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 It might be outdated or ideologically biased.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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References in periodicals archive

In 2003, Dowa Hightech came under scrutiny when it disposed of effluent containing hexamethylenetetramine, discharging it into the same Tone River system and causing formaldehyde to be generated.

UPDATE2: Gunma waste disposal firm may have discharged formaldehyde

Prophylactic and antidotal effects of hexamethylenetetramine against phosgene poisoning in rabbits.

The role of the clinical laboratory in managing chemical or biological terrorism

Metal-doped nZnO (Fe-nZnO, Co-nZnO, Ni-nZnO, and Mn-nZnO) and nondoped nZnO photocatalysts were prepared through hydrothermal method of zinc nitrate, hexamethylenetetramine, and various metal ions.

Preparation, characterization, and biotoxicity of nanosized doped ZnO photocatalyst

By crosslinking with hexamethylenetetramine, benzo-l,3,2-dioxaborolanyl containing novolac resin exhibits higher carbon yield, more excellent flame retardancy and oxidation resistance than commercial novolac resin.

Pyrolysis of Hyperbranched polyborate modified phenolic resin

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.

Application of a factorial design to study a chromate-conversion process

A mixture of 3,6-dihydroxy-9H-xanthen-9-one (4, 5.545 g, 0.024 mol) and hexamethylenetetramine (HMTA, 17.1 g, 0.12 mol) was dissolved in AcOH (60 mL).

Xanthone and Flavone Derivatives as Dual Agents with Acetylcholinesterase Inhibition and Antioxidant Activity as Potential Anti-Alzheimer Agents

The ZnO growth solution was prepared by dissolving 16 mM of zinc nitrate hexahydrate (Zn [(N[O.sub.3]).sub.2]-6[H.sub.2]O) and 25 mM of hexamethylenetetramine (HMT) into 200 mL of distilled water.

Annealing effect of ZnO seed layer on enhancing photocatalytic activity of ZnO/Ti[O.sub.2] nanostructure

This is probably due to the fact that the [T.sub.g] of phenolic novolac polymer (cured with hexamethylenetetramine) is reportedly about 120[degrees]C [27] while the neat polybenzoxazine possesses a higher [T.sub.g]s of 165[degrees]C.

Development of wood-substituted composites from highly filled polybenzoxazine-phenolic novolac alloys

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.

Structural beams from thick wood panels bonded industrially with formaldehyde-free tannin adhesives