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Triacetonamine

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: :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, as well as the radical oxidizer 4-Hydroxy-TEMPO.

Triacetonamine has known application in the synthesis of alpha-eucaine.

A continuous process for the production of triacetonamine was developed:

References

References

  1. Nabyl Merbouh. (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International.
  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. {{doi. 10.1002/047084289X.
  3. (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development.
  4. (2014). "Continuous synthesis of triacetonamine over sulfonic acid-functionalized mesoporous silicas". RSC Advances.
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piperidines cyclic-ketones
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