Triuret is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

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

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''p ...

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

. 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 compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...

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

phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, es ...

: :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 more recently as a solvent that is ...

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 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 metabolic breakdown ...

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 of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due t ...

from urea.

Related compounds

Urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

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 , where ...

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

References

Ureas Functional groups