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1-Piperazineethanamine is often used as a building block in the synthesis of pharmaceuticals, agrochemicals, and surfactants.
Additionally, 1-Piperazineethanamine can act as a ligand in coordination chemistry.
1-Piperazineethanamine is also used as a chemical intermediate and in corrosion-inhibition, asphalt, polyurethane/urethane, polyamide, mineral-processing and petroleum-related applications.
CAS Number: 140-31-8
EC Number: 205-411-0
Molecular formula: C₆H₁₅N₃
Molecular weight: 129.2034 g/mol
SYNONYMS:
Aminoethylpiperazine, N-Aminoethylpiperazine, N-(2-Aminoethyl)piperazine, 1-(2-Aminoethyl)piperazine, 1-Piperazineethanamine, Piperazine, 1-(2-aminoethyl)-, N-(β-Aminoethyl)piperazine, N-(Aminoethyl)piperazine, 1-Aminoethylpiperazine, 1-Piperazineethylamine, 2-(1-Piperazinyl)ethanamine, 2-(Piperazin-1-yl)ethanamine, 2-Piperazinylethylamine, 2-Piperazinoethylamine, 2-Piperazin-1-ylethylamine, AEP, N-AEP, D.E.H. 39, USAF DO-46, NSC 38968, D.E.H. 39, 2-(1-Piperazinyl)ethylamine, 2-Piperazinoethylamine, 1-(2-Aminoethyl)piperazine, 1-Aminoethylpiperazine, 1-Piperazineethylamine, 2-Piperazinylethylamine, 2-piperazin-1-ylethylamine, AEP, Aminoethylpiperazine, N-(.beta.-aminoethyl)piperazine), N-(2-aminoethyl)piperazine, N-(Aminoethyl)piperazine, N-(«beta»-Aminoethyl)piperazine, NSC 38968, Piperazine, 1-(2-aminoethyl)-, UN 2815, USAF DO-46, piperazine, N-(2-aminoethyl)-, 1-(2-Aminoethyl)piperazine, 1-(β-Aminoethyl)piperazine, 2-(1-Piperazinyl)ethanamine, 2-(1-Piperazinyl)ethylamine, 2-(Piperazin-1-yl)ethan-1-amine, Piperazine, 1-(2-aminoethyl)-, N-(β-Aminoethyl)piperazine, N-(Aminoethyl)piperazine, N-(2-Aminoethyl)piperazine, 1-(2-Aminoethyl)piperazine, 1-Aminoethylpiperazine, 1-Piperazineethylamine, Aminoethylpiperazine, USAF DO-46, UN 2815, 2-Piperazinylethylamine, AEP, NSC 38968, 2-piperazin-1-ylethylamine, 2-(Piperazin-1-yl)ethan-1-amine, 2-(1-Piperazinyl)ethylamine, AEP, N-AEP, N-(2-Aminoethyl)piperazine, 2-Piperazinoethylamine, 1-(2-Aminoethyl)piperazine, 1-Piperazine ethanamine, 1-Aminoethylpiperazine
1-Piperazineethanamine, also known as N-(2-aminoethyl)piperazine, is an organic compound characterized by its piperazine ring structure with an ethylamine side chain.
1-Piperazineethanamine is a colorless to pale yellow liquid at room temperature and is soluble in water and various organic solvents, which enhances its utility in chemical synthesis and formulations.
1-Piperazineethanamine (AEP) is a derivative of piperazine.
1-Piperazineethanamine contains three nitrogen atoms; one primary, one secondary and one tertiary.
1-Piperazineethanamine is an aliphatic/cycloaliphatic amine commonly known as aminoethylpiperazine (AEP) or N-(2-aminoethyl)piperazine.
1-Piperazineethanamine is a nitrogen-rich, bifunctional amine containing a piperazine ring with a 2-aminoethyl substituent.
1-Piperazineethanamine's molecular structure contains a primary amine on the side chain and a secondary amine within the piperazine ring.
USES and APPLICATIONS of 1-PIPERAZINEETHANAMINE:
Corrosion inhibitors: 1-Piperazineethanamine has been used as a corrosion inhibitor, either directly or as a component/intermediate in more complex corrosion-inhibiting formulations.
Asphalt additives: 1-Piperazineethanamine has been used as an asphalt additive and in asphalt-related chemical formulations.
Petroleum production chemicals: 1-Piperazineethanamine is used in petroleum-production-related chemical formulations, including systems where amine functionality provides surface interaction and corrosion-control properties.
Mineral processing: 1-Piperazineethanamine is used as a mineral-processing aid and as a chemical intermediate in specialty processing formulations.
Polyamide and urethane chemistry: 1-Piperazineethanamine is used in the production or formulation of polyamide resins and urethane-related chemicals and can serve as an amine building block in polymer chemistry.
Surfactant and specialty chemical production: Its reactive amino groups make 1-Piperazineethanamine useful as an intermediate in the manufacture of surface-active materials and other functionalized nitrogen-containing compounds.
Construction materials: 1-Piperazineethanamine-containing epoxy systems are used in grouts, mortars, flooring systems, chemical anchoring systems and civil-engineering applications.
Uses of 1-Piperazineethanamine include inhibition of corrosion, surface activation, and as an asphalt additive.
As 1-Piperazineethanamine 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.
1-Piperazineethanamine exhibits basic properties due to the presence of both the piperazine nitrogen atoms and the amino group, allowing it to participate in various chemical reactions, including nucleophilic substitutions and complexation with metal ions.
1-Piperazineethanamine is often used as a building block in the synthesis of pharmaceuticals, agrochemicals, and surfactants.
Additionally, 1-Piperazineethanamine can act as a ligand in coordination chemistry.
Because of this combination of amine functionalities, 1-Piperazineethanamine is a highly reactive basic compound and is particularly important as an epoxy-resin curing agent and accelerator.
1-Piperazineethanamine is also used as a chemical intermediate and in corrosion-inhibition, asphalt, polyurethane/urethane, polyamide, mineral-processing and petroleum-related applications.
-Epoxy resin curing agent uses of 1-Piperazineethanamine:
A key use of 1-Piperazineethanamine is as an epoxy curing agent.
When used as an epoxy resin curing agent, 1-Piperazineethanamine 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.
-Pharmaceutical and chemical intermediate uses of 1-Piperazineethanamine:
1-Piperazineethanamine has been reported as a chemical intermediate in the manufacture of pharmaceuticals, anthelmintics and surface-active agents.
1-Piperazineethanamine is therefore more broadly useful as a nitrogen-containing synthetic building block rather than being limited to polymer applications.
-CO₂ capture research uses of 1-Piperazineethanamine:
Because 1-Piperazineethanamine is strongly basic and contains multiple amine functionalities, it has also been investigated for carbon dioxide absorption/capture.
Research has examined aqueous piperazine/N-(2-aminoethyl)piperazine systems for CO₂ capture.
This is better considered a specialized/research application rather than 1-Piperazineethanamine's principal commercial use.
-Epoxy resin curing agent uses of 1-Piperazineethanamine:
The principal industrial application of 1-Piperazineethanamine is as an epoxy curing agent/hardener.
1-Piperazineethanamine is used to crosslink epoxy resins and is particularly relevant to protective coatings, adhesives, flooring, composites, laminates, grouts, encapsulation and related applications.
-Epoxy curing accelerator uses of 1-Piperazineethanamine:
1-Piperazineethanamine can also be incorporated as an accelerator into amine-cured epoxy systems.
1-Piperazineethanamine's use can increase curing rate and improve the ability of some formulations to cure at ambient temperature.
Historical patent literature specifically describes 1-Piperazineethanamine/alkanolamine accelerator combinations for this purpose.
-Protective coatings uses of 1-Piperazineethanamine:
1-Piperazineethanamine is used in epoxy coating formulations intended to protect metals and other substrates.
Properly formulated epoxy-amine coatings can provide adhesion, chemical resistance and corrosion protection.
1-Piperazineethanamine-containing formulations have therefore been used in maintenance paints, tank linings and industrial protective coatings.
-Adhesives uses of 1-Piperazineethanamine:
1-Piperazineethanamine-based epoxy systems can be used in industrial adhesive formulations.
1-Piperazineethanamine reacts with epoxy resin and produces a crosslinked adhesive network with strong adhesion and mechanical performance.
-Composite materials uses of 1-Piperazineethanamine:
1-Piperazineethanamine can be used as a curing component in epoxy composite systems, including tooling and structural composite applications.
Commercial 1-Piperazineethanamine-based curing agents are used for epoxy composite materials.
BENEFITS AND CHARACTERISTICS of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine's main industrial benefits arise from the combination of its high amine functionality, low molecular weight, water solubility, relatively low viscosity and chemical reactivity.
1-Piperazineethanamine's primary and secondary amine groups provide multiple reactive sites for polymerization and crosslinking.
This makes 1-Piperazineethanamine particularly effective in epoxy curing.
1-Piperazineethanamine's low viscosity can facilitate handling and mixing in resin formulations.
Its high water solubility makes 1-Piperazineethanamine useful in certain water-compatible chemical systems and facilitates aqueous processing.
Its basicity allows 1-Piperazineethanamine to neutralize acidic species and form salts.
Its multiple nitrogen atoms make 1-Piperazineethanamine a useful starting material for synthesizing more complex nitrogen-containing molecules.
In epoxy applications, 1-Piperazineethanamine can provide relatively rapid curing and can be used to modify curing kinetics.
Commercial 1-Piperazineethanamine-based curing agents are marketed for applications where short pot life and rapid curing are desired.
THERMAL AND FIRE CHARACTERISTICS of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine is a combustible liquid rather than a noncombustible material.
The flash point of 1-Piperazineethanamine is approximately 200 °F, and the autoignition temperature is approximately 315 °C.
1-Piperazineethanamine should therefore be kept away from ignition sources and excessive heat.
INDUSTRIAL IMPORTANCE of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine is particularly important because it combines the properties of a reactive amine, polymer-curing agent, chemical intermediate and functional additive in a relatively small molecule.
Its most significant commercial role is in epoxy chemistry.
In this context, 1-Piperazineethanamine can act as a curing agent, hardener or accelerator.
Commercial 1-Piperazineethanamine-based systems are used in coatings, adhesives, flooring, grouts, composites, tank linings, tooling and construction materials.
1-Piperazineethanamine's secondary importance comes from its use as an intermediate in the production of specialty chemicals, including pharmaceutical intermediates, surfactant-related materials, corrosion inhibitors and other functionalized amines.
CHARACTERISTICS of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine is a clear, colorless to slightly yellow, strongly basic, water-soluble, combustible and corrosive liquid amine.
1-Piperazineethanamine's CAS number is 140-31-8, its EC number is 205-411-0, its molecular formula is C₆H₁₅N₃, and its molecular weight is 129.20 g/mol.
1-Piperazineethanamine's molecular structure contains a piperazine ring and a primary aminoethyl group, giving the molecule three nitrogen atoms and substantial chemical reactivity.
1-Piperazineethanamine's dominant industrial application is as an epoxy resin curing agent and accelerator, where its amine groups react with epoxy functionalities to form crosslinked polymer networks.
1-Piperazineethanamine is also used in protective coatings, adhesives, flooring, grouts, laminates, composites, chemical anchoring materials, corrosion inhibitors, asphalt additives, mineral-processing chemicals, petroleum-production chemicals, polyamide and urethane chemistry, and as an intermediate for various specialty chemicals.
MOLECULAR AND STRUCTURAL CHARACTERISTICS of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine has the molecular formula C₆H₁₅N₃.
1-Piperazineethanamine's structure consists of a six-membered saturated piperazine ring containing two nitrogen atoms.
One of the ring nitrogens is substituted with a –CH₂–CH₂–NH₂ group.
The molecule therefore contains three nitrogen atoms in total.
The structure can be represented approximately as:
H₂N–CH₂–CH₂–N(CH₂CH₂)₂NH
The combination of the primary amino group and the secondary piperazine nitrogen gives 1-Piperazineethanamine strong basicity and considerable chemical reactivity.
This structure is particularly useful in epoxy chemistry because the amine hydrogens can participate in epoxy-ring-opening and crosslinking reactions, while the tertiary-like catalytic behavior of substituted amine environments can contribute to curing acceleration depending on the formulation.
Unlike a simple diamine, 1-Piperazineethanamine contains a cyclic diamine framework and a primary aminoethyl substituent.
This gives 1-Piperazineethanamine a useful combination of reactivity, basicity, water miscibility and relatively low molecular weight.,
CHEMICAL PROPERTIES of 1-PIPERAZINEETHANAMINE:
1-Piperazineethanamine is a strongly basic organic amine.
Its three nitrogen atoms give 1-Piperazineethanamine significant proton-accepting capacity, and the compound readily reacts with acids to form corresponding ammonium salts.
1-Piperazineethanamine is highly water soluble because its amine groups can hydrogen-bond with water and become protonated in aqueous media.
1-Piperazineethanaminecontains both primary and secondary amine functionality.
This is particularly important in polymer chemistry because these functional groups can react with epoxy groups and other electrophilic functionalities.
1-Piperazineethanamine can neutralize acids through exothermic acid-base reactions.
1-Piperazineethanamine can also react with acid chlorides, acid anhydrides and other reactive acyl compounds.
1-Piperazineethanamine is incompatible with a range of strong oxidizing agents and reactive electrophiles.
1-Piperazineethanamine can also react with isocyanates, epoxides, anhydrides, acid halides, alkylene oxides and epichlorohydrin.
These reactions are important industrially because some are desirable controlled reactions during polymer or resin manufacture, whereas uncontrolled contact can produce excessive heat or other hazards.
Another important chemical characteristic is 1-Piperazineethanamine's ability to act as a nucleophile.
The nitrogen atoms can attack electrophilic centers, which is the basis for 1-Piperazineethanamine's usefulness in epoxy curing, chemical synthesis and functionalization reactions.
EPOXY CURING PROPERTIES of 1-PIPERAZINEETHANAMINE:
One of the most important applications of 1-piperazineethanamine is its use as an epoxy resin curing agent/hardener.
1-Piperazineethanamine reacts with epoxide groups and causes the epoxy resin molecules to become interconnected through chemical crosslinking.
This transforms a relatively low-viscosity resin system into a solid three-dimensional polymer network.
1-Piperazineethanamine can also function as an accelerator in epoxy systems.
Its amine functionality allows 1-Piperazineethanamine to participate directly in curing while also influencing the reaction kinetics of other amine curing agents.
Historical patent literature describes 1-Piperazineethanamine in accelerator combinations designed to accelerate epoxy curing at ambient or elevated temperatures.
1-Piperazineethanamine-based epoxy systems can be used in protective coatings, adhesives, flooring, grouts, laminates, castings, potting compounds, encapsulants and sealing systems.
Commercial 1-Piperazineethanamine-based curing-agent products are also used in chemical anchoring, tank linings, mortars, tooling systems and composite materials.
An important advantage in epoxy formulations is its relatively low viscosity compared with some higher-molecular-weight amine curing agents.
This can facilitate mixing and processing.
PRODUCTION of 1-PIPERAZINEETHANAMINE:
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.
1-Piperazineethanamine is also manufactured by reacting ethylenediamine or ethanolamine/ammonia mixtures over a catalyst.
PHYSICAL and CHEMICAL PROPERTIES of 1-PIPERAZINEETHANAMINE:
Chemical name: 1-Piperazineethanamine
Common name: Aminoethylpiperazine
Abbreviation: AEP
IUPAC name: 2-(Piperazin-1-yl)ethan-1-amine
CAS Number: 140-31-8
EC Number: 205-411-0
PubChem CID: 8795
ChemSpider ID: 8465
Molecular formula: C₆H₁₅N₃
Molecular weight: 129.2034 g/mol
Molar mass: 129.20 g/mol
Exact/monoisotopic mass: approximately 129.1260 Da
InChI: InChI=1S/C6H15N3/c7-1-4-9-5-2-8-3-6-9/h8H,1-7H2
InChIKey: IMUDHTPIFIBORV-UHFFFAOYSA-N
Canonical SMILES: NCCN1CCNCC1
Physical form: Liquid
Appearance: Clear/colorless to slightly yellow liquid
Chemical family: Amines / ethyleneamines / piperazine derivatives
Transport classification: UN 2815, corrosive material, Packing Group III.
Physical state: Liquid
Appearance: Clear, colorless to slightly yellow liquid.
Odor: Ammonia-like/amine odor is reported for commercial AEP.
Melting point: Approximately −19 °C.
Boiling point: Approximately 218–222 °C.
Density: Approximately 0.985 g/mL at 25 °C; approximately 0.984 g/cm³ at 20 °C.
Vapor density: Approximately 4.4 relative to air.
Vapor pressure: Approximately 0.05 mmHg at 20 °C in ChemicalBook data.
Refractive index: Approximately n²⁰/D 1.500.
Flash point: Approximately 200 °F (about 93 °C).
Autoignition temperature: Approximately 315 °C.
Water solubility: Soluble; ChemicalBook reports >1000 g/L, and other databases describe it as fully miscible with water.
pH: Approximately 12 for a 100 g/L aqueous solution at 20 °C.
LogP: Approximately −1.48 at 20 °C.
Predicted pKa: Approximately 10.11 ± 0.10.
Explosive limits: Approximately 2.1–10.5% by volume according to ChemicalBook data.
Storage temperature: ChemicalBook recommends storage below approximately 30 °C.
Air sensitivity: Reported as air-sensitive.
Stability: Generally stable under recommended storage conditions, but chemically reactive with a number of acids,
oxidizers and other reactive compounds.
Hydrogen-bond donor count: approximately 2
Hydrogen-bond acceptor count: approximately 3
Rotatable bonds: approximately 3
Topological polar surface area: approximately 58.0 Ų
Heavy atom count: 9
Formal charge: 0 for the neutral molecule
Ring system: One saturated six-membered piperazine ring
Nitrogen atoms: 3
Carbon atoms: 6
Oxygen atoms: 0
Halogen atoms: 0
Aromatic rings: None
Double bonds: None
Triple bonds: None
CAS No.: 140-31-8
EC No.: 205-411-0
Molecular Formula: C₆H₁₅N₃
Molecular Weight: 129.2034 g/mol
PubChem CID: 8795
ChemSpider ID: 8465
InChIKey: IMUDHTPIFIBORV-UHFFFAOYSA-N
SMILES: NCCN1CCNCC1
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
FIRST AID MEASURES of 1-PIPERAZINEETHANAMINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of 1-PIPERAZINEETHANAMINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of 1-PIPERAZINEETHANAMINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of 1-PIPERAZINEETHANAMINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of 1-PIPERAZINEETHANAMINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of 1-PIPERAZINEETHANAMINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
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