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Title:Ab Initio Study of the Decomposition of 2,5-Dimethylfuran
Authors:John M. Simmie and Wayne K. Metcalfe, 2011
Abstract: The initial steps in the thermal decomposition of 2,5-dimethylfuran are identified as scission of the C–H bond in the methyl side chain and formation of β- and α-carbenes via 3,2-H and 2,3-methyl shifts, respectively. A variety of channels are explored which prise the aromatic ring open and lead to a number of intermediates whose basic properties are essentially unknown. Once the furan ring is opened demethylation to yield highly unsaturated species such as allenylketenes appears to be a feature of this chemistry. The energetics of H abstraction by the hydroxyl radical (and other abstracting species) from a number of mono- and disubstituted methyl furans has been studied. H-atom addition to 2,5-dimethylfuran followed by methyl elimination is shown to be the most important route to formation of the less reactive 2-methylfuran. Identification of 2-ethenylfuran as an C6H6O intermediate in 2,5-dimethylfuran flames is probably not correct and is more likely the isomeric 2,5-dimethylene-2,5-dihydrofuran for which credible formation channels exist.
ICHEC Project:BurnQuest: Towards a World Class Combustion Chemistry Centre
Publication:J. Phys. Chem. A, 2011, 115 (32), pp 8877–8888
URL: DOI: 10.1021/jp2039477
Status: Published

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