Solvent Induced Oxidation of Hydroxylamines

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Solvent Inducing Oxidation of Hydroxylamines

_{Shizuyo HORIYAMA,*,a Kiyoko SUWA,a Masae YAMAKI,a Hiromi KATAOKA,a Toyoshi KATAGI,a
Mitsuo TAKAYAMA,b and Takae TAKEUCHIc}

Chem. Pharm. Bull. 50(7) 996Ñ1000 (2002)

http://cpb.jstage.jst.go.jp/cgi-bin/fs.cgi/50_996.pdf?SID=55e104fd59f1dd4f416f418297c4e744

Abstract
Hydroxylamines gradually undergo oxidation to their oximes on being dissolved in organic solvent (e.g. methanol). This phenomenon was followed by 1H-NMR and liquid chromatography-mass spectrometry (LC-MS). The oxidation rate was estimated from the peak area observed on the mass chromatogram at the protonated molecule or fragment ion on LC-atmospheric pressure chemical ionization (APCI)-MS. The results showed that the oxidation rate of hydroxylamines depended on the solvent type.

Excerp......
.....the results indicate that the oxidation phenomenon of hydroxylamines depends on the solvent and that oxidation proceeded very rapidly in methylamine, slowly in ethanol, pyridine and almost not at all in benzene and toluene,hence oxidation proceeded in protic solvents more than in aprotic solvents.