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Quantification of Nonanal and Oleic Acid Formed During the Ozonolysis of Vegetable Oil Free Fatty Acids or Fatty Acid Methyl Esters

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Journal of the American Oil Chemists' Society

Abstract

The ozonolysis of unsaturated lipids is a process that has been used to generate aldehydes, acids, alcohols, and other biobased chemical intermediates. Reported here is a method that can be used to measure the formation of nonanal and oleic acid during the ozonolysis of unsaturated vegetable oil fatty acids or their methyl esters to indicate the extent of the ozonolysis reaction. Derivatization was performed using boron trifluoride in methanol solution to transform nonanal and oleic acid into nonanal dimethyl acetal and oleic acid methyl ester, respectively. Undecanal and 10-heptadecenoic acid were used as internal standards and separation was performed using gas chromatography coupled with a flame ionization detector. The method was validated by performing a standard addition procedure in which nonanal or oleic acid standards were spiked into samples collected during the ozonolysis of oleic acid or canola oil fatty acid methyl ester (FAME). Linear regression results indicated that the measured nonanal and oleic acid are in good agreement with the actual amounts of nonanal and oleic acid added to the sample with at least 98 % recovery. The application of the method was demonstrated by the successful measurement of nonanal and oleic acid formed throughout the ozonolysis process for high oleic canola oil FAME.

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Acknowledgments

We acknowledge the University of Alberta Biorefining Conversion Network and Alberta Innovates Biosolutions for support for this research. Mr. Tavassoli-Kafrani thanks Alberta Innovates-Technology Futures for providing a scholarship.

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Authors and Affiliations

  1. Lipid Chemistry Group, Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, AB, T6G 2P5, Canada

    M. H. Tavassoli-Kafrani, E. Kharraz & J. M. Curtis

  2. P2 Science Inc., 4 Research Drive, Woodbridge, CT, 06525, USA

    P. Foley

Authors
  1. M. H. Tavassoli-Kafrani
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  2. P. Foley
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  3. E. Kharraz
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  4. J. M. Curtis
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Correspondence to J. M. Curtis.

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Tavassoli-Kafrani, M.H., Foley, P., Kharraz, E. et al. Quantification of Nonanal and Oleic Acid Formed During the Ozonolysis of Vegetable Oil Free Fatty Acids or Fatty Acid Methyl Esters. J Am Oil Chem Soc 93, 303–310 (2016). https://doi.org/10.1007/s11746-015-2780-7

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  • DOI: https://doi.org/10.1007/s11746-015-2780-7

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