Biuret

Biuret
Skeletal formula of biuret
Ball-and-stick model of the biuret molecule
Space-filling model of the biuret molecule
Names
Preferred IUPAC name
2-Imidodicarbonic diamide[1]
Other names
Biuret[1]
Allophanamide[2]
Carbamylurea[2]
Allophanic acid amide[2]
Allophanimidic acid[2]
N-Carbamoylaminomethanamide
Ureidoformamide[2]
Imidodicarbonic diamide
Diurea
Identifiers
3D model (JSmol)
3DMet B00969
1703510
ChEBI
ChemSpider
ECHA InfoCard 100.003.236
EC Number 203-559-0
49702
KEGG
MeSH Biuret
UNII
Properties
C2H5N3O2
Molar mass 103.08 g·mol−1
Appearance White crystals
Odor Odourless
Density 1.467 g/cm3
Melting point 190 °C (decomposes)
Thermochemistry
131.3 J K−1 mol−1
146.1 J K−1 mol−1
−565.8–−561.6 kJ mol−1
−940.1–−935.9 kJ mol−1
Hazards
GHS pictograms
GHS signal word WARNING
H315, H319, H335
P261, P305+351+338
Related compounds
Related compounds
 urea, triuret, cyanuric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Biuret is a chemical compound with the chemical formula C2H5N3O2. It is also known as carbamylurea. It is the result of condensation of two molecules of urea and is an impurity in urea-based fertilizers. This white solid is soluble in hot water. Biuret was first prepared and studied by Gustav Heinrich Wiedemann (1826 - 1899) for his doctoral dissertation, which was submitted in 1847. His findings were reported in several articles.[3][4][5][6]

The term "biuret" also describes a family of organic compounds with the functional group -(HN-CO-)2N-. Thus dimethyl biuret is CH3HN-CO-NR'-CO-NHCH3. A variety of organic derivatives are possible.

Preparation

The parent compound can be prepared by heating urea above the melting point at which temperature ammonia is expelled:[7]

2 CO(NH2)2 → H2N-CO-NH-CO-NH2 + NH3

Under related conditions, pyrolysis of urea affords triuret ((H2N-CO-NH)2CO).[7] In general, organic biurets (those with alkyl or aryl groups in place of one or more H atoms) are prepared by trimerization of isocyanates. For example, the trimer of 1,6-hexamethylene diisocyanate is also known as HDI-biuret.

Applications

Biuret is also used as a non-protein nitrogen source in ruminant feed,[8] where it is converted into protein by gut microorganisms.[9] It is less favored than urea, due to its higher cost and lower digestibility[10] but this characteristic also slows down its digestion and so decreases the risk of ammonia toxicity.[10][11]

Biuret test

The biuret test is a chemical test for proteins and polypeptides. It is based on the biuret reagent, a blue solution that turns violet upon contact with proteins, or any substance with peptide bonds. The test and reagent do not actually contain biuret; they are so named because both biuret and proteins have the same response to the test.

References

  1. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 866. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. 1 2 3 4 5 Scifinder, version 2007.1; Chemical Abstracts Service: Columbus, OH; RN 108-19-0 (accessed June 15, 2012)
  3. ↑ Wiedemann, G. (1848). "Ueber ein neues Zersetzungsproduct des Harnstoffs" [On a new decomposition product of urea]. Annalen der Physik. 150 (5): 67–84. doi:10.1002/andp.18491500508.
  4. ↑ Wiedemann, G. (1847). "Neues Zersetzungsproduct des Harnstoffs" [New decomposition product of urea]. Journal für Praktische Chemie. 42 (3–4): 255–256. doi:10.1002/prac.18470420134. This notice reports that biuret reacts with alkaline copper sulfate to produce a red solution -- the so-called "Biuret test"
  5. ↑ Wiedemann, G. (1848). "Ueber eine neue, aus dem Harnstoff entstehende Verbindung" [On a new compound arising from urea]. Journal für Praktische Chemie. 43 (5): 271–280. doi:10.1002/prac.18480430133.
  6. ↑ Wiedemann, G. (1848). "Biuret. Zersetzungsprodukt des Harnstoffs" [Biuret: decomposition product of urea]. Justus Liebig's Annalen der Chemie. 68 (3): 323–326. doi:10.1002/jlac.18480680318.
  7. 1 2 Meessen, J. H.; Petersen, H., "Urea", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_333
  8. ↑ Beef cattle feed, Encyclopædia Britannica Online
  9. ↑ Kunkle, B.; Fletcher, J.; Mayo, D. (2013). "Florida Cow-Calf Management, 2nd Edition - Feeding the Cow Herd". IFAS Extension, University of Florida. Publication #AN117.
  10. 1 2 Oltjen, R. R.; Williams, E. E.; Slyter, L. L.; Richardson, G. V. (1969). "Urea versus biuret in a roughage diet for steers". Journal of Animal Science. 29 (5): 816–822. PMID 5391979.
  11. ↑ Fonnesbeck, P. V.; Kearl, L. C.; Harris, L. E. (1975). "Feed Grade Biuret as a Protein Replacement for Ruminants. A Review". Journal of Animal Science. 40 (6): 1150–1184.
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