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:[1]

3 (CH3)2CO + NH3 → OC(CH2CMe2)2NH + 2 H2O
Triacetone amine
Names
IUPAC name
2,2,6,6-Tetramethylpiperidinone
Other names
Triacetone amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.011.413
EC Number
  • 212-554-2
RTECS number
  • TO0127900
UNII
Properties
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)
Moderate
Solubility in other solvents Most organic solvents
Hazards
Main hazards flammable
GHS pictograms
GHS Signal word Danger
H290, H302, H314, H315, H317, H318, H319, H335, H412
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).
N verify (what is YN ?)
Infobox references

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. 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:10.1002/047084289X.
  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.
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