1,2-Diaminoethane
Ethylenediamine
CAS: 107-15-3
Molecular Formula: C2H8N2
1,2-Diaminoethane - Names and Identifiers
| Name | Ethylenediamine |
| Synonyms | EDA amerstat274 Ethylenediamine Ethylendiaminum 1,2-Diaminoethane ethane-1,2-diamine ethane-1,1-diamine 1,2-ethylenediamine beta-Aminoethylamine EDA EthylenediaMine a (E)-ethene-1,2-diamine Ethylenediamineanhydrous Ethylenediamine diacetate 1,2-Diaminoethane anhydrous ETHYLENEDIAMINE FOR SYNTHESIS Ethylenediamine and derivatives |
| CAS | 107-15-3 |
| EINECS | 203-468-6 |
| InChI | InChI=1/C2H8N2/c3-1-2-4/h1-4H2 |
| InChIKey | PIICEJLVQHRZGT-UHFFFAOYSA-N |
1,2-Diaminoethane - Physico-chemical Properties
| Molecular Formula | C2H8N2 |
| Molar Mass | 60.1 |
| Density | 0.899 g/mL at 25 °C (lit.) |
| Melting Point | 8.5 °C (lit.) |
| Boling Point | 118 °C (lit.) |
| Flash Point | 93°F |
| Water Solubility | miscible |
| Solubility | ethanol: soluble(lit.) |
| Vapor Presure | 10 mm Hg ( 20 °C) |
| Vapor Density | 2.07 (vs air) |
| Appearance | Liquid, Fuming In Air |
| Specific Gravity | 0.899 |
| Color | colorless to pale yellow |
| Odor | Strong ammoniacal odor; ammonia-like mild and ammoniacal odor. |
| Exposure Limit | TLV-TWA 10 ppm (～25 mg/m3) (ACGIH,MSHA, and OSHA); IDLH 2000 ppm(NIOSH). |
| Merck | 14,3795 |
| BRN | 605263 |
| pKa | 10.712(at 0℃) |
| PH | 12.2 (100g/l, H2O, 20℃) |
| Storage Condition | Flammables area |
| Sensitive | Air Sensitive |
| Explosive Limit | 2-17%(V) |
| Refractive Index | n20/D 1.4565(lit.) |
| Physical and Chemical Properties | Density 0.898 melting point 11°C boiling point 117-118°C refractive index 1.4555-1.4575 flash point 34°C water-soluble miscible |
| Use | For the treatment of psoriasis, Malignant lymphoma, head and neck cancer, soft tissue sarcoma also has a certain role in the relief |
1,2-Diaminoethane - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R10 - Flammable R21/22 - Harmful in contact with skin and if swallowed. R34 - Causes burns R42/43 - May cause sensitization by inhalation and skin contact. |
| Safety Description | S23 - Do not breathe vapour. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN 1604 8/PG 2 |
| WGK Germany | 2 |
| RTECS | KH8575000 |
| FLUKA BRAND F CODES | 10-34 |
| TSCA | Yes |
| HS Code | 29212110 |
| Hazard Class | 8 |
| Packing Group | II |
| Toxicity | LD50 orally in rats: 1.16 g/kg (Smyth) |
1,2-Diaminoethane - Upstream Downstream Industry
1,2-Diaminoethane - Nature
Open Data Verified Data
colorless and strongly alkaline volatile viscous liquid. Ammonia odor. Flammable. Soluble in water and ethanol, soluble in water hydrate formation. Slightly soluble in ether, insoluble in benzene. Ethylenediamine has strong alkaline, easy to salt when acid. It can absorb the moisture and carbon dioxide in the air to produce non volatile carbonate. Ethylenediamine can also form complexes with many inorganic substances. In case of open flame, high heat or contact with oxidant, there is a risk of combustion explosion. With sulfuric acid, nitric acid, hydrochloric acid and other strong acid reaction.
Last Update：2024-01-02 23:10:35
1,2-Diaminoethane - Preparation Method
Open Data Verified Data
aqueous ammonia was added to dichloroethane and the mixture was heated to 115-120 °c for reaction. The reaction solution was evaporated until crystallization started, filtered, and washed with ethanol. Anhydrous ethylenediamine was obtained by distillation in a nitrogen bath.
Last Update：2022-01-01 09:26:18
1,2-Diaminoethane - Use
Open Data Verified Data
for non-aqueous solution titration. Aminocarboxylic complexing agent. Determination of antimony, bismuth, cadmium, cobalt, copper, mercury, silver and uranium. Used as a curing agent for epoxy resin, protein, fibrin solvent.
Last Update：2022-01-01 09:26:18
1,2-Diaminoethane - Safety
Open Data Verified Data
rat oral LD50:1.16g/kg. This substance may be harmful to the environment, and special attention should be paid to the water body. Should be stored separately from oxidants and acids. Staff should be protected. If the eyes and skin are touched, they should be immediately rinsed with plenty of flowing water. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight.
Last Update：2022-01-01 09:26:19
1,2-Diaminoethane - Reference Information
| Henry's Law Constant | 1.69(x 10-9 atm?m3/mol) at 25 °C (Westheimer and Ingraham, 1956) |
| LogP | -1.6 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| The simplest diamine | Ethylenediamine is the simplest diamine, which is an aliphatic diamine with the molecular formula NH2(CH2)2NH2. It was first produced by Hofmann in 1871. It is a colorless, transparent and viscous liquid with ammonia smell. Volatile together with water vapor. Relative density 0.8995(20 ℃), melting point 8.5 ℃ (anhydrous). Boiling point 116.5 ℃, 62.5 ℃(13.332 × 103Pa). Flash point 33.9 ℃. 1.4568 refractive index. The viscosity 1.54mPa s(25 ℃). The melting point of monohydrate is 11 ℃. Boiling point 118.5 ℃. Vapor pressure 1.200 × 103Pa (20 ℃), 2.226 × 103Pa(30 ℃), 6.799 × 103Pa(50 ℃), 11.132 × 103Pa (60 ℃), 26.531 × 103Pa (80 ℃), 38.663 × 103Pa(90 ℃), 55.995 × 103Pa (100 ℃), 78.913 × 103Pa)(110 ℃). Ethylenediamine is soluble in water, ethanol and acetone, but insoluble in ether and benzene. It can form azeotropic mixture with water, n-butanol and toluene. The content of this product is (mass fraction%): 81.6, 35.7 and 30.8 respectively, and the azeotropic point is 119 ℃, 125 ℃ and 104 ℃ respectively. It forms an explosive mixture with air, and the explosion limit is 2.7 ~ 16.6% (volume fraction). Ethylenediamine is alkaline, can form water-soluble salts with inorganic acids, can absorb carbon dioxide in the air, and form non-volatile carbonates. Smoke is produced in the air. Reacts with inorganic acid to form a salt dissolved in water. Can be sulfonylated to form sulfonamide. Reacts with nitric acid to release nitrogen, which can be used to determine the amount of-NH2. Reacts with aldehyde to form Schiff base. Reacts with urea to produce ethylene urea. Reacts with carboxylic acid, acid anhydride, and acid halide to form amide. Reacts with carbon disulfide to produce ethylene dithiocarbamate. Under the action of a catalyst, it can be cyclized at high temperature to form piperazine. It can be complexed with copper salt, manganese salt and cobalt salt. It is commonly used as a solvent for casein, albumin, shellac and sulfur, a stabilizer for emulsifier and rubber emulsion, an ammonia complexing agent (EDTA), an insecticidal and bactericidal agent, an epoxy resin hardener, an anti-coagulation solution and an anticoagulant for textile lubricating oil. This product is corrosive, toxic, irritating, can strongly stimulate the eyes, skin and respiratory organs, causing allergies. Inhalation of high concentrations of vapor can lead to death. The maximum allowable concentration in the air is 10ppm. In case of fire, high temperature, oxidant, there is a risk of combustion. In case of acetic acid, acetic anhydride, carbon disulfide, chlorosulfonic acid, hydrochloric acid, nitric acid, sulfuric acid, fuming sulfuric acid, silver perchlorate, etc. react violently. |
| Uses | 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. 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. It 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. It is used to treat psoriasis, and it also has a certain relief effect on malignant lymphoma, head and neck tumors, and soft tissue sarcoma Used as analytical reagent, organic solvent, antifreeze and emulsifier Used as analytical reagent, epoxy resin curing agent, also used in organic synthesis and pharmaceutical industry |
| 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 ethylenediamine, crude triamine and polyamine mixture are obtained. Finally, crude ethylenediamine is rectified under normal pressure to obtain 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. Ethanolamine 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, 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. Ethylene oxide ammonification. 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) ethanolamine 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 ethylenediamine and piperazine from the top of the tower, and further decompose to obtain ethylenediamine finished products. NH2CH2CH2OH+NH3→NH2CH2CH2NH2+H2O |
| category | flammable liquid |
| toxicity classification | highly toxic |
| acute toxicity | oral administration-rat LD50: 500 mg/kg; Inhalation-mouse LC50: 300 mg/m3 |
| stimulation data | skin-rabbit 10 mg/24 hours severe; Eye-rabbit 0.75 mg/24 hours severe |
| explosive hazard characteristics | blastable when mixed with air |
| flammability hazard characteristics | it is more flammable when exposed to open flames, high temperatures, and oxidants; combustion produces toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and acids |
| fire extinguishing agent | dry powder, carbon dioxide, foam, 1211 fire extinguishing agent |
| occupational standard | TWA 25 mg/m3; STEL 35 mg/m3 |
| auto-ignition temperature | 716 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
| immediate life-threatening and health concentration | 1,000 ppm |
Last Update：2024-05-22 16:54:56
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Raw Materials for 1,2-Diaminoethane
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