|Jmol-3D images||Image 1|
|Molar mass||60.10 g mol−1|
|Melting point||8 °C; 46 °F; 281 K ()|
|Boiling point||116 °C; 241 °F; 389 K ()|
|Vapor pressure||1.3 kPa (at 20 °C)|
|kH||5.8 mol Pa−1 kg−1|
|Refractive index (nD)||1.4565|
|Std enthalpy of
|−63.55–−62.47 kJ mol−1|
|Std enthalpy of
|−1.8678–−1.8668 MJ mol−1|
|202.42 J K−1 mol−1|
|Specific heat capacity, C||172.59 J K−1 mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H226, H302, H312, H314, H317, H334|
|GHS precautionary statements||P261, P280, P305+351+338, P310|
|R-phrases||R10, R21/22, R34, R42/43|
|S-phrases||(S1/2), S26, S36/37/39, S45|
|Flash point||34 °C (93 °F)|
|Autoignition temperature||385 °C (725 °F)|
|LD50||1.2 g kg−1 (oral, rat)|
|Related alkanamines||1,2-Diaminopropane, 1,3-Diaminopropane|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)
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 strongly basic amine. It is a widely used building block in chemical synthesis, with approximately 500000000 kg being 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).
In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by rectification. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products.
This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts.
Ethylenediamine is used in large quantities for production of many industrial chemicals. It 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.
Chelating agent and precursor to other ligands
Ethylenediamine is a well-known chelating ligand for coordination compounds, such as [Co(ethylenediamine)3]3+. The most prominent derivative of ethylenediamine is EDTA, which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. Hydroxyethylethylenediamine is another commercially significant chelating agent. The salen ligands, derived from the condensation of salicylaldehydes and ethylenediamine, are popular chelating agents in the research laboratory although not commercially significant.
Precursor to pharmaceuticals and agrochemicals
Numerous bio-active compounds contain the N-CH2-CH2-N linkage, including aminophylline and 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.
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 dendrimers are derived from ethylenediamine.
The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil.
- 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 epoxys, and dyes.
- Ethylenediamine (Edamine) is a common organic additive to the plant in vitro culture Murashige and Skoog medium.
Ethylenediamine is the first member of the so-called polyethylene amines, other members being:
- Diethylenetriamine, abbreviated dien or DETA, (H2N-CH2CH2-NH-CH2CH2-NH2, an analog of diethylene glycol)
- Triethylenetetramine, abbreviated trien or TETA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2)
- Tetraethylenepentamine, abbreviated TEPA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2),
- Pentaethylenehexamine, abbreviated PEHA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2), up to polyethylene amine. Similarly piperazine is an analogue of dioxane.
Related derivatives of ethylenediamine include tetramethylethylenediamine (abbreviated TMEDA), (CH3)2N-CH2CH2-N(CH3)2 and tetraethylethylenediamine (abbreviated TEEDA) (C2H5)2N-CH2CH2-N(C2H5)2
Ethylenediamine, like most amines, is a skin irritant. It was used in commercially available skin products including Mycolog cream. Unless tightly contained, 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. Exposure to a relatively small amount of vapor or mist by inhalation can seriously damage health and may even result in death. Ethylenediamine has a half-life of about 30 minutes and a small volume of distribution of 0.133 liters/kg. After oral administration its bioavailability is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by urinal excretion.
- "ethylenediamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 3 May 2012.
- "32007R0129". European Union. 12 February 2007. Annex II. Retrieved 3 May 2012.
- Record in the GESTIS Substance Database from the IFA
- Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a02_001
- Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 245, Wiley VCH
- Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH
- Kotti, S. R. S. S.; Timmons, C. and Li, G. (2006). "Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry". Chemical Biology & Drug Design 67 (2): 101–114. doi:10.1111/j.1747-0285.2006.00347.x. PMID 16492158.
- Hogan DJ. (January 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem.". Dermatol Clin. 8 (1): 133–6. PMID 2137392.
- Material Safety Data Sheet
- Zuidema J. (1985-08-23). "Ethylenediamine, profile of a sensitizing excipient.". Pharmacy World & Science 7 (4): 134–40. doi:10.1007/BF02097249. PMID 3900925.