Triacetonamine

Triacetone amine
Names
	IUPAC name 2,2,6,6-Tetramethylpiperidinone
	Other names Triacetone amine
Identifiers
CAS Number	826-36-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL117614 ;
ChemSpider	12665 ;
ECHA InfoCard	100.011.413
EC Number	212-554-2;
PubChem CID	13220;
RTECS number	TO0127900;
UNII	2K4430S3XP;
CompTox Dashboard (EPA)	DTXSID4041527 ;
	InChI InChI=1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 Key: JWUXJYZVKZKLTJ-UHFFFAOYSA-N ; InChI=1/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 Key: JWUXJYZVKZKLTJ-UHFFFAOYAQ;
	SMILES O=C1CC(NC(C)(C)C1)(C)C;
Properties
Chemical formula	C9H17NO
Molar mass	155.241 g·mol−1
Appearance	Colorless low-melting solid
Density	0.882 g/cm3
Melting point	43 °C (109 °F; 316 K)
Boiling point	205 °C (401 °F; 478 K)
Solubility in water	Moderate
Solubility in other solvents	Most organic solvents
Hazards
Main hazards	flammable
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H290, H302, H314, H315, H317, H318, H319, H335, H412
GHS precautionary statements	P234, P260, P261, P264, P270, P271, P272, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P330, P332+313, P333+313, P337+313, P362, P363, P390
Flash point	73 °C; 164 °F; 346 K
Related compounds
Related compounds	Piperidine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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

Nabyl Merbouh, James M. Bobbitt, Christian Brückner (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International. 36: 1-31. doi:10.1080/00304940409355369.CS1 maint: uses authors parameter (link)
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:10.1002/047084289.
Ciriminna, Rosaria; Pagliaro, Mario (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development. 14 (1): 245–251. doi:10.1021/op900059x.

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[1] Nabyl Merbouh, James M. Bobbitt, Christian Brückner (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International. 36: 1-31. doi:10.1080/00304940409355369.CS1 maint: uses authors parameter (link)

[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:10.1002/047084289.

[3] Ciriminna, Rosaria; Pagliaro, Mario (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development. 14 (1): 245–251. doi:10.1021/op900059x.