Interfacial Oxidative Oligomerization of Catechol

Marcelo I. Guzman, Elizabeth A. Pillar-Little, Alexis J. Eugene

Research output: Contribution to journalArticlepeer-review

Abstract

The heterogeneous reaction between thin films of catechol exposed to O3(g) creates hydroxyl radicals (HO) in situ, which in turn generate semiquinone radical intermediates in the path to form heavier polyhydroxylated biphenyl, terphenyl, and triphenylene products. Herein, the alteration of catechol aromatic surfaces and their chemical composition are studied during the heterogeneous oxidation of catechol films by O3(g) molar ratios ≥ 230 ppbv at variable relative humidity levels (0% ≤ RH ≤ 90%). Fourier transform infrared micro-spectroscopy, atomic force microscopy, electrospray ionization mass spectrometry, and reverse-phase liquid chromatography with UV-visible and mass spectrometry detection provide new physical insights into understanding the surface reaction. A Langmuir-Hinshelwood mechanism is accounted to report reaction rates, half-lives, and reactive uptake coefficients for the system under variable relative humidity levels. The reactions reported explain how the oligomerization of polyphenols proceeds at interfaces to contribute to the formation of brown organic carbon in atmospheric aerosols.

Original languageEnglish
Pages (from-to)36009-36016
Number of pages8
JournalACS Omega
Volume7
Issue number40
DOIs
StatePublished - Oct 11 2022

Bibliographical note

Funding Information:
Support from the U.S. National Science Foundation under Award 1903744 to M.I.G. is gratefully acknowledged.

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

  • Chemistry (all)
  • Chemical Engineering (all)

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