Summary
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1.
A method for obtaining vinylcaprolactam in about 70% yield was found.
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2.
A new catalyst was used for vinylation of ε-caprolactam, viz., the potassium salt of ε-caprolactam (the product of reaction of potassium with ε-caprolactam).
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3.
Vinylcaprolactam is readily obtained in crystalline form; this is highly hygroscopic, and it absorbs an equimolecular amount of water when exposed to the air.
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4.
Hydrolysis of vinylcaprolactam gives acetaldehyde, ε-caprolactam, and salts of ε-aminocapronic acid.
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5.
Polymerization of vinylcaprolactam proceeds satisfactorily in presence of hydrogen peroxide at 140–150°.
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6.
A crystalline intermediate product of polymerization of vinylcaprolactam was isolated. It is formed by the action of oxygen on vinylcaprolactam, and it exhibits peroxide properties, and can serve as an initiator of the polymerization process.
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7.
The process of thermopolymerization of vinylcaprolactam proceeds only to a negligible extent.
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Shostakovsky, M.F., Medzykhovskaya, N.A. & Zelenskaya, M.G. Synthesis and polymerization of vinylcaprolactam. Russ Chem Bull 1, 627–632 (1952). https://doi.org/10.1007/BF01164929
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DOI: https://doi.org/10.1007/BF01164929