2,2,6,6-Tetramethyl-4-piperidon Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R34:Verursacht Ver?tzungen.
R22:Gesundheitssch?dlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-S?tze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Triacetonamine (CAS 826-36-8), also known as 2,2,6,6-tetramethyl-4-piperidone or TAA, is a key intermediate in the synthesis of HALS (hindered amine light stabilisers); Their ability to effectively inhibit polymer degradation by scavenging free radicals is based on their sterically hindered amine functional groups, which are capable of forming stable N-oxides as active intermediates (the Denysov cycle). TAA is also used in the synthesis of pharmaceuticals, piperidine nitroso radicals and pyrrolidone derivatives. For example, the oxidation of TAA or its derivatives yields the corresponding tetramethylpiperidine-N-oxide, namely TEMPO; the latter can be used as a polymerisation inhibitor, molecular weight regulator or oxidation catalyst[2].
Chemische Eigenschaften
white crystalline powder
Verwenden
2,2,6,6-Tetramethyl-4-piperidinone (cas# 826-36-8) is a compound useful in organic synthesis.
Synthesis Reference(s)
Synthesis, p. 735, 1976
DOI: 10.1055/s-1976-24178
Synthese
The routes of triacetonamine synthesis includes
[1]:
a. From acetone and ammonia. Triacetonamine was initially prepared by the method of Francisfrom acetone and ammonia in the presence of an acidic catalyst like calcium chloride in a 20% yield. Co-catalysts bromine or iodine combined with acid halides of the type XCH2COX acted as synergists.
b. From phorone and ammonia. Phorone reacted with ammonia to give triacetonamine via the nucleophilic addition of nitrogen to the olefi nic bond.
c. From N-oxides. Triacetonamine was formed via reduction of cation in the presence of NaOH in acetone media.
d. From alcohols. Photogenerated singlet oxygen was used in oxidation of alcohol with formation of triacetonamine under mild and facile conditions using the catalyst CoIIDPDME.
e. From dimethylamine derivatives. Dimethylamine was alkylated by methyl iodide. The following hydrolysis gave triacetonamine.
2,2,6,6-Tetramethyl-4-piperidon Upstream-Materialien And Downstream Produkte
Upstream-Materialien
4-Heptanone, 2,6-diamino-2,6-dimethyl-
2,3,4,5-Tetrahydro-2,2,4,4,6-pentamethylpyrimidin
2,2,6,6-Tetramethyl-4-piperidonoxim
2,3-Dimethyl-2,3-dinitrobutan
Downstream Produkte
2,2,6,6-Tetramethyl-4-piperidylamin
2,2,6,6-Tetramethylpiperidin
2,2,4,4,6-pentamethyl-hexahydropyrimidine
1 2 2 6 6-PENTAMETHYL-4-PIPERIDONE 97
4-Amino-4-methylpentan-2-on
N-Butyl-2,2,6,6-tetramethylpiperidin-4-amin
2,2,6,6-Tetramethylpiperidin-4-ol
