Hexamethylenetetramine

Synthesis_Hexamine.svg

Hexamethylenetetramine (also known as methenamine, urotropin, or hexamine) is a heterocyclic organic compound with the formula (CH₂)₆N₄. It is a white crystalline compound highly soluble in water and polar organic solvents.

History

Hexamethylenetetramine was first discovered by Aleksandr Butlerov in 1859. It has since been used in various applications, including as a medication, a food additive, and in the production of phenolic resins.

Chemical Structure and Properties

Hexamethylenetetramine is composed of a six-membered ring containing four nitrogen atoms and six methylene groups. Its molecular structure can be described as a cage-like structure similar to adamantane. The compound is stable under normal conditions but can decompose at high temperatures to release formaldehyde and ammonia.

Synthesis

Hexamethylenetetramine is synthesized by the reaction of formaldehyde and ammonia:

<math>4 CH₂O + 6 NH₃ → (CH₂)₆N₄ + 6 H₂O</math>

This reaction is typically carried out in an aqueous solution.

Applications

Medical Use

Hexamethylenetetramine is used as an antibiotic under the name methenamine. It is particularly effective in the treatment of urinary tract infections (UTIs). The compound works by decomposing into formaldehyde in acidic environments, which has antibacterial properties.

Industrial Use

Hexamethylenetetramine is used in the production of phenolic resins, which are important in the manufacture of molding compounds, laminates, and adhesives. It is also used as a fuel in solid fuel tablets for camping stoves.

Food Additive

In the food industry, hexamethylenetetramine is used as a preservative and is listed under the E number E239.

Safety and Handling

Hexamethylenetetramine is generally considered safe when used in accordance with prescribed guidelines. However, it can be irritating to the skin, eyes, and respiratory system. Proper safety measures, including the use of personal protective equipment, should be followed when handling the compound.

See Also

• Formaldehyde
• Ammonia
• Phenolic resin
• Urinary tract infection