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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Ethane-1,2-diamine[2] | |||
| Other names Edamine,[1] 1,2-Diaminoethane, 'en' when a ligand | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | en | ||
| 605263 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.154 | ||
| EC Number |
| ||
| 1098 | |||
| KEGG |
| ||
| MeSH | ethylenediamine | ||
| RTECS number |
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| UNII | |||
| UN number | 1604 | ||
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| Properties | |||
| 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] | ||
| miscible | |||
| logP | −2.057 | ||
| Vapor pressure | 1.3 kPa (at 20 °C) | ||
Henry's law constant (kH) | 5.8 mol Pa−1 kg−1 | ||
| |||
Refractive index (nD) | 1.4565 | ||
| Thermochemistry | |||
| 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: | |||
    | |||
| Danger | |||
| H226,H302,H311,H314,H317,H332,H334,H412 | |||
| P101,P102,P260,P273,P280,P305+P351+P338,P308+P313,P405,P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 34 °C (93 °F; 307 K)[3] | ||
| 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). | |||
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 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.
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.
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Media related toEthylenediamine at Wikimedia Commons
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