It is white hygroscopic crystalline powder or shiny colorless rhombic crystals. It is almost odorless with sweet and bitter taste. It is soluble in water and chloroform but less soluble in carbon tetrachloride, acetone, benzene and ether and insoluble in petroleum ether.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
Air & Water Reactions
Highly flammable. Burns readily on contact with a flame with a smokeless flame. Finely powdered dust is significant dust explosion hazard. Water soluble.
It is soluble in H2O (67%), CHCl3 (10%), EtOH (8%) and Et2O (0.3%), and a 0.2M solution has a pH of 8.4. Dissolve it in hot absolute EtOH (reflux, Norit), filter using a heated funnel, cool at room temperature first, then in ice. Wash the crystals with cold Et2O, dry them in air or under a vacuum. A further crop can be obtained by adding Et2O to the filtrate. It sublimes above 260o without melting. The picrate has m 179o(dec). [pK2 0 4.85: Reilley & Schmid Anal Chem 30 947 1958, pK2 0 6.30: Pummerer & Hofmann Chem Ber 56 1255 1923.] [Beilstein 26 I 306, 26 II 200, 26 III/IV 1680.]
Davis); Urotropin (Parke-Davis).
It is a therapeutic drug for treating the bacterial urinary tract infections. Hexamethylenetetramine itself has no antibacterial effect. After oral absorption, it can be secreted out by renal with being broken down into ammonia and formaldehyde in acidic urine with the later one being able to effectively inhibit the G-bacteria, especially having a strong antibacterial effect on Escherichia coli, Enterobacter aerogenes and Pseudomonas aeruginosa. It can be used for treating urinary tract infections caused by susceptible strains. When it is subject to oral administration, the patients should also take vitamin C or ammonium chloride at the same time in order to acidify the urine (pH≤5.5).
Hexamethylenetetramine has an adamantane structure with high degree of symmetry and the characteristics of tertiary amines. Each of the four nitrogen atoms has a pair of unshared electron with being able to form coordination compound with many kinds of inorganic compounds. It can have heating reaction with strong inorganic acid to generate formaldehyde and ammonium salts. In the presence of zinc powder, it can have reaction with hydrochloric acid to generate the hydrochloride salt of trimethylamine and ammonium chloride. It can also be subject to nitrification and generate RDX. It can also have reaction with nitrous acid to form N'N'-Dinitroso pentamethylene tetramine. It can have reaction with hydrogen peroxide and hydrogen cyanide. It can also have reaction with sulfur and sulfur compounds or react with the alkali metal salts, alkaline earth metal, and rare earth metal salts to form a complex. In acidic medium, it can react with alcohol. It can also react with organic acid to form salt. It can also react with halides, phenols and amides as well as some natural products such as protein and fiber. It is irritating to the skin and can cause dermatitis. Intravenous-Rats LD50: 1200 mg/kg; Intraperitoneal injection-mice LD50: 512mg/kg.
Figure 1 is the formula of hexamethylenetetramine
Odorless white crystalline powder or colorless lustrous crystals. Sublimes in a vacuum at about 505° F with some decomposition. Solutions are strong bases (pH of 0.2 molar aqueous solution is 8.4).
Used in the treatment of urinary track infection.
Hexamethylenetetramine is hygroscopic. Hexamethylenetetramine is sensitive to exposure to heat. Hexamethylenetetramine is incompatible with oxidizing agents. Hexamethylenetetramine is also incompatible with acids. Hexamethylenetetramine reacts violently with sodium peroxide. Hexamethylenetetramine reacts explosively with 1-bromopentaborane(9) at temperatures above 194° F. The complex with iodine deflagrates at 280° F. The 1:1 addition complex with iodoform has exploded at 352° F. Hexamethylenetetramine is corrosive to some metals, such as aluminum and zinc . Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot [USCG, 1999].
It can be made from the condensation reaction of formaldehyde and ammonia. Place the formaldehyde solution in a reactor, put through the ammonia with condensation reaction being carried out in alkaline solution and the reaction temperature being maintained at 50-70 ℃; the material liquid was cooled and fed into the film vacuum evaporator and subject to evaporation at 60-80 ℃ to make its concentration be increased from 24% to 38%-42%. Then the reaction mixture was filtered and subjected to vacuum evaporation and crystallization, filtration drying to derive the hexamethylenetetramine product.
Put the formaldehyde (37% aqueous solution) and excess amount of ammonia for 3 h at 38 ℃. After completion of reaction, the reaction mixture was further subject to clarification, filtration, membrane evaporation (pressure 9.806~9.866 kPa) for twice with concentrated liquid subjecting cooling and crystallization, filtration, and drying at 150 ℃ to obtain the products.
It is obtained through the reaction between formaldehyde and the calculated amount of ammonia.
Special Hazards of Combustion Products: Formaldehyde gas and ammonia may be given off when hot.
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.
Hexamethylenetetramine is used in the foundry, tire and rubber, and phenol formaldehyde resins industries
and in other applications such as a hardener in epoxy resins Bisphenol A type and as an anticorrosive agent. It is an ammonia and formaldehyde releaser sometimes used in topical medicaments and cosmetics
white crystalline powder
It can be used as the curing agent for resins and plastics, the vulcanization accelerator of rubber (accelerator H) and textiles shrink-proof agent. It can also be used for making antibacterial drug, explosives and so on. As medicine, after oral administration, it can be decomposed when coming across acidic urine to generate formaldehyde and exerts its antibacterial effect used for treating mild urinary tract infection; it can be externally used for treating ringworm, antiperspirants, and treatment of underarm odor. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks.
It can be used as a kind of anti-microbial agents.
It can be used as anti-shrinking textile finishing agent, bleaching agents of sodium chlorite and the buffer of waterproofing agents CR.
Hexamethylenetetramine is mainly used as the curing agent of plastic and resin, the catalyst and foaming agent of aminoplast, rubber vulcanization accelerator (accelerator H), and the shrink-proof agents of textiles. Hexamethylenetetramine is the raw material for organic synthesis and can be used for the production of chloramphenicol in the pharmaceutical industry. Hexamethylenetetramine can be used as the disinfectant of urinary system with itself having no antibacterial effect and being effective in treating gram-negative bacteria. Its 20% solution can be used for the treatment of underarm odor, sweaty feet, tinea and so on. Its being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks. It can also be used for the manufacture of pesticides. Hexamethylenetetramine can react with fuming nitric acid to obtain highly explosive cyclonite, briefly referred as RDX. Hexamethylenetetramine can be used as the reagent and chromatography reagents for determination of bismuth, indium, manganese, cobalt, thorium, platinum, producing magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, and iodide.
In the liver function tests, it can be used for formulating thymol turbidity, test and measurement of object such as bismuth, iron, manganese, cobalt, thorium, platinum and magnesium as well as the determination and identification of lithium, iron cyanide, iron bromide and iodide. It can also be used for the determination of copper, uranium, beryllium, tellurium etc. Moreover, it can be used as gas chromatography fixed solution (maximum usage temperature of 180 ℃ with the solvent being chloroform).
ChEBI: A polycyclic cage that is adamantane in which the carbon atoms at positions 1, 3, 5 and 7 are replaced by nitrogen atoms.