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Title: Products of the gas-phase reaction of the OH radical with the Dibasic ester Ch{sub 3}OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}

Abstract

Dibasic esters are potentially important commercial solvents and their use will lead to possible release into the atmosphere, where they will react with the hydroxyl (OH) radical and contribute to the formation of photochemical air pollution in urban and regional areas. The authors have investigated the products formed from the gas-phase reaction of the OH radical with the dibasic ester dimethyl glutarate [CH{sub 3}-OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}] in the presence of NO in large volume chambers with analysis by in situ Fourier transform infrared (FTIR) absorption spectroscopy, in situ atmospheric pressure ionization tandem mass spectrometry (API-MS), gas chromatography with flame ionization detection, and combined gas chromatography-mass spectrometry. No information was obtained concerning the reaction products using the gas chromatographic analyses. The in situ API-MS and API-MS/MS analyses indicated the formation of products with molecular weights 146, 174, and 221, and, based on plausible reaction schemes, these could be mono-methyl glutarate [CH{sub 3}OC(O)CH{sub 2}CH{sub 2}-CH{sub 2}C(O)OH], dimethyl 1,3-acetonedicarboxylate [CH{sub 3}OC(O)-CH{sub 2}C(O)CH{sub 2}C(O)OCH{sub 3}], and/or its isomers, and an organic nitrate(s), respectively. The in situ FT-IR spectroscopic analyses were consistent with these expectations, with the identification and quantification of organic nitrate(s), mono-methyl glutarate, and dimethyl 1,3-acetonedicarboxylate with formation yields of 15more » {+-} 6, 34 {+-} 16, and 28 {+-} 8 {percent}, respectively. These products therefore account for 77 {+-} 19 {percent} of the total reaction products and reaction pathways, recognizing that the quantifications of mono-methyl glutarate and dimethyl 1,3-acetonedicarboxylate are subject to significant uncertainties.« less

Authors:
; ;  [1]
  1. Univ. of California (United States). Air Pollution Research Center
Publication Date:
OSTI Identifier:
696762
Resource Type:
Journal Article
Journal Name:
Environmental Science and Technology
Additional Journal Information:
Journal Volume: 33; Journal Issue: 17; Other Information: PBD: 1 Sep 1999
Country of Publication:
United States
Language:
English
Subject:
54 ENVIRONMENTAL SCIENCES; AIR POLLUTION; ATMOSPHERIC CHEMISTRY; HYDROXYL RADICALS; ESTERS; ORGANIC SOLVENTS; PHOTOCHEMICAL OXIDANTS; PHASE STUDIES

Citation Formats

Tuazon, E.C., Aschmann, S.M., and Atkinson, R. Products of the gas-phase reaction of the OH radical with the Dibasic ester Ch{sub 3}OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}. United States: N. p., 1999. Web. doi:10.1021/es990142x.
Tuazon, E.C., Aschmann, S.M., & Atkinson, R. Products of the gas-phase reaction of the OH radical with the Dibasic ester Ch{sub 3}OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}. United States. doi:10.1021/es990142x.
Tuazon, E.C., Aschmann, S.M., and Atkinson, R. Wed . "Products of the gas-phase reaction of the OH radical with the Dibasic ester Ch{sub 3}OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}". United States. doi:10.1021/es990142x.
@article{osti_696762,
title = {Products of the gas-phase reaction of the OH radical with the Dibasic ester Ch{sub 3}OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}},
author = {Tuazon, E.C. and Aschmann, S.M. and Atkinson, R.},
abstractNote = {Dibasic esters are potentially important commercial solvents and their use will lead to possible release into the atmosphere, where they will react with the hydroxyl (OH) radical and contribute to the formation of photochemical air pollution in urban and regional areas. The authors have investigated the products formed from the gas-phase reaction of the OH radical with the dibasic ester dimethyl glutarate [CH{sub 3}-OC(O)CH{sub 2}CH{sub 2}CH{sub 2}C(O)OCH{sub 3}] in the presence of NO in large volume chambers with analysis by in situ Fourier transform infrared (FTIR) absorption spectroscopy, in situ atmospheric pressure ionization tandem mass spectrometry (API-MS), gas chromatography with flame ionization detection, and combined gas chromatography-mass spectrometry. No information was obtained concerning the reaction products using the gas chromatographic analyses. The in situ API-MS and API-MS/MS analyses indicated the formation of products with molecular weights 146, 174, and 221, and, based on plausible reaction schemes, these could be mono-methyl glutarate [CH{sub 3}OC(O)CH{sub 2}CH{sub 2}-CH{sub 2}C(O)OH], dimethyl 1,3-acetonedicarboxylate [CH{sub 3}OC(O)-CH{sub 2}C(O)CH{sub 2}C(O)OCH{sub 3}], and/or its isomers, and an organic nitrate(s), respectively. The in situ FT-IR spectroscopic analyses were consistent with these expectations, with the identification and quantification of organic nitrate(s), mono-methyl glutarate, and dimethyl 1,3-acetonedicarboxylate with formation yields of 15 {+-} 6, 34 {+-} 16, and 28 {+-} 8 {percent}, respectively. These products therefore account for 77 {+-} 19 {percent} of the total reaction products and reaction pathways, recognizing that the quantifications of mono-methyl glutarate and dimethyl 1,3-acetonedicarboxylate are subject to significant uncertainties.},
doi = {10.1021/es990142x},
journal = {Environmental Science and Technology},
number = 17,
volume = 33,
place = {United States},
year = {1999},
month = {9}
}