Hexamethylenetetramine

  • Hexamethylenetetramine
  • 1,3,5,7- tetraazaadamantane
  • Formin
  • Hexamine
  • Methenamine
  • Dry alcohol

Colorless solid with an amine-like odor

Fixed

1.33 g · cm -3

Decomposition: 263 ° C

50 MPa (20 ° C)

  • Very well in water (490 g in 1000 ml at 20 ° C), good in chloroform 199 g · l-1
  • Standard in methanol 57 g · l-1, ethanol 23 g · l -1, bad in diethyl ether, 0.4 g · l-1

Attention

Template: Infobox chemical / molecular formula search available

Urotropin (also: hexamethylenetetramine or methenamine INDEX Number: 612-101-00-2, EC number: 202-905-8 ) is a colorless crystalline powder. The structure of urotropin can be derived from adamantane, a hydrocarbon. The four points of attachment of the three six-membered rings are occupied by nitrogen atoms, which is one CH 2 group between the nitrogen atoms.

Use

Urotropin used for the production of amino and phenolic resins and as a food preservative ( E 239, rarely used, only allowed in Provolone cheese). In compressed form it is also used as solid fuel and is the main component of the fuel Esbit.

In the organic synthesis, it is used as formyl ( Duff reaction) to introduce amino groups for the synthesis of N-heterocyclic compounds, and is used in the Mannich reaction. In inorganic analysis, it serves in the cation separation process as buffer substance in the precipitation of the so-called Urotropingruppe ( which includes iron, chromium and aluminum are ) at pH 5.5. In acidic aqueous solution decomposes into hexamine formaldehyde and ammonium ions.

Urotropin is a starting material for the production of explosives RDX, HMX, and Dinitrohexamin HMTD.

In the foundry art, it is used in combination with phenol resin as a resin-hardener system for the shell mold process for the production of molds and the hollow cores.

Medically, it is under the name of methenamine (trade name: Antihydral ® ( D)) use against excessive transpiration, such as on the hands, feet or underarms.

Production

Hexamethylenetetramine formed from ammonia and formaldehyde in aqueous solution:

This reaction is used in the so-called formol titration for the determination of ammonium compounds.

Properties

  • Flash point: 250 ° C
  • Ignition temperature: 390 ° C
  • Energy density, calorific value 31.3 MJ / kg
CAS registry number PubChem Vapor pressure Dangerous Substances Directive (67/548/EEC) European Community number Aluminium Sørensen formol titration Integrated Authority File
251063
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