1,6-Diaminohexane
1,6-Hexanediamine
CAS: 124-09-4
Molecular Formula: C6H16N2
1,6-Diaminohexane - Names and Identifiers
| Name | 1,6-Hexanediamine |
| Synonyms | HMDA NCI-C61405 H2N(CH2)6NH2 Hexylenediamine 1,6-Hexanediamine 1,6-diamino-hexan 1,6-Diaminohexane hexane-1,6-diamine Hexamethylendiamine hexane-1,6-diaminium Hexamethylenediamine cyclohexane diammoniate 1,6-Hexamethylenediamine hexamethylenediamine,solid 6-aminohexan-1-aminium chloride hexamethylenediamine(1,6-hexanediamine) |
| CAS | 124-09-4 |
| EINECS | 204-679-6 |
| InChI | InChI=1/C6H12.2H2N/c1-2-4-6-5-3-1;;/h1-6H2;2*1H3 |
1,6-Diaminohexane - Physico-chemical Properties
| Molecular Formula | C6H16N2 |
| Molar Mass | 116.2 |
| Density | 0.89g/mLat 25°C(lit.) |
| Melting Point | 42-45°C(lit.) |
| Boling Point | 204-205°C |
| Flash Point | 201°F |
| Water Solubility | 490 g/L (20 ºC) |
| Solubility | alcohol: soluble(lit.) |
| Vapor Presure | 0.25 hPa (20 °C) |
| Vapor Density | 4 (vs air) |
| Appearance | Solution |
| Color | White, may discolor during storage |
| Exposure Limit | ACGIH: TWA 0.5 ppm |
| Merck | 14,4695 |
| BRN | 1098307 |
| pKa | 11.857(at 0℃) |
| PH | 12.4 (100g/l, H2O, 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, organic materials. |
| Sensitive | Hygroscopic |
| Explosive Limit | 0.9-7.6%(V) |
| Refractive Index | n20/D 1.439(lit.) |
| Physical and Chemical Properties | White flaky crystals, with ammonia odor. |
| Use | Used in organic synthesis and polymerization of high molecular compounds. Mainly used in the production of polyamide, such as nylon 66, Nylon 610, etc.; Also used in the synthesis of diisocyanate; And used as urea-formaldehyde resin, epoxy resin curing agent, organic crosslinking agent. Hexamethylene diamine can be produced from adiponitrile, hexanediol and caprolactam, but almost all processes for the large-scale production of hexamethylene diamine are based on adiponitrile. |
1,6-Diaminohexane - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R34 - Causes burns R37 - Irritating to the respiratory system R21/22 - Harmful in contact with skin and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | 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.) S22 - Do not breathe dust. S27 - Take off immediately all contaminated clothing. |
| UN IDs | UN 2735 8/PG 3 |
| WGK Germany | 3 |
| RTECS | MO1180000 |
| FLUKA BRAND F CODES | 10-34 |
| TSCA | Yes |
| HS Code | 2921 22 00 |
| Hazard Class | 8 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 850 mg/kg LD50 dermal Rabbit 1110 mg/kg |
1,6-Diaminohexane - Upstream Downstream Industry
| Raw Materials | 1,6-Hexanediamine |
1,6-Diaminohexane - Nature
Open Data Verified Data
White Flake Crystal, ammonia odor, flammable. Melting point 41~42 deg C. Boiling Point 204~205 deg C. The relative density was 0. 883. Viscosity (50 ℃)1. 46kPa -s. Refractive index 4498. Flash point 81 °c. Slightly soluble in water: O ℃,lOOmL water dissolved 2.Og, 30 ℃,lOOmL water dissolved 0.85g; Difficult to dissolve in ethanol, ether and benzene. Moisture and carbon dioxide are readily absorbed in the air.
Last Update：2024-01-02 23:10:35
1,6-Diaminohexane - Preparation Method
Open Data Verified Data
According to the different sources of starting materials used, 1,6-hexamethylene diamine production method at present, the method of hydrogenation of adiponitrile and the method of using adipic acid as raw material are used in industrial production.
- 1. Adiponitrile catalytic hydrogenation method this method is divided into low pressure and high pressure two. (1) low pressure method with adiponitrile as raw material, framework nickel as catalyst, ethanol as solvent, sodium hydroxide as co-catalyst, according to a certain proportion of the mixing tank after mixing, the reaction is carried out at a temperature of 70~90 ℃ and a pressure of 2~3MPa to obtain three kinds of materials: gas phase, liquid phase and solid phase. After filtration, the reaction solution is sent to a distillation tower and subjected to distillation and rectification, dealcoholization, dehydration, Coke removal, removal of light and heavy components, top extraction distillation to obtain fine 1,6 A hexanediamine product, the yield of up to 97%. (2) high pressure method with skeleton cobalt as catalyst, liquid ammonia as diluent, hydrogen, adiponitrile and liquid ammonia with 38:1:25(mol) respectively, the pump was sent to the preheater, and the mixture was heated to 90 ° C., and then sent to the fixed bed reactor at 90-150 ° C. And 19.6-29. Under the pressure of 4MPa, the reaction is carried out, and the gas and liquid phase are condensed and separated to obtain crude 1,6-hexamethylene diamine, which is then continuously distilled through 5 distillation columns to dehydrate, de-coke, the light and heavy components and impurities are removed and purified by rectification to obtain a finished product of 1, 6-hexanediamine with a yield of 90%-93%.
- 2. Method using adipic acid as raw material in this method, adipic acid vapor and excess ammonia are heated to 340 ℃ by silica gel and other dehydration catalysts to generate adiponitrile, and then methanol and liquid ammonia are added thereto, with diatomite nickel as catalyst, in 90~100 ℃, with 10. 1325~20. 265MPa hydrogen reduction to get the finished product
Last Update：2022-01-01 10:35:37
1,6-Diaminohexane - Use
Open Data Verified Data
This product is mostly used for the synthesis of nylon 66 and 610 resin, also used for the synthesis of polyurethane resin, ion exchange resin and hexylene diisocyanate, also used for the preparation of crosslinking agent, adhesive, aviation coatings, epoxy resin curing agent, rubber vulcanization accelerator, and used as textile and paper industry stabilizer, bleaching agent, aluminum alloy corrosion inhibitor and neoprene emulsifier.
Last Update：2022-01-01 10:35:37
1,6-Diaminohexane - Safety
Open Data Verified Data
- This product is toxic and can cause changes in nervous system, vascular tension and hematopoietic function. Inhalation of high concentrations of 1,6 hexamethylene diamine can cause severe Head Pain. Skin exposure to high concentrations of 1,6 hexamethylene diamine can cause dry or wet necrosis, and low concentrations can cause dermatitis and eczema. Splash into the eye causes redness and swelling of the eyelids, Conjunctival Congestion, and even blindness. The photosensitivity threshold for human eyes was 0.0027mg/m3 and the olfactory threshold was 0. 0033mg/m3. The maximum allowable concentration in the workplace is 1mg/m3. Inhalation should be moved to the fresh air, inhalation of 1% boric acid solution, skin contamination with 3% acetic acid solution wet, with a large amount of water. Oral administration of dilute vinegar, lemon juice gastric lavage, sent to the hospital for diagnosis and treatment.
- This product is easily deliquescent and flammable. It shall be filled in a sealed tinplate drum, 200kg per barrel. Store in a cool and ventilated place, protected from light and heat.
Last Update：2022-01-01 10:35:38
1,6-Diaminohexane - Reference Information
| LogP | 0.4 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | hexamethylene diamine is an amine-based organic compound. It is a kind of diamine, which contains a carbon chain skeleton of hexane and amino functional groups at both ends. It is a colorless solid with strong ammonia odor, similar to piperidine. |
| Application | hexamethylene diamine is an important organic chemical intermediate, which is mostly used as a raw material for the synthesis of polyamide, such as for the synthesis of nylon-6e salt, but also commonly used as urea resin and epoxy resin curing agent and crosslinking agent. At present, with the development of synthetic fiber industry, the demand for hexamethylene diamine compounds in the world is increasing, and the market demand is larger. |
| Use | used for Nylon 66, polyurethane foam raw materials and epoxy resin curing agent This product is mostly used in the synthesis of nylon 66 and 610 resin, also used in the synthesis of polyurethane resin, ion exchange resin and hexylene diisocyanate, and used as a curing agent for urea-formaldehyde resin, epoxy resin, etc., organic crosslinking agent, etc., also used as a stabilizer for textile and paper industry, bleaching agent, aluminum alloy corrosion inhibitor and chloroprene rubber emulsifier. Hexanediamine and hydrochloric acid salt below 28 °c to obtain 1, 6-hexanediamine hydrochloride ([6055-52-3]), can be used to produce bactericide chlorhexidine acetate. Hexanediamine also has some applications in the production of adhesives, aviation coatings and rubber vulcanization accelerators. used in organic synthesis and polymerization of polymer compounds. Mainly used in the production of polyamide, such as nylon 66, Nylon 610, etc.; Also used in the synthesis of diisocyanate; And used as urea-formaldehyde resin, epoxy resin curing agent, organic crosslinking agent. Hexamethylene diamine can be produced from adiponitrile, hexanediol and caprolactam, but almost all processes for the large-scale production of hexamethylene diamine are based on adiponitrile. organic synthesis, nylon 66 intermediate. |
| production method | the production of hexamethylene diamine initially uses furfural as a raw material, and there are many industrial methods for the production of hexamethylene diamine, depending on the raw materials used, there are adipic acid method, butadiene method, acrylonitrile method, hexylene glycol method and caprolactam method. Among them, the adipic acid method, the butadiene method and the acrylonitrile dimerization method are the hydrogenation of the intermediate adiponitrile to generate hexamethylene diamine. At present, almost all the methods for large-scale production of hexamethylene diamine are the catalytic hydrogenation of adiponitrile. There are two kinds of catalytic hydrogenation of adiponitrile in industry: high pressure method and low pressure method. (1) high pressure method using cobalt-copper catalyst, reaction temperature 100-135 ℃, pressure 60-65mpa; Can also use iron catalyst, reaction temperature 100-180 ℃, pressure can use liquid ammonia, sometimes aromatic hydrocarbons (e. G., toluene) are also added. The selectivity to hexamethylene diamine is about 90-95%. In production, a gas mixture of liquid hexonitrile, toluene and ammonia with hydrogen-containing ammonia and a small amount of adiponitrile and toluene is fed into a reactor equipped with a cobalt-copper catalyst, and the resulting crude hexamethylene diamine is removed, it is subjected to azeotropic distillation with water and then to vacuum distillation several times to obtain a high-purity product suitable for the manufacture of nylon 66. (2) low pressure method using framework nickel, iron-nickel or chromium-nickel catalyst, the reaction is carried out in sodium hydroxide solution. The selectivity of hexamethylene diamine can reach 99% at a reaction temperature of about 75 ℃ and a pressure of 3MPa. In order to prevent poisoning of the catalyst, the purity of the raw material adiponitrile is highly required. 2. Method using adipic acid as raw material this method is to generate adiponitrile by heating adipic acid vapor together with excess ammonia to 340 ℃ silica gel and other dehydration catalysts, Then, methanol and liquid ammonia were added thereto, and nickel diatomite was used as a catalyst for reduction at 90-100 ° C. With 10.1325-20.265MPA hydrogen to obtain a finished product. 3. Caprolactam process is generally used for the treatment of caprolactam and other small production units. It is from caprolactam and ammonia in phosphate (such as manganese, aluminum, calcium, barium or zinc phosphate) in the presence of gas phase reaction to produce amino acetonitrile, reaction temperature 350 deg C, the yield was almost 100%. The resulting aminocapronitrile is then subjected to a hydrogenation reaction to form hexamethylene diamine, a process similar to the hydrogenation of adiponitrile. |
| category | corrosive article |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 750 mg/kg; Inhalation-mouse LCL0: 750 mg/m3/10 min |
| flammability hazard characteristics | flammability; Combustion emission toxic NOx fumes |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from acids and oxidants. |
| fire extinguishing agent | foam, carbon dioxide, sand |
| Occupational Standard | TWA 1 mg/m3; Tel 2 mg/m3 |
| spontaneous combustion temperature | 305°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:44
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Raw Materials for 1,6-Diaminohexane