What Is Hexamethylenetetramine?
Hexamethylenetetramine, a heterocyclic aliphatic amine, boasts the chemical formula C6H12N4. Commonly known as hexamine, urotropine, methenamine, and 1,3,5,7-tetraazaadamantane, this compound serves various industrial and medical purposes.
It is classified under several regulations: as a Class D substance, a “Class I designated chemical substance, and as an undesignated additive.
Uses of Hexamethylenetetramine
Hexamethylenetetramine finds its use in therapeutic settings, particularly for treating cystitis and urinary tract infections. It transforms into formaldehyde in the urine, which then exhibits antiseptic properties. While used as an antiseptic preservative in food products internationally, it is not utilized as a food preservative in Japan.
Properties of Hexamethylenetetramine
This compound appears as a colorless, odorless crystal or crystalline powder that sublimates at 280°C and ignites at 410°C. It is soluble in water, ethanol, and chloroform, but insoluble in benzene, acetone, and ether.
Structure of Hexamethylenetetramine
Hexamethylenetetramine’s structure is a tetrahedral cage, similar to adamantane, with nitrogen atoms at the four vertices connected by methylene links. It features a molar mass of 140.186 g/mol and a density of 1.33 g/cm3 at 20°C.
Other Information on Hexamethylenetetramine
1. Synthetic Method
Discovered by Alexander Butlerov in 1859, hexamethylenetetramine is produced industrially via the reaction of formaldehyde and ammonia.
2. Reactions Involving Hexamethylenetetramine
It is instrumental in organic synthesis, notably in the Duff reaction for formylating aromatic rings, the Sommelet reaction for synthesizing aldehydes from benzyl halides, and the Delépine reaction for creating amines from alkyl halides.
3. Hexamethylenetetramine as a Base
Acting as an amine-like base, it undergoes protonation and N-alkylation. For instance, N-alkylation with 1,3-dichloropropene yields Quaternium-15, a quaternary ammonium salt consisting of cis and trans isomers.