Triacetonamine is an
organic compound with the formula OC(CH
2CMe
2)
2NH (where Me = CH
3). 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 (CH
3)
2CO + NH
3 → OC(CH
2CMe
2)
2NH + 2 H
2O
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
Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions ...
amine
2,2,6,6-tetramethylpiperidine, CH
2 H2C(CH3)2sub>2NH, as well as the radical oxidizer
4-Hydroxy-TEMPO
4-Hydroxy-TEMPO or TEMPOL, formally 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl, is a heterocyclic compound. Like the related TEMPO, it is used as a catalyst and chemical oxidant by virtue of being a stable aminoxyl radical. Its major appeal ov ...
.
[{{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