Triacetonamine is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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 2,2,6,6-Tetramethylpiperidine, abbreviated TMP, HTMP, or TMPH, is an organic compound of the amine class. In appearance, it is a colorless liquid and has a "fishy", amine-like odor. This amine is used in chemistry as a hindered base ( hindered am ...

, a sterically hindered base and precursor to the reagent called

TEMPO In musical terminology, tempo (Italian for 'time'; plural 'tempos', or from the Italian plural), measured in beats per minute, is the speed or pace of a given musical composition, composition, and is often also an indication of the composition ...

. Triacetonamine is formed by the poly-

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

of acetone in the presence of ammonia and

calcium chloride Calcium chloride is an inorganic compound, a Salt (chemistry), salt with the chemical formula . It is a white crystalline solid at room temperature, and it is highly soluble in water. It can be created by neutralising hydrochloric acid with cal ...

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

Reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that converts a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amine ...

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 Hindered amine light stabilizers (HALS) are chemical compounds containing an amine functional group that are used as stabilizers in plastics and polymers. These compounds are typically derivatives of tetramethylpiperidine and are primarily used ...

, but also finds use as a chemical feedstock. It is used to prepare the

hindered Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is generally a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivi ...

amine

, CH₂ H₂C(CH₃)₂sub>2NH, as well as the radical oxidizer 4-Hydroxy-TEMPO.{{cite journal, last1=Ciriminna, first1=Rosaria, last2=Pagliaro, first2=Mario, title=Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives, journal=Organic Process Research & Development, date=15 January 2010, volume=14, issue=1, pages=245–251, doi=10.1021/op900059x

References

Piperidines Cyclic ketones