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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.World demand for caprolactam was estimated to reach five million tons per year for 2015. 90% of caprolactam produced is used to make filament and fiber, 10% for plastics, and a small amount is used as a chemical intermediate. [2]
Caprolactam molecule used to synthesize Nylon 6 by ring opening polymerization. Nylon 6 or polycaprolactam is a polymer, in particular semicrystalline polyamide.Unlike most other nylons, nylon 6 is not a condensation polymer, but instead is formed by ring-opening polymerization; this makes it a special case in the comparison between condensation and addition polymers.
Although no longer economical, caprolactone was once produced as a precursor to caprolactam. Caprolactone is treated with ammonia at elevated temperatures to give the lactam: (CH 2) 5 CO 2 + NH 3 → (CH 2) 5 C(O)NH + H 2 O. Carbonylation of caprolactone gives, after hydrolysis, pimelic acid. The lactone ring is easily opened with nucleophiles ...
The peptide bond within the caprolactam is broken with the exposed active groups on each side being incorporated into two new bonds as the monomer becomes part of the polymer backbone. The 428 °F (220 °C) melting point of nylon 6 is lower than the 509 °F (265 °C) melting point of nylon 66. [61] Homopolymer nylons are derived from one monomer.
Polycaprolactone (PCL) is a synthetic, semi-crystalline, biodegradable polyester with a melting point of about 60 °C and a glass transition temperature of about −60 °C. [ 2 ] [ 3 ] The most common use of polycaprolactone is in the production of speciality polyurethanes .
The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam, which is used to produce Nylon 6: This reaction is catalyzed by sulfuric acid, [1] but industrial scale reactions use solid acids. [2] Typical of oximes, the compound can be reduced by sodium amalgam to produce ...
Their common names are β-propiolactam, γ-butyrolactam, δ-valerolactam, and ε-caprolactam. A lactam is a cyclic amide, formally derived from an amino alkanoic acid through cyclization reactions. The term is a portmanteau of the words lactone + amide.
This page contains tables of azeotrope data for various binary and ternary mixtures of solvents. The data include the composition of a mixture by weight (in binary azeotropes, when only one fraction is given, it is the fraction of the second component), the boiling point (b.p.) of a component, the boiling point of a mixture, and the specific gravity of the mixture.