Ethylenediamine (abbreviated asen when aligand) is theorganic compound with theformula C₂H₄(NH₂)₂. This colorless liquid with anammonia-like odor is abasicamine. It is a widely used building block in chemical synthesis, with approximately 500,000tonnes produced in 1998.^[6] Ethylenediamine is the first member of the so-calledpolyethylene amines.

Ethylenediamine

Names
Preferred IUPAC name Ethane-1,2-diamine[2]
Other names Edamine,[1] 1,2-Diaminoethane, 'en' when a ligand
Identifiers
CAS Number	107-15-3 Y
3D model (JSmol)	Interactive image
Abbreviations	en
Beilstein Reference	605263
ChEBI	CHEBI:30347 Y
ChEMBL	ChEMBL816 Y
ChemSpider	13835550 Y
ECHA InfoCard	100.003.154
EC Number	203-468-6
Gmelin Reference	1098
KEGG	D01114 Y
MeSH	ethylenediamine
PubChemCID	3301
RTECS number	KH8575000
UNII	60V9STC53F Y
UN number	1604
CompTox Dashboard(EPA)	DTXSID5021881
InChI InChI=1S/C2H8N2/c3-1-2-4/h1-4H2 Y Key: PIICEJLVQHRZGT-UHFFFAOYSA-N Y
SMILES NCCN
Properties
Chemical formula	C2H8N2
Molar mass	60.100 g·mol−1
Appearance	Colorless liquid[3]
Odor	Ammoniacal[3]
Density	0.90 g/cm3[3]
Melting point	8 °C (46 °F; 281 K)[3]
Boiling point	116 °C (241 °F; 389 K)[3]
Solubility in water	miscible
logP	−2.057
Vapor pressure	1.3 kPa (at 20 °C)
Henry's law constant (kH)	5.8 mol Pa−1 kg−1
Magnetic susceptibility (χ)	−46.26×10−6 cm3 mol−1 −76.2×10−6 cm3 mol−1 (HCl salt)
Refractive index (nD)	1.4565
Thermochemistry
Heat capacity(C)	172.59 J K−1 mol−1
Std molar entropy(S⦵298)	202.42 J K−1 mol−1
Std enthalpy of formation(ΔfH⦵298)	−63.55 to −62.47 kJ mol−1
Std enthalpy of combustion(ΔcH⦵298)	−1.8678 to −1.8668 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226,H302,H311,H314,H317,H332,H334,H412
Precautionary statements	P101,P102,P260,P273,P280,P305+P351+P338,P308+P313,P405,P501
NFPA 704 (fire diamond)	3 2 0
Flash point	34 °C (93 °F; 307 K)[3]
Autoignition temperature	385 °C (725 °F; 658 K)[3]
Explosive limits	2.7–16%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	500 mg/kg (oral, rat) 470 mg/kg (oral, guinea pig) 1160 mg/kg (oral, rat)[5]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 10 ppm (25 mg/m3)[4]
REL (Recommended)	TWA 10 ppm (25 mg/m3)[4]
IDLH (Immediate danger)	1000 ppm[4]
Related compounds
Related alkanamines	1,2-Diaminopropane,1,3-Diaminopropane
Related compounds	Ethylamine,Ethylenedinitramine
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Ethylenediamine is produced industrially by treating1,2-dichloroethane withammonia under pressure at 180 °C in an aqueous medium (EDC process):^[6][7]

In this reactionhydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition ofsodium hydroxide and can then be recovered byfractional distillation.Diethylenetriamine (DETA) andtriethylenetetramine (TETA) are formed as by-products.

Another industrial route to ethylenediamine involves the reaction ofethanolamine and ammonia:^[8]

This process involves passing the gaseous reactants over a bed of nickelheterogeneous catalysts.

It can be prepared in the lab by the reaction of eitherethylene glycol orethanolamine andurea, followed by decarboxylation of the ethyleneurea intermediate.^[9]

Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.^[10]

Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives withcarboxylic acids (includingfatty acids),nitriles,alcohols (at elevated temperatures), alkylating agents,carbon disulfide, andaldehydes andketones. Because of its bifunctional nature, having two amino groups, it readily forms heterocycles such asimidazolidines.

A most prominent derivative of ethylenediamine is thechelating agentEDTA, which is derived from ethylenediamine via aStrecker synthesis involvingcyanide andformaldehyde. Hydroxyethylethylenediamine is another commercially significant chelating agent.^[6] Numerous bio-active compounds and drugs contain the N–CH₂–CH₂–N linkage, including someantihistamines.^[11] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand namesManeb, Mancozeb,Zineb, and Metiram. Someimidazoline-containing fungicides are derived from ethylenediamine.^[6]

Ethylenediamine is aningredient in the commonbronchodilator drugaminophylline, where it serves to solubilize the active ingredienttheophylline. Ethylenediamine has also been used in dermatologic preparations, but has been removed from some because of causing contact dermatitis.^[12] When used as a pharmaceutical excipient, after oral administration itsbioavailability is about 0.34, due to a substantialfirst-pass effect. Less than 20% is eliminated byrenal excretion.^[13]

Ethylenediamine-derivedantihistamines are the oldest of the five classes offirst-generation antihistamines, beginning withpiperoxan aka benodain, discovered in 1933 at the Pasteur Institute in France, and also includingmepyramine,tripelennamine, andantazoline. The other classes are derivatives of ethanolamine,alkylamine,piperazine, and others (primarily tricyclic and tetracyclic compounds related tophenothiazines,tricyclic antidepressants, as well as thecyproheptadine-phenindamine family)

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 ofdendrimers are derived from ethylenediamine.^[6]

Thebleaching activatortetraacetylethylenediamine is generated from ethylenediamine. The derivativeN,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and asurfactant in gasoline and motor oil.

• as asolvent, it ismiscible with polar solvents and is used to solubilizeproteins such asalbumins andcasein. It is also used in certainelectroplating baths.
• as acorrosion inhibitor in paints andcoolants.
• ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.
• chemicals forcolor photography developing,binders,adhesives,fabric softeners,curing agents forepoxies, anddyes.
• as a compound to sensitizenitromethane into an explosive. This mixture was used atPicatinny Arsenal during World War II, giving the nitromethane and ethylenediamine mixture the nicknamePLX, or Picatinny Liquid Explosive.

Ethylenediamine is a well-knownbidentatechelatingligand forcoordination 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[Co(en)₃]³⁺ is a well studied example. Schiff base ligands easily form from ethylenediamine. For example, the diamine condenses with4-Trifluoromethylbenzaldehyde to give to the diimine.^[14] Thesalen ligands, some of which are used in catalysis, are derived from the condensation ofsalicylaldehydes and ethylenediamine.

Related derivatives of ethylenediamine includeethylenediaminetetraacetic acid (EDTA),tetramethylethylenediamine (TMEDA), andtetraethylethylenediamine (TEEDA). Chiralanalogs of ethylenediamine include1,2-diaminopropane andtrans-diaminocyclohexane.

Ethylenediamine, likeammonia 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 mucous membranes.

  Media related toEthylenediamine at Wikimedia Commons

• IRIS EPA Ethylenediamine
• CDC - NIOSH Pocket Guide to Chemical Hazards
• Chemical data