Oxidation of Secondary and Tertiary Amines at Nitrogen

The oxidation of secondary amines with dilute (6%) hydrogen peroxide at room temperature furnishes dialkylhydroxylamines. N,N-D -ethylhydroxylamine is prepared with a yield not higher than 50%. With dipropylamine, the yield is not stated [154.  

The oxidation of tertiary amines to amine oxides is carried out by peroxy compounds, most often hydrogen peroxide and peroxyacetic acid. 

Other peroxides such as fert-butyl hydroperoxide [226, 227], performic acid 247, 248], peroxytrifluoroacetic acid [/55], peroxydichloromaleic acid [339], and dimethyldioxirane [210] are used less frequently. 

Trialkylamines such as tributylamine are oxidized either with aqueous-methanolic 30-35% hydrogen peroxide at 0 °C to room temperature over 

The yields of tributylamine oxide are comparable 98 and 95%, respectively [756]. Dimethyldodecylamine oxide is prepared by heating the tertiary amine with tcrt-butyl hydroperoxide in the presence of vanadium catalysts (equation 501) [226, 227]. 

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