Triacetonamine

Structural formula
General
Surname	Triacetonamine
other names	2,2,6,6-tetramethyl-4-piperidone; TAA;
Molecular formula	C 9 H 17 NO
Brief description	white-yellow to brownish solid
External identifiers / databases
EC number	212-554-2
ECHA InfoCard	100.011.413
PubChem	13220
ChemSpider	12665
Wikidata	Q6120732
properties
Molar mass	155.24 g mol −1
Physical state	firmly
density	1.065 g cm −3
Melting point	33.2 ° C ; 63-61 ° C (monohydrate);
boiling point	209.1 ° C
solubility	Easily soluble in water (249 g l −1 at 20 ° C)
safety instructions
H and P phrases	H: 290-302-314-317-412
	P: 260-301 + 312-303 + 361 + 353-304 + 340-305 + 351 + 338-501
Toxicological data	1540 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triacetonamine is a chemical compound and a tetramethylated 4-piperidone .

Occurrence

Scented violets ( Viola odorata )

Triacetonamine was detected in the scented violet .

Extraction and presentation

Triacetonamine can be obtained by the condensation of acetone with ammonia in the presence of calcium chloride at room temperature. Syntheses by reaction of phosphorus with ammonia, by condensation of diacetone alcohol with acetone and ammonia in the presence of calcium chloride or starting from acetonin are also known .

properties

Triacetonamine is a flammable, hardly inflammable, crystalline, white-yellow to brownish solid that is easily soluble in water. The also existing monohydrate crystallizes in a monoclinic crystal structure with the space group P 2 ₁ / c (space group no. 14) . Template: room group / 14

use

Triacetone amine is used as a stabilizer for polymers .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on triacetonamine in the GESTIS substance database of the IFA , accessed on January 21, 2019(JavaScript required) .
↑ Data sheet 2,2,6,6-Tetramethyl-4-piperidone monohydrate, 99% from AlfaAesar, accessed on January 21, 2019 ( PDF )(JavaScript required) .
↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8351-4 , pp. 1872 ( limited preview in Google Book search).
↑ G. Sosnovsky, M. Konieczny: Preparation of Triacetoneamine, I. In: Zeitschrift für Naturforschung B. 32, 1977, p. 328, doi : 10.1515 / znb-1977-0319 .
↑ Andrew D. Bond: Redetermination of the twinned structure of triacetone amine monohydrate. In: Acta Crystallographica Section C Crystal Structure Communications. 58, 2002, p. O115, doi : 10.1107 / S0108270101021527 .
↑ Google Patents: US4831146A - Process for preparing triacetone amine and other oxopiperidines - Google Patents , accessed January 21, 2019.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on triacetonamine in the GESTIS substance database of the IFA , accessed on January 21, 2019(JavaScript required) .

[Alfa-2] Data sheet 2,2,6,6-Tetramethyl-4-piperidone monohydrate, 99% from AlfaAesar, accessed on January 21, 2019 ( PDF )(JavaScript required) .

[Shmuel_Yannai-3] Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8351-4 , pp. 1872 ( limited preview in Google Book search).

[DOI10.1515/znb-1977-0319-4] G. Sosnovsky, M. Konieczny: Preparation of Triacetoneamine, I. In: Zeitschrift für Naturforschung B. 32, 1977, p. 328, doi : 10.1515 / znb-1977-0319 .

[DOI10.1107/S0108270101021527-5] Andrew D. Bond: Redetermination of the twinned structure of triacetone amine monohydrate. In: Acta Crystallographica Section C Crystal Structure Communications. 58, 2002, p. O115, doi : 10.1107 / S0108270101021527 .

[google.com-6] Google Patents: US4831146A - Process for preparing triacetone amine and other oxopiperidines - Google Patents , accessed January 21, 2019.