Journal article
Mechanism of formation of volatile organic compounds from oxidation of linseed oil
Industrial & Engineering Chemistry Research, Vol.51(16), pp.5653-5661
2012
Abstract
The pathways of volatile organic compound (VOC) formation have been investigated through a computational study, employing the Gaussian 03 suite of programs. We optimized geometries and zero-point vibrational energies (ZPVEs) at the B3LYP/6-31G(d) level of theory and improved electronic energies by conducting single-point energy calculations using the large 6-311++G(3df,3pd) basis set. To describe the predominant mechanism of the linseed oil oxidation, the following sequence is proposed: hydrogen abstraction of unsaturated fatty compounds as the initiation reaction followed by the reaction of allylic-type radicals with molecular oxygen to form peroxyl radicals and finally intramolecular rearrangement through four- and five-membered rings. Quantum calculations identified low-energy pathways following cyclization resulting in the formation of major products observed, especially aldehydes and ketones. The overall energy changes taking place through the four- and five-membered rings were found to be 78 and 93 kJ mol -1 exothermic, respectively. Metal catalysts decompose hydroperoxides based on the Fenton-like mechanism into alkoxyl and peroxyl radicals.
Details
- Title
- Mechanism of formation of volatile organic compounds from oxidation of linseed oil
- Authors/Creators
- Juita (Author/Creator)B.Z. Dlugogorski (Author/Creator)E.M. Kennedy (Author/Creator)J.C. Mackie (Author/Creator)
- Publication Details
- Industrial & Engineering Chemistry Research, Vol.51(16), pp.5653-5661
- Publisher
- American Chemical Society
- Identifiers
- 991005543612407891
- Copyright
- © 2012 American Chemical Society.
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 1 Clinical & Life Sciences
- 1.68 Lipids
- 1.68.621 Virgin Olive Oil
- Web Of Science research areas
- Engineering, Chemical
- ESI research areas
- Chemistry