Triuret

Triuret
Names
	Other names Carbonyldiurea; 1,3-Dicarbamylurea; Dicarbamylurea; Diimidotricarbonic diamide; 2,4-diimidotricarbonic diamide; Tricarbonodiimidic diamide
Identifiers
CAS Number	556-99-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36955;
ChemSpider	61685;
ECHA InfoCard	100.008.317
EC Number	209-147-7;
MeSH	C017781
PubChem CID	68400;
UNII	6ID4233C3S ;
CompTox Dashboard (EPA)	DTXSID9060314 ;
	InChI 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;
	SMILES C(=O)(N)NC(=O)NC(=O)N;
Properties
Chemical formula	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

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]

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.

Related compounds

gollark: It's mostly bot roles. Which I can't remove without the hassle of removing and readding each bot, unless there's a better way, which I was asking about (Discord is known for weird poorly documented features).

gollark: > You can have up to 250 roles in a serverYes, I reached that. But removing and readding bots to make role space is inconvenient.

gollark: Can I remove this "integration" role without just removing the bot entirely? I have a few hundred of these due to reasons and it appears to have reached the role limit.

gollark: The playground thing does have buttons at the top for the weird characters, which is helpful.

gollark: This is neat apart from being impossible to type.

References

D. Carlström and H. Ringertz "The molecular and crystal structure of triuret" Acta Crystallogr. (1965. vol. 18, 307-313. doi:10.1107/S0365110X65000737
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)
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.
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.

[1] D. Carlström and H. Ringertz "The molecular and crystal structure of triuret" Acta Crystallogr. (1965. vol. 18, 307-313. doi:10.1107/S0365110X65000737

[Ullmann-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)

[Chen2012-3] 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.

[4] Alfred Schittenhelm, Karl Wiener "Carbonyldiharnstoff als Oxydationsprodukt der Harnsäure" Zeitschrift für Physiologische Chemie 1909, volume 62, 100 ff..