Hexamethylenetetramine

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The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Hexamethylenetetramine

hexamine, or urotropine, colorless crystals with a sweet taste that carbonize at 280° C and sublime in vacuum above 230° C. Hexamethylenetetramine is highly soluble in water and carbon disulfide, moderately in alcohol and chloroform, and slightly in ether and benzene.

Hexamethylenetetramine is prepared by condensing ammonia with formaldehyde: 4NH₃ + 6CH₂O⇌(CH₂)₆N₄ + 6H₂O.

This reaction is reversible and under certain conditions the equilibrium may be shifted toward the left, which makes it possible to use hexamethylenetetramine as a convenient formaldehyde source (for example, in the production of ureaformaldehyde resins). Hexamethylenetetramine is also used in the production of the powerful explosive hexogen, in analytical chemistry (for example, in the preparation of buffer solutions), and as a smokeless solid fuel (so-called solid alcohol). Hexamethylenetetramine is a medicinal preparation of the antiseptic variety. Its antimicrobial action is due to formaldehyde formation from the decomposition of hexamethylenetetramine in acid media. Hexamethylenetetramine is used internally in powders, tablets, and solutions, as well as intravenously in infectious diseases, particularly for urinary tract infections. It was first synthesized by A. M. Butlerov in 1860.

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