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Czonolysis as a method for establishing the position of olefinic linkages

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Journal of the American Oil Chemists Society

Summary

Ozonolysis and chromatographic procedures as a method for determining the position of double bonds in olefinic acids are not entirely satisfactory. Ozonolysis is seriously limited because of the secondary reactions undergone by the ozonide. Chromatographic resolution of the decomposed ozonides of oleic acid yields the expected pelargonic and azelaic acids but also yields fractions that indicate double bonds which do not exist. Fractions corresponding to pimelic, sebacic, caprylic, suberic, and capric acids appeared. The “pimelic acid” fraction resulted from the reaction of ozone with an oxidizable or hydrolyzable solvent such as acetone, methanol, or tetrachloromethane. The “sebacic” and “caprylic acid” fractions were incompletely decomposed ozonide. The suberic and capric acid fractions however were real and are believed to have resulted from 8-octadecenoic acid present in the oleic acid in amounts too small to be detected by the methods used to establish its purity.

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References

  1. Higuchi, T., Hill, U. C., and Corcoran, G. B., Anal. Chem.,24, 491 (1952).

    Article  CAS  Google Scholar 

  2. Corcoran, G. B., Anal. Chem.,23, 168 (1956).

    Article  Google Scholar 

  3. Begemann, P. H., Keppler, J. G., and Boekenoogen, H. A., Rec. Trav. Chim.,69, 439 (1950).

    Article  CAS  Google Scholar 

  4. Allen, R. R., and Kiess, A. A., J. Am. Oil Chemists’ Soc.,33, 419 (1956).

    Article  CAS  Google Scholar 

  5. Keppler, J. G., Rec. Trav. Chim.,76, 49 (1957).

    Article  CAS  Google Scholar 

  6. Knegtel, J. T., Boelhouwer, C., Tels, M., and Waterman, H. I., J. Am. Oil Chemists’ Soc.,34, 336 (1957).

    CAS  Google Scholar 

  7. Criegee, R., Kerckow, A., and Zincke, H., Ber.,88, 1878 (1955).

    Article  CAS  Google Scholar 

  8. Leffler, J. E., Chem. Rev.,45, 385 (1949).

    Article  CAS  Google Scholar 

  9. Cook, G.,et al., paper presented at the International Ozone Conference, Chicago, Ill., November 28–30, 1956.

  10. Lemieux, R. U., and von Rudolff, E., Can. J. Research,33, 1701 (1955).

    CAS  Google Scholar 

  11. von Rudolff, E., J. Am. Oil Chemists’ Soc.,33, 126 (1956).

    Article  Google Scholar 

  12. Rieche, A., Meister, R., and SauthoffAnn., 553 187 (1942).

    CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Central Research Laboratories, Armour and Company, Chicago, Illinois

    F. L. Benton, Arthur A. Kiess & H. J. Harwood

Authors
  1. F. L. Benton
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  2. Arthur A. Kiess
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  3. H. J. Harwood
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Benton, F.L., Kiess, A.A. & Harwood, H.J. Czonolysis as a method for establishing the position of olefinic linkages. J Am Oil Chem Soc 36, 457–460 (1959). https://doi.org/10.1007/BF02639640

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  • DOI: https://doi.org/10.1007/BF02639640

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