Triacetonamine Explained

Triacetonamine is an organic compound with the formula OC(CH₂CMe₂)₂NH (where Me = CH₃). 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:^[1]

3 (CH₃)₂CO + NH₃ → OC(CH₂CMe₂)₂NH + 2 H₂O

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, CH₂[CH₂C(CH₃)₂]₂NH,^[2] as well as the radical oxidizer 4-Hydroxy-TEMPO.^[3]

References

1. Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review. Nabyl Merbouh . . Christian Brückner . 2004. Organic Preparations and Procedures International. 36. 1–31. 10.1080/00304940409355369. 98117103 .
2. Sorgi, K. L. "2,2,6,6-Tetramethylpiperidine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. .
3. Ciriminna. Rosaria. Pagliaro. Mario. Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives. Organic Process Research & Development. 15 January 2010. 14. 1. 245–251. 10.1021/op900059x.