Functional group analysis during ozonation of sunflower oil methyl esters by FT-IR and NMR

Ozonation of neat sunflower oil (SFO) methyl esters was monitored by FT-IR and 1 H and 13 C NMR spectroscopy. During the early stage of ozonation, ozone absorption was essentially quantitative. This was accompanied by the formation of 1,2,4-trioxolane. IR and NMR spectra of ozonated samples showed t...

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Bibliographic Details
Published in:Chemistry and physics of lipids 2003-12, Vol.126 (2), p.133-140
Main Authors: Soriano, Nestor U, Migo, Veronica P, Matsumura, Masatoshi
Format: Article
Language:English
Subjects:
Aldehydes - analysis
Aldehydes - chemistry
Criegee mechanism
Esterification
Esters - chemistry
IR and NMR spectra
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Ozonation
Ozone - analysis
Ozone - chemistry
Plant Oils - chemistry
Spectroscopy, Fourier Transform Infrared
Sunflower Oil
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Summary:Ozonation of neat sunflower oil (SFO) methyl esters was monitored by FT-IR and 1 H and 13 C NMR spectroscopy. During the early stage of ozonation, ozone absorption was essentially quantitative. This was accompanied by the formation of 1,2,4-trioxolane. IR and NMR spectra of ozonated samples showed that scission of ozonide to give aldehyde were minimal. 1 H NMR analysis revealed that the amount of ozonide relative to aldehyde was more than 90% regardless of the extent of ozonation. Complete ozonation was attained after supplying around 0.20 g O 3/ml methyl ester after which ozone absorption suddenly dropped to around 25%. At the latter part of ozonation, ozonide and aldehyde reacted with excess ozone to give carboxylic acid. Reaction products were identified according to Criegee mechanism.
ISSN:0009-3084
1873-2941
DOI:10.1016/j.chemphyslip.2003.07.001