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PRODUCT DETAILS
OTHER CHEMICALS > Hexamine

Hexamethylenetetramine is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like structure similar to adamantane.

Formula: C6H12N4, Molar mass: 140.186 g/mol, Density: 1.33 g/cm³, Boiling point: 280 °C, IUPAC ID: 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane, Soluble in: Water

Applications

The main 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. These products are used as binders, e.g. in brake and clutch linings, abrasive products, non-woven textiles, formed parts produced by moulding processes, and fireproof materials.
Medical uses

As the mandelic acid salt (generic methenamine mandelate, USP[6]) it is used for the treatment of urinary tract infection. It decomposes at an acidic pH to form formaldehyde and ammonia, and the formaldehyde is bactericidal; the mandelic acid adds to this effect. Urinary acidity is typically ensured by co-administering vitamin C (ascorbic acid) or ammonium chloride. Its use had temporarily been reduced in the late 1990s, due to adverse effects, particularly chemically-induced hemorrhagic cystitis in overdose,[7] but its use has now been re-approved because of the prevalence of antibiotic resistance to more commonly used drugs. This drug is particularly suitable for long-term prophylactic treatment of urinary tract infection, because bacteria do not develop resistance to formaldehyde. It should not be used in the presence of renal insufficiency.[medical citation needed]
Histological stains

Methenamine silver stains are used for staining in histology, including the following types:
 

  •     Grocott's methenamine silver stain, used widely as a screen for fungal organisms.
  •     Jones' stain, a methenamine silver-Periodic acid-Schiff that stains for basement membrane, availing to view the "spiked" Glomerular basement membrane associated with membranous glomerulonephritis.


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. It burns smokelessly, has a high energy density (30.0 MJ/kg), does not liquify while burning, and leaves no ashes.

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). It is approved for usage for this purpose in the EU,[9] where it is listed under E number E239, however it is not approved in the USA, Australia, or New Zealand.

Reagent in organic chemistry

Hexamethylenetetramine is a versatile reagent in organic synthesis. It is used in the Duff reaction (formylation of arenes),[11] the Sommelet reaction (converting benzyl halides to aldehydes),[12] and in the Delepine reaction (synthesis of amines from alkyl halides).

Explosives

Hexamethylenetetramine is the base component to produce RDX and consequently, C-4[5] as well as Hexogen, Oktogen, Dinitrohexamine and HMTD.