Cyclohexanone
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 oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.
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| Names | |||
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| Preferred IUPAC name
Cyclohexanone | |||
| Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.003.302 | ||
| EC Number |
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| KEGG | |||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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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 | ||
| log P | 0.81 | ||
| Vapor pressure | 5 mmHg (20°C) | ||
| -62.04·10−6 cm3/mol | |||
Refractive index (nD) |
1.447 | ||
| Viscosity | 2.02 cP at 25 °C | ||
| Thermochemistry | |||
Std molar entropy (S⦵298) |
+229.03 J.K−1.mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) |
−270.7 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) |
−3519.3 kJmol−1 | ||
| Hazards | |||
| GHS labelling: | |||
| Danger | |||
| H226, H302, H305, H312, H315, H318, H332 | |||
| P280, P305+P351+P338 | |||
| NFPA 704 (fire diamond) | |||
| 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): | |||
LD50 (median dose) |
1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally) | ||
LC50 (median concentration) |
8000 ppm (rat, 4 hr) | ||
LCLo (lowest published) |
4706 ppm (mouse, 1.5 hr) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 50 ppm (200 mg/m3) | ||
REL (Recommended) |
TWA 25 ppm (100 mg/m3) [skin] | ||
IDLH (Immediate danger) |
700 ppm | ||
| Related compounds | |||
Related ketones |
Cyclopentanone, cycloheptanone | ||
Related compounds |
Cyclohexanol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |||
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