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 | |
| Std molar
entropy (S |
229.03 J·K−1·mol−1 |
| Std enthalpy of
formation (ΔfH |
−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): | |
| LD50 (Median dose)
|
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.
Contents
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.
