β-Ionone reactions with ozone and OH radical: Rate constants and gas-phase products
The bimolecular rate constants, k OH + β -ionone (118±30)×10 −12 cm 3 molecule −1 s −1 and k O 3 + β ‐ ionone , (0.19±0.05)×10 −16 cm 3 molecule −1 s −1, were measured using the relative rate technique for the reaction of the hydroxyl radical (OH) and ozone (O 3) with 4-(2,6,6-trimethyl-1-cyclohexen...
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| Published in: | Atmospheric environment (1994) Vol. 41; no. 38; pp. 8758 - 8771 |
|---|---|
| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Oxford
Elsevier Ltd
01.12.2007
Elsevier Science |
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| ISSN: | 1352-2310, 1873-2844 |
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| Abstract | The bimolecular rate constants,
k
OH
+
β
-ionone (118±30)×10
−12
cm
3
molecule
−1
s
−1 and
k
O
3
+
β
‐
ionone
, (0.19±0.05)×10
−16
cm
3
molecule
−1
s
−1, were measured using the relative rate technique for the reaction of the hydroxyl radical (OH) and ozone (O
3) with 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (
β-ionone) at 297±3
K and 1
atm total pressure. To more clearly define part of
β-ionone's indoor environment degradation mechanism, the products of the
β-ionone+OH
and
β-ionone+O
3 reactions were also investigated. The identified
β-ionone+OH
reaction products were: glyoxal (ethanedial, HC(=O)C(=O)H), and methylglyoxal (2-oxopropanal, CH
3C(=O)C(=O)H) and the identified
β-ionone+O
3 reaction product was 2-oxopropanal. The derivatizing agents
O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and
N,
O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) were used to propose 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde as the other major
β-ionone+OH
and
β-ionone+O
3 reaction product. The elucidation of this other reaction product was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible
β-ionone+OH
and
β-ionone+O
3 reaction mechanisms based on previously published volatile organic compound+OH
and volatile organic compound+O
3 gas-phase reaction mechanisms. The additional gas-phase products observed from the
β-ionone+OH
reaction are proposed to be the result of cyclization through a radical intermediate. |
|---|---|
| AbstractList | The bimolecular rate constants, k sub(O) sub(H) sub(?) sub(+) sub( beta ) sub(-) sub(i) sub(o) sub(n) sub(o) sub(n) sub(e) (118+/-30)x10 super(-) super(1) super(2)cm super(3)molecule super(-) super(1)s super(-) super(1) and k sub(O) sub(3) sub(+) sub( beta ) sub( approximately equal to ) sub(i) sub(o) sub(n) sub(o) sub(n) sub(e), (0.19+ /-0.05)x10 super(-) super(1) super(6)cm super(3)molecule super(-) super(1)s super(-) super(1), were measured using the relative rate technique for the reaction of the hydroxyl radical (OH) and ozone (O sub(3)) with 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one ( beta -ionone) at 297+/-3K and 1atm total pressure. To more clearly define part of beta -ionone's indoor environment degradation mechanism, the products of the beta -ionone+OH? and beta -ionone+O sub(3) reactions were also investigated. The identified beta -ionone+OH? reaction products were: glyoxal (ethanedial, HC(=O)C(=O)H), and methylglyoxal (2-oxopropanal, CH sub(3)C(=O)C(=O)H) and the identified beta -ionone+O sub(3) reaction product was 2-oxopropanal. The derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) were used to propose 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde as the other major beta -ionone+OH? and beta -ionone+O sub(3) reaction product. The elucidation of this other reaction product was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible beta -ionone+OH? and beta -ionone+O sub(3) reaction mechanisms based on previously published volatile organic compound+OH? and volatile organic compound+O sub(3) gas-phase reaction mechanisms. The additional gas-phase products observed from the beta -ionone+OH? reaction are proposed to be the result of cyclization through a radical intermediate. The bimolecular rate constants, k OH + β -ionone (118±30)×10 −12 cm 3 molecule −1 s −1 and k O 3 + β ‐ ionone , (0.19±0.05)×10 −16 cm 3 molecule −1 s −1, were measured using the relative rate technique for the reaction of the hydroxyl radical (OH) and ozone (O 3) with 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one ( β-ionone) at 297±3 K and 1 atm total pressure. To more clearly define part of β-ionone's indoor environment degradation mechanism, the products of the β-ionone+OH and β-ionone+O 3 reactions were also investigated. The identified β-ionone+OH reaction products were: glyoxal (ethanedial, HC(=O)C(=O)H), and methylglyoxal (2-oxopropanal, CH 3C(=O)C(=O)H) and the identified β-ionone+O 3 reaction product was 2-oxopropanal. The derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and N, O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) were used to propose 2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde as the other major β-ionone+OH and β-ionone+O 3 reaction product. The elucidation of this other reaction product was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible β-ionone+OH and β-ionone+O 3 reaction mechanisms based on previously published volatile organic compound+OH and volatile organic compound+O 3 gas-phase reaction mechanisms. The additional gas-phase products observed from the β-ionone+OH reaction are proposed to be the result of cyclization through a radical intermediate. |
| Author | Ham, Jason E. Forester, Crystal D. Wells, J. Raymond |
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| Keywords | Reaction products Annelation β-Ionone Oxygenated organic compounds 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one Kinetics β-Irisone Unsaturated cyclic compound Pollutant behavior Reaction product Ozone Volatile organic compound Chemical degradation Free radical reaction Chemical reaction kinetics Ozonization Atmospheric chemistry Reaction mechanism Indoor pollution Hydroxyl radicals Oxidation Enone Degradation product Organic compounds |
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| References | Sarwar, Corsi, Kimura, Allen, Weschler (bib17) 2002; 36 Atkinson, Arey (bib3) 2003; 103 Weschler, Wells, Poppendieck, Hubbard, Pearce (bib26) 2006; 114 (accessed 14.02.05). Rogers, Isola, Jeng, Lefebvre, Smith (bib16) 2005; 39 Wilson, Colome, Tian, Becker, Baker, Behrens, Billick, Garrison (bib27) 1996; 6 Martin, Tuazon, Aschmann, Arey, Atkinson (bib12) 2002; 106 Ham, Proper, Wells (bib9) 2006; 40 Atkinson, Aschmann (bib4) 1993; 27 Jarvis, Seed, Elton, Sawyer, Agius (bib11) 2005; 62 US Environmental Protection Agency, 2000. AOPWIN v1.91. Washington, DC. Yu, Flagan, Seinfeld (bib28) 1998; 32 Shangaria, Chan, Popovica, O’Brien (bib20) 2006; 71 Shu, Kwok, Tuazon, Atkinson, Arey (bib21) 1997; 31 Singer, Destaillats, Hodgson, Nazaroff (bib22) 2006; 16 Rheault, Sibi (bib15) 2003 Holt, Atkinson, Arey (bib10) 2005; 176 Anderson, Wells, Fedorowicz, Butterworth, Meade, Munson (bib1) 2007; 97 Nazaroff, Weschler (bib13) 2004; 38 Weschler, Shields (bib25) 1997; 31 Atkinson (bib2) 1989; 1 Atkinson, Carter, Winer, Pitts (bib5) 1981; 31 Semikolenov, Ilyna, Simakova (bib18) 2002; 182 Taylor, Allston, Moscato, Fazekas, Kozlowski, Takacs (bib23) 1980; 12 Sexton, Jefferies, Jang, Kamens, Doyle, Voicu, Jaspers (bib19) 2004; 16 Forester, Ham, Wells (bib8) 2007; 41 Fick, Pommer, Nilsson, Andersson (bib7) 2003; 37 Paulson, Chung, Hasson (bib14) 1999; 103 Weschler, Shields (bib24) 1996; 30 |
| References_xml | – volume: 1 start-page: 246 year: 1989 ident: bib2 article-title: Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds publication-title: Journal of Physical Chemical Reference Data, Monograph – volume: 62 start-page: 243 year: 2005 end-page: 250 ident: bib11 article-title: Relationship between chemical structure and the occupational asthma hazard of low molecular weight organic compounds publication-title: Journal of Occupational and Environmental Medicine – volume: 103 start-page: 4605 year: 2003 end-page: 4638 ident: bib3 article-title: Atmospheric degradation of volatile organic compounds publication-title: Chemical Reviews – volume: 6 start-page: 311 year: 1996 end-page: 326 ident: bib27 article-title: California residential air exchange rates and residence volumes publication-title: Journal of Exposure Analysis and Environmental Epidemiology – volume: 106 start-page: 11492 year: 2002 end-page: 11501 ident: bib12 article-title: Formation and atmospheric reactions of 4,5-dihydro-2-methylfuran publication-title: Journal of Physical Chemistry A – volume: 12 start-page: 231 year: 1980 end-page: 240 ident: bib23 article-title: Atmospheric photo-dissociation lifetimes for nitromethane, methyl nitrite, and methyl nitrate publication-title: International Journal of Chemical Kinetics – volume: 71 start-page: 1610 year: 2006 end-page: 1618 ident: bib20 article-title: Glyoxal markedly compromises hepatocyte resistance to hydrogen peroxide publication-title: Biochemical Pharmacology – reference: US Environmental Protection Agency, 2000. 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Washington, DC. 〈 – volume: 182 start-page: 383 year: 2002 end-page: 393 ident: bib18 article-title: Effect of heterogeneous and homogeneous pathways on selectivity of pinane-2-ol to linalool isomerization publication-title: Journal of Molecular Catalysis A—Chemical – volume: 41 start-page: 1188 year: 2007 end-page: 1199 ident: bib8 article-title: Geraniol (2,6-dimethyl-2,6-octadien-8-ol) reactions with ozone and OH radical: rate constants and gas-phase products publication-title: Atmospheric Environment – volume: 16 start-page: 107 year: 2004 end-page: 114 ident: bib19 article-title: Photochemical products in urban mixtures enhance inflammatory responses in lung cells publication-title: Inhalation Toxicology – volume: 114 start-page: 442 year: 2006 end-page: 446 ident: bib26 article-title: Workgroup report: indoor chemistry and health publication-title: Environmental Health Perspectives – volume: 31 start-page: 896 year: 1997 end-page: 904 ident: bib21 article-title: Products of the gas-phase reactions of linalool with OH radicals, NO publication-title: Environmental Science and Technology – volume: 103 start-page: 8125 year: 1999 end-page: 8138 ident: bib14 article-title: OH radical formation from the gas-phase reaction of ozone with terminal alkenes and the relationship between structure and mechanism publication-title: Journal of Physical Chemistry A – volume: 31 start-page: 1090 year: 1981 end-page: 1092 ident: bib5 article-title: An experimental protocol for the determination of OH radical rate constants with organics using methyl nitrite photolysis as an OH radical source publication-title: Journal of the Air Pollution Control Association – volume: 97 start-page: 355 year: 2007 end-page: 363 ident: bib1 article-title: Evaluation of the contact and respiratory sensitization potential of volatile organic compounds generated by simulated indoor air chemistry publication-title: Toxicology Sciences – start-page: 803 year: 2003 end-page: 819 ident: bib15 article-title: Radical-mediated annulation reactions publication-title: Synthesis—Stuttgart – volume: 176 start-page: 231 year: 2005 end-page: 237 ident: bib10 article-title: Effect of water vapor concentration on the conversion of a series of 1,4-hydroxycarbonyls to dihydrofurans publication-title: Journal of Photochemistry and Photobiology A—Chemistry – volume: 31 start-page: 3719 year: 1997 end-page: 3722 ident: bib25 article-title: Measurements of the hydroxyl radical in a manipulated but realistic indoor environment publication-title: Environmental Science and Technology – volume: 27 start-page: 1357 year: 1993 end-page: 1363 ident: bib4 article-title: OH radical production from the gas-phase reactions of O publication-title: Environmental Science and Technology – volume: 30 start-page: 3250 year: 1996 end-page: 3258 ident: bib24 article-title: Production of the hydroxyl radical in indoor air publication-title: Environmental Science and Technology – reference: 〉 (accessed 14.02.05). – volume: 39 start-page: 7810 year: 2005 end-page: 7816 ident: bib16 article-title: Simulated inhalation levels of fragrance materials in a surrogate air freshener formulation publication-title: Environmental Science and Technology – volume: 37 start-page: 4087 year: 2003 end-page: 4096 ident: bib7 article-title: Effect of OH radicals, relative humidity, and time on the composition of the products formed in the ozonolysis of alpha-pinene publication-title: Atmospheric Environment – volume: 16 start-page: 179 year: 2006 end-page: 191 ident: bib22 article-title: Cleaning products and air fresheners: emissions and resulting concentrations of glycol ethers and terpenoids publication-title: Indoor Air – volume: 36 start-page: 3973 year: 2002 end-page: 3988 ident: bib17 article-title: Hydroxyl radicals in indoor environments publication-title: Atmospheric Environment – volume: 32 start-page: 2357 year: 1998 end-page: 2370 ident: bib28 article-title: Identification of products containing –COOH, –OH, and –C publication-title: Environmental Science and Technology – volume: 40 start-page: 726 year: 2006 end-page: 735 ident: bib9 article-title: Gas-phase chemistry of citronellol with ozone and OH radical: rate constants and products publication-title: Atmospheric Environment – volume: 38 start-page: 2841 year: 2004 end-page: 2865 ident: bib13 article-title: Cleaning products and air fresheners: exposure to primary and secondary air pollutants publication-title: Atmospheric Environment |
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| Snippet | The bimolecular rate constants,
k
OH
+
β
-ionone (118±30)×10
−12
cm
3
molecule
−1
s
−1 and
k
O
3
+
β
‐
ionone
, (0.19±0.05)×10
−16
cm
3
molecule
−1
s
−1, were... The bimolecular rate constants, k sub(O) sub(H) sub(?) sub(+) sub( beta ) sub(-) sub(i) sub(o) sub(n) sub(o) sub(n) sub(e) (118+/-30)x10 super(-) super(1)... |
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| SubjectTerms | 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one Annelation Applied sciences Atmospheric pollution Exact sciences and technology Indoor pollution and occupational exposure Kinetics Oxygenated organic compounds Pollution Reaction products β-Ionone β-Irisone |
| Title | β-Ionone reactions with ozone and OH radical: Rate constants and gas-phase products |
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