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beta-Ionone reactions with the nitrate radical: rate constant and gas-phase products.

Authors
Harrison-JC; Ham-JE
Source
Int J Chem Kinet 2009 Oct; 41(10):629-641
NIOSHTIC No.
20035964
Abstract
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.
Keywords
Chemical-reactions; Gas-chromatography; Gases; Gas-industry; Gas-mixtures; Mass-spectrometry; Molecular-biology; Molecular-structure; Organic-chemicals; Organic-compounds
Contact
Jason E. Ham, Exposure Assessment Branch, Health Effects Laboratory Division, National Institute for Occupational Safety and Health,1095 Willowdale Road, Morgantown, WV 26505
CODEN
IJCKBO
Publication Date
20091001
Document Type
Journal Article
Email Address
bvo2@cdc.gov
Fiscal Year
2010
NTIS Accession No.
NTIS Price
Issue of Publication
10
ISSN
0538-8066
NIOSH Division
HELD
Priority Area
Services
Source Name
International Journal of Chemical Kinetics
State
WV
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