Triacetonediamine Chemical Properties

Melting point:

16-18 °C(lit.)

Boiling point:

188-189 °C(lit.)

Density 

0.912 g/mL at 25 °C(lit.)

vapor pressure 

<=20 hPa (20 °C)

refractive index 

n20/D 1.470(lit.)

Flash point:

162 °F

storage temp. 

Store below +30°C.

pka

10.83±0.10(Predicted)

form 

clear liquid

color 

Colorless to Light orange to Yellow

Specific Gravity

0.912

PH

12.3 (99g/l, H2O, 20℃)

Water Solubility 

soluble

BRN 

105038

InChIKey

FTVFPPFZRRKJIH-UHFFFAOYSA-N

LogP

0.94 at 20℃

Surface tension

67.11-68.09mN/m at 1g/L and 20℃

CAS DataBase Reference

36768-62-4(CAS DataBase Reference)

NIST Chemistry Reference

4-Piperidinamine, 2,2,6,6-tetramethyl-(36768-62-4)

EPA Substance Registry System

4-Piperidinamine, 2,2,6,6-tetramethyl- (36768-62-4)

Safety Information

Hazard Codes 

Xn,Xi,C

Risk Statements 

22-36/37/38-34-52/53-41

Safety Statements 

26-36/37-45-36/37/39-61

RIDADR 

UN 2735 8/PG 3

WGK Germany 

2

RTECS 

TM4290100

Autoignition Temperature

300 °C

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29333999

Toxicity

LD50 orally in Rabbit: 1000 mg/kg

MSDS

• Language:English Provider:Triacetonediamine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Triacetonediamine Usage And Synthesis

Chemical Properties

CLEAR SLIGHTLY YELLOW LIQUID

Uses

Additive for light and heat stability of polyamide 6 containing hindered piperidine amines and tertiary amines

Template for preparation of ammoniopiperidinium hydrogen phosphates

Fiber-reactive yellowing inhibitor for partial brightness stabilization of peroxide-bleached pulps

Reactant for thermostability of soybean / sunflower oils

Uses

Triacetonediamine have been investigated as new anticancer drugs with high activity and low toxicity.

Preparation

Triacetonediamine 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

Reactions

Triacetonediamine is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO. Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx.

Synthesis

The general procedure for the synthesis of 2,2,6,6-tetramethylpiperidinamine from 2,2,6,6-tetramethylpiperidin-4-one is as follows: Examples 1-12: 300 g of 2,2,6,6-tetramethylpiperidin-4-one, deionized water and 11 g of catalyst (sequentially using B113W nickel-based catalyst and B2112Z cobalt-based catalyst from Evonik Degussa GmbH) were added to a 1-liter stirred autoclave under argon protection. The autoclave was equipped with a paddle stirrer, an electric heating system, an air cooling unit and a hydrogen mass flow regulator. The autoclave was then flushed three times with nitrogen. The stirrer speed was set to 300 rpm and then 83 g of liquid ammonia was slowly added. The system was adjusted to the pressure and temperature conditions required for the main reaction under hydrogen atmosphere. The reaction was carried out at 150 °C and 50 bar pressure for about 3 hours. Deviations from other reaction conditions are recorded in Table 1, which shows both the process parameters and the results for each embodiment.

References

[1] Anales de Quimica, 1998, vol. 94, # 1, p. 36 - 45
[2] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[3] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[4] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191
[5] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 1, p. 182 - 191

Triacetonediamine(36768-62-4)Related Product Information

• 2,2,6,6-Tetramethyl-4-piperidinol
• 2,2,6,6-Tetramethylpiperidine
• N,N-Dimethyl-1,4-phenylenediamine
• Triacetonamine
• N,N,N',N'-Tetramethylethylenediamine
• ALTRENOGEST
• Betaine
• Glycine
• Haloperidol
• Lithium bis(trimethylsilyl)amide
• Tris(hydroxymethyl)aminomethane
• 4-Aminopiperidine
• Hexamethylenetetramine
• 4-ACETAMIDO-TEMPO
• 4-Amino-TEMPO, free radical
• Chimassorb 119
• N-BUTYL TRIACETONEDIAMINE
• AMINO ACIDS