Misplaced Pages

Triuret: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 20:54, 17 July 2014 editSpacepotato (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers27,611 edits add some names← Previous edit Latest revision as of 22:06, 1 October 2023 edit undoTrappist the monk (talk | contribs)Administrators479,921 editsm cite repair;Tag: AWB 
(21 intermediate revisions by 12 users not shown)
Line 1: Line 1:
{{chembox {{chembox
| ImageFile = Triuret.svg | ImageFile = TriuretHbond.png
| ImageSize = 230px | ImageSize = 260px
| ImageName = Structure of triuret | ImageName = Structure of triuret
| Name = Triuret | Name = Triuret
| PIN = 2,4-Diimidotricarbonic diamide<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |page=866 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| OtherNames = Carbonyldiurea<br /> 1,3-Dicarbamylurea<br />Dicarbamylurea<br />Diimidotricarbonic diamide<br />2,4-diimidotricarbonic diamide<br />Tricarbonodiimidic diamide | OtherNames = Carbonyldiurea<br /> 1,3-Dicarbamylurea<br />Dicarbamylurea<br />Diimidotricarbonic diamide<br />Tricarbonodiimidic diamide
⚫ | Summenformel = C<sub>3</sub>H<sub>6</sub>N<sub>4</sub>O<sub>3</sub>
| Section1 = {{chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 556-99-0 | CASNo = 556-99-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 68400}}
| UNII = 6ID4233C3S
⚫ | Section2 = {{chembox Properties
| UNII_Ref = {{fdacite|correct|FDA}}
| C = 3
| H = 6 | EINECS = 209-147-7
| N = 4 | PubChem = 68400
| O = 3 | ChemSpiderID = 61685
| SMILES = C(=O)(N)NC(=O)NC(=O)N
| StdInChI = 1S/C3H6N4O3/c4-1(8)6-3(10)7-2(5)9/h(H6,4,5,6,7,8,9,10)
| StdInChIKey = WNVQBUHCOYRLPA-UHFFFAOYSA-N
| MeSHName = C017781
| ChEBI = 36955}}
⚫ |Section2={{Chembox Properties
| C=3 | H=6 | N=4 | O=3
| Density = 1.547 g/cm<sup>3</sup>
}} }}
}} }}
'''Triuret''' is an ] with the formula (H<sub>2</sub>NC(O)NH)<sub>2</sub>CO. It is a product from the ] of ]. 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.<ref>D. Carlström and H. Ringertz "The molecular and crystal structure of triuret" Acta Crystallogr. (1965. vol. 18, 307-313. {{doi|10.1107/S0365110X65000737}}</ref>
'''Triuret''' is an ]. It can be produced during the pyrolysis
of ] by condensation of three urea molecules with elimination of two molecules of ].


== Properties == ==Synthesis==
The compound is typically prepared by heating thin layers of urea, the thin layers facilitating escape of ]:
Triuret is a colorless, crystalline, hygroscopic substance, slightly soluble in cold water or ether, and more soluble in hot water.
⚫ :3 (H<sub>2</sub>N)<sub>2</sub>CO → <sub>2</sub>CO + 2 NH<sub>3</sub>
It can also prepared by treatment of urea with ]:<ref name=Ullmann>{{ Ullmann |author=C. Nitschke |author2=G. Scherr | title = Urea Derivatives | year = 2012| doi = 10.1002/14356007.o27_o04}}</ref>
:2 (H<sub>2</sub>N)<sub>2</sub>CO + COCl<sub>2</sub> → <sub>2</sub>CO + 2 HCl
A similar synthesis employs urea and ] with potassium methoxide as a catalyst:<ref name="Chen2012">{{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}}</ref>
:2 (H<sub>2</sub>N)<sub>2</sub>CO + CO(OCH<sub>3</sub>)<sub>2</sub> → <sub>2</sub>CO + 2 MeOH

The original synthesis entailed oxidation of ] with hydrogen peroxide.<ref>Alfred Schittenhelm, Karl Wiener "Carbonyldiharnstoff als Oxydationsprodukt der Harnsäure" Zeitschrift für Physiologische Chemie 1909, volume 62, 100 ff.</ref>

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


== Related compounds == == Related compounds ==
* ]
* ] * ]
* ] * ]
* ]


==References==
<references />


] ]

Latest revision as of 22:06, 1 October 2023

Triuret
Structure of triuret
Names
Preferred IUPAC name 2,4-Diimidotricarbonic diamide
Other names Carbonyldiurea
1,3-Dicarbamylurea
Dicarbamylurea
Diimidotricarbonic diamide
Tricarbonodiimidic diamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.317 Edit this at Wikidata
EC Number
  • 209-147-7
MeSH C017781
PubChem CID
UNII
CompTox Dashboard (EPA)
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
Density 1.547 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Synthesis

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

3 (H2N)2CO → 2CO + 2 NH3

It can also prepared by treatment of urea with phosgene:

2 (H2N)2CO + COCl2 → 2CO + 2 HCl

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

2 (H2N)2CO + CO(OCH3)2 → 2CO + 2 MeOH

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

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

Related compounds

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 866. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. D. Carlström and H. Ringertz "The molecular and crystal structure of triuret" Acta Crystallogr. (1965. vol. 18, 307-313. doi:10.1107/S0365110X65000737
  3. C. Nitschke; G. Scherr (2012). "Urea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o04. ISBN 978-3527306732.
  4. 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.
  5. Alfred Schittenhelm, Karl Wiener "Carbonyldiharnstoff als Oxydationsprodukt der Harnsäure" Zeitschrift für Physiologische Chemie 1909, volume 62, 100 ff.
Categories: