- Title
- Non-oxidative thermal decomposition of endosulfan II. Mechanism of decomposition
- Creator
- Mackie, J. C.; Dharmarathne, W. N. K.; Kennedy, E. M.; Stockenhuber, M.
- Relation
- Australian Combustion Symposium 2015. Proceedings of the Australian Combustion Symposium 2015 (Parkville, Vic. 7-9 December, 2015) p. 120-123
- Relation
- http://www.anz-combustioninstitute.org/ACS2015/
- Publisher
- Combustion Institute, Australian and New Zealand Section
- Resource Type
- conference paper
- Date
- 2015
- Description
- The mechanism of thermal decomposition of endosulfan has been investigated by quantum chemical calculation. Under pyrolysis conditions, endosulfan initially decomposes via a retro-Diels-Alder decomposition into hexachlorocyclopentadiene (HCCP) and 4,7- dihydro-1,3,2-dioxathiepine-2-oxide (a seven-membered ring compound). The latter undergoes decomposition via two competing channels – one eliminates SO₂ and 2,5-dihydrofuran, the second also eliminates SO₂, forming additionally 3-butenal which further eliminates CO and propene. At higher temperatures, HCCP undergoes fission of a Cl atom, which promotes further decomposition of endosulfan via abstraction of a hydrogen atom to form HCl. The resulting endosulfan radical undergoes a sequence of low barrier steps leading to ring opening and finally to ring closure to a series of chlorinated styrenes and chlorobenzenes – known precursors of dioxins under oxidative conditions.
- Subject
- endosulfan; pyrolysis; quantum chemistry; reaction mechanisms
- Identifier
- http://hdl.handle.net/1959.13/1316257
- Identifier
- uon:23116
- Identifier
- ISSN:1839-8170
- Language
- eng
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