1- (2-aminoethyl) piperazine

Structural formula
General
Surname	1- (2-aminoethyl) piperazine
other names	2-piperazin-1-ylethylamine; 1- (2-aminoethyl) piperazine;
Molecular formula	C 6 H 15 N 3
Brief description	yellowish liquid with a fish-like odor
External identifiers / databases
EC number	205-411-0
ECHA InfoCard	100.004.920
PubChem	8795
Wikidata	Q3887815
properties
Molar mass	129.21 g mol −1
Physical state	liquid
density	0.9842 g cm −3 (20 ° C)
Melting point	−19 ° C
boiling point	217-218 ° C
Vapor pressure	0.07 mbar (20 ° C)
solubility	completely miscible in water
Refractive index	1.5 (20 ° C)
safety instructions
H and P phrases	H: 314-317-311-302-412
	P: 273-280-305 + 351 + 338-310
Toxicological data	867 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 2110 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 . Refractive index: Na-D line , 20 ° C

1- (2-Aminoethyl) piperazine (also less precisely: Aminoethylpiperazine ) is a chemical compound from the group of aliphatic amines that is used to crosslink epoxy resins and other polymers and as an intermediate in the chemical industry.

presentation

Aminoethylpiperazine can be made by catalytic hydrogenation of nitrilotriacetonitrile :

Another possibility is the reaction of monoethanolamine and piperazine .

properties

Aminoethylpiperazine is a yellowish liquid at room temperature with a weak, fish-like odor, at higher temperatures a pungent odor that is completely soluble in water. Your aqueous solution reacts strongly alkaline.

use

Aminoethylpiperazine can react in a polymerization both on its primary and on its secondary amino group. It is therefore used to crosslink epoxy resins. The synthesis of branched polymers (dendrimers) is also possible on its basis.

In addition, 1- (2-aminoethyl) piperazine is a valuable intermediate product in the production of hot-melt adhesive polymers and fine chemicals such as anthelmintics, insecticides and high-temperature lubricating oils, as well as other reaction products made from piperazine and an alcohol ( English alcohol-extended piperazines ) or piperazine and an amine ( amine-extended piperazines ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2-piperazin-1-ylethylamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ RN Zagidullin: Piperazinophenols as stabilizers for Unsaturated compounds and Their chloro derivative . In: Chemistry of Heterocyclic Compounds . 26, No. 10, October 1990, pp. 1140-1142. doi : 10.1007 / BF00472186 .
↑ Kangcai Wang, Daibing Luo, Dingguo Xu, Furong Guo, Lin Liu, Zhien Lin: New open-framework cobalt sulfate-oxalates based on molecular and chain-like building blocks . In: Dalton Transactions . 43, No. 36, July 29, 2014, p. 13476. doi : 10.1039 / C4DT01503G .
↑ RN Zagidullin: Synthesis of alkali and heavy metal dithio- and thiocarbamates based on N - (? - aminoethyl) piperazine . In: Chemistry of Heterocyclic Compounds . 25, No. 11, November 1989, pp. 1275-1279. doi : 10.1007 / BF00481523 .
↑ Data sheet 1- (2-Aminoethyl) piperazine, 99% from Sigma-Aldrich , accessed on July 1, 2015 ( PDF ).
↑ Entry on 2-piperazin-1-ylethylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Patent US4927931 : Preparation of alkyl-extended, alcohol-extended or amine-extended piperazines. Filed November 1, 1988 , published May 22, 1990 , Applicant: Dow Chemical, Inventor: David C. Molzahn, George E. Hartwell, Robert G. Bowman. ‌
↑ Patent US3055901 : Preparation of aminoethylpiperazine. Filed May 18, 1961 , published September 25, 1962 , Applicant: Jefferson Chem Co, Inventor: Lichtenwalter Myrl, George P Speranza. ‌
↑ Filiberto González Garcia, Bluma Guenther Soares, Maria Elena Leyva, Alexandre Zirpoli Simões: Influence of aliphatic amine epoxy hardener on the adhesive properties of blends of mono-carboxyl-terminated poly (2-ethylhexyl acrylate-co-methyl methacrylate) with epoxy resin . In: Journal of Applied Polymer Science . 2010, pp. N / a – n / a. doi : 10.1002 / app.31720 .
↑ Deyue Yan, Chao Gao: Hyper Branched Polymers Made from A and B-B 'type monomer. 1. Polyaddition of 1- (2-Aminoethyl) piperazine to Divinyl Sulfone . In: Macromolecules . 33, No. 21, October 2000, pp. 7693-7699. doi : 10.1021 / ma000438j .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2-piperazin-1-ylethylamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[2] RN Zagidullin: Piperazinophenols as stabilizers for Unsaturated compounds and Their chloro derivative . In: Chemistry of Heterocyclic Compounds . 26, No. 10, October 1990, pp. 1140-1142. doi : 10.1007 / BF00472186 .

[3] Kangcai Wang, Daibing Luo, Dingguo Xu, Furong Guo, Lin Liu, Zhien Lin: New open-framework cobalt sulfate-oxalates based on molecular and chain-like building blocks . In: Dalton Transactions . 43, No. 36, July 29, 2014, p. 13476. doi : 10.1039 / C4DT01503G .

[4] RN Zagidullin: Synthesis of alkali and heavy metal dithio- and thiocarbamates based on N - (? - aminoethyl) piperazine . In: Chemistry of Heterocyclic Compounds . 25, No. 11, November 1989, pp. 1275-1279. doi : 10.1007 / BF00481523 .

[Sigma-5] Data sheet 1- (2-Aminoethyl) piperazine, 99% from Sigma-Aldrich , accessed on July 1, 2015 ( PDF ).

[CLP_100.004.920-6] Entry on 2-piperazin-1-ylethylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[extended_piperazines-7] Patent US4927931 : Preparation of alkyl-extended, alcohol-extended or amine-extended piperazines. Filed November 1, 1988 , published May 22, 1990 , Applicant: Dow Chemical, Inventor: David C. Molzahn, George E. Hartwell, Robert G. Bowman. ‌

[8] Patent US3055901 : Preparation of aminoethylpiperazine. Filed May 18, 1961 , published September 25, 1962 , Applicant: Jefferson Chem Co, Inventor: Lichtenwalter Myrl, George P Speranza. ‌

[9] Filiberto González Garcia, Bluma Guenther Soares, Maria Elena Leyva, Alexandre Zirpoli Simões: Influence of aliphatic amine epoxy hardener on the adhesive properties of blends of mono-carboxyl-terminated poly (2-ethylhexyl acrylate-co-methyl methacrylate) with epoxy resin . In: Journal of Applied Polymer Science . 2010, pp. N / a – n / a. doi : 10.1002 / app.31720 .

[10] Deyue Yan, Chao Gao: Hyper Branched Polymers Made from A and B-B 'type monomer. 1. Polyaddition of 1- (2-Aminoethyl) piperazine to Divinyl Sulfone . In: Macromolecules . 33, No. 21, October 2000, pp. 7693-7699. doi : 10.1021 / ma000438j .