Hexamethylenetetramine


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Related to Hexamethylenetetramine: Hexamine, Hexamethylenediamine

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.

References in periodicals archive ?
The composition of the coatings was determined by means of AAS after stripping the deposits in HC1 1:3 with hexamethylenetetramine to inhibit dissolution of the steel substrate.
Hexamethylenetetramine (hexamine) has already been used industrially for the production of interior-grade tannin-bonded panels of low or no formaldehyde emission (Pizzi 1977, 1999; Pizzi et al.
In a similar case, a leading global manufacturer of belts and hoses to the automotive and industrial aftermarket had been strengthening its belts with polyester cord pre-treated with a combination of hexamethoxymelamine or hexamethylenetetramine and phenol-formaldehyde condensation product, where the phenol is usually resorcinol.
In combination with a methylene donor such as hexamethylenetetramine (HMT-80/EPR/P) or hexamethoxymethylmelamine (HMMM-50/EPR/S), the resins function as adhesion promoter additives to the rubber compound.