ETHYLENEDIAMINE

CAS NUMBER: 107-15-3

MOLECULAR WEIGHT: 60.10

EC NUMBER: 203-468-6

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. 
Ethylenediamine is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. 
Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety). 
Ethylenediamine is the first member of the so-called polyethylene amines.
Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. 
Ethylenediamine is often abbreviated "en" in inorganic chemistry. The complex [Co(ethylenediamine)3]3+ is an archetypical chiral tris-chelate complex. 
The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and ethylenediamine.

Ethylenediamine appears as a clear colorless liquid with an ammonia-like odor. 
Flash point of 91°F and a melting point of 47°F. 
Corrosive to tissue. Vapors are heavier than air. 
Produces toxic oxides of nitrogen during combustion. 
Density 7.5 lb / gal. 
Used to make other chemicals and as a fungicide.
Ethylenediamine is an alkane-alpha,omega-diamine in which the alkane is ethane. 
Ethylenediamine has a role as a GABA agonist. 
Ethylenediamine derives from a hydride of an ethane.
Ethylenediamine is an organic compound that is used as a building block for the production of many other chemical products. 
Notably, ethylenediamine is a contact sensitizer capable of producing local and generalized reactions. 
Sensitivity to ethylenediamine may be identified with a clinical patch test.

Ethylenediamine (CAS #000107-15-3, 1,2-diaminoethane) is the lowest molecular weight ethylenediamine. 
Ethylenediamine is a single-component product with two primary nitrogens. 
Ethylenediamine has an ammonia-like odor and is clear and colorless.
Ethylenediamine (EDA) is the ethyleneamine with the lowest molecular weight. 
Ethylenediamine contains two primary amine groups and is a colorless liquid. 
Ethylenediamine is commonly used as an intermediate to produce detergents, chelates, textile auxiliaries, agrochemicals and polyamides.
Ethylenediamine is an organic compound that is used as a building block for the production of many other chemical products. 

Ethylenediamine is also used as an excipient in many pharmacological preparations such as creams. 
Notably, ethylenediamine is a contact sensitizer capable of producing local and generalized reactions. 
Sensitivity to ethylenediamine may be identified with a clinical patch test.
Ethylenediamine is approved for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.
Ethylenediamine (EDA) is a clear and colorless product at normal temperature and pressure which has a characteristic smell of an amine. 
Ethylenediamine is strongly alkaline and is miscible with water and alcohol. 
Ethylenediamine is air sensitive and hygroscopic and absorbs carbon dioxide from the air. 
Ethylenediamine is incompatible with aldehydes, phosphorus halides, organic halides, oxidising agents, strong acids, copper, its alloys, and its salts.

1,2-Ethylenediamine (EDA) is used mainly as a building block for crop protection products, in the synthesis of chelating agents and for low-temperature-active bleaching agents. 
The many other applications of 1,2-ethylenediamine (EDA) include polyamides, lubricants, fuel additives and textiles.
Ethylenediamine is used as a building block for the synthesis of bleach activators, chelates and crop protection products. 
Furthermore is is used as an intermediate in applications like corrosion inhibitors, polyamide resins and lubricants/fuel additives.   
Chain extender in the production of poyurethane resin for the water PU Dispersion (PUD).
Products derived from EDA are frequently used for bleach activators and chelates in detergents and for fungicides in crop protection area.
Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper, film, and foil webs and in hot-melt, pressure-sensitive, and heat-seal adhesives for leather, paper, plastic, and metal. 
The main polyamide resin type, in addition to the liquid resins used as epoxy hardeners, is prepared generally by the condensation reaction of diamines with di- and polybasic fatty acids. 
Thermoplastic polyamides are similarly used in formulating glossy, abrasion-resistant, overprint varnishes.
Ethylenediamine is available as pure substance.

Ethylenediamine is a major industrial chemical with approximately 90 million lbs. (41,000 tonnes) produced in the US, 128 million lbs. (58,000 tonnes) produced in Western Europe and 11 million lbs. (5,000 tonnes) produced in Japan in 1994 (Somogyi et al., 1996). 
There are two plants in the US, five plants in Western Europe and two plants in Japan (Greiner, et al., 1999). 
There are two processes used to produce Ethylenediamine: The ethylene dichloride (EDC) process and the ethylene oxide/monoethanolamine (EO/MEA) process. 
In each process the starting materials are reacted with ammonia. 
In the EO/MEA process, EO reacts with ammonia to form MEA which then reacts with ammonia to form Ethylenediamine.
Since Ethylenediamine is used as an industrial intermediate, its uses are predominantly in enclosed systems and for these uses there is little occasion for human exposure. 
The greatest exposures occur during product transfer and maintenance operations. 
Due to the highly reactive nature of Ethylenediamine, it is essentially consumed during reactions. 
During these manufacturing processes, residual Ethylenediamine is typically removed by distillation. 
Low levels of EDA, typically in the low ppm range would be expected in the final product. 

Ethylenediamine is a very reactive molecule and will react with acids, oxides and other materials. 
Thus the concentration of EDA may be lower than estimated. 
Based on manufacturing processes and use conditions, significant releases are not expected to the terrestrial environment.
Ethylenediamine is used primarily as an intermediate in the production of chelating agents, such as ethylenediaminetetraacetic acid (EDTA). 
Ethylenediamine is also used as an intermediate in the production of polyamide resins, ethylene bis-stearamide, gasoline and lube oil additives, cationic surfactants and, in Europe, fungicides (Greiner et al., 1999). 
To a lesser extent Ethylenediamine has been used as an intermediate in the production of fabric softeners and bleach activators. 
In the production of these materials, Ethylenediamine is the initial reactant and may undergo one, two, three or four subsequent reactions prior to the manufacture of the final product. 
The concentration of unreacted EDA decreases with each subsequent reaction. 

Ethylenediamine is also added to refinery streams as a scavenging agent due to its high degree of reactivity.
Ethylenediamine is used within the pharmaceutical industry to produce aminophylline for the treatment of acute severe asthma (Merck, 1999). 
In the U.S., this use is restricted to consumers under medical supervision. 
At the present time, there is only one aminophylline producer (PDR, 2000) and the amount sold into this market is probably quite small. 
Ethylenediamine has been used in the past as a stabilizer in topical creams containing neomycin (Van Hecke, 1975). 
However, recent formulations of topical creams do not appear to contain ethylenediamine (PDR, 2000). 

USES:

Ethylenediamine is used in numerous industrial proces ses as a solvent for casein or albumin, as a stabilizer in rubber latex and as a textile lubricant. 
Ethylenediamine can be found in epoxy-resin hardeners, cooling oils, fungicides, and waxes. 
Contact dermatitis from ethylenediamine is almost exclusively due to topical medicaments. 
Occupational contact dermatitis in epoxy-resin systems is rather infrequent. 
Ethylenediamine can cross react with triethylenetetramine and diethylenetriamine. 
Ethylenediamine was responsible for sensitization in pharmacists handling aminophylline suppositories, in nurses preparing and administering injectable theophylline, and in a laboratory technician in the manufacture of aminophylline tab lets.

USES:

-Corrosion inhibitors
-Wet-strength resins
-Fabric softeners
-Epoxy curing agents
-Polyamide resins
-Fuel additives
-Lube oil additives
-Asphalt additives
-Ore flotation
-Corrosion inhibitors
-Ore flotation
-Asphalt
-Additives
-Corrosion inhibitors
-Epoxy curing agents
-Hydrocarbon purification
-Lube oil & fuel additives
-Mineral processing aids
-Polyamide resins
-Surfactants
-Textile additives-paper wet-strength resins
-Fabric softeners
-Surfactants
-Coatings
-Urethanes
-Fuel additives
-Chemical intermediates
-Epoxy curing agents
-Lube oils
-Wet strength resins

USAGE AREAS:

- Bleach Activator
- Chelating Agents
- Corrosion Inhibitors
- Elastomeric Fibers
- Fungicides
- Fuel Additives
- Pharmaceutical Intermediate
- Plastic Lubricants
- Polyamide Resins
- Rubber Processing additives
- Textile Additives
- Urethane Chemicals

BENEFITS:

-Consistent and predictable reaction products
-Easily derivatized
-Low vapor pressure
-High viscosity
-Low environmental impact
-Suitable for harsh conditions
-Low sensitivity
-Versatile

APPLICATION:

Ethylenediamine is used in large quantities for production of many industrial chemicals. 
Ethylenediamine forms derivatives with carboxylic acids (including fatty acids), nitriles, alcohols (at elevated temperatures), alkylating agents, carbon disulfide, and aldehydes and ketones. 
Because of its bifunctional nature, having two amines, it readily forms heterocycles such as imidazolidines.
With the two nitrogen atoms, which can donate their lone pairs of electrons, ethylenediamine is widely used as a chelating ligand for coordination chemistry to form bonds to a transition-metal ion such as nickel (II). 
The bonds form between the metal ion and the nitrogen atoms of ethylenediamine. 
Ethylenediaminetetraacetic acid (EDTA) is a derivate of ethylenediamine and it is a versatile chelating agent, which could form chelates with both transition-metal ions and main-group ions. 
Ethylenediamine is mainly used to synthesize ethylenediaminetetraacetic acid. EDTA is frequently used in soaps and detergents to form complexes with calcium and magnesium ions in hard water to improve the cleaning efficiency. Furthermore, EDTA is used extensively as a stabilizing agent in the food industry to promote color retention, to improve flavor retention, and to inhibit rancidity.

Ethylenediamine is used to facilitate the dissolution of theophylline. 
This combination is known as aminophylline and used to treat and prevent wheezing and trouble breathing caused by ongoing lung disease (e.g. asthma, emphysema, chronic bronchitis).
Ethylenediamine is evidenced that there is no molecular association between theophylline and ethylenediamine in biological media. 
The bioavailability of ethylenediamine is approximately 34% and of theophylline is about 88%.5
Ethylenediamine is used as an intermediate in the manufacture of tetraacetyl ethylenediamine (TAED), a bleaching activator, which is used in detergents and additives for laundry washing and dishwashing. 
The amount of TAED used in household cleaning products in Europe was estimated to be 61,000 t in 2001.

Ethylenediamine is in the manufacture of organic flocculants, urea resins, and fatty bisamides. 
Ethylenediamine is used in the production of formulations for use in the printed circuit board and metal finishing industries. 
Ethylenediamine is used as intermediate in the production of crop protection agents, hardeners for epoxy resins, leather industry, paint industry, fungicides in crop protection area, and textile industry. 
Ethylenediamine is also used as solvent and for the analytical chemistry. 
Ethylenediamine is used to produce photographic fixer additive.

OTHER APPLICATIONS:

-as a solvent, it is miscible with polar solvents and is used to solubilize proteins such as albumins and casein. It is also used in certain electroplating baths.
-as a corrosion inhibitor in paints and coolants.
-ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.
-chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents for epoxies, and dyes.
-as a compound to sensitize nitromethane into an explosive. This mixture was used at Picatinny Arsenal during WWII, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.

PHYSICAL AND CHEMICAL PROPERTIES:

-Boiling Point @ 760 mm Hg, °C: 117
-Freezing Point, °C: 11
-Density, g/ml @ 20°C: 0.897
-Specifi c gravity 20°/20°: 0.898
-Viscosity, cp @ 20°C: 1.8
-Kinematic viscosity, cst @ 25°C: 1.7
-Kinematic viscosity, cst @ 40°C: 1.2
-Vapor pressure @20°C, mm Hg: 10.40
-Specifi c heat, cal/g °C @ 20°C: 0.68
-Thermal conductivity cal/cm-sec-°C @ 20°C: 0.000614
-Surface tension, dynes/cm @ 20°C: 42
-Coefficient of expansion, per degree centigrade @ 20°C: 0.000108
-Dielectric constant @ 23°C and 1 kHz: 13.3
-Electrical conductivity, µmhos/cm @ 25°C: 7.52
-Heat of formation, 25 °C BTU/lb: -569
-Heat of vaporization @ 760 mm Hg, BTU/lb: 270
-Heat of combustion, BTU/lb, 25°C: -13251
-Ionization constant, K1 @ 25 °C: 0.73x10-4
-pH of 1 wt.% solution: 11.7
-Nitrogen content, wt.%: 46.6
-Amine value, mg KOH/g: 1860

PRECURSOR TO CHELATION AGENTS, DRUGS, AND AGROCHEMICALS:

A most prominent derivative of ethylenediamine is the chelating agent EDTA, which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. 
Hydroxyethylethylenediamine is another commercially significant chelating agent. 
Numerous bio-active compounds and drugs contain the N-CH2-CH2-N linkage, including some antihistamines. 
Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline-containing fungicides are derived from ethylenediamine.

PHARMACEUTICAL INGREDIENT:

Ethylenediamine is an ingredient in the common bronchodilator drug aminophylline, where Ethylenediamine serves to solubilize the active ingredient theophylline. 
Ethylenediamine has also been used in dermatologic preparations, but has been removed from some because of causing contact dermatitis. 
When used as a pharmaceutical excipient, after oral administration its bioavailability is about 0.34, due to a substantial first-pass effect. 
Less than 20% is eliminated by renal excretion.
Ethylenediamine-derived antihistamines are the oldest of the five classes of first-generation antihistamines, beginning with piperoxan aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including mepyramine, tripelennamine, and antazoline. 
The other classes are derivatives of ethanolamine, alkylamine, piperazine, and others (primarily tricyclic and tetracyclic compounds related to phenothiazines, tricyclic antidepressants, as well as the cyproheptadine-phenindamine family).

ROLE IN POLYMERES:

Ethylenediamine, because Ethylenediamine contains two amine groups, is a widely used precursor to various polymers. 
Condensates derived from formaldehyde are plasticizers. 
Ethylenediamine is widely used in the production of polyurethane fibers. 
The PAMAM class of dendrimers are derived from ethylenediamine.

SAFETY:

Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant. 
Unless tightly contained, liquid ethylenediamine will release toxic and irritating vapors into its surroundings, especially on heating. 
The vapors react with moisture in humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.

SYNONYM:

Ethane-1,2-diamine
1,2-Ethanediamine
107-15-3
1,2-Diaminoethane
Ethylene diamine
Ethylendiamine
edamine
Dimethylenediamine
1,2-Ethylenediamine
Aethaldiamin
Aethylenediamin
Ethyleendiamine
Ethylene-diamine
beta-Aminoethylamine

IUPAC NAME:

1,2,-Diaminoethane
1,2-Diaminoethane
1,2-diaminoethane
1,2-Diaminoethane , 1,2-Ethylenediamine , 1,4-Diazabutane , Dimethylenediamine
1,2-Ethanediamine
Diaminoethane
Ethane-1,2-diamine
ethane-1,2-diamine
ethane-1,2-diamine
Ethylendiamin

TRADE NAME:

Bruggolen P22
EDA
Ethylenediamine
ETHYLENEDIAMINE (EDA)
ETHYLENEDIAMINE.
Ethylenediamine.