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alpha-Terpineol reactions with the nitrate radical: rate constant and gas-phase products.

Authors
Jones-BT; Ham-JE
Source
Atmos Environ 2008 Sep; 42(27):6689-6698
NIOSHTIC No.
20034618
Abstract
The bimolecular rate constant of kNO3+a-terpineol (16 4) 10-12 cm3 molecule-1 s-1 was measured using the relative rate technique for the reaction of the nitrate radical (NO3) with a-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 a-terpineol's indoor environment degradation mechanism, the products of a-terpineol + NO3 reaction were investigated. The identified reaction products were: acetone, glyoxal (HC(O)C(O)H), and methylglyoxal (CH3C(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 a-terpineol + NO3* reaction mechanisms based on previously published volatile organic compound + NO3* 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.
Keywords
Quantitative-analysis; Sampling-methods; Air-quality; Indoor-environmental-quality; Chemical-binding; Chemical-deposition; Chemical-composition; Chemical-properties; Chemical-reactions; Chemical-synthesis; Organic-chemicals; Organic-compounds; Organic-vapors; Gases; Author Keywords: a-Terpineol; Nitrate radical; Kinetics; Reaction products; Oxygenated 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
AENVEQ
CAS No.
107-22-2; 67-64-1; 78-98-8
Publication Date
20080901
Document Type
Journal Article
Email Address
bvo2@cdc.gov
Fiscal Year
2008
NTIS Accession No.
NTIS Price
Issue of Publication
27
ISSN
1352-2310
NIOSH Division
HELD
Priority Area
Services
Source Name
Atmospheric Environment
State
WV
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