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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Surface Oxidation of Phenolic Aldehydes: Fragmentation, Functionalization, and Coupling Reactions.

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The Journal of Physical Chemistry. A
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Biomass burning releases phenolic aldehydes that transform in the atmosphere. Oxidation by ozone creates new compounds, enhancing light absorption and contributing to secondary organic aerosol formation.

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Area of Science:

  • Atmospheric Chemistry
  • Environmental Science
  • Chemical Kinetics

Background:

  • Biomass burning is a significant source of atmospheric phenolic aldehydes like syringaldehyde, vanillin, and 4-hydroxybenzaldehyde.
  • Oxidative transformation of these aldehydes during atmospheric transport can alter particulate properties, impacting climate and human health.

Purpose of the Study:

  • To investigate the oxidative transformation of solid films of syringaldehyde, vanillin, and 4-hydroxybenzaldehyde by ozone (O3(g)).
  • To elucidate the reaction mechanisms and identify the resulting products under atmospherically relevant conditions (74% relative humidity).

Main Methods:

  • Oxidation of thin solid films of phenolic aldehydes with O3(g).
  • Analysis of oxidized films using UV-vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), ion chromatography, and ultrahigh-pressure liquid chromatography (UHPLC) with UV-vis and MS detection.
  • In situ monitoring of reaction intermediates and products.

Main Results:

  • Oxidation enhanced mass absorption coefficients at wavelengths greater than 300 nm, indicating increased light absorption by aged particles.
  • Aromatic ring cleavage was confirmed for syringaldehyde and vanillin, producing various carboxylic acids (e.g., formic, glycolic, oxalic acid).
  • In situ production of hydroxyl radicals was observed, alongside demethoxylation and ipso attack, suggesting complex reaction pathways.

Conclusions:

  • Ozone oxidation of phenolic aldehydes leads to the formation of polyfunctional products and enhances light-absorbing properties of aerosols.
  • The reactivity of phenolic aldehydes towards ozone increases with the number of electron-donating methoxy substituents.
  • These findings contribute to understanding the formation and properties of secondary organic aerosol from biomass burning emissions.