Uncatalyzed, Regioselective Oxidation of Saturated Hydrocarbons in an Ambient Corona Discharge

Atmospheric pressure chemical ionization (APCI) in air or in nitrogen with just traces of oxygen is shown to yield regioselective oxidation, dehydrogenation, and fragmentation of alkanes. Ozone is produced from ambient oxygen in situ and is responsible for the observed ion chemistry, which includes...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2018-01, Vol.57 (3), p.769-773
Main Authors: Ayrton, Stephen T., Jones, Rhys, Douce, David S., Morris, Mike R., Cooks, R. Graham
Format: Article
Language:English
Subjects:
Aldehydes
Alkanes
Atmospheric chemistry
Atmospheric pressure
Chemistry
Dehydrogenation
Hydrocarbons
Ionization
Ions
Ketones
mass spectrometry
Nitrogen
Oxidation
Oxygen
Ozone
reaction mechanisms
Regioselectivity
Saturated hydrocarbons
Water loss
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Summary:Atmospheric pressure chemical ionization (APCI) in air or in nitrogen with just traces of oxygen is shown to yield regioselective oxidation, dehydrogenation, and fragmentation of alkanes. Ozone is produced from ambient oxygen in situ and is responsible for the observed ion chemistry, which includes partial oxidation to ketones and C−C cleavage to give aldehydes. The mechanism of oxidation is explored and relationships between ionic species produced from individual alkanes are established. Unusually, dehydrogenation occurs by water loss. Competitive incorporation into the hydrocarbon chain of nitrogen versus oxygen as a mode of ionization is also demonstrated. No pressure: Atmospheric pressure corona discharge ionization (APCI) in air, or in the presence of trace amounts of oxygen, is shown to yield regioselective oxidation, dehydrogenation, and fragmentation. The chemistry of oxidation is explored and relationships between the ionic species, produced from single analytes, are established. Ozone is produced from ambient oxygen in situ and dehydration is responsible for the observed dehydrogenated ketones.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201711190