triethylenediamine
1,4-Diazabicyclo[2.2.2]octane
CAS: 280-57-9
Molecular Formula: C6H12N2
triethylenediamine - Names and Identifiers
triethylenediamine - Physico-chemical Properties
| Molecular Formula | C6H12N2 |
| Molar Mass | 112.17 |
| Density | 1.02g/mL |
| Melting Point | 156-159°C(lit.) |
| Boling Point | 174 °C |
| Flash Point | 198°F |
| Water Solubility | 46 g/100 mL (26 ºC) |
| Solubility | Soluble in water (460 mg/ml) |
| Vapor Presure | 2.9 mm Hg ( 50 °C) |
| Appearance | White Crystals |
| Color | White to pale yellow |
| Merck | 14,9669 |
| BRN | 103618 |
| pKa | 3.0, 8.7(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable, but very hygroscopic. Incompatible with strong oxidizing agents, strong acids. Highly flammable. |
| Sensitive | Hygroscopic |
| Refractive Index | n20/D 1.4634(lit.) |
| MDL | MFCD00006689 |
| Physical and Chemical Properties | Density 1.14 melting point 155-160°C boiling point 174°C flash point 62°C water-soluble 46g/100 mL (26°C) |
| Use | Can be used for the production of polyurethane foam, elastomers and Coatings and Other Products |
triethylenediamine - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R41 - Risk of serious damage to eyes R36/38 - Irritating to eyes and skin. R11 - Highly Flammable |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S60 - This material and its container must be disposed of as hazardous waste. S37/39 - Wear suitable gloves and eye/face protection S3 - Keep in a cool place. S16 - Keep away from sources of ignition. S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 1325 4.1/PG 2 |
| WGK Germany | 1 |
| RTECS | HM0354200 |
| FLUKA BRAND F CODES | 3 |
| TSCA | Yes |
| HS Code | 29335920 |
| Hazard Class | 8 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 700 mg/kg |
triethylenediamine - Nature
Open Data Verified Data
colorless hygroscopic crystals, with a strong ammonia odor, rapidly sublimate at room temperature. It has a highly symmetric molecular cage-like structure. Solubility (g/log) 45, 13, 51, 77 and 26.1 of triethylenediamine in water, acetone, benzene, ethanol and butanone. An explosion occurs when exposed to hydrogen peroxide. And carbon at 230 deg C can occur spontaneous combustion. The reaction occurs in contact with nitrocellulose.
Last Update：2024-01-02 23:10:35
triethylenediamine - Preparation Method
Open Data Verified Data
with Hydroxyethyl piperazine or double Hydroxyethyl piperazine as raw material, under the action of catalyst, high temperature cyclization reaction, preparation of triethylene diamine.
Last Update：2022-01-01 09:30:21
triethylenediamine - Introduction
Soluble in water, solubility in water: 46g/100ml (26 C), soluble in conventional organic solvents such as acetone, benzene and ethanol, soluble in pentane, hexane, heptane and other linear hydrocarbons; exposed to air It is easy to absorb moisture, deliquesce and agglomerate, and can absorb CO2 in the air and yellow.
Last Update：2022-10-16 17:24:12
triethylenediamine - Use
Open Data Verified Data
used as a corrosion inhibitor in boiler water treatment. It is also used as a catalyst for polyurethane foaming and polymerization, an accelerator for curing epoxy resin, and a catalyst for acrylonitrile, ethylene and alkylene oxide.
Last Update：2022-01-01 09:30:21
triethylenediamine - Safety
Open Data Verified Data
strong alkaline, its vapor is irritating to the eyes, nostrils, throat and respiratory organs, is an allergen, may cause allergies and asthma, and can cause pain. Avoid contact during use. Avoid inhalation of vapors and mist droplets. If contact with the skin and eyes, should be immediately
Rinse with plenty of running water. Easy to absorb moisture, should be stored in a dry place, not heated. It cannot be stored and transported with the acidic substance.
Last Update：2022-01-01 09:30:22
triethylenediamine - Reference Information
| LogP | -0.49 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | triethylenediamine, also known as 1,4-diazabicyclo [2.2.2] octane, or triethylenediamine, abbreviated as DABCO or TEDA in English, and its chemical formula is C6H12N2. triethylenediamine is a very important and efficient catalyst in chemical production and is widely used in condensation reaction, polyurethane foaming catalysis, pesticide synthesis and electroplating industries. |
| Application | Triethylenediamine is an important chemical raw material, used as a catalyst for polyurethane and also used as an oil additive; used as a corrosion inhibitor in boiler water treatment, It is also used as a catalyst for polyurethane foaming and polymerization, an accelerator for epoxy resin curing, a catalyst for acrylonitrile, ethylene and alkane ethylene oxide; as a non-nucleophilic base, the reagents that split the reaction of β-mono-keto acid vinegar and the diester and dehydrohalogenation form complexes with organic magnesium, lithium, and zinc compounds to increase activity and participate in many reactions |
| preparation | (1) dissolving piperazine with methanol in advance, adding 123.9g(1.05mol) dimethyl oxalate to the reaction bottle with mechanical stirring device, adding methanol until complete dissolution, adding 4.3g sodium methoxide, and then slowly adding 86g(1mol) piperazine dissolved in methanol at a temperature of 40 ℃, after dropping, stirring for 1~2 hours, filtering, the resulting filter cake is washed with methanol and dried to obtain the intermediate product dioxytriethylenediamine;(2) Add the dioxytriethylenediamine prepared in step (1) to the high-pressure reaction kettle, add tetrahydrofuran until it is completely dissolved, add 4.3g palladium charcoal, seal the lid of the kettle tightly, raise the temperature to 175 ℃, and fill the high-pressure valve with hydrogen until the pressure reaches 5MPa, during the reaction, hydrogen is continuously filled to maintain the pressure until the pressure does not drop significantly to obtain crude triethylenediamine;(3) Open the exhaust valve of the high-pressure reaction kettle to exhaust, open the kettle cover, and drop to room temperature. The crude triethylenediamine prepared in step (2) is filtered to remove the catalyst, tetrahydrofuran is rectified, then ethanol is added to beat, filtered, and the resulting filter cake is dried to obtain the final product triethylenediamine 98.11g. The molar yield of triethylenediamine was calculated as 87.6%, and the purity of triethylenediamine detected by gas phase was 99.0%. |
| purification method | 2500g of triethylenediamine reaction solution prepared by the reaction of ethylenediamine and liquid ammonia is subjected to ordinary atmospheric distillation, the triethylenediamine reaction solution is heated to 160 ℃ until the product is evaporated, the remaining solution 1200g is used as distillation raw material, the mass percentage of triethylenediamine is 60%, and the mass of triethylenediamine is 720g, 288g of azeotropic agent 2-methyl -3-hydroxypropylamine is added to the distillation raw material, mixed evenly, added to the tower kettle of the distillation tower, the theoretical plate number of the distillation tower is 20, the distillation is started under the conditions of absolute vacuum degree of 40kPa and the temperature of the reaction liquid of the tower kettle is 130 ℃, the reflux ratio is controlled to be 0.2:1, the fraction before 120~122 ℃ is collected, the reflux ratio is continuously heated to 170 ℃, and the reflux ratio is controlled to be 5:1. Collect the 140~141 ℃ fraction, reduce the 140~141 ℃ fraction to room temperature, crystallize and filter to obtain 615g of triethylenediamine, and the purity detected by gas chromatography is 99.6%. |
| use | can be used for the production of polyurethane foam, elastomer, coating and other products catalyst and petroleum additive for the preparation of polyurethane foam. |
| production method | 1,2-dichloroethane and ammonia are sent into a tubular reactor, and hot-pressed ammoniation reaction is carried out at 150-250 ℃ and 392kPa pressure. The reaction solution is neutralized with alkali to obtain mixed free amine, which is concentrated to remove sodium chloride, and then the crude is distilled under reduced pressure to collect different fractions for separation. At the same time as the product is obtained, ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine and polyethylenepolyamine are produced in parallel. The product can be obtained by fractionation from the mother liquor of piperazine hexahydrate, and about 3-4t of triethylenediamine hexahydrate can be obtained from the first production of 100t of piperazine hexahydrate. |
| spontaneous combustion temperature | 350°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:11
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