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Polyamide synthesis from 6-aminocapronitrile, part 1: N-alkyl amide formation by amine amidation of a hydrolyzed nitrile.

The synthesis of N-hexylpentanamide from a stoichiometric amount of pentanenitrile and hexylamine has been studied as a model reaction for the synthesis of nylon-6 from 6-aminocapronitrile. The reaction was carried out under mild hydrothermal conditions and in the presence of a homogeneous ruthenium catalyst. For the mild hydrothermal conditions the presence of hexylamine distinctively increases the nitrile hydrolysis compared to the nitrile hydrolysis in the absence of hexylamine. Amine-catalyzed nitrile hydrolysis mainly produces the N-substituted amide. A clear product development is observed, consisting of first the terminal amide formation and second the accumulation of N-hexylpentanamide. With a maximum conversion of only 80 % after 18 h, the nitrile hydrolysis rate at 230 degrees C is still much too low for nylon-6 synthesis. Ruthenium dihydride phosphine was therefore used as a homogeneous catalyst, which significantly increases the nitrile hydrolysis rate. At a temperature of 140 degrees C and with only 0.5 mol % [RuH(2)(PPh(3))(4)] a 60 % nitrile conversion is already reached within 2 h. Initially the terminal amide is the sole product, which is gradually converted into N-hexylpentanamide. The reaction has a high initial rate, however, for higher conversions a strong decrease in hydrolysis rate is observed. This is ascribed to product inhibition, which results from the equilibrium nature of the reaction.[1]

References

  1. Polyamide synthesis from 6-aminocapronitrile, part 1: N-alkyl amide formation by amine amidation of a hydrolyzed nitrile. van Dijk, A.J., Heyligen, T., Duchateau, R., Meuldijk, J., Koning, C.E. Chemistry (2007) [Pubmed]
 
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