Triacetonamine

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title: "Triacetonamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["piperidines", "cyclic-ketones"] topic_path: "general/piperidines" source: "https://en.wikipedia.org/wiki/Triacetonamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470612896 | Name = Triacetone amine | ImageFile = Triacetonamine-Structural formula V1.svg | ImageName = | PIN = 2,2,6,6-Tetramethylpiperidin-4-one | OtherNames = Triacetone amine |Section1={{Chembox Identifiers | SMILES = O=C1CC(NC(C)(C)C1)(C)C | ChemSpiderID_Ref = | ChemSpiderID = 12665 | PubChem = 13220 | InChI = 1/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 | InChIKey = JWUXJYZVKZKLTJ-UHFFFAOYAQ | ChEMBL_Ref = | ChEMBL = 117614 | StdInChI_Ref = | StdInChI = 1S/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3 | StdInChIKey_Ref = | StdInChIKey = JWUXJYZVKZKLTJ-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 826-36-8 | RTECS = TO0127900 | EC_number = 212-554-2 | UNII = 2K4430S3XP |Section2={{Chembox Properties | C=9|H=17|N=1|O=1 | MolarMass = | Appearance = Colorless low-melting solid | Density = 0.882 g/cm3 | Solubility = Moderate | Solvent = other solvents | SolubleOther = Most organic solvents | MeltingPtC = 43 | BoilingPtC = 205 | pKb = | Viscosity = |Section3={{Chembox Structure | Dipole = |Section7={{Chembox Hazards | ExternalSDS = | MainHazards = flammable | FlashPtF = 164 | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = |Section8={{Chembox Related | OtherCompounds = Piperidine

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: :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, as well as the radical oxidizer 4-Hydroxy-TEMPO.

Triacetonamine has known application in the synthesis of alpha-eucaine.

A continuous process for the production of triacetonamine was developed:

References

References

  1. Nabyl Merbouh. (2004). "Preparation of Tetramethylpiperdine-1-oxoammonlum Salts and Their Use as Oxidants in Organic Chemistry. A Review". Organic Preparations and Procedures International.
  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. (15 January 2010). "Industrial Oxidations with Organocatalyst TEMPO and Its Derivatives". Organic Process Research & Development.
  4. (2014). "Continuous synthesis of triacetonamine over sulfonic acid-functionalized mesoporous silicas". RSC Advances.

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piperidinescyclic-ketones