Lipids

, Volume 6, Issue 12, pp 919–925 | Cite as

Alcoholysis, saponification and the preparation of fatty acid methyl esters

  • R. L. Glass
Article

Abstract

Evidence is offered to support the contention that methanolysis precedes the saponification of esters in methanolic solutions of sodium hydroxide. This results from the hydroxide-alkoxide equilibrium which greatly favors methoxide formation even in the presence of rather considerable amounts of water. Saponification-reesterification methods of methyl ester formation are shown to be actually extensions of methanolysis procedures. A simplified method is proposed for the preparation of fatty acid methyl esters.

Keywords

Methyl Ester Fatty Acid Methyl Ester Methoxide Sodium Hydroxide Methyl Linoleate 

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References

  1. 1.
    Pardee, A.M., and E.E. Reid, J. Ind. Eng. Chem. 12:129 (1920).CrossRefGoogle Scholar
  2. 2.
    Formo, M.W., JAOCS 31:548 (1954).Google Scholar
  3. 3.
    “Fatty Acids, Their Chemistry, Properties, Production, and Uses”, 2nd Edition, part 2, Edited by K.S. Markley, Interscience Publishers, Inc., New York, 1961.Google Scholar
  4. 4.
    Kurz, H., Fette Seifen, 44:144 (1937).CrossRefGoogle Scholar
  5. 5.
    Rowe, G.K., J. Soc. Chem. Ind (London) 52:49T (1933).Google Scholar
  6. 6.
    Toyama, Y., T. Tsuchiya and T. Ishikawa, J. Soc. Chem. Ind. (Japan) 36, Suppl. binding 230B-231B, 231B–232B (1933).Google Scholar
  7. 7.
    Anderson, E., and H.B. Pierce, J. Phys. Chem. 22:44 (1918).CrossRefGoogle Scholar
  8. 8.
    Bender, M.L., and W.A. Glassom, J. Am. Chem. Soc. 81:1590 (1959).CrossRefGoogle Scholar
  9. 9.
    Caldin, E.F., and G. Long, J. Chem. Soc. (London) 1954: 3737.Google Scholar
  10. 10.
    Noller, C.R. “Chemistry of Organic Compound”, Third Edition, Saunders, Philadelphia, 1965, p. 195.Google Scholar
  11. 11.
    March, J., “Advanced Organic Chemistry—Reactions, Mechanisms and Structure”, McGraw-Hill, New York, 1968, p. 309.Google Scholar
  12. 12.
    Metcalfe, L.D., A.A. Schmitz and J.R. Pelka, Anal. Chem. 38:514 (1966).CrossRefGoogle Scholar
  13. 13.
    Methods of Analysis. Ass. Off. Anal. Chem 11th Edition, 1970, p. 454.Google Scholar
  14. 14.
    Mason, M.E., M.E. Eager and G.R. Waller, Anal. Chem. 36:587 (1964).CrossRefGoogle Scholar
  15. 15.
    Lorette, N.B., and J.H. Brown, Jr., J. Org. Chem. 24:261 (1959).CrossRefGoogle Scholar
  16. 16.
    Luddy, F.E., R.A. Barford and R.W. Riemenschneider, JAOCS 37:447 (1960).Google Scholar
  17. 17.
    Christopherson, S.W., and Glass, R.L., J. Dairy Sci. 52:1289 (1970).CrossRefGoogle Scholar

Copyright information

© American Oil Chemists’ Society 1972

Authors and Affiliations

  • R. L. Glass
    • 1
  1. 1.Department of Biochemistry, College of Biological SciencesUniversity of MinnesotaSt. Paul

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