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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.
Caprolactam (CPL) is an organic compound with the formula (CH 2) 5 C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid.Global demand for this compound is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics.
Type 6,6 Nylon 101 is the most common commercial grade of nylon, and Nylon 6 is the most common commercial grade of molded nylon. [94] [95] For use in tools such as spudgers, nylon is available in glass-filled variants which increase structural and impact strength and rigidity, and molybdenum disulfide-filled variants which increase lubricity.
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. Other acids, such as sulfuric acid, polyphosphoric acid, and hydrogen fluoride have all been used.
General scheme ionic propagation. Propagating center can be radical, cationic or anionic. In polymer chemistry, ring-opening polymerization (ROP) is a form of chain-growth polymerization in which the terminus of a polymer chain attacks cyclic monomers to form a longer polymer (see figure).
Approximately 95% of hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6. [10] The treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam (3). [21] The latter can then undergo a ring-opening polymerization to yield Nylon 6. [22]
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In this equation, P is the polymer while x represents degree of polymerization, * means active center of chain-growth polymerization, M is the monomer which will react with active center, and L may be a low-molar-mass by-product obtained during chain propagation.