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Uncatalyzed, Regioselective Oxidation of Saturated Hydrocarbons in an Ambient Corona Discharge
Author(s) -
Ayrton Stephen T.,
Jones Rhys,
Douce David S.,
Morris Mike R.,
Cooks R. Graham
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711190
Subject(s) - dehydrogenation , chemistry , oxygen , ozone , atmospheric pressure chemical ionization , corona discharge , regioselectivity , photochemistry , hydrocarbon , ionic bonding , ionization , inorganic chemistry , nitrogen , chemical ionization , organic chemistry , ion , catalysis , electrode
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.