In the present work, we have evaluated whether isomeric C5-alkene diols (1,2-dihydroxy-2-methyl-3-butene, 1,2-dihydroxy-3-methyl-3-butene, and 1,4-dihydroxy-2-methyl-2-butene (cis + trans)), which have first been detected upon photooxidation of isoprene in the absence of NO and are known to be formed in the ambient atmosphere, can serve as precursors for the 2-methyltetrols, C5-alkene triols, and 2-methylglyceric acid under low-NO(x) conditions. The C5-alkene diols were prepared following published synthesis procedures. It is shown that under the applied chamber conditions the isomeric C5-alkene diols give rise to 2-methyltetrols with different threo/erythro abundance ratios and that certain diols produce 2-methylglyceric acid, but that they do not form C5-alkene triols. Furthermore, it is shown that the photooxidation of isoprene under the applied chamber conditions employing photolysis of H2O2 under dry conditions yields relatively small amounts of C5-alkene triols compared to those of the 2-methyltetrols, unlike under ambient conditions. It is argued that the chamber conditions are not optimal for the formation of C5-epoxydiols, which serve as gas-phase precursors for the C5-alkene triols, and likely as in some previous studies favor the formation of C5-alkene diols as a result of RO2 + RO2 reactions.
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http://dx.doi.org/10.1039/c3fd00092c | DOI Listing |
Environ Sci Process Impacts
November 2018
Department of Environmental Sciences and Engineering, Gillings School of Global Public Health, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, USA.
Acid-catalyzed multiphase chemistry of isoprene epoxydiols (IEPOX) on sulfate aerosol produces substantial amounts of water-soluble secondary organic aerosol (SOA) constituents, including 2-methyltetrols, methyltetrol sulfates, and oligomers thereof in atmospheric fine particulate matter (PM2.5). These constituents have commonly been measured by gas chromatography interfaced to electron ionization mass spectrometry (GC/EI-MS) with prior derivatization or by reverse-phase liquid chromatography interfaced to electrospray ionization high-resolution mass spectrometry (RPLC/ESI-HR-MS).
View Article and Find Full Text PDFFaraday Discuss
March 2014
Department of Pharmaceutical Sciences, University of Antwerp, Belgium.
In the present work, we have evaluated whether isomeric C5-alkene diols (1,2-dihydroxy-2-methyl-3-butene, 1,2-dihydroxy-3-methyl-3-butene, and 1,4-dihydroxy-2-methyl-2-butene (cis + trans)), which have first been detected upon photooxidation of isoprene in the absence of NO and are known to be formed in the ambient atmosphere, can serve as precursors for the 2-methyltetrols, C5-alkene triols, and 2-methylglyceric acid under low-NO(x) conditions. The C5-alkene diols were prepared following published synthesis procedures. It is shown that under the applied chamber conditions the isomeric C5-alkene diols give rise to 2-methyltetrols with different threo/erythro abundance ratios and that certain diols produce 2-methylglyceric acid, but that they do not form C5-alkene triols.
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