From Wikipedia, the free encyclopedia
Aminoethylpiperazine
Names
Preferred IUPAC name
2-(Piperazin-1-yl)ethan-1-amine
Other names
2-(1-Piperazinyl)ethylamine, AEP, N-AEP, N-(2-Aminoethyl)piperazine, 2-Piperazinoethylamine, 1-(2-Aminoethyl)piperazine, 1-Piperazine ethanamine, 1-Aminoethylpiperazine
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.004.920
EC Number
RTECS number
UNII
UN number
2815
InChI=1S/C6H15N3/c7-1-4-9-5-2-8-3-6-9/h8H,1-7H2
Y Key: IMUDHTPIFIBORV-UHFFFAOYSA-N
Y InChI=1/C6H15N3/c7-1-4-9-5-2-8-3-6-9/h8H,1-7H2
Key: IMUDHTPIFIBORV-UHFFFAOYAV
Properties
C 6 H 15 N 3
Molar mass
129.207 g·mol−1
Appearance
Colourless to yellowish liquid
Density
0.984 g/cm3 at 20 °C
Melting point
−19 °C (−2 °F; 254 K)
Boiling point
222 °C (432 °F; 495 K)
miscible
Vapor pressure
0.076 mmHg @ 20 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
harmful, corrosive, sensitizing
GHS labelling :
Danger
H302 ,
H312 ,
H314 ,
H317 ,
H412
P260 ,
P261 ,
P264 ,
P270 ,
P272 ,
P273 ,
P280 ,
P301+P312 ,
P301+P330+P331 ,
P302+P352 ,
P303+P361+P353 ,
P304+P340 ,
P305+P351+P338 ,
P310 ,
P312 ,
P321 ,
P322 ,
P330 ,
P333+P313 ,
P363 ,
P405 ,
P501
NFPA 704 (fire diamond)
Flash point
93 °C (199 °F; 366 K)
315 °C (599 °F; 588 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Aminoethylpiperazine (AEP) is a derivative of
piperazine . This
ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause
pulmonary edema as a result of inhalation. It is
REACH and
TSCA registered.
[1]
Production
Ethylene dichloride is reacted with ammonia as a main method of production. This process produces various ethylene amines which can then be purified by distillation. These include
ethylenediamine ,
diethylenetriamine ,
triethylenetetramine ,
tetraethylenepentamine , other
higher homologues and aminoethyl piperazine.
[2]
[3] AEP is also manufactured by reacting ethylenediamine or
ethanolamine /
ammonia mixtures over a
catalyst .
Epoxy resin curing agent
A key use of AEP is as an
epoxy curing agent.
[4] When used as an epoxy resin curing agent, it is usually used in conjunction with other amines as an accelerator as it only has 3 amine hydrogens for cross-linking. The tertiary amine on the molecule acts as an accelerator and the other three amine hydrogens allow sites for crosslinking the epoxy.
[5] This then allows coating systems to be formulated that prevent
corrosion of
steel and other substrates.
[6] Novolac resins may also be cured by this material and blends.
[7]
Other uses
Uses include inhibition of
corrosion , surface activation, and as an
asphalt additive. As AEP is alkaline and
carbon dioxide is weakly acidic, it has been researched as a carbon dioxide sequestrant.
[8] This is part of ongoing research in
Carbon capture and storage .
[9]
[10]
Toxicology
The toxicology has been extensively studied and is well understood.
[11]
[12]
See also
References
^ PubChem.
"1-(2-Aminoethyl)piperazine" . pubchem.ncbi.nlm.nih.gov . Retrieved 2023-05-03 .
^ Eller K, Henkes E, Rossbacher R, Höke H (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH.
doi :
10.1002/14356007.a02_001 .
ISBN
3527306730 .
^ Brydson JA (1999). "Epoxide Resins". In Brydson JA (ed.).
Plastics Materials (Seventh ed.). Oxford: Butterworth-Heinemann. pp.
744 –777.
doi :
10.1016/B978-075064132-6/50067-X .
ISBN
9780750641326 .
^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" Master of Science Thesis April 1997 Imperial College London
^ May, Clayton (2017).
Epoxy Resins : Chemistry and Technology, 2nd Edition . London.
ISBN
978-1-351-44996-0 .
OCLC
1004366333 . {{
cite book }}
: CS1 maint: location missing publisher (
link )
^ Garcia, Filiberto González; Soares, Bluma G.; Pita, Victor J. R. R.; Sánchez, Rubén; Rieumont, Jacques (2007-11-05).
"Mechanical properties of epoxy networks based on DGEBA and aliphatic amines" . Journal of Applied Polymer Science . 106 (3): 2047–2055.
doi :
10.1002/app.24895 .
^ Atta, Ayman M.; Abdou, M. I.; Elsayed, Abdel-Atif A.; Ragab, Mohamed E. (2008-11-01).
"New bisphenol novolac epoxy resins for marine primer steel coating applications" . Progress in Organic Coatings . 63 (4): 372–376.
doi :
10.1016/j.porgcoat.2008.06.013 .
ISSN
0300-9440 .
^ Choi, Jeong Ho; Kim, Young Eun; Nam, Sung Chan; Yun, Soung Hee; Yoon, Yeo Il; Lee, Jung-Hyun (2016-11-01).
"CO2 absorption characteristics of a piperazine derivative with primary, secondary, and tertiary amino groups" . Korean Journal of Chemical Engineering . 33 (11): 3222–3230.
doi :
10.1007/s11814-016-0180-9 .
ISSN
1975-7220 .
S2CID
99511394 .
^ Du, Yang; Li, Le; Namjoshi, Omkar; Voice, Alexander K.; Fine, Nathan A.; Rochelle, Gary T. (2013-01-01).
"Aqueous Piperazine/N-(2-Aminoethyl) Piperazine for CO2 Capture" . Energy Procedia . GHGT-11 Proceedings of the 11th International Conference on Greenhouse Gas Control Technologies, 18-22 November 2012, Kyoto, Japan. 37 : 1621–1638.
doi :
10.1016/j.egypro.2013.06.038 .
ISSN
1876-6102 .
^ Li, Le; Voice, Alexander K.; Li, Han; Namjoshi, Omkar; Nguyen, Thu; Du, Yang; Rochelle, Gary T. (2013).
"Amine blends using concentrated piperazine" . Energy Procedia . 37 : 353–369.
doi :
10.1016/j.egypro.2013.05.121 .
^ Leung, Hon-Wing (1994-01-01).
"Evaluation of the genotoxic potential of alkyleneamines" . Mutation Research/Genetic Toxicology . 320 (1): 31–43.
doi :
10.1016/0165-1218(94)90057-4 .
ISSN
0165-1218 .
PMID
7506385 .
^ PubChem.
"1-(2-Aminoethyl)piperazine" . pubchem.ncbi.nlm.nih.gov . Retrieved 2023-05-03 .
External links
Simple piperazines(no additional rings)
Phenylpiperazines
2C-B-PP
3,4-CFP
Acaprazine
Antrafenine
Aripiprazole
Batoprazine
Bifeprunox
BRL-15,572
Ciprofloxacin
CSP-2503
Dapiprazole
DCPP
DMPP
Diphenylpiperazine
Dropropizine
EGIS-12,233
Elopiprazole
Eltoprazine
Enpiprazole
Ensaculin
Etoperidone
Flesinoxan
Fluanisone
Flibanserin
Fluprazine
Itraconazole
Ketoconazole
Levodropropizine
Lorpiprazole
mCPP
Mefway
MeOPP
Mepiprazole
Naftopidil
Naluzotan
Naphthylpiperazine
Nefazodone
Niaprazine
Oxypertine
Pardoprunox
pCPP
pFPP
Posaconazole
S-14,506
S-14,671
S-15,535
SB-258,585
SB-271,046
SB-357,134
SB-399,885
Sonepiprazole
TFMPP
Tolpiprazole
Trazodone
Urapidil
Vesnarinone
Vilazodone
Vortioxetine
WAY-100,135
WAY-100,635
Benzylpiperazines
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolyl
piperazines
Tricyclics (piperazine attached via side chain) Others/Uncategorized