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Journal of the American Oil Chemists' Society

, Volume 89, Issue 11, pp 1951–1960 | Cite as

Monitoring the Epoxidation of Canola Oil by Non-aqueous Reversed Phase Liquid Chromatography/Mass Spectrometry for Process Optimization and Control

  • Sabiqah Tuan Anuar
  • Yuan Yuan Zhao
  • Samuel M. Mugo
  • Jonathan M. CurtisEmail author
Original Paper

Abstract

Non-aqueous reversed phase liquid chromatography/electrospray mass spectrometry (NARP-LC/ESI–MS) was used to monitor the epoxidation of canola oil by performic acid. The reaction was sampled at regular intervals over 28 h and analyzed by NARP-LC/ESI–MS in order to observe the formation of partially epoxidized reaction intermediates and the fully epoxidized products. The experiment focused on the transformation of triacylglycerols (TAG) with 54 carbons in the fatty acyl chains and between 2 and 7 double bonds which account for >93 % of the oil. NARP-LC/ESI–MS allowed determination of the time required for full epoxidation of the oil. It was shown that complete epoxidation of TAG with low numbers of double bonds occurs more rapidly than for those with many double bonds. Furthermore, it was observed that epoxidation of multiply unsaturated TAG occurs via a sequential process in which partially epoxidized intermediates are consumed to form other more highly epoxidized compounds as the reaction proceeds. Data obtained by flow-injection ESI–MS was found to be comparable to that obtained from NARP-LC/ESI–MS for monitoring intermediates and products and could be adapted for in-process reaction monitoring.

Keywords

Canola oil Epoxidation LC/MS Reaction monitoring Oxiranes Non-aqueous reversed phase LC 

Abbreviations

C18:0

Stearic acid

C18:1

Oleic acid

C18:2

Linoleic acid

C18:3

Linolenic acid

Epo

Epoxide

ESI/MS

Electrospray mass spectrometry

EVO

Epoixidized vegetable oil

FID

Flame ionization detector

FTIR

Fourier transform infra-red

GC

Gas chromatography

HPLC

High performance liquid chromatography

LC/MS

Liquid chromatography/mass spectrometry

NARP-LC/ESI–MS

Non-aqueous reversed phased liquid chromatography/electrospray–mass spectrometry

NMR

Nuclear magnetic resonance

PU

Polyurethanes

PVC

Polyvinyl chloride

TAG

Triacylglycerol

TAG [54:x]

Triacylglycerol 54 carbon with x-number of double bonds

TAG [54:x (yepo)]

Triacylglycerol 54 carbon with x-double bonds in the starting oil and y-epoxy

TIC

Total ion chromatogram

Notes

Acknowledgments

This work was partly supported by an NSERC Discovery grant 197273 awarded to J. M. Curtis and a Malaysian Ministry of Higher Education grant supporting the graduate research of Sabiqah Tuan Anuar. The authors would also like to thank the Alberta Crop Industry Development Fund (ACIDF) for ongoing support and members of the University of Alberta Lipid Chemistry Group for their assistance.

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Copyright information

© AOCS 2012

Authors and Affiliations

  • Sabiqah Tuan Anuar
    • 1
    • 2
  • Yuan Yuan Zhao
    • 1
  • Samuel M. Mugo
    • 3
  • Jonathan M. Curtis
    • 1
    Email author
  1. 1.Lipid Chemistry Group, Department of Agricultural, Food and Nutritional Science (AFNS)University of AlbertaEdmontonCanada
  2. 2.Department of Chemical SciencesUniversiti Malaysia TerengganuTerengganuMalaysia
  3. 3.Department of Physical Sciences (Chemistry)Grant MacEwan UniversityEdmontonCanada

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