Aminoethylpiperazine

Aminoethylpiperazine
Skeletal formula of aminoethylpiperazine
Ball-and-stick model of the aminoethylpiperazine molecule
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.920 Edit this at Wikidata
EC Number
  • 205-411-0
RTECS number
  • TK8050000
UNII
UN number 2815
  • InChI=1S/C6H15N3/c7-1-4-9-5-2-8-3-6-9/h8H,1-7H2 checkY
    Key: IMUDHTPIFIBORV-UHFFFAOYSA-N checkY
  • InChI=1/C6H15N3/c7-1-4-9-5-2-8-3-6-9/h8H,1-7H2
    Key: IMUDHTPIFIBORV-UHFFFAOYAV
  • NCCN1CCNCC1
Properties
C6H15N3
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:
GHS05: CorrosiveGHS07: Exclamation mark
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
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).
checkY verify (what is checkY☒N ?)

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

  1. ^ PubChem. "1-(2-Aminoethyl)piperazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-05-03.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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
  5. ^ 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)
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ PubChem. "1-(2-Aminoethyl)piperazine". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-05-03.

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