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
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.]
