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Alkali-catalyzed alcoholysis of crambe oil and camelina oil for the preparation of long-chain esters

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Journal of the American Oil Chemists' Society

Abstract

The alcoholysis of crambe and camelina oils was carried out with oleyl alcohol, alcohols derived from crambe and camelina oils, and n-octanol using potassium hydroxide as catalyst to prepare alkyl esters. Conversions to alkyl esters were about 0% with oleyl alcohol, 20–45% with crambe and camelina alcohols, and 60% with n-octanol. The conversion to esters for crambe and camelina oil with oleyl alcohol and n-octanol increased with increasing molar excess of alcohol. Composition of the alkyl esters formed was as expected from the composition of the reaction partners.

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References

  1. Bondioli, P., L. Inzaghi, G. Postorino, and P. Quartuccio, Crambe abyssinica Oil and Its Derivatives as Renewable Lubricants: Synthesis and Characterization of Different Esters Based on Crambe Fatty Acids, Riv. Ital. Sost. Grasse 74:137–141 (1997).

    CAS  Google Scholar 

  2. Yaniv, Z., E. Shabelsky, D. Schafferman, I. Granot, and T. Kipnis, Oil and Fatty Acid Changes in Sinapis and Crambe Seeds During Germination and Early Development, Ind. Crops Prod. 9:1–8 (1998).

    Article  CAS  Google Scholar 

  3. Leonard, E.C., Camelina Oil: α-Linolenic Source, INFORM 9: 830–838 (1998).

    Google Scholar 

  4. Freedman, B., R.O. Butterfield, and E.H. Pryde, Transesterification Kinetics of Soybean Oil, J. Am. Oil Chem. Soc. 63: 1375–1380 (1986).

    CAS  Google Scholar 

  5. Haas, M.J., and K.M. Scott, Combined Nonenzymatic-Enzymatic Method for the Synthesis of Simple Alkyl Fatty Acid Esters from Soapstock, Ibid. 73:1393–1401 (1996).

    Article  CAS  Google Scholar 

  6. Christie, W.W., Preparation of Ester Derivatives of Fatty Acids for Chromatographic Analysis, in Advances in Lipid Technology, edited by W.W. Christie, Vol. 2, The Oily Press, Dundee, 1993, pp. 69–81.

    Google Scholar 

  7. Komers, K., R. Stloukal, J. Machek, F. Skopal, and A. Komersová, Biodiesel from Rapeseed Oil, Methanol, and KOH. Analytical Methods in Research and Production, Fett/Lipid 100: 507–512 (1998).

    Article  CAS  Google Scholar 

  8. Bryant, K.K., C.P. Nwaonicha, M.A. Anderson, and F.O. Ayorinde, Acid-Catalyzed Alcoholysis of Vernonia galamensis Oil, J. Am. Oil Chem. Soc. 69:1023–1026 (1992).

    CAS  Google Scholar 

  9. Kildiran, G., S.Ö. Yücel, and S. Türkay, In-situ Alcoholysis of Soybean Oil, Ibid. 73:225–228 (1996).

    Article  CAS  Google Scholar 

  10. Busson-Breysse, J., M. Farines, and J. Soulier, Jojoba Wax: Its Esters and Some of Its Minor Components, Ibid. 71:999–1002 (1994).

    CAS  Google Scholar 

  11. Coteron, A., N. Sánchez, M. Marinez, and J. Aracil, Optimization of the Synthesis of an Analogue of Jojoba Oil Using a Fully Central Composite Design, Can. J. Chem. Eng. 71:485–488 (1993).

    Article  CAS  Google Scholar 

  12. Aracil, J., M. Martinez, N. Sánchez, and A. Corma, Formation of a Jojoba Oil Analog by Esterification of Oleic Acid Using Zeolites as Catalyst, Zeolites 12:233–236 (1992).

    Article  CAS  Google Scholar 

  13. Wisniak, J., Potential Use of Jojoba Oil and Meal—A Review, Ind. Crops Prod. 3:43–68 (1994).

    Article  CAS  Google Scholar 

  14. McCrae, A., E.-L. Roehl, and H.M. Brand, Bio-Ester—Bio-Esters, Seifen Öle Fette Wachse 116:201–205 (1990).

    CAS  Google Scholar 

  15. De, B.K., D.K. Bhattacharyya, and C. Bandhu, Enzymatic Synthesis of Fatty Esters by Alcoholysis, J. Am. Oil Chem. Soc. 76: 451–453 (1999).

    CAS  Google Scholar 

  16. Decagny, B., S. Jan, J.C. Vuillemard, C. Sarazin, J.P. Séguin, C. Gosselin, J.N. Barbotin, and F. Ergan, Synthesis of Wax Ester Through Triolein Alcoholysis: Choice of the Lipase and Study of the Mechanism, Enzyme Microb. Technol. 22:578–582 (1998).

    Article  CAS  Google Scholar 

  17. Schuch, R., and K.D. Mukherjee, Interesterification of Lipids Using an Immobilized sn-1,3-Specific Triacylglycerol Lipase, J. Agric. Food Chem. 35:1005–1008 (1987).

    Article  CAS  Google Scholar 

  18. Mukherjee, K.D., and I. Kiewitt, Preparation of Esters Resembling Natural Waxes by Lipase-Catalyzed Reactions, Ibid. 36: 1333–1336 (1988).

    Article  CAS  Google Scholar 

  19. Steinke, G., R. Kirchhoff, and K.D. Mukherjee, Lipase-Catalyzed Alcoholysis of Crambe Oil and Camelina Oil for the Preparation of Long-Chain Esters, J. Am. Oil Chem. Soc. 77:361–366 (2000).

    CAS  Google Scholar 

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Correspondence to Kumar D. Mukherjee.

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Presented as part of the doctoral thesis of Georg Steinke to the University of Münster, Münster, Germany.

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Steinke, G., Schönwiese, S. & Mukherjee, K.D. Alkali-catalyzed alcoholysis of crambe oil and camelina oil for the preparation of long-chain esters. J Amer Oil Chem Soc 77, 367–371 (2000). https://doi.org/10.1007/s11746-000-0060-2

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  • DOI: https://doi.org/10.1007/s11746-000-0060-2

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