EFFECT OF TERT-BUTYLHYDROQUINONE (TBHQ) ON THE FORMATION OF NITROSAMINES IN THE REACTION OF SECONDARY-AMINES WITH NITRITE

tert-Butylhydroquinone (TBHQ), an antioxidant for edible fats and oil, inhibited nitrosamine formation in the reaction of secondary amines w ith nitrite under acidic conditions. The inhibitory effect may be due to the loss of nitrite available for nitrosation. TBHQ was oxidized wi th nitrite into 2-tert-butyl-P-benzoquinone (TBQ), which was active in enhancing nitrosamine formation in the presence of an adequate amount of available nitrite. TBQ readily reacted with secondary amines to fo rm 1:1 secondary amine-TBQ adducts whose structures were established t o be 2-tert-butyl-5 (and 6)-amino-p-benzoquinones. The adducts may be nitrosated to be transformed into the nitrosamines, or they may cataly tically enhance the nitrosamine formation.