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1,2-Ethylenediamine is a clear and colorless product at normal temperature and pressure which has a characteristic smell of an amine.
1,2-Ethylenediamine is strongly alkaline and is miscible with water and alcohol.
1,2-Ethylenediamine is air sensitive and hygroscopic and absorbs carbon dioxide from the air.
CAS: 107-15-3
MF: C2H8N2
MW: 60.1
EINECS: 203-468-6
1,2-Ethylenediamine 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.
1,2-Ethylenediamine is incompatible with aldehydes, phosphorus halides, organic halides, oxidising agents, strong acids, copper, its alloys, and its salts.
1,2-Ethylenediamine can be found in epoxy-resin hardeners, cooling oils, fungicides, and waxes.
Contact dermatitis from 1,2-Ethylenediamine is almost exclusively due to topical medicaments.
Occupational contact dermatitis in epoxy-resin systems is rather infrequent.
1,2-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.
An alkane-alpha,omega-diamine in which the alkane is ethane.
An organic compound, H2NCH2CH2NH2.
1,2-Ethylenediamine 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 1,2-Ethylenediamine is given the abbreviation en.
1,2-Ethylenediamine is a linear aliphatic diamine, widely used as a building block in organic synthesis.
1,2-Ethylenediamine readily forms heterocyclic imidazolidine derivatives, because of its bifunctional nature, having two amines.
1,2-Ethylenediamine is also utilized as a raw material for the synthesis of chelating agents, polymers, agrochemicals and pharmaceutical intermediates.
1,2-Ethylenediamine is the organic compound with the formula C2H4(NH2)2.
This colorless liquid with an ammonia-like odor is a basic amine.
1,2-Ethylenediamine is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998.
1,2-Ethylenediamine is the first member of the so-called polyethylene amines.
1,2-Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when 1,2-Ethylenediamine acts as a ligand.
1,2-Ethylenediamine is often abbreviated "en" in inorganic chemistry.
The complex [Co(ethylenediamine)3]3+ is an archetypical chiral tris-chelate complex.
The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and 1,2-Ethylenediamine.
1,2-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: n20/D 1.4565(lit.)
Fp: 93 °F
Storage temp.: Flammables area
Solubility ethanol: soluble(lit.)
pka: 10.712(at 0℃)
Form: Liquid, Fuming In Air
Specific Gravity: 0.899
Color: colorless to pale yellow
PH: 12.2 (100g/l, H2O, 20℃)
Odor: Strong ammoniacal odor; ammonia-like mild and ammoniacal odor.
Explosive limit: 2-17%(V)
Water Solubility: miscible
Sensitive: Air Sensitive
Merck: 14,3795
BRN: 605263
Henry's Law Constant: 1.69(x 10-9 atm?m3/mol) at 25 °C (Westheimer and Ingraham, 1956)
Exposure limits: TLV-TWA 10 ppm (～25 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 2000 ppm (NIOSH).
InChIKey: PIICEJLVQHRZGT-UHFFFAOYSA-N
LogP: -1.6 at 20℃
CAS DataBase Reference: 107-15-3(CAS DataBase Reference)
NIST Chemistry Reference: 1,2-Ethylenediamine (107-15-3)
EPA Substance Registry System: 1,2-Ethylenediamine (107-15-3)
1,2-Ethylenediamine, a polyamine, is a strongly alkaline, colorless, clear, thick liquid.
Ammonia odor.
1,2-Ethylenediamine is a solid below 8.5℃.
The Odor Threshold is 1.0 ppm
Clear, 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.
Application
With the two nitrogen atoms, which can donate their lone pairs of electrons, 1,2-Ethylenediamine is widely used as a chelating ligand for coordination chemistry to form bonds to a transition-metal ion such as nickel (II).
The bonds form between the metal ion and the nitrogen atoms of 1,2-Ethylenediamine. Ethylenediaminetetraacetic acid (EDTA) is a derivate of 1,2-Ethylenediamine and it is a versatile chelating agent, which could form chelates with both transition-metal ions and main-group ions.
1,2-Ethylenediamine is mainly used to synthesize ethylenediaminetetraacetic acid.
1,2-Ethylenediamine is frequently used in soaps and detergents to form complexes with calcium and magnesium ions in hard water to improve the cleaning efficiency.
Furthermore, 1,2-Ethylenediamine is used extensively as a stabilizing agent in the food industry to promote color retention, to improve flavor retention, and to inhibit rancidity.
Pharmaceutical ingredient
1,2-Ethylenediamine is used to facilitate the dissolution of theophylline.
1,2-Ethylenediamine 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).
1,2-Ethylenediamine is evidenced that there is no molecular association between theophylline and ethylenediamine in biological media.
The bioavailability of 1,2-Ethylenediamine is approximately 34% and of theophylline is about 88%.
1,2-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.
Other applications
1,2-Ethylenediamine is in the manufacture of organic flocculants, urea resins, and fatty bisamides.
1,2-Ethylenediamine is used in the production of formulations for use in the printed circuit board and metal finishing industries.
1,2-Ethylenediamine 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.
1,2-Ethylenediamine is also used as solvent and for the analytical chemistry.
1,2-Ethylenediamine is used to produce photographic fixer additive
Uses
1,2-Ethylenediamine is used as a stabilizerfor rubber latex, as an emulsifier, as aninhibitor in antifreeze solutions, and intextile lubricants.
1,2-Ethylenediamine is also used as a solvent for albumin, shellac, sulfur, and othersubstances.
Intermediate in the manufacture of 1,2-Ethylenediamine; catalytic agent in epoxy resins; dyes, solvent stabilizer; neutralizer in rubber products
1,2-Ethylenediamine 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).
1,2-Ethylenediamine 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).
1,2-Ethylenediamine is also an important ingredient in hair-settings, cold wave lotions, and nail polish (Arena 1979).
1,2-Ethylenediamine is used in large quantities for production of many industrial chemicals.
1,2-Ethylenediamine 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, 1,2-Ethylenediamine readily forms heterocycles such as imidazolidines.
1,2-Ethylenediamine is a strongly basic amine useful as a building block in chemical synthesis.
1,2-Ethylenediamine is used as a solvent to dissolve proteins such as albumins and casein.
1,2-Ethylenediamine is widely used for color photography developers, binders, adhesives, fabric softeners, curing agents for epoxys and dyes.
As a corrosion inhibitor, 1,2-Ethylenediamine plays a vital role in paints and coolants.
1,2-Ethylenediamine is used as an intermediate in the preparation of polyamide resins, fuel additives and lubricants.
1,2-Ethylenediamine acts as a precursor for many polymers like polyurethane fibers and poly(amidoamine), ethylenediamine dihydroiodide (EDDI) as well as the bleaching activator, tetraacetylethylenediamine.
1,2-Ethylenediamine is an important chelating ligand used in the preparation of coordination compounds viz. tris(ethylenediamine)cobalt(III) chloride.
1,2-Ethylenediamine is also involved in the manufacture of many industrial chemicals and forms derivatives with carboxylic acids, nitriles, alcohols, alkylating agents, carbon disulfide, aldehydes and ketones.
1,2-Ethylenediamine is a basic building block to prepare heterocyclic compound such as imidazolidines.
Used in medicine, pesticides, dyes, plastics, rubber and other industries
Ethylenediamine, also known as 1, 2-diaminoethane, is an intermediate for fungicides such as amonium, zine and mancozeb, and is also the raw material for the pesticide imidacloprid.
1,2-Ethylenediamine is an important chemical raw material, which is widely used to manufacture organic compounds, polymer compounds, drugs, etc, used in the production of pesticide fungicides (zinc, ammonium), pesticides, herbicides, dyes, dye fixing agents, synthetic emulsifiers, demulsifiers, fiber surfactants, water quality stabilizers, descaling agents, electroplating brighteners, paper wetting enhancers, adhesives, metal chelating agents EDTA, epoxy resin curing agents, rubber vulcanization accelerators, acid gas purifiers, photographic development additives, ultra-high pressure lubricating oil stabilizers, welding flux, Amino resin, ethylenediamine urea-formaldehyde resin, etc.
1,2-Ethylenediamine is also used in organic solvents and chemical analysis reagents, as well as for the identification of beryllium, cerium, lanthanum, magnesium, nickel, thorium, uranium and other metals, antimony, bismuth, cadmium, cobalt, copper, mercury, nickel, silver and uranium Determination etc.
1,2-Ethylenediamine is used to treat psoriasis, and it also has a certain relief effect on malignant lymphoma, head and neck tumors, and soft tissue sarcoma.
1,2-Ethylenediamine used as analytical reagent, organic solvent, antifreeze and emulsifier.
1,2-Ethylenediamine used as analytical reagent, epoxy resin curing agent, also used in organic synthesis and pharmaceutical industry.
Synthesis
1,2-Ethylenediamine can be synthesized from ethanolamine (EA) with ammonia over acidic types of zeolite catalyst.
1,2-Ethylenediamine is produced industrially by the reaction of 1,2-dichloroethane with ammonia in a liquid base under high temperature and high presseure.
The synthesis of 1,2-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.
Reactivity Profile
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.
1,2-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.
1,2-Ethylenediamine reacts violently with ethylene chlorohydrin.
Health Hazard
1,2-Ethylenediamine 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 1,2-Ethylenediamine's 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 1,2-Ethylenediamine.
The acute oral toxicity value in animalswas low to moderate.
An oral LD50 value inrats is 500 mg/kg (NIOSH 1986).
Human 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 1,2-Ethylenediamine 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 burn.
1,2-Ethylenediamine, in addition, is a potent allergen causing hypersensitization in exposed individuals (HSDB 1988).
Because of such reactions, 1,2-Ethylenediamine has been difficult to establish threshold limits that will prevent the hypersensitization response.
Allergic reactions to 1,2-Ethylenediamine 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 1,2-Ethylenediamine 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 1,2-Ethylenediamine 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 1,2-Ethylenediamine (Prystowsky et al 1979).
Fire Hazard
Burning 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.
Contact allergens
1,2-Ethylenediamine is used in numerous industrial processes as a solvent for casein or albumin, as a stabilizer in rubber latex, and as a textile lubricant.
1,2-Ethylenediamine can be found in epoxy resin hardeners, cooling oils, fungicides, and waxes.
Contact dermatitis from 1,2-Ethylenediamine is almost exclusively due to topical medicaments. Occupational contact dermatitis in epoxy resin systems is rather infrequent.
1,2-Ethylenediamine can crossreact with triethylenetetramine and diethylenetriamine. 1,2-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.
Production Method
1. dichloroethane ammonification method: 1,2-dichloroethane and liquid ammonia are sent to the reactor, and the thermal ammonolysis reaction is carried out at a temperature of 120-180 ℃ and a pressure of 1.98-2.47MPa. the reaction liquid is evaporated with part of water and excess ammonia, then sent to the neutralizer, and neutralized with 30% liquid alkali, after concentration, desalination and crude distillation, crude 1,2-Ethylenediamine, crude triamine and polyamine mixture are obtained.
Finally, crude 1,2-Ethylenediamine is rectified under normal pressure to obtain 1,2-Ethylenediamine finished product with a content of 70%, and then pressurized distillation can obtain 90% finished product.
The reaction process also produces diethylenetriamine by-products, and the reaction continues to produce triethylenetetramine, tetraethylenepenamine and other polyethylenepolyamines.
2. 1,2-Ethylenediamine ammonification method: ethanolamine, cobalt catalyst and water are added to the reactor, and then ammonia and hydrogen are introduced into the reactor, and the reaction is carried out at 20MPa and 170-230 ℃.
After 5-10h, 1,2-Ethylenediamine can be prepared, and its conversion rate reaches 69%.
The side reactions of the reaction process also generate diethylenetriamine, piperazine, aminoethyl piperazine, hydroxyethyl piperazine, etc.
3. In addition, ethylenediamine can also be fractionated from the mother liquor of piperazine hexahydrate, a pharmaceutical product.
The preparation methods include dichloroethane method and ethanolamine method.
(1) Dichloroethane method is directly synthesized by dichloroethane and ammonia, and is carried out in a molybdenum-titanium stainless steel reaction pipeline.
The reaction temperature is controlled at 160~190 ℃, the pressure is 2.452 MPa, and the reaction time is 1.5min.
The synthesized liquid after the reaction is evaporated with a part of water and excess ammonia into a neutralizer, and is neutralized with 30% alkali solution, then through concentration, desalination, crude distillation to obtain a mixture of crude ethylenediamine, crude triamine, crude polyamine, etc., and finally the crude ethylenediamine is rectified at normal pressure to obtain ethylenediamine finished product, the content is 70%, and the product with 90% purity can be obtained by distillation under pressure.
The reaction equation is shown in the figure:$SClCH2CH2Cl + 2NH4OH → HCl · H2NCH2CH2NH2 · HCl + 2H2O[2NaOH]→ NH2CH2CH2NH2 + 2Nacl(2)
1,2-Ethylenediamine method evaporates ethanolamine, ammonia and circulating materials into a gas phase mixture and passes into a fixed bed reactor.
The reaction is carried out in a hydrogen stream at a reaction temperature of 300 ℃ and a pressure of 25 MPa.
After partial condensation of the reaction product, ammonia and hydrogen in the gas phase are separated and returned to the reactor after compression, after deamination, the liquid phase reactants enter the rectification tower after deamination, and evaporate 1,2-Ethylenediamine and piperazine from the top of the tower, and further decompose to obtain ethylenediamine finished products.
NH2CH2CH2OH+NH3→NH2CH2CH2NH2+H2O
Synonyms
ethylenediamine
Ethane-1,2-diamine
107-15-3
1,2-Ethanediamine
1,2-Diaminoethane
Ethylene diamine
Ethylendiamine
edamine
Dimethylenediamine
1,2-Ethylenediamine
Aethaldiamin
Aethylenediamin
Ethyleendiamine
Ethylene-diamine
beta-Aminoethylamine
1,2-Diaminoaethan
Algicode 106L
Amerstat 274
1,2-Diamino-ethaan
1,2-Diamino-ethano
Ethylenediamine [JAN]
NCI-C60402
Edamine [INN]
ETHYLENEDIAMINE ANHYDROUS
CHEBI:30347
CHEMBL816
H2NCH2CH2NH2
ETHANE,1,2-DIAMINO
60V9STC53F
27308-78-7
2-Aminoethylammonium chloride
1, 2-Diaminoethane
NCGC00091527-01
1,2-diaminoethane phase II
EN
1,2-diaminoethane phase I beta
Aethaldiamin [German]
Caswell No. 437
1,2-diaminoethane phase I alpha
Ethyleendiamine [Dutch]
Aethylenediamin [German]
Ethylene-diamine [French]
Ethane-1,2-diammonium bromide
CAS-107-15-3
Ethylenediamine, ReagentPlus(R), >=99%
1,2-Diaminoaethan [German]
1,2-Diamino-ethaan [Dutch]
CCRIS 5224
HSDB 535
1,2-Diamino-ethano [Italian]
Aminophylline Injection
EINECS 203-468-6
UN160
EPA Pesticide Chemical Code 004205
Ethylenediamine [USP:JAN]
BRN 0605263
UNII-60V9STC53F
ethylenediarnine
AI3-24231
2-aminoethylamine
ethylene di amine
1,4-diazabutane
1,2-diaminoethan
ethylene - diamine
EDN
1,2-ethylendiamine
MFCD00008204
1,2-diamino-ethane
ethane 1,2-diamine
N,N'-ethylenediamine
Ethylenediamine, 8CI
1,2-ethylene diamine
1,2-ethylene-diamine
Ethylenediamine [UN1604] [Corrosive]
.beta.-Aminoethylamine
ethane-1, 2-diamine
N,N'-ethylene diamine
Ethylenediamine, BioXtra
Epitope ID:117724
EC 203-468-6
ETHYLENEDIAMINE [II]
ETHYLENEDIAMINE [MI]
4-04-00-01166 (Beilstein Handbook Reference)
Ethylenediamine (USP/JP15)
Ethylenediamine (USP/JP17)
ETHYLENEDIAMINE [HSDB]
ETHYLENEDIAMINE [INCI]
BDBM7972
NH2(CH2)2NH2
ETHYLENEDIAMINE [MART.]
DTXSID5021881
ETHYLENEDIAMINE [WHO-DD]
624-59-9 (di-hydrobromide)
333-18-6 (di-hydrochloride)
5700-49-2 (di-hydriodide)
Ethylenediamine, analytical standard
STR00309
Tox21_111145
Tox21_201202
STL264241
ZINC37253587
ETHYLENEDIAMINE [EP MONOGRAPH]
AKOS000118850
DB14189
ETHYLENEDIAMINE [USP MONOGRAPH]
UN 1604
Ethylenediamine, for synthesis, 99.0%
NCGC00091527-02
NCGC00258754-01
BP-20367
Ethylenediamine [UN1604] [Corrosive]
E0077
E0081
EN300-19398
D01114
Ethylenediamine, SAJ special grade, >=99.0%
Ethylenediamine, meets USP testing specifications
Ethylenediamine, Vetec(TM) reagent grade, >=98%
Q411362
J-001723
Ethylenediamine, purified by redistillation, >=99.5%
TIZANIDINE HYDROCHLORIDE IMPURITY H [EP IMPURITY]
Z104473714
Ethylenediamine, puriss. p.a., absolute, >=99.5% (GC)
QuadraPure(R) AEA, 100-400 mum particle size, extent of labeling: 1.3 mmol/g loading, 1 % cross-linked with divinylbenzene
