Ethylenediamine (abbreviated as en when a

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...

) is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the formula C₂H₄(NH₂)₂. This colorless liquid with an

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous wa ...

-like odor is a basic

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

. It is a widely used building block in chemical synthesis, with approximately 500,000

tonnes The tonne ( or ; symbol: t) is a unit of mass equal to 1000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton to distinguish it from the non-metric units of the short ton (United States c ...

produced in 1998.Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. Ethylenediamine is the first member of the so-called polyethylene amines.

Synthesis

Ethylenediamine is produced industrially by treating

1,2-dichloroethane The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vin ...

with

under pressure at 180 °C in an aqueous medium:Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 245, Wiley VCH : Ethylendiamin Darstellung

In this reaction

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by .

Diethylenetriamine Diethylenetriamine (abbreviated and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. ...

(DETA) and

triethylenetetramine Triethylenetetramine (TETA and trien), also known as trientine (INN) when used medically, is an organic compound with the formula H2NHCH2CH2NH2sub>2. The pure freebase is a colorless oily liquid, but, like many amines, older samples assume a yel ...

(TETA) are formed as by-products. Another industrial route to ethylenediamine involves the reaction of

ethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid w ...

and ammonia:Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH : EDA synthesis from MEOA

This process involves passing the gaseous reactants over a bed of nickel

heterogeneous catalyst In chemistry, heterogeneous catalysis is catalysis where the phase of catalysts differs from that of the reactants or products. The process contrasts with homogeneous catalysis where the reactants, products and catalyst exist in the same phase. P ...

s. It can be produced in the lab by the reaction of

ethylene glycol Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...

and

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

. Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.

Applications

Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids (including

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...

s), nitriles, alcohols (at elevated temperatures), alkylating agents,

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...

, and

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

s and ketones. Because of its bifunctional nature, having two amines, it readily forms heterocycles such as

imidazolidine Imidazolidine is a heterocyclic compound (CH2)2(NH)2CH2. The parent imidazolidine is lightly studied, but related compounds substituted on one or both nitrogen centers are more common. Generally, they are colorless, polar, basic compounds. Imida ...

Precursor to chelation agents, drugs, and agrochemicals

A most prominent derivative of ethylenediamine is the

chelating Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

agent

EDTA Ethylenediaminetetraacetic acid (EDTA) is an aminopolycarboxylic acid with the formula H2N(CH2CO2H)2sub>2. This white, water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes ev ...

, which is derived from ethylenediamine via a

Strecker synthesis The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with ammonia in the presence of potassium cyanide. The condensation reaction yields an α- ...

involving

cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...

and

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...

. Hydroxyethylethylenediamine is another commercially significant chelating agent. Numerous bio-active compounds and drugs contain the N-CH₂-CH₂-N linkage, including some

antihistamine Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provid ...

s. Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names

Maneb Maneb is a fungicide and a polymeric complex of manganese with the ethylene bis(dithiocarbamate) anionic ligand.Arno H. Reidies "Manganese Compounds" Ullmann's Encyclopedia of Chemical Technology 2007; Wiley-VCH, Weinheim. Applications It can ...

, Mancozeb,

Zineb Zineb is the chemical compound with the formula n. Structurally, it is classified as a coordination polymer and a dithiocarbamate complex. This pale yellow solid is used as fungicide. Production and applications It is produced by treating ethyle ...

, and Metiram. Some

imidazoline Imidazoline is a class of heterocycles formally derived from imidazoles by the reduction of one of the two double bonds. Three isomers are known, 2-imidazolines, 3-imidazolines, and 4-imidazolines. The 2- and 3-imidazolines contain an imine In ...

-containing fungicides are derived from ethylenediamine.

Pharmaceutical ingredient

Ethylenediamine is an ingredient in the common

bronchodilator A bronchodilator or broncholytic (although the latter occasionally includes secretory inhibition as well) is a substance that dilates the bronchi and bronchioles, decreasing resistance in the respiratory airway and increasing airflow to the lung ...

drug aminophylline, where it serves to solubilize the active ingredient

theophylline Theophylline, also known as 1,3-dimethylxanthine, is a phosphodiesterase inhibiting drug used in therapy for respiratory diseases such as chronic obstructive pulmonary disease (COPD) and asthma under a variety of brand names. As a member of the ...

. 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 In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. Ho ...

is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by

renal The kidneys are two reddish-brown bean-shaped organs found in vertebrates. They are located on the left and right in the retroperitoneal space, and in adult humans are about in length. They receive blood from the paired renal arteries; bloo ...

excretion. Ethylenediamine-derived

antihistamines Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provides re ...

are the oldest of the five classes of

first-generation antihistamines First generation, ''Generation I'' or variants may refer to: History * 1G, the first generation of wireless telephone technology * First generation of video game consoles, 1972–1983 * First generation computer, a vacuum-tube computer Music * ...

, beginning with

piperoxan Piperoxan, also known as benodaine, was the first antihistamine to be discovered. This compound, derived from benzodioxan, was prepared in the early 1930s by Daniel Bovet and Ernest Fourneau at the Pasteur Institute in France. Formerly investiga ...

aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including mepyramine,

tripelennamine Tripelennamine, sold under the brand name Pyribenzamine by Novartis, is a drug that is used as an antipruritic and first-generation antihistamine. It can be used in the treatment of asthma, hay fever, rhinitis, and urticaria, but is now less ...

, and antazoline. The other classes are derivatives of ethanolamine, alkylamine,

piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...

, and others (primarily tricyclic and tetracyclic compounds related to

phenothiazines Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. Th ...

tricyclic antidepressants Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants, which is important for the management of depression. They are second-line drugs next to SSRIs. TCAs were discovered in the early 1950s and wer ...

, as well as the

cyproheptadine Cyproheptadine, sold under the brand name Periactin among others, is a first-generation antihistamine, first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties. It was patented in 1959 an ...

- phenindamine family)

Role in polymers

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

dendrimer Dendrimers are highly ordered, branched polymeric molecules. Synonymous terms for dendrimer include arborols and cascade molecules. Typically, dendrimers are symmetric about the core, and often adopt a spherical three-dimensional morphology. The ...

s are derived from ethylenediamine.

Tetraacetylethylenediamine

The bleaching activator

tetraacetylethylenediamine Tetraacetylethylenediamine, commonly abbreviated as TAED, is an organic compound with the formula (CH3C(O))2NCH2CH2N(C(O)CH3)2. This white solid is commonly used as a bleach activator in laundry detergents and for paper pulp. It is produced by ac ...

is generated from ethylenediamine. The derivative ''N'',''N''-ethylenebis(stearamide) (EBS) is a commercially significant mold-

release agent A release agent (also mold release agent, release coating, or mold release coating) is a chemical used to prevent other materials from bonding to surfaces. It can provide a solution in processes involving mold release, die-cast release, plastic r ...

and a surfactant in gasoline and motor oil.

Other applications

*as a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

, it is miscible with polar solvents and is used to solubilize

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...

s such as albumins and

casein Casein ( , from Latin ''caseus'' "cheese") is a family of related phosphoproteins ( αS1, aS2, β, κ) that are commonly found in mammalian milk, comprising about 80% of the proteins in cow's milk and between 20% and 60% of the proteins in hum ...

. It is also used in certain electroplating baths. *as a

corrosion inhibitor In chemistry, a corrosion inhibitor or anti-corrosive is a chemical compound that, when added to a liquid or gas, decreases the corrosion rate of a material, typically a metal or an alloy, that comes into contact with the fluid. The effectiveness ...

in paints and

coolant A coolant is a substance, typically liquid, that is used to reduce or regulate the temperature of a system. An ideal coolant has high thermal capacity, low viscosity, is low-cost, non-toxic, chemically inert and neither causes nor promotes corrosi ...

s. *

ethylenediamine dihydroiodide Ethylenediamine dihydroiodide (EDDI) is a water-soluble salt derived from ethylenediamine and hydroiodic acid. It is a colorless to light yellow crystalline powder. The salt consists of the ethylenediammonium dication C2H4(NH3)22+ and iodide anio ...

(EDDI) is added to animal feeds as a source of iodide. *chemicals for color photography developing, binders, adhesives,

fabric softener A fabric softener (American English) or fabric conditioner (British English) is a conditioner that is applied to laundry during the rinse cycle in a washing machine to reduce harshness in clothes that are dried in air after machine washing. In con ...

s, curing agents for

epoxies The Epoxies were an American new wave band from Portland, Oregon, formed in 2000. Heavily influenced by new wave, the band jokingly described themselves as robot garage rock. Members included FM Static on synthesizers, guitarist Viz Spectrum, ...

, and dyes. *as a compound to sensitize

nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...

into an explosive. This mixture was used at

Picatinny Arsenal The Picatinny Arsenal ( or ) is an American military research and manufacturing facility located on of land in Jefferson and Rockaway Township in Morris County, New Jersey, United States, encompassing Picatinny Lake and Lake Denmark. The Ar ...

during WWII, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.

Coordination chemistry

Ethylenediamine is a well-known bidentate

for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. It is often abbreviated "en" in inorganic chemistry. The complex o(ethylenediamine)₃sup>3+ is an archetypical

chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is distinguishable from i ...

tris-chelate complex. The

salen ligand Salen refers to a tetradentate C2-symmetric ligand synthesized from salicylaldehyde (sal) and ethylenediamine (en). It may also refer to a class of compounds, which are structurally related to the classical salen ligand, primarily bis-Schiff base ...

s, some of which are used in catalysis, are derived from the condensation of

salicylaldehyde Salicylic aldehyde (2-hydroxybenzaldehyde) is the organic compound with the formula (C7 H6 O2) C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. This colorless oily ...

s and ethylenediamine.

Related ligands

Related derivatives of ethylenediamine include ethylenediaminetetraacetic acid (EDTA),

tetramethylethylenediamine Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four amine hydrogens with four methyl groups. It is a colorless liquid, ...

(TMEDA), and tetraethylethylenediamine (TEEDA). Chiral analogs of ethylenediamine include 1,2-diaminopropane and ''trans''-diaminocyclohexane.

Safety

Ethylenediamine, like

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 absorb moisture from humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.

References

External links

IRIS EPA Ethylenediamine
{{Authority control Diamines Amine solvents Chelating agents Fuel antioxidants Corrosion inhibitors Commodity chemicals Ethyleneamines Foul-smelling chemicals Organic compounds with 2 carbon atoms