Competing Reactions in the Ozonation of Anthracene

Bailey, Philip S.; Kolsaker, Per; Sinha, Biswajit; Ashton, Joseph B.; Dobinson, Frank; Batterbee, J. E.

doi:10.1021/jo01029a034

Cited by 26 publications

(10 citation statements)

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“…of ozone. 14 We, like Briner6 and Dick,8 have found that some autoxidation occurs when molecular oxygen is present in the ozonation gas. Table II, experiments 1 and 2 (in comparison with each other and with experiments 1 and 2, Table I), shows that the greater the oxygen-ozone ratio, the less the ozone actually consumed, but the greater the perbenzoic acid yield.…”

Section: IVmentioning

confidence: 86%

Ozonation of Aromatic Aldehydes¹

White¹,

Bailey²

1965

J. Org. Chem.

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Section: IVmentioning

confidence: 86%

Ozonation of Aromatic Aldehydes¹

White¹,

Bailey²

1965

J. Org. Chem.

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“…It is generally known that PAHs are not oxidized readily under mild conditions. Several stringent chemical decomposition methods have been reported for this purpose, for example (with respect to anthracene oxidation), photocatalytic,3a–f photo‐electrochemical,3g and sono‐electrochemical oxidation,3f Fenton reagent coupled biodegradation,4a–d electro‐enzymatic oxidation,5a–d gamma‐ray irradiation,6 the ozonization reaction,7a,b high‐temperature vapor‐phase oxidation on a catalytic surface (≈300 °C),8a,b and liquid‐phase catalytic chemical oxidation at approximately 90 °C 9a,b. Electrochemical oxidation of PAHs has rarely been achieved because of their particularly unreactive character.…”

Section: Methodsmentioning

confidence: 99%

Facile Electrochemical Oxidation of Polyaromatic Hydrocarbons to Surface‐Confined Redox‐Active Quinone Species on a Multiwalled Carbon Nanotube Surface

Barathi

Kumar

2013

Chemistry A European J

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Polyaromatic hydrocarbon (PAH) oxidation: PAHs, which are considered major environmental pollutants, are carcinogenic, and cannot be electrochemically oxidized on conventional electrodes (gold, platinum, and glassy carbon), can be electrochemically oxidized on multiwalled carbon nanotube surfaces at a potential of 1 V versus Ag/AgCl at pH 7. This results in the formation of stable surface-confined quinone systems (see scheme; AN = anthracene; AQ = anthraquinone).

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“…The mechanism suggested for coronene oxidation by O 3 is based upon ozonolysis pathways for similar PAH molecules such as anthracene 57 and benzo[a]pyrene. 58 Results from benzo[a]pyrene + O 3 show that after an initial electrophilic attack by ozone, the PAH can undergo loss of O 2 and a proton transfer reaction to form an alcohol.…”

Section: Functional Group Distribution Vs Ozone Reaction Timementioning

confidence: 99%

Competitive reaction pathways for functionalization and volatilization in the heterogeneous oxidation of coronene thin films by hydroxyl radicals and ozone

Mysak

Smith

Ashby

et al. 2011

Phys. Chem. Chem. Phys.

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X-ray photoelectron spectroscopy (XPS) is used to monitor the heterogeneous reaction of hydroxyl radicals (OH) and ozone with thin films (∼5 Å) of coronene. Detailed elemental and functional group analysis of the XPS spectra reveals that there is a competition between the addition of oxygenated functional groups (functionalization) and the loss of material (volatilization) to the gas phase. Measurements of the film thickness and elemental composition indicate that carbon loss is as important as the formation of new oxygenated functional groups in controlling how the oxygen-to-carbon ratio (O/C) of the coronene film evolves during the surface reaction. When the O/C ratio of the film is small (∼0.1) the addition of functional groups dominates changes in film thickness, while for more oxygenated films (O/C > 0.3) carbon loss is an increasingly important reaction pathway. Decomposition of the film occurs via the loss of both carbon and oxygen atoms when the O/C ratio of the film exceeds 0.5. These results imply that chemically reduced hydrocarbons, such as primary organic aerosol, age in the atmosphere by forming new oxygenated functional groups, in contrast to oxygenated secondary organic aerosol, which decompose by a heterogeneous loss of carbon and/or oxygen.

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Competing Reactions in the Ozonation of Anthracene

Cited by 26 publications

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Ozonation of Aromatic Aldehydes¹

Ozonation of Aromatic Aldehydes¹

Facile Electrochemical Oxidation of Polyaromatic Hydrocarbons to Surface‐Confined Redox‐Active Quinone Species on a Multiwalled Carbon Nanotube Surface

Competitive reaction pathways for functionalization and volatilization in the heterogeneous oxidation of coronene thin films by hydroxyl radicals and ozone

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Competing Reactions in the Ozonation of Anthracene

Cited by 26 publications

References 0 publications

Ozonation of Aromatic Aldehydes1

Ozonation of Aromatic Aldehydes1

Facile Electrochemical Oxidation of Polyaromatic Hydrocarbons to Surface‐Confined Redox‐Active Quinone Species on a Multiwalled Carbon Nanotube Surface

Competitive reaction pathways for functionalization and volatilization in the heterogeneous oxidation of coronene thin films by hydroxyl radicals and ozone

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Ozonation of Aromatic Aldehydes¹

Ozonation of Aromatic Aldehydes¹