Amide interchange reactions

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Abstract
(1) Sebacamide and N,N′‐diacetylhexamethylenediamine interchange to produce acetamide and polyhexamethylene sebacamide. (2) The rate is proportional to the concentrations of the two reacting species and to the square root of carboxyl group concentration. (3) The rate increases with increasing concentration of water. Reagents which had been held in the molten state under high vacuum were still capable of reaction. (4) N‐Substitution decreases the rate constant; the isobutyl group is more effective than methyl in this respect. (5) As an indication of the amount of interchange occurring during a typical polymerization, it is computed that at least 42% of the amide links interchange during the 66 nylon synthesis. This means that it is not feasible to make nonrandom copolyamides by polymerizing together low molecular weight homopolyamides. Interchange does provide for the production of nonrandom copolymers from two or more high molecular weight homopolyamides.

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