2726. Cyclohexanone

Nomenclature

CAS number: 108-94-1
Ketohexamethylene; pimelic ketone; Hytrol O; Anone; Nadone.
C6H10O; mol wt 98.14.
C 73.43%, H 10.27%, O 16.30%.

Description and 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.

Chemical structure

Properties

Oily liquid with characteristic odor reminiscent of peppermint and acetone. Flammable. 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): 111°F (44°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. See: H. F. Smyth et al., Am. Ind. Hyg. Assoc. J. 30, 470 (1969).

Derivative

2,4-Dinitrophenylhydrazone.

Nomenclature

CAS number: 1589-62-4
2-(2,4-Dinitrophenyl)hydrazone cyclohexanone.
C12H14N4O4; mol wt 278.26.
C 51.80%, H 5.07%, N 20.13%, O 23.00%.

Properties

Golden yellow needles, mp 160°. uv max (CHCl3): 262 nm (ε 22500); (0.01N NaOH): 435 nm (ε 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

Organic 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.