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Epoxidation of Canola Oil with Hydrogen Peroxide Catalyzed by Acidic Ion Exchange Resin

  • Original Paper
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Journal of the American Oil Chemists' Society

Abstract

Canola oil with an iodine value of 112/100 g, and containing 60% oleic acid and 20% linoleic acid, was epoxidised using a peroxyacid generated in situ from hydrogen peroxide and a carboxylic acid (acetic or formic acid) in the presence of an acidic ion exchange resin (AIER), Amberlite IR 120H. Acetic acid was found to be a better oxygen carrier than formic acid, as it produced about 10% more conversion of ethylenic unsaturation to oxirane than that produced by formic acid under otherwise identical conditions. A detailed process developmental study was then performed with the acetic acid/AIER combination. The parameters optimised were temperature (65 °C), acetic acid to ethylenic unsaturation molar ratio (0.5), hydrogen peroxide to ethylenic unsaturation molar ratio (1.5), and AIER loading (22%). An iodine conversion of 88.4% and a relative conversion to oxirane of 90% were obtained at the optimum reaction conditions. The heterogeneous catalyst, AIER, was found to be reusable and exhibited a negligible loss in activity.

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Acknowledgment

Financial support from the Saskatchewan Canola Development Commission (SCDC) and the Natural Sciences and Engineering Research Council of Canada (NSERC) for this work is gratefully acknowledged.

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Authors and Affiliations

  1. Catalysis and Chemical Reaction Engineering Laboratories, Department of Chemical Engineering, University of Saskatchewan, 57 Campus Drive, Saskatoon, SK, S7 N 5A9, Canada

    Rubeena Mungroo, Narayan C. Pradhan, Vaibhav V. Goud & Ajay K. Dalai

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  1. Rubeena Mungroo
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  2. Narayan C. Pradhan
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  3. Vaibhav V. Goud
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  4. Ajay K. Dalai
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Correspondence to Ajay K. Dalai.

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Mungroo, R., Pradhan, N.C., Goud, V.V. et al. Epoxidation of Canola Oil with Hydrogen Peroxide Catalyzed by Acidic Ion Exchange Resin. J Am Oil Chem Soc 85, 887–896 (2008). https://doi.org/10.1007/s11746-008-1277-z

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  • DOI: https://doi.org/10.1007/s11746-008-1277-z

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