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. The ...
with the formula (H
2NC(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 ''py ...
of
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 r ...
. 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 nitrogenous was ...
:
:3 (H
2N)
2CO →
2NC(O)NHsub>2CO + 2 NH
3
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, espe ...
:
:2 (H
2N)
2CO + COCl
2 →
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 (H
2N)
2CO + CO(OCH
3)
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 of ...
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 r ...
*
Biuret
*
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 bleach ...
References
Ureas
Functional groups