β-Ionone reactions with ozone and OH radical: Rate constants and gas-phase products

Forester, Crystal D.; Ham, Jason E.; Wells, J. R.

doi:10.1016/j.atmosenv.2007.07.047

Cited by 11 publications

(10 citation statements)

References 26 publications

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“…The measured k NO 3 ·+β-ionone of (9. [28] and its corresponding calculated value of 238 × 10 −12 cm 3 molecule −1 s −1 , using AOPWIN estimation software [30]. Primary reactions are expected to occur at both double bonds of β-ionone; however, the measured rate constant (k OH •) suggests that only one of the double bonds interacts with OH•.…”

Section: Discussionmentioning

confidence: 99%

“…Several oxidation products were generated from β-ionone/NO 3 • reactions that were similar to those previously observed from β-ionone/OH• or β-ionone/O 3 gas-phase reactions [28]. The mechanisms for the formation of these specific products were detailed by Forester et al [28] and only a brief description will be provided here.…”

Section: Equivalent or Structurally Analogous Products Observed From mentioning

confidence: 90%

“…A comparison of this value to a typical indoor air exchange rate of 0.6 h −1 [39] suggests that nitrate radical chemistry is the most likely removal mechanism for β-ionone. When compared with the pseudo-first-order rate constants of the hydroxyl radical (k OH•+β-Ionone = 118 × [28], it is evident that nitrate radical chemistry could play a critical role in the transformation of β-ionone in the indoor environment.…”

Section: Indoor Nitrate Radical Chemistrymentioning

confidence: 98%

“…The mechanisms for the formation of these specific products were detailed by Forester et al [28] and only a brief description will be provided here. The mechanism for the formation of the product observed at 20.8 min, (2E)-5-acetyl-2-ethylidene-3-methylcyclopentyl nitrate, is analogous to the similar product, 1-[(3E)-3-ethylidene-2-hydroxy-4-methylcyclopentyl]ethanone observed from β-ionone/OH•, except NO 3 • adds to the carbon-carbon double bond (labeled A, Structure 1) with subsequent annelation of the alkyl radical leading to the five-membered ring.…”

Section: Equivalent or Structurally Analogous Products Observed From mentioning

confidence: 99%

“…The chromatographic peaks for the oxime observed at 24.1 and 24.4 min have been described previously [18,28].…”

Section: Glyoxal (Hc( O)c( O)h)mentioning

confidence: 99%

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β‐Ionone reactions with the nitrate radical: Rate constant and gas‐phase products

Harrison

Ham

2009

Int J of Chemical Kinetics

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The bimolecular rate constant of k N O 3 ·+β-ionone (9.4 ± 2.4 × 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 (β-ionone) at (297 ± 3) K and 1 atmosphere total pressure. In addition, the products of β-ionone + NO 3 • reaction were also investigated. The identified reaction products were 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-1-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 β-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-methylcyclopentyl nitrate, 1-(1-hydroxy-7,7-dimethyl-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-methylcyclopentanone are proposed to be the result of cyclization through a reaction intermediate. glyoxal (HC( O)C( O)H), and methylglyoxal (CH 3 C( O)C( O)H). Derivatizing agents

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Section: Discussionmentioning

confidence: 99%

Section: Equivalent or Structurally Analogous Products Observed From mentioning

confidence: 90%

Section: Indoor Nitrate Radical Chemistrymentioning

confidence: 98%

Section: Equivalent or Structurally Analogous Products Observed From mentioning

confidence: 99%

“…The chromatographic peaks for the oxime observed at 24.1 and 24.4 min have been described previously [18,28].…”

Section: Glyoxal (Hc( O)c( O)h)mentioning

confidence: 99%

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β‐Ionone reactions with the nitrate radical: Rate constant and gas‐phase products

Harrison

Ham

2009

Int J of Chemical Kinetics

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Rate constants for the gas-phase reactions of nitrate radicals with geraniol, citronellol, and dihydromyrcenol

Harrison¹,

Ham²

2010

Int. J. Chem. Kinet.

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Terpenes and terpene alcohols are prevalent compounds found in a wide variety of consumer products including soaps, flavorings, perfumes, and air fresheners used in the indoor environment. Knowing the reaction rate of these chemicals with the nitrate radical is an important factor in determining their fate indoors. In this study, the bimolecular rate constants of k NO 3 • +geraniol (16.6 ± 4.2) × 10 −12 , k NO 3 • +citronellol (12.1 ± 3) × 10 −12 , and k NO 3 • +dihydromyrcenol (2.3 ± 0.6) × 10 −14 cm 3 molecule −1 s −1 were measured using the relative rate technique for the reaction of the nitrate radical (NO 3 • ) with 2,6-dimethyl-2,6-octadien-8-ol (geraniol), 3,7-dimethyl-6-octen-1-ol (citronellol), and 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol) at (297 ± 3) K and 1 atmosphere total pressure. Using the geraniol, citronellol, or dihydromyrcenol + NO 3 • rate constants reported here, pseudo-first-order rate lifetimes (k ) of 1.5, 1.1, and 0.002 h −1 were determined, respectively. C 2010 Wiley Periodicals, Inc. * Int J Chem Kinet 42: [669][670][671][672][673][674][675] 2010

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Rate Constants for the Gas‐Phase Reactions of Ozone and Nitrate Radicals with the Sesquiterpenes: Valencene and Farnesol

Ham

2013

Int J of Chemical Kinetics

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Sesquiterpenes are constituents of a variety of essential oils that are used in flavorings, perfumes, personal care, and cleaning products. Two sesquiterpenes that are commonly used as indoor fragrances are valencene and farnesol. Knowing the reaction rate constants of these chemicals with ozone (O 3 ) and nitrate radical (NO • 3 ) is an important factor in determining their fate indoors. In this study, the bimolecular rate constants of k O 3 +valencene (0.35 ± 0.9) × 10 −16 , k O 3 +farnesol (21 ± 5.2) × 10 −16 , k NO • 3 +valencene (7.9 ± 2.0) × 10 −12 , and k NO • 3 +farnesol (44 ± 11) × 10 −12 cm 3 molecule −1 s −1 were measured using the relative rate technique at 297 ± 3 K and 1 atm total pressure. Using the rate constants reported here and measured/modeled indoor concentrations of O 3 and NO • 3 (20 ppb and 1 ppt, respectively), pseudo-first-order-rate lifetimes k O 3 +valencene (0.06), k O 3 +farnesol (3.8), k NO 3 +valencene(0.7), and k NO 3 ·+farnesol (3.9)h −1 were determined. C 2013 Wiley Periodicals, Inc.

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β-Ionone reactions with ozone and OH radical: Rate constants and gas-phase products

Cited by 11 publications

References 26 publications

β‐Ionone reactions with the nitrate radical: Rate constant and gas‐phase products

β‐Ionone reactions with the nitrate radical: Rate constant and gas‐phase products

Rate constants for the gas-phase reactions of nitrate radicals with geraniol, citronellol, and dihydromyrcenol

Rate Constants for the Gas‐Phase Reactions of Ozone and Nitrate Radicals with the Sesquiterpenes: Valencene and Farnesol

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