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Preparation and purity of linoleic acid from commercial corn, cottonseed, and safflower oils

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  • Published:
Journal of the American Oil Chemists Society

Abstract

Linoleic acid from commercial corn, cottonseed, and safflower oils was prepared by low temperature crystallization using acetone and petroleum ether as solvents; temperatures ranged between −70 and 50C. This method has the advantages of simple equipment and of flexibility in preparatory capacity. The crystalline fraction obtained at −55C was shown to be “pure” linoleic acid.

Isomerization with potassium tertiary butoxide, oxidative cleavage by periodate-permanganate, and analysis by liquid-liquid and gas-liquid partition chromatography were used to ascertain the purity and the presence of isomers in the final product. This fraction was found to contain 90 to 95%, 9,12 dienoic acid; approximately 5% of dienes with the first double bond at the C8 position and the second bond either at the C12 or C13 positions; and small amounts of nonconjugatable 9,15cis,cis dienes. Linoleic acid from these oils was similar in composition, except that from corn oil showed the presence of diene with the first double bond at the C11 position.

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References

  1. Hilditch, T. P., “The Chemical Coustitution of Natural Fats,” pp. 526–530, John Wiley and Sons. Inc., New York, 1956.

    Google Scholar 

  2. Frankel, J. S., W. Stoneburner, and J. B. Brown, J. Am. Chem. Soc.,65, 259 (1943).

    Article  CAS  Google Scholar 

  3. Swift, C. F., W. G. Rose, and G. S. Jamieson, Oil & Soap,20, 249 (1943).

    CAS  Google Scholar 

  4. Mitchell, J. H., Jr., H. R. Kraybill, and F. P. Zscheile, Ind. Eng. Chem., Anal. Ed.,15, 1 (1943).

    Article  CAS  Google Scholar 

  5. Riemenschneider, R. W., S. F. Herb, and P. I. Nichols, Jr., JAOCS,26, 371 (1949).

    CAS  Google Scholar 

  6. Swern, D., and W. E. Parker,Ibid.,,30, 5 (1953).

    CAS  Google Scholar 

  7. Beal, R. E., and O. L. Brekke,Ibid.,,36, 397 (1959).

    CAS  Google Scholar 

  8. Allen, R. R., and A. A. Kiess,Ibid.,,33, 355 (1956).

    CAS  Google Scholar 

  9. Cousins, E. R., W. A. Guice, and R. O. Feuge,Ibid.,,36, 24 (1959).

    Article  CAS  Google Scholar 

  10. Scholfield, C. R., J. Nowakowska, and H. J. Dutton,Ibid.,,37, 27 (1960).

    CAS  Google Scholar 

  11. Sreenivasan, B. S., and J. B. Brown,Ibid.,,35, 89 (1958).

    CAS  Google Scholar 

  12. Lemieux, R. U., and E. von Rudloff, Can. J. Chem.,33, 1701 (1955).

    Article  CAS  Google Scholar 

  13. Jones, E. P., and J. A. Stolp JAOCS,35, 71 (1958).

    CAS  Google Scholar 

  14. Nowakowska, J., E. H. Melvin, R. Wiebe,Ibid.,,34, 411 (1957).

    CAS  Google Scholar 

  15. Brown, J. B., D. K. Kolb, R. T. Holman, W. O. Lundberg, and T. Malkin, in “Progress in the Chemistry of Fats,” Vol. 3, pp. 66–70, Pergamon Press Ltd., London, 1955.

    Google Scholar 

  16. Allen, G., and E. F. Caldin, Quart. Rev. (London)7, 255 (1953).

    CAS  Google Scholar 

  17. Shreve, O. D., M. R. Heether, H. B. Knight, and D. Swern, Anal. Chem.,22, 1261 (1950).

    Article  CAS  Google Scholar 

  18. AOCS “Official and Tentative Methods,” Cd-7-58. 2d Edition. Revised 1959.

  19. Scholfield, C. R., E. P. Jones, J. Nowakowska, E. Selke, and H. J. Dutton, JAOCS,38, 208 (1961).

    CAS  Google Scholar 

  20. Benton, F. L., A. A. Kiess, and H. J. Harwood,Ibid., 36, 457 (1959).

    CAS  Google Scholar 

  21. Brice, B. A., M. L. Swain, S. F. Herb, P. L. Nichols, Jr., and R. W. Riemenschneider,Ibid., 29, 279 (1952).

    CAS  Google Scholar 

  22. Matthews, N. L., W. R. Brode, and J. B. Brown, J. Am. Chem. Soc.,63, 1064 (1941).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Physiological Chemistry, Ohio State University, Columbus

    B. Sreenivasan & J. B. Brown

  2. Northern Regional Research Laboratory, Peoria, Illinois

    E. P. Jones, V. L. Davison & Janina Nowakowska

Authors
  1. B. Sreenivasan
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  2. J. B. Brown
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  3. E. P. Jones
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  4. V. L. Davison
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  5. Janina Nowakowska
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Additional information

A laboratory of the Northern Utilization Research and Development Division, U.S.D.A.

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Sreenivasan, B., Brown, J.B., Jones, E.P. et al. Preparation and purity of linoleic acid from commercial corn, cottonseed, and safflower oils. J Am Oil Chem Soc 39, 255–259 (1962). https://doi.org/10.1007/BF02631705

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  • DOI: https://doi.org/10.1007/BF02631705

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