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| 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 | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.920 
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| EC Number |
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| PubChem CID | |
| RTECS number |
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| UNII | |
| UN number | 2815 |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C6H15N3 |
| Molar mass | 129.207 g·mol |
| Appearance | Colourless to yellowish liquid |
| Density | 0.984 g/cm at 20 °C |
| Melting point | −19 °C (−2 °F; 254 K) |
| Boiling point | 222 °C (432 °F; 495 K) |
| Solubility in water | miscible |
| Vapor pressure | 0.076 mmHg @ 20 °C |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
| Main hazards | harmful, corrosive, sensitizing |
| GHS labelling: | |
| Pictograms |  
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| Signal word | Danger |
| Hazard statements | H302, H312, H314, H317, H412 |
| Precautionary statements | 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) |
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| Flash point | 93 °C (199 °F; 366 K) |
| Autoignition temperature |
315 °C (599 °F; 588 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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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.
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. 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. 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. This then allows coating systems to be formulated that prevent corrosion of steel and other substrates. Novolac resins may also be cured by this material and blends.
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. This is part of ongoing research in Carbon capture and storage.
Toxicology
The toxicology has been extensively studied and is well understood.
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
- Catalytic method for the conjoint manufacture of N-aminoethylpiperazine
- Safety MSDS Data
- Safety data sheet
- Data sheet