ChemicalBook > Product Catalog > Biochemical Engineering > Inhibitors > Immunosuppressants > Ethylenediamine
Ethylenediamine Chemical Properties
- Melting point:8.5 °C(lit.)
- Boiling point:118 °C(lit.)
- Density 0.899 g/mL at 25 °C(lit.)
- vapor density 2.07 (vs air)
- vapor pressure 10 mm Hg ( 20 °C)
- refractive index n
- Flash point:93 °F
- storage temp. Flammables area
- solubility ethanol: soluble(lit.)
- pka10.712(at 0℃)
- form Liquid, Fuming In Air
- color colorless to pale yellow
- Specific Gravity0.899
- OdorStrong ammoniacal odor; ammonia-like mild and ammoniacal odor.
- PH12.2 (100g/l, H2O, 20℃)
- explosive limit2-17%(V)
- Water Solubility miscible
- Sensitive Air Sensitive
- Merck 14,3795
- BRN 605263
- Henry's Law Constant1.69(x 10-9 atm?m3/mol) at 25 °C (Westheimer and Ingraham, 1956)
- Exposure limitsTLV-TWA 10 ppm (～25 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 2000 ppm (NIOSH).
- CAS DataBase Reference107-15-3(CAS DataBase Reference)
- NIST Chemistry ReferenceEthylenediamine(107-15-3)
- EPA Substance Registry SystemEthylenediamine (107-15-3)
- Hazard Codes C
- Risk Statements 10-21/22-34-42/43
- Safety Statements 23-26-36/37/39-45
- RIDADR UN 1604 8/PG 2
- WGK Germany 2
- RTECS KH8575000
- F 10-34
- Autoignition Temperature716 °F
- TSCA Yes
- HazardClass 8
- PackingGroup II
- HS Code 29212110
- Hazardous Substances Data107-15-3(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 1.16 g/kg (Smyth)
Ethylenediamine Usage And Synthesis
- DescriptionEthylenediamine (EDA) is a clear and colorless product at normal temperature and pressure which has a characteristic smell of an amine. It is strongly alkaline and is miscible with water and alcohol. It is air sensitive and hygroscopic and absorbs carbon dioxide from the air. It is incompatible with aldehydes, phosphorus halides, organic halides, oxidising agents, strong acids, copper, its alloys, and its salts.
- synthesisEthylenediamine can be synthesized from ethanolamine (EA) with ammonia over acidic types of zeolite catalyst.2 It is produced industrially by the reaction of 1,2-dichloroethane with ammonia in a liquid base under high temperature and high presseure.3 The synthesis of ethylenediamine from 1,2-dichloroethane is ClCH2CH2Cl + 2NH3 → NH2CH2CH2NH2*2HCl
ClCH2CH2Cl + NH2CH2CH2NH2*2HCl + 2NH3 → NH2CH2C H2NHCH2CH2NH3*3HCl + NH4HCl
Nevertheless, there are too many byproducts during the reaction. The key of this synthesis is to improve the selectivity of reaction product and the application of advanced separation methods to obtain high product purity.
- ApplicationLigands in coordination chemistry
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).3 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).4 It 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.6 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. It is used in the production of formulations for use in the printed circuit board and metal finishing industries. It 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.7 Ethylenediamine is also used as solvent and for the analytical chemistry. It is used to produce photographic fixer additive
- References Formation of metal complexes with ethylenediamine: a critical survey of equilibrium constants, enthalpy and entropy values, Pure & Applied Chemistry, vol. 56, 1984, pp.491-522
 K. Segawa, S. Mizuno, M. Sugiura, S. Nakata, Selective synthesis of ethylenediamine from ethanolamine over modified H-mordenite catalyst, Studies in Surface Science and Catalysis, vol. 101, 1996, pp. 267-276
 Norbert Rietbrock, B. G. Woodcock, A. H. Staib, Theophylline and other Methylxanthines, 1981, ISBN 978-3-663-05269-2
 Ian A. Cotgreave, John Caldwell, Comparative plasma pharmacokinetics of theophylline and ethylenediamine after the administration of aminophylline to man, Journal of Pharmacy and Pharmacology, vol. 35, 1983, pp. 378-382
- DescriptionEthylenediamine 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. It 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.
- Chemical PropertiesEthylenediamine, a polyamine, is a strongly alkaline, colorless, clear, thick liquid. Ammonia odor. A solid below 8.5℃. The Odor Threshold is 1.0 ppm
- Physical propertiesClear, colorless, volatile, slight viscous, hygroscopic liquid with a sweet, ammonia-like odor. The average least detectable odor threshold concentrations in water at 60 °C and in air at 40 °C were 12 and 52 mg/L, respectively (Alexander et al., 1982).
- UsesEthylenediamine is used as a stabilizerfor rubber latex, as an emulsifier, as aninhibitor in antifreeze solutions, and intextile lubricants. It is also used as a solvent for albumin, shellac, sulfur, and othersubstances.
- UsesIntermediate in the manufacture of EDTA; catalytic agent in epoxy resins; dyes, solvent stabilizer; neutralizer in rubber products
- Uses[Note—Edamine is the recommended contraction for the ethylenediamine radical.].
- DefinitionChEBI: An alkane-alpha,omega-diamine in which the alkane is ethane.
- Production MethodsThe production of ethylene-1,2-diamine (EDA) is by the catalytic amination of monoethanolamine or the reaction of aqueous ammonia with 1,2-dichloroethane (Spitz 1979). U.S. Production is estimated at greater than 33,000 tons in 1975.
- DefinitionAn organic compound, H2NCH2CH2NH2. It is important in inorganic chemistry because it may function as a bidentantate ligand, coordinating to a metal ion by the lone pairs on the two nitrogen atoms. In the names of complexes it is given the abbreviation en.
- Air & Water ReactionsHighly flammable. Hygroscopic. Fumes in the air. Water soluble. Biodegrades readily.
- Reactivity ProfileA base. Highly reactive with many compounds. Can react violently with acetic acid, acetic anhydride, acrolein, acrylic acid, acrylonitrile, allyl chloride, carbon disulfide, chlorosulfonic acid, epichlorohydrin, ethylene chlorohydrin, hydrogen chloride, mesityl oxide, nitric acid, oleum, AgClO4, sulfuric acid, beta-propiolactone and vinyl acetate. Incompatible with strong acids, strong oxidizers (perchlorate salts), and chlorinated organic compounds. Ethylenediamine is also incompatible with halogenated organic compounds and metal halides. May react with nitromethane and diisopropyl peroxydicarbonate. May ignite on contact with cellulose nitrate. Readily absorbs carbon dioxide from the air to give crusty solid deposits. . Ethylenediamine reacts violently with ethylene chlorohydrin. (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 1554.).
- HazardToxic by inhalation and skin absorption, strong irritant to skin and eyes. Flammable, moderate fire risk. Questionable carcinogen.
- Health HazardEthylenediamine is a severe skin irritant, producing sensitization, an allergic reaction andblistering on the skin. Pure liquid on contact with the eyes can damage vision. A25% aqueous solution can be injurious to theeyes. Inhalation of its vapors can producea strong irritation to the nose and respiratory tract leading to chemical pneumonitis and pulmonary edema. Such irritation inhumans with symptoms of cough and dis tressed breathing may be noted at concentrations of >400 ppm. Repeated exposure tohigh concentrations of this substance in airmay cause lung, liver, and kidney damage.The toxicity of this compound, however, is much less than that of ethylenimine.The acute oral toxicity value in animalswas low to moderate. An oral LD50 value inrats is 500 mg/kg (NIOSH 1986).
- Health HazardHuman subjects found 100 p.p.m. EDA for a few seconds to be inoffensive but
higher concentrations of 200 and 400 p.p.m. produced noticeable irritation of the
nasal mucosa (HSDB 1988). Acute EDA ingestion will cause burns of the mouth,
esophagus and possibly stomach. Eye contact would be expected to produce a
serious burn due to the corrosiveness of the compound. Acute exposure to the skin
is likely to produce a skin burn, while chronic exposure will cause a serious
EDA, in addition, is a potent allergen causing hypersensitization in exposed individuals (HSDB 1988). Because of such reactions, it has been difficult to establish threshold limits that will prevent the hypersensitization response. Allergic reactions to EDA in hair and nail care products have been observed among beauty operators, patrons and their husbands (Arena 1979). In the lacquer and shellac industries, exposure to EDA used as a solvent or paint thinner has produced wheezing, heaviness in the chest, severe asthma, allergic coryza and skin rashes (Arena 1979). Workmen exposed to EDA occasionally see halos around objects and have some blurring of vision, presumably due to the effects on the corneal epithelium (Grant 1974). In a study population of 1158 paid volunteers given a patch test, 0.43% showed a positive reaction to EDA (Prystowsky et al 1979).
- Fire HazardBurning rate: 2.2 mm/minute. When exposed to heat or flame, the material has a moderate fire potential. The material can react readily with oxidizing materials. Containers may explode in heat of fire. Material emits nitrogen oxides when burned. Avoid carbon disulfide, silver perchlorate, imines, oxidizing materials. Stable. Hazardous polymerization may not occur.
- Chemical ReactivityReactivity with Water Gives off heat, but reaction is not hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Industrial usesEDA functions as a reactive intermediate in the synthesis of carbamate fungicides and in the preparation of dyes, synthetic waxes, resins, insecticides and asphalt wetting agents (Parmeggiani 1983). EDA is a solvent for casein, albumin, shellac, and sulfur; an emulsifier; a stabilizer for rubber latex; an inhibitor in antifreeze solutions; and a pharmaceutic aid (aminophylline injection stabilizer) (Windholz 1983). It is also an important ingredient in hair-settings, cold wave lotions, and nail polish (Arena 1979).
- Contact allergensEthylenediamine is used in numerous industrial processes as a solvent for casein or albumin, as a stabilizer in rubber latex, and as a textile lubricant. It 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 crossreact with triethylenetetramine and diethylenetriamine. Ethylenediamine was found to be 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 tablets
- Safety ProfileA human poison by inhalation. Experimental poison by inhalation, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by ingestion and skin contact, Experimental reproductive effects. Corrosive. A severe skin and eye irritant. An allergen and sensitizer. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. Can react violently with acetic acid, acetic anhydride, acrolein, acrylic acid, acrylonitrile, allyl chloride, CS2, chlorosulfonic acid, epichlorohydrin, ethylene chlorohydrin, HCl, mesityl oxide, HNO3, oleum, AgClO4, H2SO4, Ppropiolactone, or vinyl acetate. To fight fwe, use CO2, dry chemical, alcohol foam. When heated to decomposition it emits toxic fumes of NOx and NH3. See also MINES.
- Potential ExposureEthylenediamine is used as an intermediate; as a urine acidifier; as a solvent; an emulsifier for casein and shellac solutions; a stabilizer in rubber late. A chemical intermediate in the manufacture of dyes; corrosion inhibitors; synthetic waxes; fungicides, resins, insecticides, asphalt wetting agents; and pharmaceuticals. Ethylenediamine is a degradation product of the agricultural fungicide Maneb.
- Environmental FateChemical/Physical. Absorbs carbon dioxide forming carbonates (Patnaik, 1992; Windholz et al.,
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 893 mg/L. The adsorbability of the carbon used was 21 mg/g carbon (Guisti et al., 1974).
- MetabolismEDA is absorbed through the skin (Beard and Noe 1981). The penetration rates,
distribution and excretion of topically applied [14C]-ethylenediamine have been
studied in the rat (Yang et al 1987). Male Wistar rats were percutaneously exposed
to solutions of 10, 25 or 50% EDA over about 10% of the body surface.
Absorption of EDA was concentration dependent, with about 12, 55 and 61%
being absorbed at the 70, 25 and 50% concentration respectively. The terminal
plasma half-life of EDA was approximately 4.5 h and the major route of excretion
was via the urine. The authors concluded that skin absorption is relatively low and
the reduced absorption at higher EDA concentrations may be due to epidermal
When male rats were given 5, 50 or 500 mg/kg doses of [14C]-EDA by oral, endotracheal and i.v. routes, urinary excretion accounted for 42-65% of the administered radioactivity (Yang and Tallant 1982). Fecal excretion amounted to 5-32% of the dose, depending on the route and 6-9% was eliminated in expired air as 14CO2. As the dosage increased from 5 to 50 to 500 mg/kg, there was a pattern of accumulated tissue EDA with a corresponding decrease in metabolite formation. The route of administration did not appear to change the metabolic profile. The major urinary metabolite in the rat was N-acetylethylenediamine (Yang and Tallant 1982). Cotgreave and Caldwell (1983) found that EDA was not detectable in the plasma 2 h after oral and i.v. administration of aminophylline in three healthy human subjects. Davies et al (1983) observed that ethylenediamine uptake in rat brain slices was temperature-dependent and appeared to take place by both sodium dependent and sodium independent mechanisms. Yang et al (1984a) demonstrated age- and, to a lesser extent, sex-related differences in the pharmacokinetics of EDA in Fischer 344 rats.
- ShippingUN1604 Ethylenediamine, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid
- Purification MethodsIt forms a constant-boiling (b 118.5o, monohydrate, m 10o) mixture with water (23w/w%). [It is hygroscopic and miscible with water.] Recommended purification procedure [Asthana & Mukherjee in J.F.Coetzee (ed), Purification of Solvents, Pergamon Press, Oxford, 1982 cf p 53]: to 1L of ethylenediamine is added 70g of type 5A Linde molecular sieves and shaken for 12hours. The liquid is decanted and shaken for a further 12hours with a mixture of CaO (50g) and KOH (15g). The supernatant is fractionally distilled (at 20:1 reflux ratio) in contact with freshly activated molecular sieves. The fraction distilling at 117.2o /760mm is collected. Finally it is fractionally distilled from sodium metal. All distillations and storage of ethylenediamine should be carried out under nitrogen to prevent reaction with CO2 and water. The material containing 30% water is dried with solid NaOH (600g/L) and heated on a water bath for 10hours. Above 60o, separation into two phases takes place. The hot ethylenediamine layer is decanted off, refluxed with 40g of sodium for 2hours and distilled [Putnam & Kobe Trans Electrochem Soc 74 609 1938]. Ethylenediamine is usually distilled under nitrogen. Alternatively, it is dried over type 5A Linde molecular sieves (70g/L), then a mixture of 50g of CaO and 15g of KOH/L, with further dehydration of the supernatant with molecular sieves followed by distillation from molecular sieves and, finally, from sodium metal. A spectroscopically improved material is obtained by shaking with freshly baked alumina (20g/L) before distillation. [Beilstein 4 IV 1166.]
- IncompatibilitiesVapor may form explosive mixture with air. Ethylenediamine is a medium strong base. Violent reaction with strong acids; strong oxidizers; chlorinated organic compounds; acetic acid; acetic anhydride; acrolein, acrylic acid; acrylonitrile, allyl chloride; carbon disulfide; chlorosulfonic acid; epichlorohydrin, ethylene chlorohydrin, oleum, methyl oxide; vinyl acetate. Also incompatible with silver perchlorate, 3-propiolactone, mesityl oxide; ethylene dichloride; organic anhydrides; isocyanates, acrylates, substituted allyls; alkylene oxides; ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks aluminum, copper, lead, tin, zinc, and alloys; some plastics, rubber, and coatings.
- Waste DisposalControlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices).
Ethylenediamine Preparation Products And Raw materials
- Preparation Products2-(2-Aminoethylamino)ethanolC-(1H-INDOL-5-YL)-METHYLAMINEReactive Blue 198Imidocarbdimethyl p-octadecyl phenylsulfonyl amino propyl ammoium propylsulfonateN,N'-BIS(ETHYLENE)-P-TOLUENESULFONAMIDELofexidineacid washing corrosion inhibitor Sx-12-Nitroaminoimidazoline2-Methylpyrazine2,3-Dimethylpyrazine2-Phenyl-2-imidazolinelaurylamide propionate JHZ-101N,N'-Ethylenebis(stearamide)NABAMETHYLEN-BIS-(4,6-DIMETHYL-TETRAHYDRO-1,3,5-THIADIAZIN-2-THION)MoxonidineCURING AGENT (POLYAMIDE BASE LIQUID) FOR EPOXY RESamidoamino acidnoncyanide zinc plating additive XD-1EthyleneureaETHYLENEDIAMINE DIACETATEadditive EQD-3N-Acetylethylenediamine1-Boc-3-oxopiperazineReactive Blue 231leveler DA2-Ethyl-3-methylpyrazineN-(1-Naphthyl)ethylenediamine dihydrochlorideCibenzolineEthylenediamine dihydrochlorideN,N'-Dibenzyl ethylenediamine diacetatenoncyanide zinc plating bright additive5,6,7,8-Tetrahydroquinoxaline2,3-Diethylpyrazinehydrodewaxing catalysts for diesel fuel(series)GlycylglycineN,N,N',N'-Tetrakis(2-hydroxypropyl)ethylenediamine3-(2-Aminoethylamino)propyl-dimethoxymethylsilane
- Raw materialsAmmonium hydroxideAmmonia1,4-DiazacyclohexaneEthanolamine1,2-Dichloroethane DichloroethaneTITANIUMPIPERAZINE HEXAHYDRATEN-AminoethylpiperazinePolyamine N7
- Ethylene glycol TEA Diaminomaleonitrile Ethylenediaminetetraacetic acid disodium salt Ethylenediamine Ethylamine 4,4'-Methylenedianiline Disodium edetate dihydrate Iminodiacetonitrile Ethylenediaminetetraacetic acid N,N-Dimethyl-1,4-phenylenediamine N,N,N',N'-Tetramethylethylenediamine N-ACETYL-L-PHENYLALANYL-3,5-DIIODO-L-TYROSINE Bis(cyclohexanone)oxaldihydrazone L-LEUCYL-L-ALANINE AC-TYR-NH2 1,2-Diaminocyclohexane N-ACETYL-ALA-ALA-ALA