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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 ...
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.
The archetypal Beckmann rearrangement [4] is the conversion of cyclohexanone to caprolactam via the oxime. Caprolactam is the feedstock in the production of Nylon 6. [5] The Beckmann solution consists of acetic acid, hydrochloric acid and acetic anhydride, and was widely used to catalyze the rearrangement.
For this reason it is effective in treatment of certain bleeding disorders, and it is sold under the brand name Amicar. [3] Aminocaproic acid is also an intermediate in the polymerization of Nylon-6, where it is formed by ring-opening hydrolysis of caprolactam. The crystal structure determination showed that the 6-aminohexanoic acid is present ...
Although a derivative of 12-aminododecanoic acid, it is made from cyclododecatriene.The triene is hydrogenated to the saturated alkane, cyclododecane.For the production of laurolactam, cyclododecane is oxidized with air or oxygen in the presence of boric acid and transition metal salts (e.g. cobalt(II) acetate), obtaining a mixture [3] of cyclododecanol and cyclododecanone.
The monomers can be amides themselves (usually in the form of a cyclic lactam such as caprolactam), α,ω-amino acids or a stoichiometric mixture of a diamine and a diacid. Both these kinds of precursors give a homopolymer. Polyamides are easily copolymerized, and thus many mixtures of monomers are possible which can in turn lead to many ...