Skip to main content
Log in

Urea-based fractionation of seed oil samples containing fatty acids and acylglycerols of polyunsaturated and hydroxy fatty acids

  • Published:
Journal of the American Oil Chemists' Society

Abstract

The selectivity and efficiency of urea complex (UC) formation-based fractionation of free fatty acids (FFA) were examined. A rapid, simple, and inexpensive procedure recently developed for urea fractionation was applied to lipid mixtures containing various polyunsaturated and hydroxy FFA species. Urea treatment proved useful for isolating polyunsaturated FFA (PUFA) from FFA derived from fish, borage, and linseed oils by removal of saturated and monounsaturated FFA, but was not effective for isolating hydroxy FFA from the FFA derived from castor, Lesquerella, and Dimorphotheca oils. In situations where FFA within the crystalline or UC phase were rich in PUFA, the urea/FFA mole ratio of the UC was relatively higher, with lower recovery of FFA in this phase. The distribution of urea between the crystalline phase and the solvent was not significantly affected by the FFA composition of feed nor the overall ratio of FFA to urea. It was strongly dependent on the overall mass fraction of solvent. Phospholipids and mono-, di-, and triacylglycerols were poor templates for UC formation relative to FFA. Their inclusion in acylglycerol mixtures containing FFA reduced UC formation.

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. Swern, D., Urea and Thiourea Complexes in Separating Organic Compounds, Ind. Engr. Chem. 47:216–221 (1955).

    Article  CAS  Google Scholar 

  2. Ackman, R.G., W.M.N. Ratnayake, and B. Olsson, The “Basic” Fatty Acid Composition of Atlantic Fish Oils: Potential Similarities Useful for Enrichment of Polyunsaturated Fatty Acids by Urea Complexation, J. Am. Oil Chem. Soc. 65:136–138 (1988).

    CAS  Google Scholar 

  3. Ratnayake, W.M.N., B. Olsson, D. Matthews, and R.G. Ackman, Preparation of Omega-3-PUFA Concentrates from Fish Oils via Urea Complexation, Fat Sci. Technol. 90:381–386 (1988).

    CAS  Google Scholar 

  4. Cartens, M., E. Molina Grima, A. Robles Medina, A. Gimenez-Gimenez, and J. Ibanez Gonzalez, Eicosapentaenoic Acid (20∶5n−3) from the Marine Microalga Phaeodactylum tricornutum, J. Am. Oil Chem. Soc. 73:1025–1031 (1996).

    Article  CAS  Google Scholar 

  5. Ju, Y.H., F.C. Huang, and C.H. Fang, The Incorporation of n−3 Polyunsaturated Fatty Acids into Acylglycerols of Borage Oil via Lipase-Catalyzed Reactions, 75:961–965 (1998).

    CAS  Google Scholar 

  6. Traitler, H., H.J. Willie, and A. Studer, Fractionation of Black-currant Seed Oil, 65:755–760 (1988).

    CAS  Google Scholar 

  7. Shimada, Y., N. Sakai, A. Sugihara, H. Fujita, Y. Honda, and Y. Tominaga, Large-Scale Purification of γ-Linolenic Acid by Selective Esterification Using Rhizopus delemar Lipase, 75:1539–1544 (1998).

    CAS  Google Scholar 

  8. Swern, D., and W.E. Parker, Application of Urea Complexes in the Purification of Fatty Acids, Esters, and Alcohols. III. Concentrates of Natural Linoleic and Linolenic Acids, 30:5–7 (1953).

    CAS  Google Scholar 

  9. Newey, H.A., E.C. Shokal, A.C. Mueller, T.F. Bradley, and L.C. Fetterly, Drying Oils and Resins. Segregation of Fatty Acids and Their Derivatives by Extractive Crystallization with Urea, Ind. Engr. Chem. 42:2538–2541 (1950).

    Article  CAS  Google Scholar 

  10. Fehling, E., S. Schönwiese, E. Klein, K.D. Mukherjee, and N. Weber, Preparation of Malvalic and Sterculic Acid Methyl Esters from Bombax munguba and Sterculia foetida Seed Oils, J. Am. Oil Chem. Soc. 75:1755–1760 (1998).

    Google Scholar 

  11. Hayes, D.G., Y.C. Bengtsson, J. Van Alstine, and F. Setterwall, Urea Complexation for the Rapid, Cost Effective, Ecologically Responsible Fractionation of Fatty Acid from Seed Oil, 75:1403–1409 (1998).

    CAS  Google Scholar 

  12. Canas, B.J., and M.P. Yurawecz, Ethyl Carbamate Formation During Urea Complexation for Fractionation of Fatty Acids, 76:537 (1999).

    CAS  Google Scholar 

  13. Hayes, D.G., and R. Kleiman, 1,3-Specific Lipolysis of Lesquerella fendleri Oil by Immobilized and Reverse Micellar Encapsulated Lipases, 70:1121–1127 (1993).

    CAS  Google Scholar 

  14. Hayes, D.G., K.D. Carlson, and R. Kleiman, The Isolation of Hydroxy Acids from Lesquerella Oil Lipolysate Using a Saponification/Extraction Technique (SAPEX), 73:1113–1119 (1996).

    Article  CAS  Google Scholar 

  15. Hayes, D.G., R. Kleiman, and B.S. Phillips, The Triglyceride Composition, Structure, and Presence of Estolides in the Oils of Lesquerella and Related Species, 72:559–569 (1995).

    CAS  Google Scholar 

  16. Muuse, B.G., F.P. Cuperus, and J.T.P. Derksen, Extraction and Characterization of Dimorphotheca pluvialis Seed Oil, 71:313–317 (1994).

    CAS  Google Scholar 

  17. Muuse, B.G., F.P. Cuperus, and J.P.T. Derksen, Composition and Physical Properties of Oils from New Oilseed Crops, Ind. Crops Prod. 1:57–65 (1992).

    Article  CAS  Google Scholar 

  18. Foglia, T.A., K. Petruso, and S.H. Feairheller, Enzymatic Interesterification of Tallow-Sunflower Oil Mixtures, J. Am. Oil Chem. Soc. 70:281–285 (1993).

    CAS  Google Scholar 

  19. American Oil Chemists’ Society, Free Fatty Acids: AOCS official method Ca 5a-40, 1977.

  20. Syed Rahmatullah, M.S.K., V.K.S. Shukla, and K.D. Mukherjee, γ-Linolenic Acid Concentrates from Borage and Evening Primrose Oil Fatty Acids via Lipase-Catalyzed Esterification, J. Am. Oil Chem. Soc. 71:563–567 (1994).

    Google Scholar 

  21. Hayes, D.G., and R. Kleiman, The Isolation and Recovery of Fatty Acids with Δ5 Unsaturation from Meadowfoam Oil Using Lipase-Catalyzed Hydrolysis and Esterification, 70: 555–560 (1993).

    CAS  Google Scholar 

  22. Schlenk, H., and R.T. Holman, Separation and Stabilization of Fatty Acids by Urea Complexes, J. Am. Chem. Soc. 72:5001–5004 (1950).

    Article  CAS  Google Scholar 

  23. Knight, H.B., L.P. Witnauer, J.E. Coleman, W.R. Noble Jr., and D. Swern, Dissociation Temperatures of Urea Complexes of Long-Chain Fatty Acids, Esters, and Alcohols, Anal. Chem. 24:1331–1334 (1952).

    Article  CAS  Google Scholar 

  24. Zimmerschied, W.J., R.A. Dinerstein, A.W. Weitkamp, and R.F. Marschner, Crystalline Adducts of Urea with Linear Aliphatic Compounds: A New Separation Process, Ind. Eng. Chem. 42:1300–1306 (1950).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to James M. Van Alstine.

About this article

Cite this article

Hayes, D.G., Van Alstine, J.M. & Setterwall, F. Urea-based fractionation of seed oil samples containing fatty acids and acylglycerols of polyunsaturated and hydroxy fatty acids. J Amer Oil Chem Soc 77, 207–213 (2000). https://doi.org/10.1007/s11746-000-0033-5

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-000-0033-5

Key words

Navigation