Catalytic synthesis of nitriles

Communication 3. Preparation of aromatic nitriles
  • M. A. Popov
  • N. I. Shuikin
Article
  • 25 Downloads

Summary

  1. 1.

    The optimum conditions were found for the synthesis of benzonitrile, phenylacetonitrile, and hydrocinnamonitrile by reaction of ammonia with benzyl, phenethyl, and 3-phenylpropyl alcohols over a nickelalumina catalyst in a flow system.

     
  2. 2.

    In presence of a 3% nickel-alumina catalyst at 390° the yield of benzonitrile attains 51.7%. The maximum yields of phenylacetonitrile (at 300°) and hydrocinnamonitrile (at 330°) are obtained by carrying out the nitrile formation over a 1.5% nickel-alumina catalyst and are 44.8 and 50.8%, respectively.

     
  3. 3.

    A hypothesis was advanced on the mechanism of the formation of a small amount of amines and aromatic hydrocarbons as by-products in the nitrile synthesis.

     

Keywords

Alcohol Ammonia Hydrocarbon Optimum Condition Nitrile 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. Mitchell, and E. Emmet Reid, J. Am. Chem. Soc.53, 321 (1931).Google Scholar
  2. 2.
    H. P. Coldwell and H. D. Chapman, German Fed. Republic Patent 881,342, June 29, 1953; Referat. Zhur. Khim., 10769, 4 (1956).Google Scholar
  3. 3.
    W. Ritter and J. Schmidt, German Fed. Republic Patent 893,500, October 15, 1953; Referat. Zhur. Khim., 30302, 10 (1956).Google Scholar
  4. 4.
    A. V. Willett and J. R. Pailtrop, French Patent 1,062,324, April 21, 1954; Referat. Zhur. Khim., 4873, 2 (1956).Google Scholar
  5. 5.
    E. L. Reilly, U. S. Patent 2,769,832, November 6, 1956; Referat. Zhur. Khim., 5126, 15 (1958).Google Scholar
  6. 6.
    C. H. Keever and J. W. Nemec, U.S. Patent 2,770,641, February 13, 1956; Referat. Zhur. Khim., 54,898, 16 (1958).Google Scholar
  7. 7.
    M. A. Popov and N. I. Shuikin, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk6, 713 (1958); 1992 (1959).Google Scholar
  8. 8.
    I. F. Norris and A. A. Ashdown, J Am. Chem. Soc.47, 845 (1925).Google Scholar
  9. 9.
    Ph. Landrieu, F. Baylocq, and I. R. Johnson, Bull. Soc. Chim. France [4],45, 46 (1929).Google Scholar
  10. 10.
    V. Grignard, Compt. rend.141, 44 (1905).Google Scholar
  11. 11.
    H. D. Law, J. Chem. Soc., 101, 1030 (1912).Google Scholar
  12. 12.
    J. W. Bruhl, Liebigs Ann. Chem.200, 191 (1880).Google Scholar
  13. 13.
    J. H. Mathews, J. Am. Chem. Soc.48, 569 (1926).Google Scholar
  14. 14.
    J. Timmermans, Bull. Soc. chim. beiges.25, 300 (1911); Chem. Zbl.,11, 1016 (1911).Google Scholar
  15. 15.
    W. E. St. Turner and E. W. Merry, J. Chem. Soc.,97, 2075 (1910).Google Scholar
  16. 16.
    A. Cotton and H. Mouton, Ann. Chim. Phys. [8],28, 214 (1913).Google Scholar
  17. 17.
    F. V. Grimm and W. A. Patrick, J. Am. Chem. Soc.45, 2799 (1923).Google Scholar
  18. 18.
    L. Wolf and K. Greulich, Liebigs Ann. Chem.394, 44 (1912).Google Scholar
  19. 19.
    T. W. Richards and F. Barry, J. Am. Chem. Soc.37, 1000 (1915).Google Scholar
  20. 20.
    T. W. Richards and J. W. Shipley, J. Am. Chem. Soc.38, 996 (1916).Google Scholar
  21. 21.
    F. I. Wilson and W. M. Hyslop, J. Chem. Soc.,123, 2616 (1923).Google Scholar
  22. 22.
    A. W. Hofmann, Ber.7, 520 (1874).Google Scholar
  23. 23.
    V. Grignard, Compt. rend.138, 1049 (1904).Google Scholar
  24. 24.
    P. Sabatier and J. B. Senderens, Compt. rend.140, 486 (1905).Google Scholar

Copyright information

© Consultants Bureau Enterprises, Inc. 1961

Authors and Affiliations

  • M. A. Popov
    • 1
  • N. I. Shuikin
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

Personalised recommendations