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Mechanism of the formation of secondary and tertiary amines in the course of the catalytic hydrogenation of adiponitrile to 1,6-hexanediamine

  • L. Kh. Freidlin
  • T. A. Sladkova
Organic and Biological Chemistry

Summary

  1. 1.

    Among the products of the hydrogenation of adiponitrile the following previously undescribed compounds containing a tertiary nitrogen atom were isolated: 1-(6-aminohexyl)hexamethylenimine, 1,1′-hexamethylenebis (hexamethylenimine), and hexahydro-1-azepinehexanenitrile.

     
  2. 2.

    Under the optimum conditions for the hydrogenation of adiponitrile to 1,6-hexanediamine (temperature 80–100°, initial hydrogen pressure 100 atm), the primary and primary-secondary amines formed do n of under-go any change.

     
  3. 3.

    In the process investigated, the amines containing a secondary or tertiary nitrogen atom are formed n of by deamination, but by the aldimine mechanism: reaction of the intermediately formed 6-iminohexylamine with 1,6-hexanediamine to give 6,6′-iminobishexylamine, and its reaction with hexamethylenimine to give 1-(6-aminohexyl) hexamethylenimine.

     

Keywords

Hydrogenation Nitrogen Optimum Condition Nitrogen Atom Tertiary Amine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau Enterprises, Inc. 1962

Authors and Affiliations

  • L. Kh. Freidlin
    • 1
  • T. A. Sladkova
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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