epsiloncaprolactam

Epsilon-caprolactam, also called azepan-2-one, is a cyclic amide (a lactam) consisting of a seven-membered ring that contains one nitrogen atom and six carbon atoms. Its molecular formula is C6H11NO. It is a colorless solid at room temperature and serves as the principal monomer for the production of nylon-6, a widely used polyamide.

Industrial production and processes: The dominant industrial route is the Beckmann rearrangement of cyclohexanone oxime, which itself is derived from cyclohexanone. Under acidic conditions, the oxime rearranges to caprolactam, which is then purified by distillation and crystallization. This monomer is subsequently polymerized to Nylon-6 via ring-opening polymerization, yielding high-strength fibers and engineering plastics.

Uses and applications: The primary use of epsilon-caprolactam is as the precursor to Nylon-6. Nylon-6 finds extensive application in fibers for textiles, tire cord, and specialty plastics, as well as molded components and films. The monomer can also be involved in the synthesis of related polyamides and copolymers for specialized materials.

Properties and safety: Caprolactam is a solid at ambient conditions and has a relatively high melting point for a lactam. It can irritate skin and eyes, and appropriate personal protective equipment and handling practices are advised. Environmental controls are recommended to minimize release to water and soil.

See also: Nylon-6, polyamides, lactams, Beckmann rearrangement.