Caprolactam

Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is alactam(a cyclic amide) of caproic acid. Approximately 4.5 billion kilograms are produced annually. Caprolactam is the precursor to Nylon 6, a widely used synthetic polymer.

Structure:

Chemical formula: C6H11NO

Molar mass: 113.16 g•mol−1

Appearance: White solid

Density: 1.01 g/cm3

Melting point: 69.2 °C (156.6 °F; 342.3 K)

Boiling point: 270.8 °C (519.4 °F; 544.0 K) at 1013.25 hPa

Solubility in water: 866.89 g/L (22 °C)

Vapor pressure: 0.00000008 mmHg (20° C)[1]

Caprolactam was first described in the late 1800s when it was prepared by the cyclization of ε-aminocaproic acid, the product of the hydrolysis of caprolactam. Given the commercial significance of Nylon-6, many methods have been developed for the production of caprolactam.

Almost all caprolactam produced goes into the manufacture of Nylon-6. The conversion entails a ring-opening polymerization:

n (CH₂)₅C(O)NH → [(CH₂)₅C(O)NH]_n

Nylon-6 is widely used in fibers and plastics.

In situ anionic polymerization is employed for cast nylon production where conversion from ε-caprolactam to Nylon-6 takes place inside a mold. In conjunction with endless fiber processing the term thermoplastic resin transfer molding (T-RTM) is often used.

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