Triacetonamine is an organic compound with the formula OC(CH<sub>2</sub>CMe<sub>2</sub>)<sub>2</sub>NH (where Me = CH<sub>3</sub>). It is a colorless or white solid that melts near room temperature. The compound is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO. Triacetonamine is formed by the poly-aldol condensation of acetone in the presence of ammonia and calcium chloride:
Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine.
It is primarily used as a stabilizer for plastics, typically via its conversion to number of hindered amine light stabilizers, but also finds use as a chemical feedstock. It is used to prepare the hindered amine 2,2,6,6-tetramethylpiperidine, CH<sub>2</sub>[CH<sub>2</sub>C(CH<sub>3</sub>)<sub>2</sub>]<sub>2</sub>NH, as well as the radical oxidizer 4-Hydroxy-TEMPO.
Triacetonamine has known application in the synthesis of alpha-eucaine. A surprising use of triacetonamine was in the synthesis of Elexacaftor.
A continuous process for the production of triacetonamine was developed: