Triacetone amine

Triacetone amine
Names
IUPAC name
2,2,6,6-Tetramethylpiperidinone
Other names
Triacetone amine
Identifiers
826-36-8 N
3D model (Jmol) Interactive image
ChEMBL ChEMBL117614 YesY
ChemSpider 12665 YesY
ECHA InfoCard 100.011.413
PubChem 13220
RTECS number TO0127900
Properties
C9H17NO
Molar mass 155.23 g/mol
Appearance Colorless low-melting solid
Density ? 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
R-phrases 22-36/37/38
S-phrases 26-36/37
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 YesYN ?)
Infobox references

Triacetone amine is the heterocycle that arises via the condensation of acetone and ammonia according to the following equation:

3 CH3C(O)CH3 + NH3 OC(CH2C(CH3)2)2NH + 2 H2O

It is primarily used as a light stabilizer for plastics 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,[1] as well as the radical oxidizer 4-Hydroxy-TEMPO.[2]

References

  1. 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.
  2. 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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