1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane
Methenamine
CAS: 100-97-0
Molecular Formula: C6H12N4
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Names and Identifiers
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Physico-chemical Properties
| Molecular Formula | C6H12N4 |
| Molar Mass | 140.19 |
| Density | 1.33 |
| Melting Point | 280 °C (subl.) (lit.) |
| Boling Point | 246.7°C (rough estimate) |
| Flash Point | 482°F |
| Water Solubility | 895 g/L (20 ºC) |
| Solubility | H2O: 1M at20°C, clear, colorless |
| Vapor Presure | <0.01 mm Hg ( 20 °C) |
| Vapor Density | 4.9 (vs air) |
| Appearance | Solid |
| Color | white |
| Odor | Odorless |
| Merck | 14,5966 |
| BRN | 2018 |
| pKa | 5.1(at 25℃) |
| PH | 7-10 (100g/l, H2O, 20℃) |
| Storage Condition | 贮存于阴凉、干燥处，避免日晒、雨淋；有效贮存期12个月。运输时要与氧化物隔离。 |
| Stability | Stable. Incompatible with strong acids, strong oxidizing agents. |
| Sensitive | Hygroscopic |
| Refractive Index | 1.4260 (estimate) |
| Physical and Chemical Properties | White crystalline powder or colorless, lustrous crystals. Almost odorless. Has a stimulating effect on the skin. Relative density 1.27(25 degrees C). Sublimation and partial decomposition at about 263 °c. Flash point 250°C. Water-soluble 895g/L (20°C) soluble in water, ethanol and chloroform, insoluble in ether. The combustion flame was colorless. |
| Use | It is used as a curing agent for resins and plastics, a vulcanization accelerator (accelerator H) for rubbers, a shrinkage inhibitor for textiles, and is used in the manufacture of bactericides, explosives, and the like. When the drug, after the acidic urine decomposition to produce formaldehyde and bactericidal effect, for mild urinary tract infection; External for tinea, antiperspirant, cure axillary osmidrosis. Mixed with caustic soda and sodium phenolate, used in gas masks as phosgene absorbers. |
| Caution | Moderately toxic, irritating to the skin, can cause dermatitis, operators should wear protective equipment. |
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Risk and Safety
| Risk Codes | R11 - Highly Flammable R42/43 - May cause sensitization by inhalation and skin contact. R43 - May cause sensitization by skin contact |
| Safety Description | S16 - Keep away from sources of ignition. S22 - Do not breathe dust. S24 - Avoid contact with skin. S37 - Wear suitable gloves. |
| UN IDs | UN 1328 4.1/PG 3 |
| WGK Germany | 1 |
| RTECS | MN4725000 |
| FLUKA BRAND F CODES | 9-23 |
| TSCA | Yes |
| HS Code | 2933 69 40 |
| Hazard Class | 4.1 |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 9200 mg/kg |
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Nature
Open Data Verified Data
white to pale yellow crystalline powder. Flammable. Almost odorless, sweet and bitter. Soluble in water, ethanol, chloroform and other organic solvents, difficult to dissolve in benzene, carbon tetrachloride, insoluble in ether, gasoline. When the temperature is raised to 300 ° C, hydrogen cyanide is released, and when the temperature is continued, it is decomposed into methane, hydrogen and nitrogen. It is decomposed into ammonia and formaldehyde in a weak acid solution. When in contact with a flame, it burns immediately and produces a smokeless flame. Volatile. Flammable in case of open flame and high heat. Mixing with an oxidizing agent can form an explosive mixture. Large-Area contact with nitric acid fibers can cause combustion. Contact with sodium peroxide reacts vigorously. Its vapor is heavier than air, easy to gather in the low.
Last Update：2024-01-02 23:10:35
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Preparation Method
Open Data Verified Data
The condensation reaction between formaldehyde and excess ammonia water occurs under certain conditions. After the reaction is completed, the filtrate is vacuum evaporated to paste, filtered and dried.
Last Update：2022-01-01 09:30:01
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Standard
Authoritative Data Verified Data
This product is hexamethylenetetramine. Calculated as dry product, containing no less than 99.0% of C6H12N4.
Last Update：2024-01-02 23:10:35
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Trait
Authoritative Data Verified Data
- This product is a colorless, shiny crystal or white crystalline powder; Almost odorless; Fire can burn, smoke-free flame; Aqueous solution alkaline reaction.
- This product is soluble in water, soluble in ethanol or chloroform, slightly soluble in ether.
Last Update：2022-01-01 11:32:55
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Use
Open Data Verified Data
One of the commonly used corrosion inhibitors for hydrochloric acid pickling of large boilers. It can be well adsorbed on the metal surface to form a protective film to inhibit the corrosion of hydrochloric acid on the metal. When used for hydrochloric acid washing corrosion inhibitor, the dosage is 0. 5%.
Last Update：2022-01-01 09:30:01
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Differential diagnosis
Authoritative Data Verified Data
- take about 0.5g of this product, add 5ml of dilute sulfuric acid to dissolve it, and then heat it to produce extra odor of formaldehyde, which can make the wet ammonia silver nitrate test paper black; Add excess sodium hydroxide test solution, ammonia odor is produced, which can change the wetted red litmus paper to blue.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 45).
Last Update：2022-01-01 11:32:55
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Safety
Open Data Verified Data
rats were injected intravenously with LD50: 9200mg/kg. Irritation of the skin and cause dermatitis. Staff should be protected, the workplace should be well ventilated, when skin contact, the application of a large number of water rinse. Store in a cool, ventilated warehouse. Keep away from fire and heat source. Protection from direct sunlight. Keep the container sealed. Should be stored separately from oxidants and acids.
Last Update：2022-01-01 09:30:01
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Exam
Authoritative Data Verified Data
pH
Take 5.0g of this product, add 50ml of water to dissolve, take 5.0ml of solution, add 0.1ml of acid phthalein indicator solution, and use hydrochloric acid titration solution (0.lmol/L) or sodium hydroxide titration solution (0.lmol/L) titration, consumption of titrant volume should not exceed 0.2.
clarity and color of solution
take 2.0g of this product and add 20ml of New boiling cold water to dissolve. The solution should be clear and colorless.
chloride
take 2.5g of this product and check it according to law (General rule 0801). Compared with the control solution made of 0.002% of standard sodium chloride solution, it should not be more concentrated ().
sulfate
take 1.0g of this product, add 50ml of water to dissolve, take 10ml of solution, add 5 drops of dilute hydrochloric acid to acidify, add 5 drops of barium chloride test solution, and no turbidity occurs within 1 minute.
ammonium salts and paraformaldehyde
take 0.50g of this product, Add 10ml of ammonia-free distilled water to dissolve, immediately add 1.0ml of alkaline potassium iodide test solution, shake well, and place it at 20-25°C for 2 minutes, the color of the solution should not be deeper than that of the control solution (1.0 of alkaline potassium iodide solution, 10ml of ammonia-free distilled water); In case of turbidity, the color should be lower than that of the control solution (0.60 of standard potassium sulfate solution), add 7ml of water and 1ml of dilute hydrochloric acid, shake well, add 2ml of 25% barium chloride solution, shake well, and place for 10 minutes).
loss on drying
take this product, put the phosphorus pentoxide dryer to dry to constant weight, weight loss shall not exceed 1.5% (General rule 0831).
Heavy metals
take 4.0g of this product, add 20ml of water to dissolve, filter if necessary, add several drops of ammonia test solution to the filtrate, add water to make 25ml, and check according to law (General rule 0821 method), heavy metals should not exceed 5 parts per million.
Last Update：2022-01-01 11:32:56
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Content determination
Authoritative Data Verified Data
take about 0.lg of this product, Add 30ml of methanol to dissolve, according to the potentiometric titration method (General 0701), with perchloric acid titration solution (0.1 mol/L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 14.02mg of C6H12N4.
Last Update：2022-01-01 11:32:57
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Category
Authoritative Data Verified Data
Disinfection antiseptic.
Last Update：2022-01-01 11:32:57
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:32:57
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane - Reference Information
| trait | hexamethylenetetramine is colorless or white crystal, odorless, soluble in water, alcohol and chloroform. Hexamethylenetetramine is irritating to the skin, easy to heat sublimation and decomposition, flammable, soluble in water, insoluble in ether, aromatic hydrocarbons, etc. |
| Use | hexamethylenetetramine (hexamethylenetetramine) is widely used as a preservative in National Defense Medicine, rubber, plastic, chemical and food industries. It is used as a buffer agent for anti-shrinkage finishing of textiles, sodium chlorite bleach activator, water repellent CR. It is used as a curing agent for resins and plastics, a vulcanization accelerator for rubber (accelerator H), a shrinkage inhibitor for textiles, and a bactericide. When the drug, after the acidic urine decomposition to produce formaldehyde and bactericidal effect, for mild urinary tract infection; External for tinea, antiperspirant, treatment of axillary osmidrosis. Mixed with caustic soda and sodium phenolate, used in gas masks as phosgene absorbers. Urotropine is also a commonly used corrosion inhibitor used to slow the corrosion of metallic materials. Widely used in national defense medicine, rubber, plastic, chemical, food and other industries. Assay and determination of bismuth, iron, manganese, cobalt, thorium, platinum and magnesium. Test lithium, bromide, determination of used as resin and plastic curing agent, rubber vulcanization accelerator, textile shrinkage inhibitor, and for the system of fungicides, explosives, etc. used as analytical reagents and vulcanization accelerators used as curing agents for resins and plastics, rubber vulcanization accelerators (accelerators H), anti-shrinkage agents for textiles, and used in the preparation of fungicides, explosives, etc. When the drug, after the acidic urine decomposition to produce formaldehyde and bactericidal effect, for mild urinary tract infection; External for tinea, antiperspirant, cure axillary osmidrosis. Mixed with caustic soda and sodium phenolate, used in gas masks as phosgene absorbers. antimicrobial agent. used as anti-shrinkage finishing agent for textiles, sodium chlorite bleach activator, water repellent CR buffer. hexamethylenetetramine is mainly used as a curing agent for resins and plastics, a catalyst and a foaming agent for aminoplastics, an accelerator for rubber vulcanization (accelerator H), an anti-shrinkage agent for textiles, etc. Hexamethylenetetramine is a raw material for organic synthesis and is used in the pharmaceutical industry to produce chloramphenicol. Hexamethylenetetramine can be used as a disinfectant for the urinary system, which itself has no antibacterial effect and is effective against gram-negative bacteria. Its 20% solution can be used for the treatment of bromhidrosis, sweat feet, body tinea, etc. It is mixed with sodium hydroxide and sodium phenolate and can be used as a phosgene absorber in a gas mask. And used in the manufacture of pesticides and pesticides. Hexamethylenetetramine and fuming nitric acid, can be produced by explosive cyclone explosive, referred to as RDX. Hexamethylenetetramine can also be used for the determination of bismuth, indium, manganese, cobalt, thorium, platinum, magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, reagents such as iodide and chromatographic analysis reagents. in the liver function test, thymol turbidity solution was prepared, and the substances bismuth, iron, manganese, cobalt, thorium, platinum and magnesium were tested and determined, and lithium, Iron cyanide bromide and iodide were tested, and copper, uranium, beryllium, tellurium, gas chromatography stationary liquid (the highest temperature of 180 degrees C, the solvent for chloroform). |
| Chemical properties | urotropine has an adamantane structure, which is highly symmetric and has characteristics of a tertiary amine. Each of the four nitrogen atoms has a pair of non-common electrons and can form coordination compounds with many inorganic substances. With the inorganic strong acid heating reaction, can produce formaldehyde and ammonium salt. In the presence of zinc powder, and hydrochloric acid reaction, can produce ammonium chloride and trimethylamine hydrochloride. It can be nitrated to produce cyclone explosive. It can also react with nitrous acid to generate dinitro-methylenetetramine. Can react with hydrogen peroxide, hydrogen cyanide. It can also react with sulfur and sulfide, and react with alkali metal salts, alkaline earth metal salts, rare earth metals and their salts to form complexes. It can react with alcohol in acidic medium. Reaction with organic acids to form salts. It can also react with halides, phenols and amides. It can also react with some natural substances such as proteins, cellulose, etc. Irritant to the skin, can cause dermatitis. Rats were intravenously injected with LD501200mg/kg. Mice were intraperitoneally injected with LD50512mg/kg. FIG. 1 shows the structural formula of urotropine. A white hygroscopic crystalline powder or a colorless, lustrous, rhomboid crystal. Almost odorless, sweet and bitter. Soluble in water and chloroform. Insoluble in carbon tetrachloride, acetone, benzene and ether, insoluble in petroleum ether. |
| pharmacological action | a drug for the treatment of bacterial urinary tract infections. Urotropine itself had no antibacterial effect. After oral absorption, it is excreted through the kidney and decomposed into ammonia and formaldehyde in acidic urine, which can effectively inhibit G-bacteria, especially against Escherichia coli, enterobacter aerogenes and Pseudomonas aeruginosa aeroginosa have strong antibacterial activity. Can be used to treat urinary tract infections caused by sensitive bacteria. For oral use, vitamin C or ammonium chloride should be taken to acidify the urine (pH ≤ 5.5). |
| production method | prepared by condensation of formaldehyde and ammonia. The formaldehyde solution is placed in the reactor, ammonia, condensation reaction is carried out in alkaline solution, the reaction temperature is maintained at 50-70 deg C, liquid is cooled into the liquid film vacuum evaporator, 60-80 deg C evaporation, the concentration was increased from 24% to 38%-42%, and then the reaction solution was filtered, crystallized by vacuum evaporation, and dried by Suction filtration to obtain the final product urotropine. formaldehyde (37% aqueous solution) and excess aqueous ammonia were reacted for 3 h at 38 °c. After completion of the reaction, after clarification, filtration, membrane evaporation (pressure 9.806~9.866 kPa) twice, the concentrated solution is cooled to crystallize, filtered, and dried at 150 °c to obtain a finished product. results from the reaction of formaldehyde with calculated amounts of ammonia. |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| spontaneous combustion temperature | 770 ° F. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:55:45
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