Triuret

Chemical compound From Wikipedia, the free encyclopedia

Triuret is an organic compound with the formula (H2NC(O)NH)2CO. It is a product from the pyrolysis of urea. Triuret is a colorless, crystalline, hygroscopic solid, slightly soluble in cold water or ether, and more soluble in hot water. It is a planar molecule. The central carbonyl is hydrogen-bonded to both terminal amino groups.[2]

Quick facts Names, Identifiers ...
Triuret
Structure of triuret
Structure of triuret
Names
Preferred IUPAC name
2,4-Diimidotricarbonic diamide[1]
Other names
Carbonyldiurea
1,3-Dicarbamylurea
Dicarbamylurea
Diimidotricarbonic diamide
Tricarbonodiimidic diamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.317 Edit this at Wikidata
EC Number
  • 209-147-7
MeSH C017781
UNII
  • InChI=1S/C3H6N4O3/c4-1(8)6-3(10)7-2(5)9/h(H6,4,5,6,7,8,9,10)
    Key: WNVQBUHCOYRLPA-UHFFFAOYSA-N
  • C(=O)(N)NC(=O)NC(=O)N
Properties
C3H6N4O3
Molar mass 146.106 g·mol−1
Density 1.547 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

The compound is typically prepared by heating thin layers of urea, the thin layers facilitating escape of ammonia:

3 (H2N)2CO → [H2NC(O)NH]2CO + 2 NH3

It can also prepared by treatment of urea with phosgene:[3]

2 (H2N)2CO + COCl2 → [H2NC(O)NH]2CO + 2 HCl

A similar synthesis employs urea and dimethyl carbonate with potassium methoxide as a catalyst:[4]

2 (H2N)2CO + CO(OCH3)2 → [H2NC(O)NH]2CO + 2 MeOH

The original synthesis entailed oxidation of uric acid with hydrogen peroxide.[5]

Triuret is a complicating by-product in the industrial synthesis of melamine from urea.

Related compounds

References

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