Triuret

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.[1]

Triuret
Names
Other names
Carbonyldiurea
1,3-Dicarbamylurea
Dicarbamylurea
Diimidotricarbonic diamide
2,4-diimidotricarbonic diamide
Tricarbonodiimidic diamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.317
EC Number
  • 209-147-7
MeSH C017781
UNII
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).
Infobox references

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:[2]

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

A similar synthesis employs urea and dimethyl carbonate with potassium methoxide as a catalyst:[3]

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

The original synthesis entailed oxidation of uric acid with hydrogen peroxide.[4]

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

References
  1. D. Carlström and H. Ringertz "The molecular and crystal structure of triuret" Acta Crystallogr. (1965. vol. 18, 307-313. doi:10.1107/S0365110X65000737
  2. C. Nitschke, G. Scherr (2012). "Urea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o04.CS1 maint: uses authors parameter (link)
  3. Chen, Jianchao; Zhao, Peihua; Liu, Yaqing; Liu, Hua; Zhu, Futian (2012). "Clean and facile synthesis of triuret from urea and dimethyl carbonate (DMC) under mild conditions". Korean Journal of Chemical Engineering. 29 (3): 288–290. doi:10.1007/s11814-011-0172-8. S2CID 94537937.
  4. Alfred Schittenhelm, Karl Wiener "Carbonyldiharnstoff als Oxydationsprodukt der Harnsäure" Zeitschrift für Physiologische Chemie 1909, volume 62, 100 ff..
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.