Products of the Gas-Phase Reactions of the OH Radical with 1-Methoxy-2-propanol and 2-Butoxyethanol

Glycol ethers are used as solvents and are hence liable to be released to the atmosphere, where they react and contribute to the formation of photochemical air pollution. In this work, products of the gas-phase reactions of the OH radical with 1-methoxy-2-propanol and 2-butoxyethanol in the presence...

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Veröffentlicht in:Environmental Science and Technology 1998-11, Vol.32 (21), p.3336-3345
Hauptverfasser: Tuazon, Ernesto C, Aschmann, Sara M, Atkinson, Roger
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Aschmann, Sara M
Atkinson, Roger
description Glycol ethers are used as solvents and are hence liable to be released to the atmosphere, where they react and contribute to the formation of photochemical air pollution. In this work, products of the gas-phase reactions of the OH radical with 1-methoxy-2-propanol and 2-butoxyethanol in the presence of NO have been investigated at 298 ± 2 K and 740 Torr total pressure of air by gas chromatography, in situ Fourier transform infrared spectroscopy, and in situ atmospheric pressure ionization tandem mass spectrometry. The products observed from 1-methoxy-2-propanol were methyl formate, methoxyacetone, and acetaldehyde with molar formation yields of 0.59 ± 0.05, 0.39 ± 0.04, and 0.56 ± 0.07, respectively. The products observed and quantified from 2-butoxyethanol were n-butyl formate, 2-hydroxyethyl formate, propanal, 3-hydroxybutyl formate, and an organic nitrate (attributed to CH3CH2CH2CH2OCH(ONO2)CH2OH and its isomers), with molar formation yields of 0.57 ± 0.05, 0.22 ± 0.05, 0.21 ± 0.02, 0.07 ± 0.03, and 0.10 ± 0.03, respectively. An additional product of molecular weight 132, attributed to one or more hydroxycarbonyl products, was also observed from the 2-butoxyethanol reaction by atmospheric pressure ionization mass spectrometry. For both glycol ethers, the majority of the reaction products and reaction pathways are accounted for, and detailed reaction mechanisms are presented which account for the observed products.
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In this work, products of the gas-phase reactions of the OH radical with 1-methoxy-2-propanol and 2-butoxyethanol in the presence of NO have been investigated at 298 ± 2 K and 740 Torr total pressure of air by gas chromatography, in situ Fourier transform infrared spectroscopy, and in situ atmospheric pressure ionization tandem mass spectrometry. The products observed from 1-methoxy-2-propanol were methyl formate, methoxyacetone, and acetaldehyde with molar formation yields of 0.59 ± 0.05, 0.39 ± 0.04, and 0.56 ± 0.07, respectively. The products observed and quantified from 2-butoxyethanol were n-butyl formate, 2-hydroxyethyl formate, propanal, 3-hydroxybutyl formate, and an organic nitrate (attributed to CH3CH2CH2CH2OCH(ONO2)CH2OH and its isomers), with molar formation yields of 0.57 ± 0.05, 0.22 ± 0.05, 0.21 ± 0.02, 0.07 ± 0.03, and 0.10 ± 0.03, respectively. An additional product of molecular weight 132, attributed to one or more hydroxycarbonyl products, was also observed from the 2-butoxyethanol reaction by atmospheric pressure ionization mass spectrometry. For both glycol ethers, the majority of the reaction products and reaction pathways are accounted for, and detailed reaction mechanisms are presented which account for the observed products.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/es980455c</identifier><identifier>CODEN: ESTHAG</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AIR POLLUTION ; Applied sciences ; Atmosphere ; Atmospheric pollution ; Chemical composition and interactions. Ionic interactions and processes ; Chemical reactions ; Earth, ocean, space ; ENVIRONMENTAL SCIENCES ; ETHERS ; Exact sciences and technology ; External geophysics ; GAS CHROMATOGRAPHY ; HYDROXYL RADICALS ; INFRARED SPECTRA ; MASS SPECTROSCOPY ; Meteorology ; PHASE STUDIES ; PHOTOCHEMICAL REACTIONS ; Pollutants physicochemistry study: properties, effects, reactions, transport and distribution ; Pollution ; Solvents</subject><ispartof>Environmental Science and Technology, 1998-11, Vol.32 (21), p.3336-3345</ispartof><rights>Copyright © 1998 American Chemical Society</rights><rights>1998 INIST-CNRS</rights><rights>Copyright American Chemical Society Nov 1, 1998</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-d9219d93b00364f1ac33b645a774d8150073c578eb5b68cbcc40f128a11ccdd33</citedby><cites>FETCH-LOGICAL-a377t-d9219d93b00364f1ac33b645a774d8150073c578eb5b68cbcc40f128a11ccdd33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/es980455c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/es980455c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,885,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=2437251$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/323751$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Tuazon, Ernesto C</creatorcontrib><creatorcontrib>Aschmann, Sara M</creatorcontrib><creatorcontrib>Atkinson, Roger</creatorcontrib><title>Products of the Gas-Phase Reactions of the OH Radical with 1-Methoxy-2-propanol and 2-Butoxyethanol</title><title>Environmental Science and Technology</title><addtitle>Environ. Sci. Technol</addtitle><description>Glycol ethers are used as solvents and are hence liable to be released to the atmosphere, where they react and contribute to the formation of photochemical air pollution. In this work, products of the gas-phase reactions of the OH radical with 1-methoxy-2-propanol and 2-butoxyethanol in the presence of NO have been investigated at 298 ± 2 K and 740 Torr total pressure of air by gas chromatography, in situ Fourier transform infrared spectroscopy, and in situ atmospheric pressure ionization tandem mass spectrometry. The products observed from 1-methoxy-2-propanol were methyl formate, methoxyacetone, and acetaldehyde with molar formation yields of 0.59 ± 0.05, 0.39 ± 0.04, and 0.56 ± 0.07, respectively. The products observed and quantified from 2-butoxyethanol were n-butyl formate, 2-hydroxyethyl formate, propanal, 3-hydroxybutyl formate, and an organic nitrate (attributed to CH3CH2CH2CH2OCH(ONO2)CH2OH and its isomers), with molar formation yields of 0.57 ± 0.05, 0.22 ± 0.05, 0.21 ± 0.02, 0.07 ± 0.03, and 0.10 ± 0.03, respectively. An additional product of molecular weight 132, attributed to one or more hydroxycarbonyl products, was also observed from the 2-butoxyethanol reaction by atmospheric pressure ionization mass spectrometry. For both glycol ethers, the majority of the reaction products and reaction pathways are accounted for, and detailed reaction mechanisms are presented which account for the observed products.</description><subject>AIR POLLUTION</subject><subject>Applied sciences</subject><subject>Atmosphere</subject><subject>Atmospheric pollution</subject><subject>Chemical composition and interactions. 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Ionic interactions and processes</topic><topic>Chemical reactions</topic><topic>Earth, ocean, space</topic><topic>ENVIRONMENTAL SCIENCES</topic><topic>ETHERS</topic><topic>Exact sciences and technology</topic><topic>External geophysics</topic><topic>GAS CHROMATOGRAPHY</topic><topic>HYDROXYL RADICALS</topic><topic>INFRARED SPECTRA</topic><topic>MASS SPECTROSCOPY</topic><topic>Meteorology</topic><topic>PHASE STUDIES</topic><topic>PHOTOCHEMICAL REACTIONS</topic><topic>Pollutants physicochemistry study: properties, effects, reactions, transport and distribution</topic><topic>Pollution</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tuazon, Ernesto C</creatorcontrib><creatorcontrib>Aschmann, Sara M</creatorcontrib><creatorcontrib>Atkinson, Roger</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>OSTI.GOV</collection><jtitle>Environmental Science and Technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tuazon, Ernesto C</au><au>Aschmann, Sara M</au><au>Atkinson, Roger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Products of the Gas-Phase Reactions of the OH Radical with 1-Methoxy-2-propanol and 2-Butoxyethanol</atitle><jtitle>Environmental Science and Technology</jtitle><addtitle>Environ. Sci. Technol</addtitle><date>1998-11-01</date><risdate>1998</risdate><volume>32</volume><issue>21</issue><spage>3336</spage><epage>3345</epage><pages>3336-3345</pages><issn>0013-936X</issn><eissn>1520-5851</eissn><coden>ESTHAG</coden><abstract>Glycol ethers are used as solvents and are hence liable to be released to the atmosphere, where they react and contribute to the formation of photochemical air pollution. In this work, products of the gas-phase reactions of the OH radical with 1-methoxy-2-propanol and 2-butoxyethanol in the presence of NO have been investigated at 298 ± 2 K and 740 Torr total pressure of air by gas chromatography, in situ Fourier transform infrared spectroscopy, and in situ atmospheric pressure ionization tandem mass spectrometry. The products observed from 1-methoxy-2-propanol were methyl formate, methoxyacetone, and acetaldehyde with molar formation yields of 0.59 ± 0.05, 0.39 ± 0.04, and 0.56 ± 0.07, respectively. The products observed and quantified from 2-butoxyethanol were n-butyl formate, 2-hydroxyethyl formate, propanal, 3-hydroxybutyl formate, and an organic nitrate (attributed to CH3CH2CH2CH2OCH(ONO2)CH2OH and its isomers), with molar formation yields of 0.57 ± 0.05, 0.22 ± 0.05, 0.21 ± 0.02, 0.07 ± 0.03, and 0.10 ± 0.03, respectively. An additional product of molecular weight 132, attributed to one or more hydroxycarbonyl products, was also observed from the 2-butoxyethanol reaction by atmospheric pressure ionization mass spectrometry. For both glycol ethers, the majority of the reaction products and reaction pathways are accounted for, and detailed reaction mechanisms are presented which account for the observed products.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/es980455c</doi><tpages>10</tpages></addata></record>
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subjects AIR POLLUTION
Applied sciences
Atmosphere
Atmospheric pollution
Chemical composition and interactions. Ionic interactions and processes
Chemical reactions
Earth, ocean, space
ENVIRONMENTAL SCIENCES
ETHERS
Exact sciences and technology
External geophysics
GAS CHROMATOGRAPHY
HYDROXYL RADICALS
INFRARED SPECTRA
MASS SPECTROSCOPY
Meteorology
PHASE STUDIES
PHOTOCHEMICAL REACTIONS
Pollutants physicochemistry study: properties, effects, reactions, transport and distribution
Pollution
Solvents
title Products of the Gas-Phase Reactions of the OH Radical with 1-Methoxy-2-propanol and 2-Butoxyethanol
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