Cyclohexanone
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| Names | |||
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Preferred IUPAC name
Cyclohexanone
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| Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
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| Identifiers | |||
108-94-1 
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| 3D model (Jmol) | Interactive image | ||
| ChEBI |
CHEBI:17854
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| ChEMBL |
ChEMBL18850
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| ChemSpider |
7679
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| DrugBank |
DB02060
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| ECHA InfoCard | 100.003.302 | ||
| KEGG |
C00414
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| PubChem | 7967 | ||
| UNII |
5QOR3YM052
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| Properties | |||
| C6H10O | |||
| Molar mass | 98.15 g/mol | ||
| Appearance | Colorless liquid | ||
| Odor | peppermint or acetone-like | ||
| Density | 0.9478 g/mL, liquid | ||
| 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 in all organic solvents | Miscible | ||
| Vapor pressure | 5 mmHg (20°C) | ||
| -62.04·10−6 cm3/mol | |||
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Refractive index (nD)
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1.447 | ||
| Viscosity | 2.02 cP at 25 °C | ||
| Thermochemistry | |||
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Std molar
entropy (S |
+229.03 J.K−1.mol−1 | ||
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Std enthalpy of
formation (ΔfH |
−270.7 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−3519.3 kJmol−1 | ||
| Hazards | |||
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EU classification (DSD)
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Harmful (Xn) | ||
| R-phrases | R10, R20 | ||
| S-phrases | (S2), S25 | ||
| NFPA 704 | |||
| Flash point | 44 °C (111 °F; 317 K) | ||
| 420 °C (788 °F; 693 K) | |||
| Explosive limits | 1.1-9.4% | ||
| Lethal dose or concentration (LD, LC): | |||
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LC50 (median concentration)
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8000 ppm (rat, 4 hr) | ||
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LCLo (lowest published)
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4706 ppm (mouse, 1.5 hr) | ||
| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 50 ppm (200 mg/m3) | ||
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REL (Recommended)
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TWA 25 ppm (100 mg/m3) [skin] | ||
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IDLH (Immediate danger)
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700 ppm | ||
| Related compounds | |||
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Related ketones
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Cyclopentanone, cycloheptanone | ||
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Related compounds
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Cyclohexanol | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| Infobox references | |||
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.
Cyclohexanone is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:
This process co-forms cyclohexanol, and this mixture, called "KA Oil" for ketone-alcohol oil, is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. In some cases, purified cyclohexanol, obtained by hydration of cyclohexene, is the precursor. Alternatively, cyclohexanone can be produced by the partial hydrogenation of phenol:
This process can also be adjusted to favor the formation of cyclohexanol.
Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide (Jones oxidation). An alternative method utilizes the safer and more readily available oxidant sodium hypochlorite.
The great majority of cyclohexanone is consumed in the production of precursors to Nylon 6,6 and Nylon 6. About half of the world's supply is converted to adipic acid, one of two precursors for nylon 6,6. For this application, the KA oil (see above) is oxidized with nitric acid. The other half of the cyclohexanone supply is converted to cyclohexanone oxime. In the presence of sulfuric acid catalyst, the oxime rearranges to caprolactam, a precursor to nylon 6:
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