Azacyclotridecan-2-one

Dry PowderSolid; very faintly beige crystalline lumps. Virtually insol in water.

ChEBI: Laurolactam is an azamacrocycle and a keratan 6'-sulfate.

One route to dodecyllactam is from butadiene as follows:

Butadiene is trimerized with a Ziegler-Natta catalyst to give 1,5,9-cyclododecatriene which is then hydrogenated to cyclododecane. Dodecyllactam is then obtained by a series of reactions similar to those used to prepare caprolactam from cyclohexane.

The acute oral LD50 was 2,330 mg/kg bw (rat) with central nervous system stimulation (trembling, convulsive twitches, ataxia) as the main clinical sign appearing at about 1,580 mg/kg bw. The dermal LD50 was greater than 2,000 mg/kg bw (rat). Decreased food consumption and stagnation of body weight development were noted. Validacute inhalation studies are not available. Azacyclotridecan-2-one was not irritating to the rabbit skin or eye (OECD TG 404, 405). It was not sensitizing in aguinea pig maximization test (OECD TG 406; 1981).

Azacyclotridecan-2-one crystallises from CHCl3 and is stored over P2O5 in a vacuum desiccator. [Beilstein 26/1 V 566.]