Cyclohexanone

Title: Cyclohexanone
CAS Registry Number: 108-94-1
Additional Names: Ketohexamethylene; pimelic ketone
Trademarks: Hytrol O; Anone; Nadone
Molecular Formula: C6H10O
Molecular Weight: 98.14
Percent Composition: C 73.43%, H 10.27%, O 16.30%
Literature References: Obtained from cyclohexanol by catalytic dehydrogenation or by oxidation (which yields cyclohexanone and adipic acid) or from cyclohexane by oxidation (yielding cyclohexanone and cyclohexanol): GB 310055 (1928 to Schering-Kahlbaum); US 2223493; US 2223494; US 2285914 (1940, 1940, 1942 to Du Pont). Review of manuf processes: Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 304-309. Toxicity: Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969).
Properties: Oily liq. Odor reminiscent of peppermint and acetone. d420 0.9478; d425 0.9421. mp -32.1°. bp760 155.6°; bp400 132.5°; bp200 110.3°; bp100 90.4°; bp60 77.5°; bp40 67.8°; bp20 52.5°; bp10 38.7°; bp5 26.4°; bp1.0 1.4°. nD20 1.4507. Flash pt closed cup: 147°F (63°C). Soly in water: 150 g/l at 10°; 50 g/l at 30°. Soly of water in cyclohexanone: 87 g/l at 20°. Sol in alcohol, ether and in other common organic solvents. LD50 orally in rats: 1.62 ml/kg (Smyth).
Melting point: mp -32.1°
Boiling point: bp760 155.6°; bp400 132.5°; bp200 110.3°; bp100 90.4°; bp60 77.5°; bp40 67.8°; bp20 52.5°; bp10 38.7°; bp5 26.4°; bp1.0 1.4°
Flash point: Flash pt closed cup: 147°F (63°C)
Index of refraction: nD20 1.4507
Density: d420 0.9478; d425 0.9421
Toxicity data: LD50 orally in rats: 1.62 ml/kg (Smyth)
Derivative Type: 2,4-Dinitrophenylhydrazone
Properties: Golden yellow needles, mp 160°. uv max (CHCl3): 262 nm (e 22500); (0.01N NaOH): 435 nm (e 19000).
Melting point: mp 160°
Absorption maximum: uv max (CHCl3): 262 nm (e 22500); (0.01N NaOH): 435 nm (e 19000)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin and mucous membranes; headache; narcosis, coma; dermatitis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 84.
Use: Solvent for cellulose acetate, nitrocellulose, natural resins, vinyl resins, crude rubber, waxes, fats, shellac, DDT. In the production of adipic acid for nylon. In the prepn of cyclohexanone resins. 2,4-Dinitrophenylhydrazone deriv as standard in elemental analysis.
Cyclohexene Cycloheximide Cyclohexyl Bromide Cyclohexyl Chloride Cyclohexylamine

Cyclohexanone[1][2]
Skeletal formula of cyclohexanone Ball-and-stick model of cyclohexanone
Skeletal formula viewed side-on, showing the non-planar conformation
Identifiers
CAS number 108-94-1 YesY
PubChem 7967
ChemSpider 7679 YesY
UNII 5QOR3YM052 YesY
DrugBank DB02060
KEGG C00414 YesY
ChEBI CHEBI:17854 YesY
ChEMBL CHEMBL18850 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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 ([4])
Boiling point 155.65 °C; 312.17 °F; 428.80 K
Solubility in water 8.6 g/100 mL (20 °C)
Solubility in all organic solvents Miscible
Refractive index (nD) 1.447
Viscosity 2.02 cP at 25 °C[3]
Thermochemistry
Std molar
entropy So298
+229.03 J.K−1.mol−1
Std enthalpy of
formation ΔfHo298
−270.7 kJ mol−1
Std enthalpy of
combustion ΔcHo298
−3519.3 kJmol−1
Hazards
EU classification Harmful (Xn)
R-phrases R10, R20
S-phrases (S2), S25
NFPA 704
NFPA 704.svg
2
1
0
Flash point 44 °C; 111 °F; 317 K
Autoignition temperature 420 °C; 788 °F; 693 K
Explosive limits 1.1-9.4%
Related compounds
Related ketones Cyclopentanone, cycloheptanone
Related compounds Cyclohexanol
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Except where noted otherwise, 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. 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, but miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.[5]