Related Experiment Video
Updated: Feb 23, 2026

Analyzing the Photo-oxidation of 2-propanol at Indoor Air Level Concentrations Using Field Asymmetric Ion Mobility Spectrometry
Published on: June 14, 2018
Epoxide formation from heterogeneous oxidation of benzo[a]pyrene with gas-phase ozone and indoor air
Shouming Zhou1, Leo W Y Yeung, Matthew W Forbes
1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada. szhou@chem.utoronto.ca leo.yeung@oru.se.
Abstract:
The formation of two classes of epoxide products from the heterogeneous reaction of benzo[a]pyrene (BaP) with gas-phase ozone was demonstrated. BaP was coated on a Pyrex glass tube and oxidized with different concentrations of ozone. After oxidation, the epoxide products were derivatized by N-acetylcystein (NAC) and then analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The results show that in addition to mono-epoxides, diol-epoxides were also formed. BaP exposed to genuine indoor air also produces mono- and diol-epoxides, having similar chromatograms to those produced by oxidation of BaP by low concentrations of ozone. Although it is well recognized that diol-epoxides are formed from BaP oxidation in the human body and that they exhibit carcinogenicity via formation of adducts with DNA, this is the first demonstration that such classes of compounds can be formed by abiotic heterogeneous oxidation.
Related Concept Videos
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Reactions at the Benzylic Position: Oxidation and Reduction
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Radical Autoxidation
Autoxidation of Ethers to Peroxides and Hydroperoxides
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...

