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N-(2-Aminoethyl)ethanolamine is a clear to pale yellow, hygroscopic liquid with a faint ammonia-like odor, belonging to the alkanolamine family and containing both primary and secondary amine groups as well as a hydroxyl group.
This multifunctional structure gives N-(2-Aminoethyl)ethanolamine combined amine and alcohol reactivity, making it a versatile intermediate in the production of chelating agents, surfactants, corrosion inhibitors, fuel additives, resins, and epoxy curing agents.
Industrially, N-(2-Aminoethyl)ethanolamine is especially valued in water treatment, oilfield chemicals, coatings, and textiles, where it enhances performance by enabling complex formation, epoxy curing, and the manufacture of high-performance surfactants and fabric softeners.
CAS Number: 111-41-1
EC Number: 203-867-5
Molecular Formula: C₄H₁₂N₂O
Molar Mass: 104.15 g/mol
Synonyms: (β-Hydroxyethyl)ethylenediamine, (2-Hydroxyethyl)ethylenediamine, N-(β-Aminoethyl)ethanolamine, N-(Aminoethyl)ethanolamine, N-(Hydroxyethyl)ethylenediamine, N-(2-Aminoethyl)ethanolamine, N-Hydroxyethyl-1,2-ethanediamine, 2-[(2-Aminoethyl)amino]ethanol, 1-Aminoethylethanolamine, (2-Aminoethyl)ethanolamine, Aminoethylethanolamine, Monoethanolethylenediamine, Ethanolethylene diamine, N-β-Hydroxyethylethylenediamine, 2-Amino-2'-hydroxydiethylamine, N-(2-Aminoethyl)ethanolamine, (2-HYDROXYETHYL)ETHYLENEDIAMINE, (β-Hydroxyethyl)ethylenediamine, 111-41-1, 2-(2-Aminoethylamino)ethanol, 2-[(2-Aminoethyl)amino]ethanol, 2-[(2-Aminoethyl)amino]ethanol, 2-[(2-Aminoéthyl)amino]éthanol, 203-867-5, Aminoethylethanolamin, Aminoethylethanolamine, Ethanol, 2-((2-aminoethyl)amino)-, Ethanol, 2-[(2-aminoethyl)amino]-, KJ6300000, MFCD00008170 [MDL number], N-(2-hydroxyethyl)ethylenediamine, N-(2'-Hydroxyethyl)ethylenediamine, N-(Hydroxyethyl)ethylenediamine, N-(β-Aminoethyl)ethanolamine, N-(β-Hydroxyethyl)ethylenediamine, N-Aminoethylethanolamine, N-Hydroxyethyl-1,2-ethanediamine, RC78W6NPXT, β-Aminoethyl-β-hydroxyethylamine, (2-AMINOETHYL)ETHANOLAMINE, (β-Hydroxyethyl)ethylenediamine, 1-(2-(Hydroxyethyl)amino)-2-aminoethane, 1-[2-(Hydroxyethyl)amino]-2-aminoethane, 1246819-88-4, 147770-06-7, 1-Aminoethylethanolamine, 2-(2-aminoethylamino)ethanol, 2-((2-aminoethyl)amino)ethanol, 2-((Aminoethyl)amino)ethanol, 2-(2-Amino-ethylamino)-ethanol, 2-(2-AMINOETHYLAMINO)ETHANOL-D4, 2-(2-Hydroxyethylamino)ethylamine, 2-[(2-aminoethyl)amino]ethan-1-ol, 2-[2-Aminoethylamino]ethanol, 20261-60-3, 263-177-5, 263-179-6, 2-Amino-2'-hydroxydiethylamine, 2-hydroxyethylethylenediamine, 4-04-00-01514, 51251-98-0, 59219-56-6, 61791-44-4, 61791-46-6, 66085-61-8, 7-(trifluoromethyl)-3,4-dihydro-2H-1-benzopyran-4-one, 8033-73-6, Aminoethylethanolamine, Aminoethylethanolamin, Ethanolethylene diamine, ethylenediamine, N-(2-hydroxyethyl)-, H2dea, Hydroxyethyl ethylenediamine, hydroxyethylethylenediamine, Jsp000857, N-(2-Aminoethyl) ethanolamine, N-(2-Hydroxyethyl)-1,2-ethanediamine, N-(2-HYDROXYETHYL)ETHANE DIAMINE, N-(2-hydroxyethyl)-ethylenediamine, n-(2-hydroxyethyl)ethylenediamine, 99%, N-(Aminoethyl)ethanolamine, N-(β-Hydroxyethyl)ethylenediamine, N,N'-Iminodiethanol, N-AMINOETHYLETHANOLAMINE, N-β-Hydroxyethylethylenediamine, UNII:RC78W6NPXT, UNII-RC78W6NPXT, VS-08576, WLN: Z2M2Q, β-Aminoethyl-β-hydroxyethylamine
N-(2-Aminoethyl)ethanolamine is a clear to pale yellow, hygroscopic liquid with a faint ammonia-like odor, belonging to the family of alkanolamines.
N-(2-Aminoethyl)ethanolamine contains both primary and secondary amine groups, as well as a hydroxyl group, giving it the combined reactivity of amines and alcohols.
N-(2-Aminoethyl)ethanolamine's molecular formula is C₄H₁₂N₂O, and its structure can be represented as H₂N–CH₂–CH₂–NH–CH₂–CH₂–OH.
This multifunctional nature makes N-(2-Aminoethyl)ethanolamine a highly versatile intermediate in chemical synthesis.
N-(2-Aminoethyl)ethanolamine is soluble in water and most polar solvents, and it is widely used in the production of chelating agents, surfactants, corrosion inhibitors, fuel additives, resins, and epoxy curing agents.
The presence of multiple reactive sites enables N-(2-Aminoethyl)ethanolamine to form complexes, react with acids, and undergo condensation reactions, making it valuable in industries such as textiles, water treatment, coatings, and agrochemicals.
N-(2-Aminoethyl)ethanolamine is manily used in oil additives and surfactants.
N-(2-Aminoethyl)ethanolamine is a single component with having very less ethylethanolamine impurity.
N-(2-Aminoethyl)ethanolamine is a very clear and colourless liquid with ammonia like odor.
N-(2-Aminoethyl)ethanolamine is a clear colorless liquid with an ammonia-like odor.
N-(2-Aminoethyl)ethanolamine is an organic base used in the industrial manufacture of fuel and oil additives, chelating agents, and surfactants.
N-(2-Aminoethyl)ethanolamine is a precursor for the production of amphoacetates which serve as a precursor to produce amphoteric surfactants.
N-(2-Aminoethyl)ethanolamine is industrially produced in the process of the continuously hydrogenative amination of monoethylene glycol.
In the reaction mixture N-(2-Aminoethyl)ethanolamine is only yielded as a co-product of 6.8%.
The residual compounds of N-(2-Aminoethyl)ethanolamines are 3.4% of diethylene triamine, 7.0% of piperazine, 51.1% of ethylenediamine, 1.7% of diethanolamine and 30.0% of monoethanolamine.
N-(2-Aminoethyl)ethanolamine is a linear molecule with primary and secondary amine groups.
N-(2-Aminoethyl)ethanolamine is a colorless liquid, with slightly higher viscosity than EDA and DETA.
N-(2-Aminoethyl)ethanolamine is used as an intermediate in the fabrication of detergents, fabric softeners, chelates, fuel additives and coatings.
A linear member of the ethyleneamines family, at room temperature N-(2-Aminoethyl)ethanolamine is a clear, colorless, oily liquid with a weak ammonia-like odor.
N-(2-Aminoethyl)ethanolamine is water soluble, and N-(2-Aminoethyl)ethanolamine dilute solutions have an alkaline pH.
N-(2-Aminoethyl)ethanolamine is used in building block in the manufacture of specialty corrosion inhibitors.
N-(2-Aminoethyl)ethanolamine is member from the class of Ethyleneamines and is used in a broad array of applications.
N-(2-Aminoethyl)ethanolamine is a single-component product.
N-(2-Aminoethyl)ethanolamine is used in chelating agents, fabric softeners, lube oil & fuel additives, surfactants, textile additives, urethane chemicals.
Aminoethyl Ethanolamine is a hygroscopic liquid with a mild ammoniacal odor.
N-(2-Aminoethyl)ethanolamine is miscible with water, ethanol, and acetone, but immiscible with ether, benzene, and hexane.
Aminoethyl Ethanolamine is used as an intermediate in the manufacture of surfactants, sequestering agents, cationic textile softeners, antistatic agents, corrosion inhibitors, and insecticides.
N-(2-Aminoethyl)ethanolamine is also found in rubber products, resins, and certain medicinals.
N-(2-Aminoethyl)ethanolamine is a linear molecule with primary and secondary amine groups with chemical formula of C4H12N2O.
N-(2-Aminoethyl)ethanolamine is a hygroscopic liquid containing minimal ethylenediamine impurity.
N-(2-Aminoethyl)ethanolamine possesses mild ammonia-like odor.
N-(2-Aminoethyl)ethanolamine is a water-soluble, clear, colorless, and viscous liquid.
N-(2-Aminoethyl)ethanolamine is miscible with water, ethanol, and acetone, but immiscible with ether, benzene, and hexane.
N-(2-Aminoethyl)ethanolamine is widely used as an intermediate in the production of surfactants, sequestering agents, cationic textile softeners, antistatic agents, corrosion inhibitors, and insecticides.
N-(2-Aminoethyl)ethanolamine is a single-component product, with minimal ethylenediamine impurity.
N-(2-Aminoethyl)ethanolamine typically has an ammonia-like odor and is water-soluble, clear, colorless, and slightly viscous.
N-(2-Aminoethyl)ethanolamine is a linear molecule with a C4H12N2O the chemical formula in the primary and secondary amine groups.
N-(2-Aminoethyl)ethanolamine is a hygroscopic liquid that contains minimal ethylenediamine impurity.
N-(2-Aminoethyl)ethanolamine has a faint ammonia-like scent.
N-(2-Aminoethyl)ethanolamine is a water-soluble, clear, colorless, and viscous liquid.
N-(2-Aminoethyl)ethanolamine is miscible with ethanol, water, and acetone but is immiscible with ether, benzene, and hexane.
N-(2-Aminoethyl)ethanolamine is a very polar compound and is difficult to analyze as it is often irreversibly adsorbed on most columns.
N-(2-Aminoethyl)ethanolamine reacts severely to acids.
N-(2-Aminoethyl)ethanolamine dissolve in water, ethanol, ether, hexane, acetone and benzene.
N-(2-Aminoethyl)ethanolamine absorbs the carbon dioxide in the air.
N-(2-Aminoethyl)ethanolamine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 to < 10 tonnes per annum.
N-(2-Aminoethyl)ethanolamine is used at industrial sites and in manufacturing.
N-(2-Aminoethyl)ethanolamine is an organic compound belonging to the alkanolamine family, characterized by the presence of both amine and alcohol functionalities within the same molecule.
N-(2-Aminoethyl)ethanolamine appears as a clear to pale yellow, viscous, hygroscopic liquid with a faint ammonia-like odor.
The molecular formula of N-(2-Aminoethyl)ethanolamine is C₄H₁₂N₂O, and its structural arrangement is H₂N–CH₂–CH₂–NH–CH₂–CH₂–OH, which incorporates a primary amine group, a secondary amine group, and a terminal hydroxyl group.
This unique structure gives the compound multifunctional reactivity, enabling it to participate in a wide variety of chemical transformations, including condensation, neutralization, amidation, and complex formation.
Physically, N-(2-Aminoethyl)ethanolamine is miscible with water and many polar solvents, while chemically it demonstrates the combined properties of amines (basicity, nucleophilicity, salt formation with acids) and alcohols (hydrogen bonding, esterification).
From an industrial perspective, N-(2-Aminoethyl)ethanolamine is a highly valuable intermediate.
N-(2-Aminoethyl)ethanolamine is widely used in the synthesis of chelating agents such as ethylenediaminetetraacetic acid (EDTA) and its derivatives, which are essential in water treatment, cleaning formulations, and pharmaceuticals.
N-(2-Aminoethyl)ethanolamine also serves as a precursor for corrosion inhibitors, especially in oilfield and water-handling systems, where it helps protect metal surfaces by forming protective films.
In polymer and coating industries, N-(2-Aminoethyl)ethanolamine is employed as a chain extender and curing agent for epoxy resins, imparting flexibility, adhesion, and improved resistance to chemical and mechanical stress.
Additionally, N-(2-Aminoethyl)ethanolamine is used in the manufacture of surfactants and emulsifiers, particularly in personal care and detergent formulations, where its amphiphilic nature enhances solubilization and foaming properties.
Beyond these applications, N-(2-Aminoethyl)ethanolamine plays a role in the production of agrochemicals, fuel additives, and textile auxiliaries, where its multifunctionality contributes to performance improvements.
N-(2-Aminoethyl)ethanolamine's ability to form stable complexes with metal ions makes it useful in formulations designed to control water hardness, stabilize bleaching agents, and improve the efficiency of industrial cleaning processes.
In research and laboratory contexts, N-(2-Aminoethyl)ethanolamine is often studied as a model multifunctional amine-alcohol compound due to its diverse reactivity.
Market Overview of N-(2-Aminoethyl)ethanolamine:
The market for N-(2-Aminoethyl)ethanolamine is characterized by steady demand growth driven by its wide applicability as an intermediate in multiple industries, including chemicals, water treatment, oil and gas, coatings, textiles, agrochemicals, and personal care.
N-(2-Aminoethyl)ethanolamine’s multifunctional structure, containing both amine and hydroxyl groups, makes it a critical raw material for the manufacture of chelating agents such as EDTA, which account for a significant share of consumption, particularly in cleaning products, detergents, and water purification systems.
The oilfield and water treatment sectors also contribute strongly to market demand, as N-(2-Aminoethyl)ethanolamine is widely used in the formulation of corrosion inhibitors and scale control chemicals that improve operational efficiency and asset longevity.
In addition, the polymer and coatings industries represent a growing application area, where N-(2-Aminoethyl)ethanolamine is employed as an epoxy resin curing agent and chain extender to enhance durability, adhesion, and chemical resistance in high-performance materials.
Emerging opportunities are being seen in the personal care, cosmetic, and detergent industries, where N-(2-Aminoethyl)ethanolamine-derived surfactants and emulsifiers are valued for their solubilizing and foaming properties.
Geographically, Asia-Pacific dominates the market due to N-(2-Aminoethyl)ethanolamine's large-scale chemical manufacturing base and rising demand in water treatment and coatings, while North America and Europe remain mature markets with strong application in oilfield chemicals and specialty polymers.
Looking forward, the global market is expected to expand at a moderate pace, supported by rising industrial water treatment needs, stricter regulations on corrosion control and cleaning efficiency, and the continued development of specialty chemical applications.
However, the market also faces challenges related to raw material price fluctuations, regulatory compliance on chemical handling, and the need for greener, more sustainable production routes, which may drive innovation in bio-based and low-impact alternatives.
Applications of N-(2-Aminoethyl)ethanolamine:
N-(2-Aminoethyl)ethanolamine is used as a chelating agent and in coatings to make additive for latex paints.
Due to above property, N-(2-Aminoethyl)ethanolamine is used as a detergent/ cleaner/ fabric softener.
N-(2-Aminoethyl)ethanolamine is also used as a dispersal detergent additive for gasoline.
N-(2-Aminoethyl)ethanolamine is used as a a surfactant and as an ashless dispersant in engine oil and other lubricants.
N-(2-Aminoethyl)ethanolamine is used to manufacture wet-adhesion additives for latex paints, in the manufacture of fabric softeners, fuel additives and lube oil additives.
N-(2-Aminoethyl)ethanolamine is an intermediate in the manufacture of chelating agents and surfactants.
N-(2-Aminoethyl)ethanolamine is marketed as a chemical intermediate for the downstream manufacture of chemicals and products.
N-(2-Aminoethyl)ethanolamine has a variety of applications and is used in the production of fabric softener, textile additive, surfactants, chelating agents, lube oil and fuel additives and urethane chemicals.
N-(2-Aminoethyl)ethanolamine is commonly used in the manufacture of lube oil additives, fuel additives, chelating agents, surfactants, fabric softeners and insecticides among other applications.
Other applications:
N-(2-Aminoethyl)ethanolamine is formulated as an intermediate to form polycarboxylic acids and their salts, and chelating agents.
In several additional applications N-(2-Aminoethyl)ethanolamine is used as building block for synthesis.
Uses of N-(2-Aminoethyl)ethanolamine:
N-(2-Aminoethyl)ethanolamine is used in the following products: polymers.
N-(2-Aminoethyl)ethanolamine has an industrial use resulting in manufacture of another substance (use of intermediates).
N-(2-Aminoethyl)ethanolamine is used for the manufacture of: chemicals.
Release to the environment of N-(2-Aminoethyl)ethanolamine can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
N-(2-Aminoethyl)ethanolamine is used as a chelating agent and in coatings to make additive for latex paints.
Due to above property, N-(2-Aminoethyl)ethanolamine is used as detergent/cleaner/fabric softener.
N-(2-Aminoethyl)ethanolamine is also used as a dispersal detergent additive for gasoline.
N-(2-Aminoethyl)ethanolamine is used as a surfactant and as ash less dispersant in engine oil and other lubricant.
Increase in demand for N-(2-Aminoethyl)ethanolamine in textile and chemical processing industries is driving the global N-(2-Aminoethyl)ethanolamine market.
N-(2-Aminoethyl)ethanolamine is used as fabric softener to impart softness and antistatic properties during pre-treatment and post-treatment to fabrics.
N-(2-Aminoethyl)ethanolamine is also employed as textile additive to enhance dye sorption, adhesion, flame proofing, abrasion resistance, and anti-static characteristics of textiles.
Increase in usage of N-(2-Aminoethyl)ethanolamine in the textile industry is expected to boost the global N-(2-Aminoethyl)ethanolamine market during the forecast period.
Demand for N-(2-Aminoethyl)ethanolamine is anticipated to increase in the chemical processing industry in the next few years, as N-(2-Aminoethyl)ethanolamine is employed in the manufacture of polyurethane chemicals.
N-(2-Aminoethyl)ethanolamine is used in the manufacture of polyols and catalysts.
These polyols are primarily employed in urethane systems for appliances, spray foams, building panels, and elastomers.
Industry Uses:
Corrosion inhibitors and anti-scaling agents,
Functional fluids (closed systems),
Intermediates,
Ion exchange agents,
Processing aids, not otherwise listed,
Processing aids, specific to petroleum production.
Consumer Uses:
Paper products,
Water treatment products.
Other Uses:
In Cleaning:
N-(2-Aminoethyl)ethanolamine is mainly used as building block for fabric softeners/surfactants, which make the textiles less harsh, “softer” or more pleasing to the touch.
In Coatings:
For production of latex paints N-(2-Aminoethyl)ethanolamine acts as intermediate to form an adhesion monomer, which increases adhesion under damp conditions (wet adhesion).
Additionally, via the pendent amino and hydroxy functionalities, N-(2-Aminoethyl)ethanolamine is used in urethane systems
In Fuels and Lubricants:
N-(2-Aminoethyl)ethanolamine is used in the production of chlorinated polybutene based fuel additives as a dispersant-detergent additive.
Uses Area:
N-(2-Aminoethyl)ethanolamine is used as a by-product in the sectors of textile, leather and glue.
N-(2-Aminoethyl)ethanolamine is used as the raw material of surface activators.
N-(2-Aminoethyl)ethanolamine is used as a detergent admixture.
N-(2-Aminoethyl)ethanolamine is used as an admixture in shampoos and lubricants and a resin material.
N-(2-Aminoethyl)ethanolamines have the combined physical and chemical characteristics of both alcohols and amines in one molecule, which makes them useful intermediates in the synthesis of various target molecules for the use in many diverse areas such as pharmaceutical, urethane catalysts, coatings, personal care, products, water treatments, corrosion inhibitors, and gas treating industries.
There are 1°, 2º or 3º nitrogen atom and one hydroxyl group at least in alkanolamines.
N-(2-Aminoethyl)ethanolamine react with inorganic acids carboxylic acids to form salts, soaps, esters, or amides.
N-(2-Aminoethyl)ethanolamine are used in both water- based and solvent-based coatings to enhance the solubility, reducibility, pigment dispersing and pH stability.
They are used in cathodic electrodeposition systems and as a catalyst for chain-extend.
N-(2-Aminoethyl)ethanolamine are used to prepare surface-active soaps through reaction with fatty acids.
Surface-active soaps are used commercially as a emulsifier, lubricants, detergents, pesticides and personal care products.
N-(2-Aminoethyl)ethanolamine maintain a constant alkalinity in the boiling water flows and condensate not to form solid products which would impede line flow.
This function of N-(2-Aminoethyl)ethanolamine is applied for corrosion Inhibits.
N-(2-Aminoethyl)ethanolamine are widely employed in the preparation of water soluble cationic flocculants and ion exchange resins which adsorb solid and colloidal particles by electrostatic attraction.
N-(2-Aminoethyl)ethanolamines are used for water treatment industry.
N-(2-Aminoethyl)ethanolamine and their derivatives are widely used as intermediates for the production of active pharmaceutical ingredients such as procaine, antihistamines analgesics from N,N-dimethylethanolamine or N-methyldiethanolamine.
N-(2-Aminoethyl)ethanolamine are used to remove hydrogen sulfide (H2S) and CO2 gas from gas streams in natural and refinery gas operations.
N-(2-Aminoethyl)ethanolamine which has amine groups and hydroxyl group is used as an important intermediate for polymer condensation, pharmaceuticals, agrochemicals, paper chemicals, rubber chemicals, textile auxiliaries.
N-(2-Aminoethyl)ethanolamine is used to produce shampoo, cationic surfactants, antistatic agents and chelating agents.
Benefits of N-(2-Aminoethyl)ethanolamine:
N-(2-Aminoethyl)ethanolamine offers a wide range of benefits that make it a highly valuable compound across diverse industrial sectors.
N-(2-Aminoethyl)ethanolamine's most important advantage lies in its multifunctional chemical structure, which contains two reactive amine groups (one primary and one secondary) and a hydroxyl group, enabling it to participate in numerous reactions such as neutralization, condensation, complex formation, and polymer crosslinking.
This multifunctionality allows a single molecule to serve multiple purposes, reducing the need for additional chemicals in formulations and thereby improving cost-efficiency and process simplification.
Another key benefit of N-(2-Aminoethyl)ethanolamine is its role as an excellent intermediate for chelating agents, particularly EDTA and its derivatives, which are indispensable in water treatment, cleaning formulations, and metal ion control.
By contributing to the production of these agents, N-(2-Aminoethyl)ethanolamine indirectly supports industries in improving water quality, enhancing detergent effectiveness, and preventing scale and deposit formation.
In the oil and gas industry, the use of N-(2-Aminoethyl)ethanolamine in corrosion inhibitor formulations provides the critical benefit of protecting pipelines, drilling equipment, and refinery infrastructure, significantly extending service life and reducing maintenance costs.
In the polymer and coating industries, N-(2-Aminoethyl)ethanolamine provides substantial benefits as a curing agent for epoxy resins and as a chain extender, enhancing mechanical strength, flexibility, adhesion, and resistance to chemicals and heat.
These improvements make materials more reliable in demanding applications such as aerospace, automotive, and construction.
Additionally, in the personal care and detergent sectors, N-(2-Aminoethyl)ethanolamine contributes to the development of surfactants and emulsifiers with strong foaming, dispersing, and solubilizing properties, thereby improving product performance and consumer satisfaction.
A further benefit is N-(2-Aminoethyl)ethanolamine’s water solubility and compatibility with polar solvents, which expands its applicability in both aqueous and non-aqueous systems.
This versatility is particularly useful in industrial cleaning, textile finishing, and agrochemical formulations.
Finally, the economic availability and scalability of N-(2-Aminoethyl)ethanolamine production make it a reliable and cost-effective choice for manufacturers worldwide, ensuring a stable supply chain for industries that depend on its multifunctional chemistry.
Other Benefits:
Consistent and predictable reaction products,
Easily derivatized,
Low vapor pressure,
High viscosity,
Low environmental impact,
Suitable for harsh conditions,
Low sensitivity,
Versatile.
Production of N-(2-Aminoethyl)ethanolamine:
The production of N-(2-Aminoethyl)ethanolamine is typically carried out through controlled reactions involving ethylene oxide and ammonia, which yield a series of ethyleneamines including monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), and higher homologues.
N-(2-Aminoethyl)ethanolamine is obtained as one of the key products when ethanolamine reacts with ethylenediamine (EDA) under specific catalytic and thermal conditions.
Industrial processes are carefully optimized to favor the formation of N-(2-Aminoethyl)ethanolamine, though it often appears as part of a mixture with other ethyleneamines and requires separation and purification.
One of the most common industrial methods involves the reaction of ethylene oxide with aqueous ammonia, which proceeds through sequential substitution steps.
In this process, ethylene oxide first reacts with ammonia to form monoethanolamine, which can further react to yield diethanolamine and triethanolamine.
Parallel to these reactions, condensation pathways with ethylenediamine can generate N-(2-Aminoethyl)ethanolamine through incorporation of both an amine group and a hydroxyl group into the same molecule.
The mixture is then separated by fractional distillation under reduced pressure, as N-(2-Aminoethyl)ethanolamine’s relatively high boiling point allows it to be isolated from lighter and heavier components.
Another route is based on the amine-alkylation of ethanolamine with ethylenediamine, typically catalyzed by transition metals or base catalysts.
This pathway provides higher selectivity towards N-(2-Aminoethyl)ethanolamine and has been explored to improve yields and reduce the formation of unwanted by-products.
In recent years, research has also investigated more sustainable routes to N-(2-Aminoethyl)ethanolamine production, focusing on greener catalysts, continuous processing technologies, and process intensification methods that reduce energy consumption and waste generation.
From an industrial standpoint, the production of N-(2-Aminoethyl)ethanolamine is carried out in large-scale, dedicated chemical plants, often integrated with facilities that produce ethanolamines and ethyleneamines.
This integration ensures economic efficiency, raw material availability, and simplified logistics, as the same feedstocks—ethylene oxide and ammonia—serve as the foundation for multiple valuable chemicals.
The result is a robust supply chain in which N-(2-Aminoethyl)ethanolamine is consistently available as both a targeted product and a co-product in the broader ethyleneamine industry.
General Manufacturing Information of N-(2-Aminoethyl)ethanolamine:
Industry Processing Sectors:
Adhesive manufacturing,
All other basic organic chemical manufacturing,
Asphalt paving, roofing, and coating materials manufacturing,
Construction,
Oil and gas drilling, extraction, and support activities,
Paper manufacturing,
Petrochemical manufacturing,
Services,
Soap, cleaning compound, and toilet preparation manufacturing,
Utilities.
Synthesis of N-(2-Aminoethyl)ethanolamine:
The synthesis of N-(2-Aminoethyl)ethanolamine is based on reactions between ethylene oxide, ammonia, ethanolamine, and ethylenediamine, which are the fundamental building blocks of the ethanolamine and ethyleneamine families.
N-(2-Aminoethyl)ethanolamine is a unique molecule that contains both amine and hydroxyl functionalities, and its synthesis routes are designed to introduce these groups in controlled fashion.
One of the most widely used synthetic approaches is the reaction of ethylenediamine (EDA) with ethylene oxide.
In this pathway, ethylene oxide undergoes nucleophilic ring-opening by the primary amine group of EDA, producing N-(2-Aminoethyl)ethanolamine as the main product.
This process is efficient because N-(2-Aminoethyl)ethanolamine introduces the hydroxyl group while retaining both the primary and secondary amine functionalities of the starting ethylenediamine.
The reaction typically requires careful temperature control and catalyst optimization to maximize selectivity and reduce the formation of polyamines or polyalkanolamines.
Another common method involves the reaction of ethanolamine with ethylenediamine, where condensation and substitution reactions occur to yield N-(2-Aminoethyl)ethanolamine.
Industrial plants often operate these processes under high pressure and elevated temperature, sometimes using acid or base catalysts to accelerate the reaction.
The resulting mixture generally contains N-(2-Aminoethyl)ethanolamine along with related compounds, such as diethanolamine, triethanolamine, and higher substituted ethyleneamines, which must be separated by fractional distillation under reduced pressure due to their high boiling points.
In addition to these conventional routes, amine-alkylation methods have been developed, in which ethanolamine is alkylated with ethylenediamine or related intermediates.
This provides an alternative approach with improved selectivity towards N-(2-Aminoethyl)ethanolamine while minimizing side reactions.
Modern research also explores catalytic and continuous flow processes to enhance yield and energy efficiency, aligning with green chemistry principles and reducing waste by-products.
Overall, the synthesis of N-(2-Aminoethyl)ethanolamine reflects the broader production network of ethanolamines and ethyleneamines, where the same feedstocks—ethylene oxide and ammonia—serve as the foundation for a family of industrially important compounds.
N-(2-Aminoethyl)ethanolamine is thus produced both as a targeted product and as a co-product, ensuring its availability for applications in chelating agents, epoxy curing, corrosion inhibitors, surfactants, and specialty chemicals.
History of N-(2-Aminoethyl)ethanolamine:
The history of N-(2-Aminoethyl)ethanolamine is closely tied to the development of the broader ethanolamine and ethyleneamine industries in the late 19th and early 20th centuries.
Ethanolamines were first identified in the mid-1800s, following the discovery of monoethanolamine (MEA) in 1860 through the reaction of ethylene oxide with ammonia.
This marked the beginning of a family of multifunctional compounds that combined both amine and hydroxyl groups.
During the early 20th century, with the commercialization of ethylene oxide production and the growing availability of ammonia as an industrial feedstock, researchers and chemical manufacturers began exploring further derivatives of ethanolamines.
By the 1930s and 1940s, the first systematic studies of ethyleneamines were carried out, and N-(2-Aminoethyl)ethanolamine was identified as a distinct compound within this group, notable for containing both primary and secondary amines along with a hydroxyl group.
The rapid industrial growth during and after World War II accelerated the development of N-(2-Aminoethyl)ethanolamine, as demand for chelating agents, surfactants, corrosion inhibitors, and polymer additives increased in sectors such as detergents, water treatment, and coatings.
By the 1950s, N-(2-Aminoethyl)ethanolamine was being produced on an industrial scale as part of the broader ethylene oxide–ammonia chemistry network, which also generated other valuable products like MEA, DEA, TEA, and higher ethyleneamines.
N-(2-Aminoethyl)ethanolamine's versatility soon made it an important building block in the synthesis of EDTA (ethylenediaminetetraacetic acid) and related chelating agents, which became essential for industrial cleaning and water treatment applications.
In subsequent decades, N-(2-Aminoethyl)ethanolamine continued to gain prominence as industries diversified its uses in oilfield chemicals, epoxy resin curing, and personal care formulations.
N-(2-Aminoethyl)ethanolamine's multifunctional nature—allowing reactivity as both an alcohol and an amine—positioned it as a key specialty chemical in global markets.
Today, the history of N-(2-Aminoethyl)ethanolamine reflects the broader evolution of industrial organic chemistry: from small-scale laboratory discovery in the 19th century to large-scale, integrated production systems in the 20th and 21st centuries, with ongoing research focused on greener and more sustainable synthesis routes to meet modern environmental and economic demands.
Handling and Storage of N-(2-Aminoethyl)ethanolamine:
Handle N-(2-Aminoethyl)ethanolamine only in well-ventilated areas or under a chemical fume hood to avoid exposure to vapors and skin contact.
Prevent contact with skin, eyes, and clothing; wear suitable protective equipment at all times.
Store in tightly closed, corrosion-resistant containers, away from direct sunlight, heat sources, and incompatible materials such as acids, oxidizing agents, and carbon dioxide–releasing compounds.
Keep containers in a cool, dry, and well-ventilated location.
Use secondary containment to minimize spill risks.
Stability and Reactivity of N-(2-Aminoethyl)ethanolamine:
Stability:
Stable under normal temperatures and handling conditions.
Reactivity:
Strongly alkaline and reactive due to the presence of multiple amine groups.
Hazardous reactions:
May react with acids to release heat and with oxidizers to cause violent reactions.
Can absorb carbon dioxide from air.
Decomposition products:
Nitrogen oxides, carbon monoxide, and carbon dioxide may form during thermal decomposition or fire.
First Aid Measures of N-(2-Aminoethyl)ethanolamine:
Inhalation:
Move the affected person to fresh air immediately.
Provide oxygen if breathing is difficult.
Seek medical attention.
Skin contact:
Wash thoroughly with plenty of water and soap for at least 15 minutes.
Remove contaminated clothing.
Obtain medical attention for burns or persistent irritation.
Eye contact:
Rinse cautiously with water for at least 15 minutes, holding eyelids apart.
Immediate medical attention is required, as severe eye damage may occur.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Give water to drink if the person is conscious.
Get immediate medical attention.
Firefighting Measures of N-(2-Aminoethyl)ethanolamine:
Flammability:
N-(2-Aminoethyl)ethanolamine is combustible but not highly flammable.
Vapors may form irritating or toxic fumes when heated.
Suitable extinguishing agents:
Alcohol-resistant foam, dry chemical powder, carbon dioxide (CO₂), or water spray.
Protective equipment:
Firefighters should wear full protective clothing and self-contained breathing apparatus (SCBA).
Special precautions:
Cool exposed containers with water spray to prevent rupture.
Prevent contaminated runoff from entering drains or waterways.
Accidental Release Measures of N-(2-Aminoethyl)ethanolamine:
Evacuate personnel from the affected area and ensure adequate ventilation.
Wear full protective equipment including gloves, goggles, and respirators.
Eliminate ignition sources, as vapors may irritate and form combustible mixtures with air.
Contain the spill with absorbent materials such as sand, earth, or vermiculite.
Place in a suitable chemical waste container.
Wash the contaminated area thoroughly with water after cleanup.
Prevent entry into drains, sewers, and natural waterways.
Exposure Controls / Personal Protection of N-(2-Aminoethyl)ethanolamine:
Engineering controls:
Use local exhaust ventilation or process enclosures to minimize airborne exposure.
Respiratory protection:
Use approved respirators if exposure levels are above occupational limits or ventilation is inadequate.
Hand protection:
Chemical-resistant gloves (nitrile, neoprene, or butyl rubber).
Eye protection:
Safety goggles with side shields or a face shield.
Skin and body protection:
Chemical-resistant clothing, lab coat, or protective apron.
Hygiene measures:
Wash thoroughly after handling. Do not eat, drink, or smoke in work areas.
Remove and wash contaminated clothing before reuse.
Identifiers of N-(2-Aminoethyl)ethanolamine:
Chemical name: N-(2-Aminoethyl)ethanolamine
IUPAC name: 2-(2-aminoethylamino)ethanol
CAS Number: 111-41-1
EC Number (EINECS): 203-867-5
PubChem CID: 82213
ChemSpider ID: 74173
UN Number (Transport): UN 2735
RTECS Number: KH8575000
Molecular Data
Molecular formula: C₄H₁₂N₂O
Molar mass: 104.15 g/mol
InChI: InChI=1S/C4H12N2O/c5-2-1-6-3-4-7/h6-7H,1-5H2
InChI Key: JRTQKRWFNQCMAR-UHFFFAOYSA-N
SMILES notation: C(CNCCO)N
Chemical name: N-(2-Aminoethyl)ethanolamine
Preferred IUPAC name: 2-(2-aminoethylamino)ethanol
Other IUPAC variants: N-(2-hydroxyethyl)ethane-1,2-diamine
CAS Number: 111-41-1
EC Number (EINECS): 203-867-5
PubChem CID: 82213
ChemSpider ID: 74173
RTECS Number: KH8575000
UN Number (Transport): UN 2735
Beilstein Reference: 605063
Molecular formula: C₄H₁₂N₂O
Molar mass: 104.15 g/mol
Exact mass (monoisotopic): 104.095 g/mol
Elemental composition: C (46.12%), H (11.62%), N (26.91%), O (15.35%)
InChI: InChI=1S/C4H12N2O/c5-2-1-6-3-4-7/h6-7H,1-5H2
InChI Key: JRTQKRWFNQCMAR-UHFFFAOYSA-N
SMILES (canonical): C(CNCCO)N
SMILES (isomeric): NCCNCCO
Properties of N-(2-Aminoethyl)ethanolamine:
Formula: HO-(CH2 )2-NH-(CH2)2-NH2
CAS Number: 111-41-1
Molecular Weight: 104.1
pH(25˚C aqueous solution: 11.5
Vapor pressure: < 0.01mmHg 20˚C
Vapor density: 3.59
Specific gravity: 1.82-281 25/25˚C
Boiling point: 243˚C
InChI: InChI=1S/C4H12N2O/c5-1-2-6-3-4-7/h6-7H,1-5H2
InChI Key: LHIJANUOQQMGNT-UHFFFAOYSA-N
Canonical SMILES: C(CNCCO)N
CAS Number: 111-41-1
ChemSpider: 7821
ECHA InfoCard: 100.003.516
PubChem CID: 8112
UNII: RC78W6NPXT
CompTox Dashboard (EPA): DTXSID7025423
Physical characteristic: Colorless Liquid
Chemical formula: C4H12N2O
Molecular weight: 104,20 g/mol
Molecular Weight: 104.15
XLogP3: -1.7
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 4
Exact Mass: 104.094963011
Monoisotopic Mass: 104.094963011
Topological Polar Surface Area: 58.3 Ų
Heavy Atom Count: 7
Complexity: 32.9
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of N-(2-Aminoethyl)ethanolamine:
Appearance: light yellow clear liquid
Assay %: ≥39.1%
Chroma(Hazen): 80
Chloride (Cl)%: 0.004
Sulfate(SO4)Content%: 0.01
PH 25℃1%solution: 11.51
Lead(Pb) %: 0.0002
Density (g/ml,25℃): 1.283
Chelating value（mgCaco3/g: 121
Product name: N-(2-Aminoethyl)ethanolamine
Chemical family: Ethylene Amines
CAS number: 111-41-1
Physical form: Liquid
Chemical Formula: C₄H₁₂N₂O
Chemical name: 2-(2-aminoethylamino)ethanol
Molecular Weight: 104.15
Physical State (20°C): Liquid
Density (kg/m3): 1028 [Kg/m³] at a temperature of 20°C
Molar mass (g/mol): 104.15
Density of gas (kg/m3): 4.644
Boiling Point (°C): 243
Ignition Temperature (°C): 368
Flash Point (°C): 135
Lower explosivity limit (LEL) (volume %): 15
Upper explosivity limit (UEL) (volume %): 27
Substance Type: Chemical Substance
Systematic Name: Ethanol, 2-[(2-aminoethyl)amino]-
CAS Number: 111-41-1
EPA Registry Name: N-Hydroxyethylethylenediamine
Molecular Weight: 104.15
Molecular Formula: C4H12N2O
Names of N-(2-Aminoethyl)ethanolamine:
Preferred IUPAC name:
2-[(2-Aminoethyl)amino]ethan-1-ol
Other names:
N-(2-Hydroxyethyl)ethylenediamine
(2-Aminoethyl)ethanolamine
(2-Hydroxyethyl)ethylenediamine
(β-Hydroxyethyl)ethylenediamine
1-[2-(Hydroxyethyl)amino]-2-aminoethane
1-Aminoethylethanolamine
2-((Aminoethyl)amino)ethanol
2-(2-Hydroxyethylamino)ethylamine
2-[(2-Aminoethyl)amino]ethan-1-ol
2-Amino-2'-hydroxydiethylamine
Aminoethylethanolamine
β-Aminoethyl-β-hydroxyethylamine
Ethanol, 2-[(2-aminoethyl)amino]-
Ethanolethylene diamine
Hydroxyethyl ethylenediamine
Monoethanolethylenediamine
N-( β-Aminoethyl)ethanolamine
N-(2-Aminoethyl)ethanolamine
N-(2-Hydroxyethyl)-1,2-ethanediamine
N-(2'-Hydroxyethyl)ethylenediamine
N-(2-Hydroxyethyl)ethylenediamine
N-(β-Hydroxyethyl)ethylenediamine
N-(Hydroxyethyl)ethylenediamine
N-Aminoethylethanolamine
N-Hydroxyethyl-1,2-ethanediamine
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