EDA ETHYLENEDIAMINE

EDA Ethylenediamine is the organic compound C₂H₄(NH₂)₂, the lowest molecular weight member of the ethyleneamine family, a colorless to pale yellow, hygroscopic liquid with a strong ammonia-like odor that is miscible with water and most polar organic solvents.
EDA Ethylenediamine contains two primary amine groups (-NH₂) joined by a two-carbon ethylene chain, which makes it a bifunctional building block that readily forms derivatives and heterocycles.
EDA Ethylenediamine is a key intermediate for chelating agents, polyamide resins, polyurethanes, agrochemicals, pharmaceuticals, epoxy curing agents, surfactants, corrosion inhibitors and fuel and lubricant additives, with roughly 500,000 tonnes produced a year.

CAS Number: 107-15-3
EC Number: 203-468-6
Molecular Formula: C₂H₈N₂
Molecular Weight: 60.10 g/mol

Synonyms: Ethylenediamine, Ethylene Diamine, EDA, 1,2-Diaminoethane, Ethane-1,2-diamine, 1,2-Ethanediamine, Diaminoethane, Edamine, Beta-Aminoethylamine, en (ligand abbreviation), Ethylenediamine Anhydrous, Ethylendiaminum, Ethyliminum, NCI-C60402, CAS 107-15-3

EDA Ethylenediamine forms derivatives with carboxylic acids, nitriles, alcohols, alkylating agents, carbon disulfide, aldehydes and ketones, and readily forms heterocycles such as imidazolidines.
EDA Ethylenediamine is the first member of the polyethyleneamine family.

EDA Ethylenediamine is a well-known bidentate chelating ligand in coordination chemistry, abbreviated "en", whose two nitrogen atoms donate their lone pairs of electrons to metal centers.
EDA Ethylenediamine forms the well-studied complex [Co(en)₃]³⁺ and is a precursor to Schiff base ligands, salen ligands used in catalysis, and EDTA.

EDA Ethylenediamine vapors absorb moisture from humid air to form a white mist that is extremely irritating to skin, eyes, lungs and mucous membranes.
EDA Ethylenediamine liquid releases toxic and irritating vapors into its surroundings unless tightly contained, especially on heating.

Uses of EDA Ethylenediamine:
EDA Ethylenediamine is the primary building block for EDTA (ethylenediaminetetraacetic acid), the most widely used chelating agent, made by Strecker synthesis.
EDA Ethylenediamine is also the starting point for hydroxyethylethylenediamine, a commercially significant chelating agent used in water treatment, industrial cleaning and metal ion sequestration.

EDA Ethylenediamine is a precursor of ethylenebisdithiocarbamate fungicides, which are commercially significant crop protection products.
EDA Ethylenediamine is also a precursor of imidazoline-containing fungicides and other agrochemical active ingredients.

EDA Ethylenediamine is used as a curing and cross-linking agent for epoxy resins, reacting with epoxy groups to form a three-dimensional network.
EDA Ethylenediamine gives the cured resin good mechanical properties, chemical resistance and insulation performance for coatings, adhesives, electronic packaging and construction, including the protection of buildings, bridges and infrastructure.

EDA Ethylenediamine is used to make polyamide resins by reacting with diacids, giving polyamide chains with excellent mechanical properties, wear resistance and corrosion resistance for fibers and engineering plastics.
EDA Ethylenediamine is also used in the production of polyurethane fibers and flexible polyurethane foams.

EDA Ethylenediamine is a pharmaceutical ingredient of the common bronchodilator aminophylline, where it solubilizes the active ingredient theophylline for the treatment of respiratory difficulties caused by bronchial asthma and cardiogenic pulmonary edema.
EDA Ethylenediamine has an oral bioavailability of approximately 0.34 after administration because of a substantial first-pass effect.

EDA Ethylenediamine is the structural basis of the ethylenediamine-derived first-generation antihistamines, the oldest of the five classes of first-generation antihistamines.
EDA Ethylenediamine-derived antihistamines began with piperoxan (1933, Pasteur Institute) and include mepyramine, tripelennamine and antazoline.

EDA Ethylenediamine is used in amine gas purification processes in the petrochemical and natural gas industry to remove hydrogen sulfide and carbon dioxide from natural gas and refinery streams.
EDA Ethylenediamine is the precursor of tetraacetylethylenediamine (TAED), the bleaching activator used in laundry detergents, textiles and paper bleaching.

EDA Ethylenediamine is also the precursor of N,N'-ethylenebis(stearamide) (EBS), a commercially significant mold-release agent and surfactant used in gasoline and motor oil.
EDA Ethylenediamine is used as a corrosion inhibitor in paints, coolants, metalworking fluids and industrial cleaning formulations, where it forms protective layers on metal surfaces.

EDA Ethylenediamine is used in industrial cleaning to remove rust and scale from metal surfaces.
EDA Ethylenediamine is used in the electroplating industry as a chelating agent that regulates the concentration and stability of metal ions in plating solutions, making the plated layer more uniform and dense.

EDA Ethylenediamine is used in the textile industry in dyeing and printing as a textile auxiliary and pH regulator, and as a fabric softener and lubricant additive in textile processing.
EDA Ethylenediamine is used in wet-strength resin production for paper.

EDA Ethylenediamine is used to make lube oil additives and fuel additives for internal combustion engines and in the production of elastomeric fibers.
EDA Ethylenediamine is also used in mineral processing and ore flotation.

EDA Ethylenediamine is the basis of PAMAM (polyamidoamine) dendrimers, which are used in drug delivery, gene therapy and nanotechnology.
EDA Ethylenediamine is used as a solvent, miscible with polar solvents, to solubilize proteins such as albumins and casein.

EDA Ethylenediamine is used in certain electroplating baths and in color photography developing.
EDA Ethylenediamine is used for the deacidification of fats and oils by removing free fatty acids, and as a basic reagent to adjust acidity and alkalinity in organic syntheses that need alkaline conditions.

EDA Ethylenediamine derivatives are used in cosmetics and personal care products for pH adjustment and as intermediates for surfactants and conditioning agents.
EDA Ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.

Benefits or Advantages of EDA Ethylenediamine:
EDA Ethylenediamine gives consistent and predictable reaction products because of its well-defined bifunctional diamine chemistry.
EDA Ethylenediamine is easily derivatized with a wide range of functional groups, including carboxylic acids, nitriles, alcohols, aldehydes, ketones and alkylating agents.

EDA Ethylenediamine has strong chelating properties thanks to the bidentate coordination of its two amine nitrogen atoms with metal ions.
EDA Ethylenediamine is therefore an excellent starting material for chelating agents such as EDTA, which bind and remove metal ions from solution over a wide range of pH and temperature.

EDA Ethylenediamine is completely miscible with water, so it can be added to aqueous industrial formulations without co-solvents or special dispersion equipment.
EDA Ethylenediamine is readily biodegradable (approximately 94% after 28 days), which gives it a favorable degradation profile compared with many synthetic chelating agents.

EDA Ethylenediamine is not expected to bioaccumulate significantly, given its log Kow of -1.62.

Features of EDA Ethylenediamine:
EDA Ethylenediamine is a colorless to pale yellow, hygroscopic, fuming liquid with a strong ammoniacal odor.
EDA Ethylenediamine has a density of about 0.897–0.90 g/cm³ at 20°C, a refractive index of 1.4565 (n20/D), a pH of about 12.2 at 100 g/L in water and a dynamic viscosity of 1.265 mPa·s at 25°C.

EDA Ethylenediamine has a melting point of about 8–11°C, a boiling point of 116–117°C and a flash point of 38–42°C (closed cup).
EDA Ethylenediamine has an autoignition temperature of about 385–405°C, explosive limits of 2–17% (v/v), a vapor pressure of about 12 hPa at 20°C and a vapor density of 2.1 (air = 1), which confirm its flammable liquid character.

EDA Ethylenediamine is miscible with water, ethanol and most polar organic solvents, and slightly soluble in diethyl ether.
EDA Ethylenediamine dissolves in benzene only when absolutely dry, and it forms azeotropic mixtures with water, n-butanol and toluene.

EDA Ethylenediamine is hygroscopic and absorbs carbon dioxide from the air.
EDA Ethylenediamine containers must be kept tightly sealed to prevent moisture absorption and contamination.

Chemical Properties of EDA Ethylenediamine:
EDA Ethylenediamine has the IUPAC name ethane-1,2-diamine and the structure H₂N-CH₂-CH₂-NH₂, with two primary amine groups separated by a two-carbon ethylene bridge.
EDA Ethylenediamine has the InChIKey PIICEJLVQHRZGT-UHFFFAOYSA-N and the SMILES NCCN.

EDA Ethylenediamine has a heat capacity (C) of 172.59 J·K⁻¹·mol⁻¹, a standard molar entropy (S°298) of 202.42 J·K⁻¹·mol⁻¹ and a specific heat capacity of 2.87 J/(g·K) at 25°C.
EDA Ethylenediamine has a standard enthalpy of formation (ΔfH°298) of -63.55 to -62.47 kJ·mol⁻¹ and a standard enthalpy of combustion (ΔcH°298) of -1.8678 to -1.8668 MJ·mol⁻¹.

EDA Ethylenediamine is incompatible with, and may react violently with, aldehydes, strong acids, acrylic acid, acetic acid, acetic anhydride, perchlorates, certain halogenated hydrocarbons, strong oxidizing agents, carbon disulfide and hydrogen chloride gas.
EDA Ethylenediamine may undergo strong exothermic reactions with these materials.

EDA Ethylenediamine requires compatibility checks with aluminium, iron, copper, bronze, brass and zinc.
EDA Ethylenediamine vapors may form flammable or explosive mixtures with air and may travel along floors and accumulate in low-lying locations.

Production of EDA Ethylenediamine:
EDA Ethylenediamine is produced industrially mainly by the EDC process, in which 1,2-dichloroethane is treated with excess ammonia under pressure at 180°C in an aqueous medium.
EDA Ethylenediamine forms in this process together with hydrogen chloride, which forms a salt with the amine; the amine is liberated with sodium hydroxide and recovered by fractional distillation, with DETA and TETA as by-products.

EDA Ethylenediamine is also produced by reacting ethanolamine with ammonia over nickel heterogeneous catalysts at elevated temperatures.
EDA Ethylenediamine can also be obtained by the hydrolysis of ethylene oxide with ammonia.

EDA Ethylenediamine commercial grade has an assay of ≥99.5 wt%, a color of ≤15 Hazen and a water content of ≤0.3 wt%.
EDA Ethylenediamine is supplied worldwide in drums as a single-component, colorless to light yellow liquid of ≥99.5% purity.

EDA Ethylenediamine must be stored in tightly sealed containers in a cool, dry, well-ventilated area at 15–25°C, away from ignition sources and oxidizing agents.
EDA Ethylenediamine is listed on major chemical inventories, including TSCA (US), DSL (Canada), IECSC (China), CSCL-ENCS (Japan), KECI (Korea), PICCS (Philippines), NZIoC (New Zealand) and INSQ (Mexico).

SDS of EDA Ethylenediamine:

Stability and Reactivity of EDA Ethylenediamine:

Chemical stability:
EDA Ethylenediamine is stable under normal ambient conditions and recommended storage conditions.

Reactivity:
EDA Ethylenediamine is a reactive chemical, and heating may increase vapor formation and create ignition hazards.
EDA Ethylenediamine may react violently with aldehydes, strong acids, acrylic acid, acetic anhydride, perchlorates and halogenated hydrocarbons.
EDA Ethylenediamine may react strongly exothermically with acetic acid, acetic anhydride, strong oxidizing agents, acids, carbon disulfide and hydrogen chloride.

Conditions to avoid:
EDA Ethylenediamine should be kept away from heat, hot surfaces, open flames, sparks and other ignition sources.
EDA Ethylenediamine should be protected from electrostatic discharge and kept out of poorly ventilated places where vapors can accumulate.
EDA Ethylenediamine should be kept away from incompatible materials, moisture and air, since it is hygroscopic and absorbs CO₂ from air.

Incompatible materials:
EDA Ethylenediamine is incompatible with strong acids, strong oxidizing agents and aldehydes.
EDA Ethylenediamine is incompatible with halogenated hydrocarbons, perchlorates, acrylic acid, acetic acid, acetic anhydride, carbon disulfide and hydrogen chloride.
EDA Ethylenediamine requires compatibility checks with aluminium, iron, copper, bronze, brass and zinc.

Hazardous decomposition products:
EDA Ethylenediamine may release nitrogen oxides, carbon monoxide and carbon dioxide.
EDA Ethylenediamine may release irritating and toxic combustion fumes.

Handling and Storage of EDA Ethylenediamine:

Handling:
EDA Ethylenediamine should be used only with sufficient local and general ventilation and kept away from all ignition sources, with no smoking, open flames or sparks.
EDA Ethylenediamine skin and eye contact should be avoided, and vapor or aerosol should not be inhaled.
EDA Ethylenediamine use should not be accompanied by eating, drinking or smoking, and hands and exposed skin should be washed thoroughly afterwards.
EDA Ethylenediamine contaminated clothing should be removed immediately.
EDA Ethylenediamine handling calls for precautions against electrostatic discharge, with containers and transfer equipment grounded and bonded where appropriate.

Storage:
EDA Ethylenediamine should be stored in a cool, dry, well-ventilated area at 15–25°C, with containers tightly closed and locked up.
EDA Ethylenediamine should be stored away from heat, flames, sparks and other ignition sources, and away from strong oxidizing agents and incompatible chemicals.
EDA Ethylenediamine storage areas must provide adequate permanent extraction where harmful vapors may be released, and chemically compatible containers should be used.

First Aid Measures of EDA Ethylenediamine:

Inhalation:
After inhalation of EDA Ethylenediamine vapor, immediately move the person to fresh air and keep them at rest in a position comfortable for breathing.
EDA Ethylenediamine exposure that causes coughing, breathing difficulty, irritation or allergic symptoms calls for medical attention, and respiratory sensitization may cause asthma-like symptoms on later low-level exposure.

Skin contact:
After skin contact with EDA Ethylenediamine, immediately remove contaminated clothing and footwear and wash the skin with large quantities of water, continuing to rinse thoroughly.
EDA Ethylenediamine skin contact requires immediate medical treatment, because corrosive burns may progress and heal poorly if untreated.

Eye contact:
After eye contact with EDA Ethylenediamine, immediately rinse the eyes with large quantities of flowing water for at least 10–15 minutes, holding the eyelids open.
EDA Ethylenediamine eye contact calls for removal of contact lenses if easy, protection of the unaffected eye and immediate examination by an ophthalmologist.

Ingestion:
After ingestion of EDA Ethylenediamine, rinse the mouth immediately, and if the person is conscious allow thorough rinsing with water.
EDA Ethylenediamine ingestion should not be followed by induced vomiting unless medical personnel instruct it, and immediate medical attention is needed because it may cause severe corrosive injury and perforation of the esophagus or stomach.

Firefighting Measures of EDA Ethylenediamine:

Suitable extinguishing media:
EDA Ethylenediamine fires can be fought with water spray, alcohol-resistant foam, dry chemical powder, BC extinguishing powder or carbon dioxide.

Unsuitable extinguishing media:
EDA Ethylenediamine fires should not be fought with a direct water jet, which may spread the burning liquid.

Specific hazards:
EDA Ethylenediamine is a flammable liquid (flash point 38–42°C), and its vapors may form explosive mixtures with air.
EDA Ethylenediamine vapors may travel along floors and accumulate in poorly ventilated areas, pits and low-lying locations, and containers exposed to fire may rupture.
EDA Ethylenediamine combustion produces nitrogen oxides, carbon monoxide, carbon dioxide and irritating and toxic fumes.

Protective equipment for firefighters:
EDA Ethylenediamine fires require firefighters to wear self-contained breathing apparatus (SCBA) and full chemical protective clothing.

Firefighting instructions:
EDA Ethylenediamine fires should be approached from a safe distance, and exposed containers cooled with water spray when safe.
EDA Ethylenediamine firefighting run-off should be kept out of drains, surface waters and groundwater.

Accidental Release Measures of EDA Ethylenediamine:

Personal precautions:
EDA Ethylenediamine spills call for evacuation of unnecessary personnel, elimination of all ignition sources and adequate ventilation.
EDA Ethylenediamine vapors, aerosols and mist should not be breathed, skin, eye and clothing contact should be avoided, and appropriate chemical protective equipment should be worn with precautions against static discharge.

Environmental precautions:
EDA Ethylenediamine must be kept out of drains, sewage systems, surface water and groundwater.
EDA Ethylenediamine releases of significant quantities into waterways or sewage systems should be reported to the appropriate environmental authorities.

Methods for cleaning up:
EDA Ethylenediamine leaks should be stopped if safe, and spilled material contained.
EDA Ethylenediamine liquid should be absorbed with sand, diatomaceous earth or a suitable chemical-binding material and collected in suitable, chemically resistant, properly labeled containers.
EDA Ethylenediamine spill areas should be ventilated thoroughly, and contaminated materials disposed of as hazardous waste.

Exposure Controls / Personal Protective Equipment of EDA Ethylenediamine:

Engineering controls:
EDA Ethylenediamine operations need effective local exhaust ventilation, with general mechanical ventilation where vapors may accumulate.
EDA Ethylenediamine airborne concentrations should be kept below occupational exposure limits (TWA: 10 ppm / 25 mg/m³), using closed or contained transfer systems for large quantities.

Eye protection:
EDA Ethylenediamine handling calls for chemical-resistant safety goggles with side protection, and a face shield where splashing is possible.

Hand protection:
EDA Ethylenediamine handling calls for butyl rubber gloves ≥0.7 mm for prolonged contact (breakthrough time >480 min).
EDA Ethylenediamine short-term splash protection can use nitrile rubber gloves ≥0.4 mm.

Skin and body protection:
EDA Ethylenediamine handling calls for chemical-resistant protective clothing, suitable protective footwear and a chemical-resistant apron where splashing may occur, with contaminated clothing removed promptly.

Respiratory protection:
EDA Ethylenediamine vapors call for a Type A filter for organic gases and vapors (boiling point >65°C).
EDA Ethylenediamine at high concentrations or in confined spaces calls for self-contained breathing apparatus (SCBA).

Hygiene measures:
EDA Ethylenediamine handling should be followed by thorough hand washing, and eating, drinking or smoking should not take place where it is handled.
EDA Ethylenediamine contaminated work clothing should not leave the workplace.

Properties of EDA Ethylenediamine:
Physical state: Liquid
Appearance: Colorless to pale yellow, hygroscopic, fuming liquid
Odor: Strong ammoniacal; ammonia-like and fishy
Melting point: 8–11°C
Boiling point: 116–118°C at 1013 hPa
Flash point: 38–42°C (closed cup)
Autoignition temperature: 385–405°C
Explosive limits: Lower 2.0–2.5% / Upper 16.3–17.0% (v/v)
Density: ~0.897–0.90 g/cm³ at 20°C
Vapor pressure: 12 hPa at 20°C
Vapor density (air = 1): 2.07–2.1
Refractive index (n20/D): 1.4565
Dynamic viscosity: 1.265 mPa·s at 25°C
pH: ~12.2 (100 g/L in water, 20°C); 12.8 (25% solution)
Solubility in water: Miscible (~1000 g/L)
Solubility in ethanol: Soluble
Solubility in ether: Slightly soluble
Log Kow: -1.62 (pH >12, 25°C)
Henry's Law Constant: ~0.6 Pa·m³/mol at 25°C
Specific heat capacity: 2.87 J/(g·K) at 25°C
Dielectric constant: 16.0 at 18°C
Biodegradability: Readily biodegradable (~94% after 28 days)
GHS Classification (reviewed supplier data): Danger; H226, H302, H311, H314, H317, H318, H332, H334, H412

Specifications of EDA Ethylenediamine:
Assay: ≥99.5 wt%
Color: ≤15 Hazen
Water content: ≤0.3 wt%
Appearance: Colorless to light yellow liquid
Storage temperature: 15–25°C
Storage: Cool, dry, well-ventilated; tightly sealed; away from ignition sources and oxidizing agents

Names of EDA Ethylenediamine:
EDA Ethylenediamine
Ethylenediamine
EDA
1,2-Diaminoethane
Ethane-1,2-diamine
1,2-Ethanediamine
Diaminoethane