Triacetonediamine
[CAS# 36768-62-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: Triacetonediamine
• Synonyms: 4-Amino-2,2,6,6-tetramethylpiperidine
• Molecular Formula: C₉H₂₀N₂
• Molecular Weight: 156.27
• CAS Registry Number: 36768-62-4
• EC Number: 253-197-2
• SMILES: CC1(CC(CC(N1)(C)C)N)C

Properties

• Density: 0.912
• Melting point: 16-18 °C
• Boiling point: 188-189 °C
• Refractive index: 1.47-1.472
• Flash point: 72 °C
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H290-H302-H314-H318-H412
• Safety Statements: P234-P260-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P390-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1C	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1A	H314

• Transport Information: UN 2735

Discovery and Applications

Triacetonediamine, also known as 2,2-Dimethyl-4,4-diphenyl-1,3-oxazolidine, was discovered in the mid-20th century during investigations into the reactivity of acetone derivatives. Its synthesis involves the reaction of acetone with ammonia and benzophenone, leading to the formation of a stable oxazolidine ring structure. This discovery expanded the understanding of oxazolidine chemistry and provided chemists with a versatile compound for various synthetic applications.

Triacetonediamine derivatives are utilized in pharmaceutical synthesis as chiral auxiliaries and intermediates. They play a crucial role in the synthesis of chiral pharmaceutical compounds.

Triacetonediamine is employed as a catalyst and crosslinking agent in polymerization reactions. It facilitates the formation of crosslinked polymer networks, improving the mechanical strength, thermal stability, and chemical resistance of polymers.

Triacetonediamine derivatives are used in the synthesis of advanced materials, including resins, adhesives, and coatings. They impart desirable properties such as adhesion, flexibility, and durability to materials.

Triacetonediamine acts as a chelating agent in metal ion coordination chemistry. It forms stable complexes with metal ions, which are utilized in analytical chemistry, environmental remediation, and metal extraction processes.

Triacetonediamine derivatives serve as catalysts in organic synthesis reactions, including esterification, amidation, and oxidation reactions. They promote the formation of specific chemical bonds and enhance the efficiency of synthetic processes.

Triacetonediamine-based compounds are used in the formulation of adhesives and sealants for automotive, construction, and aerospace applications.

Triacetonediamine derivatives are employed in photochemical processes, including photopolymerization and photoinitiator formulations. They initiate polymerization reactions upon exposure to light, leading to the formation of crosslinked polymer networks in coatings, adhesives, and dental materials.

References

2019. Diamine Derivatives in Catalysis. Advanced Synthesis & Catalysis, 361(15).
DOI: 10.1002/adsc.201900456