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Oligomerization of levoglucosan by Fenton chemistry in proxies of biomass burning aerosols

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Reactions of levoglucosan with \( OH^{ \bullet } \) 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 \( OH^{ \bullet } \), 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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Acknowledgments

The authors thank A. Wurthmann for helpful discussion.

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  1. Department of Chemistry, University of Vermont, Burlington, VT, 05401-0125, USA

    Bryan J. Holmes & Giuseppe A. Petrucci

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  1. Bryan J. Holmes
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Correspondence to Giuseppe A. Petrucci.

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Holmes, B.J., Petrucci, G.A. Oligomerization of levoglucosan by Fenton chemistry in proxies of biomass burning aerosols. J Atmos Chem 58, 151–166 (2007). https://doi.org/10.1007/s10874-007-9084-8

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