Skip to main content
Log in

Three-, six- and nine-carbon ozonolysis products from cottonseed oil and crudechlorella lipids

  • Published:
Journal of the American Oil Chemists’ Society

Abstract

Two naturally occurring lipids were subjected to ozonolysis. Isolated cottonseed oil and crude, mixed lipid extracts of the algaChlorella yielded three-, six-, and nine-carbon compounds. Both mono-and difunctional acids and aldehydes were quantifiable. Monofunctional C9 compounds occur in higher than expected yields, apparently at the expense of difunctional C3 and C9 compounds. Yields of the compounds of interest varied from ca. 35 to 150%, depending on exact conditions. The possibility of utilizing ozonolysis of natural lipids for the production of reactive organic chemicals helps justify further research in algal lipid production.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Krauss, R.W., Am. J. Bot. 49:425 (1962).

    Article  Google Scholar 

  2. Oswald, W.J., and C.G. Golueke, Adv. Applied Microbiol. 2:223 (1960).

    CAS  Google Scholar 

  3. Burlew, J.S., Algal Culture from Laboratory to Pilot Plant, Publication 600, Carnegie Institution of Washington, Washington, DC, 1953.

    Google Scholar 

  4. Benemann, J.R., J.C. Weissman, B.L. Koopman and W.J. Oswald, Nature 268:19 (1977).

    Article  CAS  Google Scholar 

  5. Ratledge, C., Chem. Soc. Rev. (London) 8:283 (1979).

    CAS  Google Scholar 

  6. Lipinsky, E.S., Science 199:644 (1978).

    Article  Google Scholar 

  7. Spoehr, H.A., and H.W. Milner, Plant Physiol. 24:120 (1949).

    Article  CAS  Google Scholar 

  8. Bennemann, J.R., R.R. Goebel and J.C. Weissman, Production of Lipid Hydrocarbon Fuels and Chemicals from Freshwater Microalgae, Final Report No. X13-0-9253-1 to the Solar Energy Research Institute, Golden, CO, 1981.

  9. Waygood, E.R., A. Hussian, H.R. Godavari, Y.C. Tai and S.S. Badour, Environ. Pollut. Ser. A. 23:179 (1980).

    Article  CAS  Google Scholar 

  10. Graff, G., and W.E.M. Lands, Chem. Phys. Lipids 17:301 (1976).

    Article  CAS  Google Scholar 

  11. Pryde, E.H., and J.C. Cowan, in Condensation Monomers, John Wiley and Sons, Inc., New York, 1972, pp. 1–153.

    Google Scholar 

  12. Anon., Chem. Eng. (NY) 59(9):246 (1952).

    Google Scholar 

  13. Suzuki, T., A. Takegawa and K. Hasegawa, Agric. Biol. Chem. 37:2653 (1973).

    CAS  Google Scholar 

  14. Kates, M., J. Lipid Res. 5:132 (1964).

    CAS  Google Scholar 

  15. Fitton, P., E.H. Pryde and J.C. Cowan, JAOCS 42:14 (1965).

    Article  CAS  Google Scholar 

  16. Sebidio, J.-L., and R.G. Ackman, Can. J. Chem. 56:2480 (1978).

    Article  Google Scholar 

  17. Pryde, E.H., P.E. Anders, H.M. Teeter and J.C. Cowan, J. Org. Chem. 25:618(1960).

    Article  CAS  Google Scholar 

  18. Privett, O.S., and E.C. Nickell, JAOCS 41:72 (1964).

    Article  CAS  Google Scholar 

  19. Anders, D.E., E.H. Pryde and J.C. Cowan, JAOCS 42:236 (1965).

    Article  CAS  Google Scholar 

  20. Neumeister, J., H. Keul, M.P. Soxena, and K. Griesbaum, Angew. Chem. Int. Ed. Engl. 17:939 (1978).

    Article  Google Scholar 

  21. Pryde, E.H., in Crop Resources, Academic Press, New York, 1977, pp. 25–45.

    Google Scholar 

  22. Khoe, T.H., L.E. Gast, E.N. Frankel and J.C. Cowan, JAOCS 49:134(1972).

    Article  CAS  Google Scholar 

  23. Fedeli, E., and F. Camurati, Riv. Ital. Sostanze Grasse 55:205 (1978).

    CAS  Google Scholar 

  24. Bailey, P.S., Ozonation in Organic Chemistry, Academic Press, New York, 1978, pp. 220–222.

    Google Scholar 

  25. Privett, O.S., and E.C. Nickeil, JAOCS 43:393 (1966).

    Article  CAS  Google Scholar 

  26. Kharasch, M., F. Kawahara and W. Nudenberg, J. Org. Chem. 19:1977 (1954).

    Article  Google Scholar 

  27. Swern, D., Organic Peroxides, Vol. 2, Wiley-Interscience, New York, 1971, pp. 192–260.

    Google Scholar 

  28. Griesbaum, K., and H. Keul, Angew. Chem. Int. Ed. Engl. 14: 716 (1975).

    Article  Google Scholar 

  29. Molerio, J., S. Menendez and R. Ramos, Rev. CENIC. 11:103 (1980).

    CAS  Google Scholar 

  30. Kingston, D.G.I., J.T. Bursey and M.M. Bursey, Chem. Rev. 74:215 (1974).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Burris, N. Three-, six- and nine-carbon ozonolysis products from cottonseed oil and crudechlorella lipids. J Amer Oil Chem Soc 60, 806–811 (1983). https://doi.org/10.1007/BF02787432

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02787432

Keywords

Navigation