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HEXAMETHYLENETETRAMINE

CAS NO: 100-97-0
EC NUMBER: 202-905-8


Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. 
This white crystalline compound is highly soluble in water and polar organic solvents. 
Hexamethylenetetramine has a cage-like structure similar to adamantane. 
Hexamethylenetetramine is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives. 
Hexamethylenetetramine sublimes in vacuum at 280 °C
Hexamethylenetetramine is a hardener in epoxy resins of the bisphenol A type and can also be used as an anticorrosive agent. 
Hexamethylenetetramine is a sensitizing agent in ceramics workers.
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).
Hexamethylenetetramine (HMTA) is a water soluble, heterocyclic organic compound with a cage-like structure resembling adamantane. It is commonly used in treating urinary tract infection.

Hexamethylenetetramine was discovered by Aleksandr Butlerov in 1859.
Hexamethylenetetramine is prepared industrially by combining formaldehyde and ammonia.
The reaction can be conducted in gas phase and in solution.

The molecule has a symmetric tetrahedral cage-like structure, similar to adamantane, whose four "corners" are nitrogen atoms and "edges" are methylene bridges. 
Although the molecular shape defines a cage, no void space is available at the interior for binding other atoms or molecules, unlike crown ethers or larger cryptand structures.

Applications
The dominant use of hexamethylenetetramine is in the production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where it is added as a hardening component.
Hexamethylenetetramine is used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials.

It has been proposed that hexamethylenetetramine could work as a molecular building block for self-assembled molecular crystals.

Medical uses
As the mandelic acid salt (generic methenamine mandelate, USP) it is used for the treatment of urinary tract infection. 
A systematic review of its use for this purpose in adult women found there was no good evidence of benefit.

Solid fuel
Together with 1,3,5-trioxane, hexamethylenetetramine is a component of hexamine fuel tablets used by campers, hobbyists, the military and relief organizations for heating camping food or military rations. 
Hexamethylenetetramine burns smokelessly, has a high energy density of 30.0 megajoules per kilogram (MJ/kg), does not liquify while burning, and leaves no ashes, although its fumes are toxic.

Standardized 0.149 g tablets of methenamine (hexamine) are used by fire-protection laboratories as a clean and reproducible fire source to test the flammability of carpets and rugs.

Food additive
Hexamethylene tetramine or hexamine is also used as a food additive as a preservative (INS number 239).
Hexamethylenetetramine is approved for usage for this purpose in the EU, where it is listed under E number E239.

Reagent in organic chemistry
Hexamethylenetetramine is a versatile reagent in organic synthesis.
Hexamethylenetetramine is used in the Duff reaction (formylation of arenes), the Sommelet reaction (converting benzyl halides to aldehydes), and in the Delepine reaction (synthesis of amines from alkyl halides).

Explosives
Hexamethylenetetramine is the base component to produce RDX and, consequently, C-4[4] as well as Octogen, hexamine dinitrate, hexamine diperchlorate and HMTD.

Historical uses
Hexamethylenetetramine was first introduced into the medical setting in 1899 as a urinary antiseptic.
However, Hexamethylenetetramine was only used in cases of acidic urine, whereas boric acid was used to treat urinary tract infections with alkaline urine.
Scientist De Eds found that there was a direct correlation between the acidity of hexamethylenetetramine's environment and the rate of its decomposition.
Therefore, its effectiveness as a drug depended greatly on the acidity of the urine rather than the amount of the drug administered.
In an alkaline environment, hexamethylenetetramine was found to be almost completely inactive.

Hexamethylenetetramine was also used as a method of treatment for soldiers exposed to phosgene in World War I.
Subsequent studies have shown that large doses of hexamethylenetetramine provide some protection if taken before phosgene exposure but none if taken afterwards.


About Hexamethylenetetramine

Hexamethylenetetramine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 tonnes per annum.
Hexamethylenetetramine is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
Hexamethylenetetramine is used in the following products: 
washing & cleaning products, fuels and cosmetics and personal care products.
Other release to the environment of Hexamethylenetetramine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use.
Article service life
Other release to the environment of Hexamethylenetetramine is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment). 
Hexamethylenetetramine can be found in products with material based on: rubber (e.g. tyres, shoes, toys) and plastic (e.g. food packaging and storage, toys, mobile phones).

Widespread uses by professional workers
Hexamethylenetetramine is used in the following products: fuels, pH regulators and water treatment products, laboratory chemicals and polymers.
Hexamethylenetetramine is used in the following areas: health services and scientific research and development.
Other release to the environment of Hexamethylenetetramine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).

Hexamethylenetetramine is used in the following products: adhesives and sealants and polymers.
Release to the environment of Hexamethylenetetramine can occur from industrial use: formulation of mixtures and formulation in materials.

Uses at industrial sites
Hexamethylenetetramine is used in the following products: fillers, putties, plasters, modelling clay, adhesives and sealants, fuels, pH regulators and water treatment products, laboratory chemicals and polymers.
Hexamethylenetetramine has an industrial use resulting in manufacture of another substance (use of intermediates).
Hexamethylenetetramine is used in the following areas: scientific research and development.
Hexamethylenetetramine is used for the manufacture of: metals, fabricated metal products, electrical, electronic and optical equipment and machinery and vehicles.
Release to the environment of Hexamethylenetetramine can occur from industrial use: as processing aid, as processing aid, in the production of articles, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and for thermoplastic manufacture.

Manufacture
Release to the environment of Hexamethylenetetramine can occur from industrial use: manufacturing of the substance.

Hexamethylenetetramine is a heterocyclic organic compound with antibiotic activity. 
In the body, Hexamethylenetetramine is converted to formaldehyde, a nonspecific bactericidal agent. 
Hexamethylenetetramine is typically used long-term to treat chronic urinary tract infections and to prevent the recurrence of infections.
Hexamethylenetetramine is typically used long-term to treat chronic urinary tract infections and to prevent the recurrence of infections.

Physical Description
Hexamethylenetetramine appears as 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).

Uses at Household Products
Household & Commercial/Institutional Products
Information on 15 consumer products that contain Hexamethylenetetramine in the following categories is provided:

• Commercial / Institutional
• Inside the Home
• Personal Care
• Pesticides

Uses
•Agent for soaking up liquid
•General adhesives and binding agents for a variety of uses
•Adhesion of molecules to a surface
•Relating to agricultural, including the raising and farming of animals and growing of crops
•Related to animals (but non-veterinary) e.g., animal husbandry, farming of animals/animal production, raising of animals for food or fur, animal feed, products for household pets 
•Relatived to the maintenance and repair of automobiles, products for cleaning and caring for automobiles (auto shampoo, polish/wax, undercarriage treatment, brake grease) 
•Binding agents, used in paint, sand, etc
•General bleaching agents, bleaching agents for textiles.
•Related to the building or construction process for buildings or boats
•Materials used in the building process, such as flooring, insulation, caulk, tile, wood, glass, etc.
•Modifier used for chemical, when chemical is used in a laboratory    
•Related to products specifically designed for children (e.g. toys, children's cosmetics, etc)
•Term used for colorants, dyes, or pigments; includes colorants for drugs, textiles, personal care products.
•Plastic products, industry for plastics, manufacturing of plastics, plastic additives
•Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet.
•Related to photography, film, photographic equipment, photographic laboraties, photochemicals, and developing of photographs
•Fertilizer for consumer or industrial use, and manufacturing of fertilizers
•Fillers for paints, textiles, plastics, etc
•Related to the activity of fishing
•Fire extinguishing agents, for use after the fire has started
•Fire prevention materials, or additives/coatings to prevent flammability in paints, textiles, plastics, etc.
•Includes antifoaming agents, coagulating agents, dispersion agents, emulsifiers, flotation agents, foaming agents, viscosity adjustors, etc
•Includes spices, extracts, colorings, flavors, etc added to food for human consumption
•General fuels, fuel additives, motor/automotive fuels    
•Additive for products to promote hardening, used in paints and varnishes, plastics, etc.
•Industrial fluids such as hydraulic fluids, lubricating agents, functional fluids, etc

Industry Uses
•Adhesives and sealant chemicals
•Automotive parts ingredient (brake pads)
•Corrosion inhibitors and anti-scaling agents
•Curing Accelerator
•Explosive Materials
•Finishing agents
•Intermediates
•Ion exchange agents
•Making phenolic resins
•Overlays
•Plating agents and surface treating agents
•Process regulators
•Processing aids, not otherwise listed
•Processing aids, specific to petroleum production
•Propellants and blowing agents

Consumer Uses
•Adhesives and sealants
•Agricultural products (non-pesticidal)
•Automotive Sound Insulation Material
•Automotive care products
•Building/construction materials not covered elsewhere
•Explosive materials
•Fuels and related products
•Metal products not covered elsewhere
•Plastic and rubber products not covered elsewhere
•Rubber Tires

Methods of Manufacturing
Formaldehyde and ammonia can be converted into hexamethylenetetramine in the gas phase, in aqueous solution, or in a suspension in an inert solvent, although the most important of these procedures is that carried out in water. 
The usual process gives a pure product in yields near 90% and includes an economical drying step.


General Manufacturing Information

Industry Processing Sectors
Adhesive manufacturing
All other chemical product and preparation manufacturing
Computer and electronic product manufacturing
Custom compounding of purchased resin
Electrical equipment, appliance, and component manufacturing
Explosives manufacturing
Fabricated metal product manufacturing
Lightbulb manufacturing
Mining (except oil and gas) and support activities
Miscellaneous manufacturing
Nonmetallic mineral product manufacturing (includes clay, glass, cement, concrete, lime, gypsum, and other nonmetallic mineral product manufacturing.
Oil and gas drilling, extraction, and support activities
Pesticide, fertilizer, and other agricultural chemical manufacturing
Petrochemical manufacturing
Plastic material and resin manufacturing
Rubber product manufacturing
Services

IDENTIFICATION AND USE: 
Hexamethylenetetramine is a white or colourless crystalline solid. It is an anti-infective agent. 
Hexamethylenetetramine hippurate tablets, USP are indicated for prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary. 
Non-medical uses include the following: in adhesives, coatings, and sealing compounds, as cross-linking agent for hardening phenol-formaldehyde resin and vulcanizing rubber, as corrosion inhibitor for steel, as fuel tablets for camping stoves, as a stabilizer for lubricating and insulating oils, in the chemical detection of metals, in the preservation of hides, as dye fixative, for the manufacture of explosive compounds, antimicrobial food additive. 

Chemical Properties    
Hexamethylenetetramine has an adamantane structure with a high degree of symmetry and the characteristics of tertiary amines. 
Each of the four nitrogen atoms has a pair of unshared electrons with being able to form coordination compounds with many kinds of inorganic compounds. 
Hexamethylenetetramine can have a heating reaction with a strong inorganic acid to generate formaldehyde and ammonium salts. 
In the presence of zinc powder, Hexamethylenetetramine can have a reaction with hydrochloric acid to generate the hydrochloride salt of trimethylamine and ammonium chloride. 
Hexamethylenetetramine can also be subject to nitrification and generate RDX.
Hexamethylenetetramine can also have a reaction with nitrous acid to form N'N'-Dinitroso pentamethylene tetramine. 
Hexamethylenetetramine can have a reaction with hydrogen peroxide and hydrogen cyanide. 
Hexamethylenetetramine can also have a 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 an acidic medium, it can react with alcohol. 
Hexamethylenetetramine can also react with an organic acid to form a salt. 
Hexamethylenetetramine is white hygroscopic crystalline powder or shiny colorless rhombic crystals. 
Hexamethylenetetramine is almost odorless with sweet and bitter taste.
Hexamethylenetetramine is soluble in water and chloroform but less soluble in carbon tetrachloride, acetone, benzene and ether and insoluble in petroleum ether.


Pharmacological effects
Hexamethylenetetramine is a therapeutic drug for treating the bacterial urinary tract infections.
Hexamethylenetetramine itself has no antibacterial effect. 
After oral absorption, Hexamethylenetetramine can be secreted out by renal with being broken down into ammonia and formaldehyde in acidic urine with the latter being able to effectively inhibit the G-bacteria, especially having a strong antibacterial effect on Escherichia coli, Enterobacter aerogenes and Pseudomonas aeruginosa.
Hexamethylenetetramine can be used for treating urinary tract infections caused by susceptible strains. 
When Hexamethylenetetramine 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).

Formula: C6H12N4
Molecular mass: 140.2
Sublimation point: ~260°C
Density: 1.33 g/cm³
Solubility in water: good
Relative vapour density (air = 1): 4.9
Flash point: 250°C c.c.
Auto-ignition temperature: 390°C
Octanol/water partition coefficient as log Pow: -2.84  


Uses    
Hexamethylenetetramine can be used as the curing agent for resins and plastics, the vulcanization accelerator of rubber (accelerator H) and textiles shrink-proof agent. 
Hexamethylenetetramine can also be used for making antibacterial drugs, explosives and so on. 
As a medicine, after oral administration, Hexamethylenetetramine can be decomposed when coming across acidic urine to generate formaldehyde and exerts its antibacterial effect used for treating mild urinary tract infection.
Hexamethylenetetramine can be externally used for treating ringworm, antiperspirants, and treatment of underarm odour. 
Hexamethylenetetramine's being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks.
Hexamethylenetetramine can be used as a kind of anti-microbial agent.
Hexamethylenetetramine can be used as an 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 the urinary system with itself having no antibacterial effect and being effective in treating gram-negative bacteria. 
Hexamethylenetetramine 20% solution can be used for the treatment of underarm odour, sweaty feet, tinea and so on. 
Hexamethylenetetramine's being mixed with caustic soda and sodium phenol can be used as the phosgene absorber of gas masks. 
Hexamethylenetetramine 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 the determination of bismuth, indium, manganese, cobalt, thorium, platinum, producing magnesium, lithium, copper, uranium, beryllium, tellurium, bromide, and iodide.
In the liver function tests, Hexamethylenetetramine 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. 
Hexamethylenetetramine can also be used for the determination of copper, uranium, beryllium, tellurium etc. 
Moreover, Hexamethylenetetramine can be used as gas chromatography fixed solution (maximum usage temperature of 180 ℃ with the solvent being chloroform).
Used in the treatment of urinary track infection.
antibacterial, tuberculostatic
Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction, the Sommelet reaction, and in the Delepine reaction.

Hexamethylenetetramine (HMTA) may be used as:
-Raw material in the synthesis of blue emitting boron carbon oxynitride (BCNO) phosphors and Zinc oxide (ZnO) nanorods.
-Catalyst in the synthesis of 2-amino-4H-pyran derivatives.
-Surfactant in the synthesis of HMTA capped transition metals doped ZnS nanoparticles.
-Precipitant and template in the synthesis of Ni(OH)2.


Hexamethylenetetramine preserves food products such as fish and marinated mussels.
Hexamethylenetetramine hydrolysed in acidic medium to produce formaldehyde, which is a broad-spectrum antimicrobial agent. 
However, Hexamethylenetetramine's relatively high toxicity limits its application to provolone cheese. 
Hexamethylenetetramine can be easily determined by acidification of an aqueous extract, followed by a characteristic reaction, for instance, with chronotropic acid and subsequent spectrophotometry at 570 nm.

Hexamethylenetetramine is a polypeptide bacteriocin that exhibits antibacterial activity against a wide range of Gram-positive bacteria. 
Hexamethylenetetramine is permitted to use in cream products, beer, salad dressings, cheese and cheese products, and so on. 
The determination of Hexamethylenetetramine in foods is typically carried out using immunoassay or bioassay. 
Recently, a chromatographic method involving LC-MS/MS has been developed for this additive.

Hexamethylenetetramine has a polyene structure and is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis. 
Hexamethylenetetramine is used to protect food from mould and yeast growth. 


IUPAC NAMES: 
1,3,5,7-Tetraazaadamantan
1,3,5,7-Tetraazaadamantane
1,3,5,7-tetraazatricyclo(3.3.1.1(sup37))decane
1,3,5,7-tetraazatricyclo[3,3,1,1. ]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1 3,7]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane
1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1.(3,7)]decane
1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane
1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
1,3,5,7-Tetraazatricyclo[3.3.1.1^(3,7)]decane
1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane
1,3,5,7-tetraazatricyclo[3.3.1.1³,7]decane
1,3,5,7-Tetraazatricyclodecane
1,3,5,7-tetraazotriciklo-(3.3.1.1)dekanas; metenaminas
HEXA
HEXAMETHYLENE TETRAMINE
Hexamethylene tetramine
Hexamethylenetetramine
hexamethylenetetramine
Hexamethylenetetramine
hexamethylenetetramine methenamine
Hexamethylenetetramine, Hexamine
hexamethylenetretramine
Hexametilén-tetramin
HEXAMINE
Methamine
Methenamin
METHENAMINE
Methenamine
methenamine
Methenamine
methenamine
methenamine; hexamethylenetetramine
MethenamineHexamethylenetetramine

SYNONYMS:
methenamine;
Hexamethylenetetramine;
100-97-0;
Hexamine;
Urotropine;
Aminoform;
Urotropin;
Hexamethylenamine;
1,3,5,7-Tetraazaadamantane;
Methenamin;
HMTA;
Hexamethylenetetraamine;
Hexamethylene tetramine;
Formamine;
Uritone;
Aminoformaldehyde;
Ammonioformaldehyde;
Ammoform;
Antihydral;
Cystamin;
Cystogen;
Duirexol;
Hexaform;
Hexaloids;
Metramine;
Resotropin;
Uratrine;
Urodeine;
Xametrin;
Formin;
Heterin;
Hexasan;
Uramin;
Preparation AF;
Hexamethyleneamine;
Hexilmethylenamine;
Hexa-Flo-Pulver;
Ekagom H;
methenaminum;
Aceto HMT;
Herax UTS;
Hexamethylentetramin;
Metenamina;
Hexaminum;
Formin (heterocycle)
;Nocceler H;
Sanceler H;
 

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