α-Terpineol reactions with the nitrate radical: Rate constant and gas-phase products

The bimolecular rate constant of k NO 3 + α-terpineol (16 ± 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 α-terpineol (2-(4-methyl-1-cyclohex-3-enyl)propan-2-ol) at 297 ± 3 K and 1 atmosphere total pressure. To m...

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Veröffentlicht in:	Atmospheric environment (1994) Jg. 42; H. 27; S. 6689 - 6698
Hauptverfasser:	Jones, Brian T., Ham, Jason E.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Oxford Elsevier Ltd 01.09.2008 Elsevier Science
Schlagworte:	Applied sciences Atmospheric pollution Exact sciences and technology Indoor pollution and occupational exposure Kinetics Nitrate radical Oxygenated organic compounds Pollution Reaction products α-Terpineol Reaction products Oxygenated organic compounds Kinetics Nitrate radical α-Terpineol Pollutant behavior Reaction product Alcohol Volatile organic compound Nitrates Low volatile compound Free radical reaction Reaction mechanism Indoor pollution Gaseous phase reaction Organic compounds Inorganic radical anion
ISSN:	1352-2310, 1873-2844
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Abstract	The bimolecular rate constant of k NO 3 + α-terpineol (16 ± 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 α-terpineol (2-(4-methyl-1-cyclohex-3-enyl)propan-2-ol) at 297 ± 3 K and 1 atmosphere total pressure. To more clearly define part of α-terpineol's indoor environment degradation mechanism, the products of α-terpineol + NO 3 reaction were investigated. The identified reaction products were: acetone, glyoxal (HC( O)C( O)H), and methylglyoxal (CH 3C( O)C( O)H). The use of derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and N, O-bis(trimethylsilyl) trifluoroacetamide (BSTFA) were used to propose the other major reaction products: 6-hydroxyhept-5-en-2-one, 4-(1-hydroxy-1-methylethyl)-1-methyl-2-oxocyclohexyl nitrate, 5-(1-hydroxy-1-methylethyl)-2-oxocyclohexyl nitrate, 1-formyl-5-hydroxy-4-(hydroxymethyl)-1,5-dimethylhexyl nitrate, and 1,4-diformyl-5-hydroxy-1,5-dimethylhexyl nitrate. The elucidation of these products was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible α-terpineol + NO 3 reaction mechanisms based on previously published volatile organic compound + NO 3 gas-phase mechanisms. The additional gas-phase products (2,6,6-trimethyltetrahydro-2 H-pyran-2,5-dicarbaldehyde and 2,2-dimethylcyclohexane-1,4-dicarbaldehyde) are proposed to be the result of cyclization through a reaction intermediate.
AbstractList	The bimolecular rate constant of k sub(N) sub(O) sub(3) sub(?) sub(+) sub( alpha ) sub(-) sub(t) sub(e) sub(r) sub(p) sub(i) sub(n) sub(e) sub(o) sub(l) (16+ /-4)x10 super(-) super(1) super(2)cm super(3)molecule super(-) super(1)s super(-) super(1) was measured using the relative rate technique for the reaction of the nitrate radical (NO sub(3)?) with alpha -terpineol (2-(4-methyl-1-cyclohex-3-enyl)propan-2-ol) at 297+/-3K and 1atmosphere total pressure. To more clearly define part of alpha -terpineol's indoor environment degradation mechanism, the products of alpha -terpineol+NO sub(3)? reaction were investigated. The identified reaction products were: acetone, glyoxal (HC(?O)C(?O)H), and methylglyoxal (CH sub(3)C(?O)C(?O)H). The use of derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and N,O-bis(trimethylsilyl) trifluoroacetamide (BSTFA) were used to propose the other major reaction products: 6-hydroxyhept-5-en-2-one, 4-(1-hydroxy-1-methylethyl)-1-methyl-2-oxocyclohexyl nitrate, 5-(1-hydroxy-1-methylethyl)-2-oxocyclohexyl nitrate, 1-formyl-5-hydroxy-4-(hydroxymethyl)-1,5-dimethylhexyl nitrate, and 1,4-diformyl-5-hydroxy-1,5-dimethylhexyl nitrate. The elucidation of these products was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible alpha -terpineol+NO sub(3)? reaction mechanisms based on previously published volatile organic compound+NO sub(3)? gas-phase mechanisms. The additional gas-phase products (2,6,6-trimethyltetrahydro-2H-pyran-2,5-dicarbaldehyde and 2,2-dimethylcyclohexane-1,4-dicarbaldehyde) are proposed to be the result of cyclization through a reaction intermediate. The bimolecular rate constant of k NO 3 + α-terpineol (16 ± 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 α-terpineol (2-(4-methyl-1-cyclohex-3-enyl)propan-2-ol) at 297 ± 3 K and 1 atmosphere total pressure. To more clearly define part of α-terpineol's indoor environment degradation mechanism, the products of α-terpineol + NO 3 reaction were investigated. The identified reaction products were: acetone, glyoxal (HC( O)C( O)H), and methylglyoxal (CH 3C( O)C( O)H). The use of derivatizing agents O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine (PFBHA) and N, O-bis(trimethylsilyl) trifluoroacetamide (BSTFA) were used to propose the other major reaction products: 6-hydroxyhept-5-en-2-one, 4-(1-hydroxy-1-methylethyl)-1-methyl-2-oxocyclohexyl nitrate, 5-(1-hydroxy-1-methylethyl)-2-oxocyclohexyl nitrate, 1-formyl-5-hydroxy-4-(hydroxymethyl)-1,5-dimethylhexyl nitrate, and 1,4-diformyl-5-hydroxy-1,5-dimethylhexyl nitrate. The elucidation of these products was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible α-terpineol + NO 3 reaction mechanisms based on previously published volatile organic compound + NO 3 gas-phase mechanisms. The additional gas-phase products (2,6,6-trimethyltetrahydro-2 H-pyran-2,5-dicarbaldehyde and 2,2-dimethylcyclohexane-1,4-dicarbaldehyde) are proposed to be the result of cyclization through a reaction intermediate.
Author	Ham, Jason E. Jones, Brian T.
Author_xml	– sequence: 1 givenname: Brian T. surname: Jones fullname: Jones, Brian T. organization: Case Western Reserve University, 10900 Euclid Avenue, Cleveland, OH 44106-7078, USA – sequence: 2 givenname: Jason E. surname: Ham fullname: Ham, Jason E. email: bvo2@cdc.gov organization: Exposure Assessment Branch, Health Effects Laboratory Division, National Institute for Occupational Safety and Health, 1095 Willowdale Road, Morgantown, WV 26505, USA
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Keywords	Reaction products Oxygenated organic compounds Kinetics Nitrate radical α-Terpineol Pollutant behavior Reaction product Alcohol Volatile organic compound Nitrates Low volatile compound Free radical reaction Reaction mechanism Indoor pollution Gaseous phase reaction Organic compounds Inorganic radical anion
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Snippet	The bimolecular rate constant of k NO 3 + α-terpineol (16 ± 4) × 10 −12 cm 3 molecule −1 s −1 was measured using the relative rate technique for the reaction... The bimolecular rate constant of k sub(N) sub(O) sub(3) sub(?) sub(+) sub( alpha ) sub(-) sub(t) sub(e) sub(r) sub(p) sub(i) sub(n) sub(e) sub(o) sub(l) (16+...
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SubjectTerms	Applied sciences Atmospheric pollution Exact sciences and technology Indoor pollution and occupational exposure Kinetics Nitrate radical Oxygenated organic compounds Pollution Reaction products α-Terpineol
Title	α-Terpineol reactions with the nitrate radical: Rate constant and gas-phase products
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