Oligomerization of levoglucosan by Fenton chemistry in proxies of biomass burning aerosols |
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| Authors: | Bryan J Holmes Giuseppe A Petrucci |
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| Institution: | (1) Department of Chemistry, University of Vermont, Burlington, VT 05401-0125, USA |
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| Abstract: | Reactions of levoglucosan with  produced from Fenton chemistry were studied in solution serving as a proxy for biomass burning aerosols. Two modes of oligomerization
(≤2000 u) were observed for reaction times between 1 and 7 days using matrix-assisted laser desorption time-of-flight mass
spectrometry (MALDI-TOF-MS) and laser desorption ionization time-of-flight mass spectrometry (LDI-TOF-MS). Single-mass unit
continuum mass distributions with dominant −2 u patterns were measured and superimposed by a +176/+162 u oligomer series.
This latter oligomer pattern was attributed to a Criegee rearrangement (+14 u) of levoglucosan, initiated by  , forming a lactone (176 u). The acid-catalyzed reaction of any ROH from levoglucosan (+162 u) forms an ester through transesterification
of the lactone functionality, whereupon propagation forms polyesters. Proposed products and chemical mechanisms are suggested
as sources and precursors of humic-like substances (HULIS), which are known to possess a large saccharic component and are
possibly formed from biomass burning aerosols (Andreae, Global Biomass Burning, MIT Press, Cambridge, Massachusetts, 3–21,
1991). |
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| Keywords: | Biomass burning aerosol Fenton Hydroxyl radical Levoglucosan Oligomerization |
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