 
150 g/L (10 ºC)
Merck 
14,2726
JECFA Number
1100
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)
Exposure limits
TLV-TWA 100 mg/m3 (25 ppm) (ACGIH); IDLH 5000 ppm (NIOSH).
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference
108-94-1(CAS DataBase Reference)
NIST Chemistry Reference
Cyclohexanone(108-94-1)
EPA Substance Registry System
Cyclohexanone(108-94-1)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS05,GHS02,GHS06,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H311+H331-H319-H335-H336-H341-H351-H361-H370-H371-H372-H332-H226-H302+H312+H332-H315-H318
Precautionary statements  P261-P280a-P303+P361+P353-P304+P340-P501a-P280-P305+P351+P338-P201-P202-P210-P233-P240-P241+P242+P243-P260-P264-P270-P271-P301+P312+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P307+P311-P370+P378-P403+P233-P405
Hazard Codes  Xn
Risk Statements  10-20-41-38-20/21/22
Safety Statements  25-36/37/39-26
RIDADR  UN 1915 3/PG 3
WGK Germany  1
RTECS  GW1050000
Autoignition Temperature 788 °F
TSCA  Yes
HS Code  2914 22 00
HazardClass  3
PackingGroup  III
Toxicity LD50 orally in rats: 1.62 ml/kg (Smyth)

NFPA 704

Diamond Hazard Value Description
2
0
Health  
Flammability   2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur and multiple finely divided suspended solids that do not require heating before ignition can occur. Flash point between 37.8 and 93.3 °C (100 and 200 °F). (e.g. diesel fuel, sulfur)
Instability   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)
Special  

(NFPA, 2010)

Cyclohexanone price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 02482 Cyclohexanone analytical standard 108-94-1 1ml $20.6 2018-11-13 Buy
Sigma-Aldrich 29135 Cyclohexanone Selectophore , ≥99.5% 108-94-1 10ml $35.3 2018-11-13 Buy
TCI Chemical C0489 Cyclohexanone >99.0%(GC) 108-94-1 25mL $17 2018-11-22 Buy
TCI Chemical C0489 Cyclohexanone >99.0%(GC) 108-94-1 500mL $20 2018-11-22 Buy
Alfa Aesar 033309 Cyclohexanone, ACS, 99+% 108-94-1 1L $41.4 2018-11-16 Buy

Cyclohexanone Chemical Properties,Uses,Production

Chemical properties

Colorless, clear liquid with soil smell; its impure product appears as light yellow color. Easily soluble in ethanol and ether.

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.

Chemical Properties

colourless liquid

Chemical Properties

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.

Chemical Properties

Peppermint or acetone-like odor.

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..

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.

Air & Water Reactions

Flammable. Soluble in water.

Reactivity Profile

Cyclohexanone forms an explosive peroxide with H2O2, and reacts vigorously with oxidizing materials (nitric acid).

Health Hazard

Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis.

Health Hazard

The toxicity of cyclohexanone in test specieswas found to be low to moderate. Exposureto its vapors can produce irritation in the eyesand throat. Splashing into the eyes can damagethe cornea. Throat irritation in humansmay occur from 3–5 minute exposure to a50-ppm concentration in air. The symptomsof chronic toxicity in animals from its inhalationwere liver and kidney damage, as wellas weight loss. However, its acute toxicitywas low below 3000 ppm. The symptomsin guinea pigs were lacrimation, salivation,lowering of heart rate, and narcosis. Exposureto 4000 ppm for 4–6 hours was lethalto rats and guinea pigs.
The oral toxicity of this compound waslow. Ingestion may cause narcosis and depressionof the central nervous system. It canbe absorbed through the skin.
LD50 value, dermal (rabbits): 1000 mg/kg
LD50 value, intraperitoneal (rats): 1130 mg/kg.

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.

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.

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

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.

Chemical Synthesis

It may be synthesized on a laboratory scale by the oxidation of cyclohexanol.

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.

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).

Shipping

UN1915 Cyclohexanone, Hazard Class: 3; Labels: 3-Flammable liquid.

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.]

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.

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.

Cyclohexanone Preparation Products And Raw materials

Raw materials

Preparation Products


Cyclohexanone Suppliers

Global( 377)Suppliers
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View Lastest Price from Cyclohexanone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-04-02 Cyclohexanone Manufacturer; In stock GMP Factory
108-94-1
US $1.00 / KG 1KG High quality manufacturer TOP 3 largest production factory in China Chemwill Asia Co.,Ltd.
2019-08-22 cyclohexanone
108-94-1
US $1.00 / g 1g 99% 500 tons Cangzhou Wanyou New Material Technology Co.,Ltd
2018-07-23 Cyclohexanone
108-94-1
US $2.00-1.00 / KG 1000KG 99.5% 100MT/Monthly or Customized career henan chemical co

Cyclohexanone Spectrum


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