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hexamethylenetetramine

Product name hexamethylenetetramine
Synonyms urotropine
hexamine
methenamine
GOST 1381-73
CAS 100-97-0

Hexamethylenetetramine is a colorless, odorless crystallline solid, soluble in water, methanol and ethanol. Practically insoluble in ether, benzene and carbon tetrachloride. Hexamine sublimes in vacuum above 230°C, on air above 280°C become charred. Being treated with fuming nitric acid in presence of ammonium nitrate and acetaldehyde gives hexogene (explosive).

Production.

Main industrial method is evaporation of formaldehyde and ammonia mixture in vacuum.

4NH3 + 4CH2O --> C6H12N4(urotropine) + 4H2O

Uses.

  • Methenamine hippurate is mainly used for the prophylaxis (prevention) of urinary tract infections, where it is hydrolysed in the acidic pH of the urine to form formaldehyde.
  • As a food additive, hexamine is used as a preservative in cheeses. It has E number E239. In some countries, such as Russia, it is banned for this use.
  • Hexamine is used as a component with 1,3,5-trioxane in hexamine fuel tablets (often called Esbit). This solid fuel in tablet form is used by campers, hobbyists, the military and relief organizations for heating camping food or military rations. It burns smokelessly, has a high energy density, does not liquify while burning and leaves no ashes.
  • production of powdery or liquid preparations of phenolic resins and phenolic resin moulding compounds, where hexamine 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.
  • It is used in rubber and textile adhesives, in paints and lacquers, in the photographic industry, in the production of explosives such as RDX, as a corrosion inhibitor, as a protein modifier, as a reagent in chemical analysis, and in the production of deodorants and hair fixers, among many other uses.

  • Manufacturer(s) JSC AZOT
    JSC Metafrax
    JSC Severodonetsk Azot Association
    CJSC Tokem
    Chemical structure of urotropine

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