Triacetonediamine

Product NameTriacetonediamine
CAS36768-62-4
MFC9H20N2
MW156.27
EINECS253-197-2
MOL File36768-62-4.mol

Chemical Properties

Melting point	17 °C (63 °F; 290 K)
Boiling point	188.5 °C (371.3 °F; 461.6 K)
Density	0.8966 g/cm3
vapor pressure	<=20 hPa (20 °C)
refractive index	1.47
Flash point	81 °C
storage temp.	Store below +30°C.
pka	10.83±0.10(Predicted)
form	liquid
Specific Gravity	0.912
color	colorless
PH	12.3 (99g/l, H2O, 20℃)
Water Solubility	soluble
BRN	105038
InChI	1S/C9H20N2/c1-8(2)5-7(10)6-9(3,4)11-8/h7,11H,5-6,10H2,1-4H3
InChIKey	FTVFPPFZRRKJIH-UHFFFAOYSA-N
SMILES	CC1(C)CC(N)CC(C)(C)N1
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	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29333999
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Acute Tox. 4 Oral Aquatic Chronic 3 Met. Corr. 1 Skin Corr. 1C
Toxicity	LD50 orally in Rabbit: 1000 mg/kg

MSDS

Provider	Language
Triacetonediamine	English
SigmaAldrich	English
ACROS	English
ALFA	English

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

826-36-8

36768-62-4

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

Triacetonediamine

Chemical Properties

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MSDS

Usage And Synthesis

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