Cyclohexanone

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Cyclohexanone
Names
IUPAC name
Cyclohexanone
Other names
Cyclohexyl ketone
Hexanon
Ketocyclohexane
Ketohexamethylene
Oxocyclohexane
Pimelic ketone
Sextone
Properties
C6H10O
Molar mass 98.15 g/mol
Appearance Colorless liquid
Odor Peppermint or acetone-like
Density 0.9478 g/cm3 (20 °C)
Melting point −47 °C (−53 °F; 226 K)
Boiling point 155.65 °C (312.17 °F; 428.80 K)
8.6 g/100 mL (20 °C)
Solubility Miscible with acetone, ethanol, THF, toluene
Vapor pressure 5 mmHg (20 °C)
Thermochemistry
229.03 J·K−1·mol−1
−270.7 kJ·mol−1
Hazards
Safety data sheet Sigma-Aldrich
Flash point 44 °C (111 °F; 317 K)
Lethal dose or concentration (LD, LC):
1.620 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cyclohexanone is the organic compound with the formula (CH2)5CO.

Properties

Chemical

Cyclohexanone and hydroxylamine will form cyclohexanone oxime, which can be converted via Beckmann rearrangement to caprolactam or reduced with sodium amalgam to cyclohexylamine.

Physical

Cyclohexanone is a colorless liquid, slightly soluble in water, but miscible with organic solvents.

Availability

Cyclohexanone is sold by chemical suppliers. It is sometimes found in PVC cements, along with THF.

Cyclohexanone has been used in the illicit production of phencyclidine (PCP) and its analogues and as such it may be subject to additional checks before purchase, depending on the country.

Preparation

Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide. Sodium hypochlorite can also be used.

Cyclohexanone can also be produced by the oxidation of cyclohexane in air, typically using cobalt catalysts.

Projects

  • Make caprolactam and Nylon 6

Handling

Safety

Cyclohexanone is irritant. With a flash point of 44 °C, it's not very flammable.

Storage

In closed bottles.

Disposal

Should be mixed with a more flammable solvent and burned in an incinerator or outside.

References

Relevant Sciencemadness threads