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Lignin pyrolysis products, which include a variety of substitutedmethoxyphenols, constitute a major component of organics released by biomasscombustion, and may play a central role in the formation of atmospheric browncarbon. Understanding the atmospheric fate of these compounds upon exposureto trace gases is therefore critical to predicting the chemical and physicalproperties of biomass burning aerosol. We used diffuse reflectance infraredspectroscopy to monitor the heterogeneous ozonolysis of 4-propylguaiacol,eugenol, and isoeugenol adsorbed on NaCl and α-Al2O3 substrates.Adsorption of gaseous methoxyphenols onto these substrates produced near-monolayer surface concentrations of3 × 1018 molecules m−2. The subsequent darkheterogeneous ozonolysis of adsorbed 4-propylguaiacol cleaved the aromaticring between the methoxy and phenol groups with the product conclusivelyidentified by GC-MS and 1H-NMR. Kinetic analysis of eugenol andisoeugenol dark ozonolysis also suggested the formation of ring-cleavedproducts, although ozonolysis of the unsaturated substituent groups formingcarboxylic acids and aldehydes was an order of magnitude faster. Averageuptake coefficients for NaCl-adsorbed methoxyphenols wereγ = 2.3 (± 0.8) × 10−7 and2 (± 1) × 10−6 for ozonolysis of the aromatic ring andthe unsaturated side chain, respectively, and reactions onα-Al2O3 were approximately two times slower. UV–visibleradiation (λ > 300 nm) enhanced eugenol ozonolysis of thearomatic ring by a factor of 4(± 1) but had no effect on ozonolysis ofthe alkene side chain

Ozonolysis of surface-adsorbed methoxyphenols: kinetics of aromatic ring cleavage vs. alkene side-chain oxidation