Aminoethylpiperazine

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Aminoethylpiperazine - Wikipedia

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
CAS Number	140-31-8^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL209790^Y
ChemSpider	8465^Y
ECHA InfoCard	100.004.920
EC Number	205-411-0
PubChem CID	8795
RTECS number	TK8050000
UNII	I86052F9F6
UN number	2815
CompTox Dashboard (EPA)	DTXSID2021997
InChI 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
SMILES NCCN1CCNCC1
Properties
Chemical formula	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)
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
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)	2 2 0
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 [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

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]

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

v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
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	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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