Description
2,2,6,6-Tetramethylpiperidine is a product that is used for the most diverse purposes because of its strong basicity, for example, as a light stabilizer for polyolefins, as a cocatalyst in olefin polymerizations (Ziegler catalysts), as a building block for the synthesis of pharmaceuticals and crop protection products, as a cocatalyst in the synthesis of dichloroacetyl chloride. The 4-unsubstituted 2.2.6,6-tetramethylpiperidine is generally prepared from the corresponding 4-oxo compound. It is known that triacetonamine can be converted by hydrazine to the hydrazone, which is then cleaved in the presence of alkali into 2,26,6-tetramethylpiperidine and nitrogen.
Chemical Properties
orange crystals or powder
Characteristics
2,2,6,6-Tetramethylpiperidinooxy(TEMPO) has the characteristics of high yield, good selectivity, good stability, and recyclable use.
Uses
TEMPO(2,2,6,6-Tetramethylpiperidinooxy) is a stable radical prepared through the oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO has a wide range of applications including use as a free radical scavenger, a reagent in organic synthe sis and as a structural probe in electron spin resonance spectroscopy. TEMPO can also be used as a mediator in free radical polymerization.
Uses
In organic chemistry as a radical trap, 2,2,6,6-Tetramethylpiperidinooxy can be used as a catalyst and in polymerization mediation.
Uses
TEMPO can be used:
- As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.
- As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.
- For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene.
- In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.
Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air
General Description
For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our
technology spotlight.
Purification Methods
Purify TEMPO by sublimation (33o, water aspirator) [Hay & Fincke J Am Chem Soc 109 8012 1987, Keana Chem Rev 78 37 1978].
