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beta-Ionone reactions with the nitrate radical: rate constant and gas-phase products.
Harrison JC; Ham JE
Int J Chem Kinet 2009 Oct; 41(10):629-641
The bimolecular rate constant of k(NO(3)(.)+beta-ionone) (9.4 +/- 2.4 x 10(-12) cm(3) molecule(-1) s(-1) was measured using the relative rate technique for the reaction of the nitrate radical (NO(3)(.)) with 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (beta-ionone) at (297 +/- 3) K and I atmosphere total pressure. in addition, the products of beta-ionone + NO(3)(.) reaction were also investigated. The identified reaction products were glyoxal (HC(=O)C(=O)H), and methylglyoxal (CH3C(=O)C(=O)H). Derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine and N,O-bis(trimethylsilyl)trifluoroacetamide were used to propose the other major reaction products: 3-oxobutane-1,2-diyl nitrate, 2,6,6-trimethylcyclohex-1-ene-carbaldehyde, 2-oxo-1-(2,6,6-trimethylcyclohex-i-en-1-yl)ethyl nitrate, pentane-2,4-dione, 3-oxo-1-(2,6,6-trimethylcyclohex-1-en-1-yl)butane-1,2-diyl dinitrate, 3,3-dimethylcyclohexane-1,2-dione, and 4-oxopent-2-enal. The elucidation of these products was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible beta-ionone + NO(3)(.) reaction mechanisms based on previously published volatile organic compound + NO(3)(.) gas-phase mechanisms. The additional gas-phase products 5-acetyl-2-ethylidene-3-methyicyclopentyl nitrate, 1-(1-hydroxy-7,7-dimetliyl-2,3,4,5,6,7-hexahydro-1H-inden-2-yl)ethanone, 1-(1-hydroxy-3a,7-dimethyl-2,3,3a,4,5,6,-hexahydro-1H-inden-2-yl)ethanone, and 5-acetyl-2-ethylidene-3-methylcyclopenta none are proposed to be the result of cyclization through a reaction intermediate.
Chemical-reactions; Gas-chromatography; Gases; Gas-industry; Gas-mixtures; Mass-spectrometry; Molecular-biology; Molecular-structure; Organic-chemicals; Organic-compounds
Jason E. Ham, Exposure Assessment Branch, Health Effects Laboratory Division, National Institute for Occupational Safety and Health,1095 Willowdale Road, Morgantown, WV 26505
Issue of Publication
International Journal of Chemical Kinetics
Page last reviewed: September 2, 2020
Content source: National Institute for Occupational Safety and Health Education and Information Division