Triuret is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula (H₂NC(O)NH)₂CO. It is a product from the

pyrolysis Pyrolysis is a process involving the Bond cleavage, separation of covalent bonds in organic matter by thermal decomposition within an Chemically inert, inert environment without oxygen. Etymology The word ''pyrolysis'' is coined from the Gree ...

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

. 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.

Synthesis

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

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

: :3 (H₂N)₂CO → ₂NC(O)NHsub>2CO + 2 NH₃ It can also prepared by treatment of urea with

phosgene Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...

: :2 (H₂N)₂CO + COCl₂ → ₂NC(O)NHsub>2CO + 2 HCl A similar synthesis employs urea and

dimethyl carbonate Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion ba ...

with potassium methoxide as a catalyst:{{cite journal, last1=Chen, first1=Jianchao, last2=Zhao, first2=Peihua, last3=Liu, first3=Yaqing, last4=Liu, first4=Hua, last5=Zhu, first5=Futian, title=Clean and facile synthesis of triuret from urea and dimethyl carbonate (DMC) under mild conditions, journal=Korean Journal of Chemical Engineering, date=2012, volume=29, issue=3, pages=288–290, doi=10.1007/s11814-011-0172-8, s2cid=94537937 :2 (H₂N)₂CO + CO(OCH₃)₂ → ₂NC(O)NHsub>2CO + 2 MeOH The original synthesis entailed oxidation of

uric acid Uric acid is a heterocyclic compound of carbon, nitrogen, oxygen, and hydrogen with the Chemical formula, formula C5H4N4O3. It forms ions and salts known as urates and acid urates, such as ammonium acid urate. Uric acid is a product of the meta ...

with hydrogen peroxide.Alfred Schittenhelm, Karl Wiener "Carbonyldiharnstoff als Oxydationsprodukt der Harnsäure" Zeitschrift für Physiologische Chemie 1909, volume 62, 100 ff. Triuret is a complicating by-product in the industrial synthesis of

melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer (chemistry), trimer of cyanamide, with a 1,3,5-Triazine, 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives ha ...

from urea.

Related compounds

Urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

Biuret Biuret ( ) is a chemical compound with the chemical formula . It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula , ...

Cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...

References

Ureas Functional groups