Biuret

Biuret is a chemical compound with the chemical formula [H2NC(O)]2NH. It is a white solid that is soluble in hot water. The term "biuret" also describes a family of organic compounds with the functional group -(HN-CO-)2N-. Thus, dimethyl biuret is [Me(H)NC(O)]2NH. A variety of organic derivatives are known. Also known as carbamylurea, it results from the condensation of two equivalents of urea. As such, it is an undesirable impurity in urea-based fertilizers.

Biuret
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
1703510
ChEBI
ChemSpider
ECHA InfoCard 100.003.236
EC Number
  • 203-559-0
49702
KEGG
MeSH Biuret
UNII
Properties
C2H5N3O2
Molar mass 103.081 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
Std enthalpy of
formation (ΔfH⦵298)
 −565.8–−561.6 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −940.1–−935.9 kJ mol−1
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 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

Preparation and structure

The parent compound can be prepared by heating urea above the melting point at which temperature ammonia is expelled:[3]

2 CO(NH2)2 → H2N-CO-NH-CO-NH2 + NH3

Under related conditions, pyrolysis of urea affords triuret ((H2N-CO-NH)2CO).[3] 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.

In the anhydrous material, the molecule is planar and unsymmetrical in the solid state owing to intramolecular hydrogen bonding. The terminal C-N distances of 1.327 and 1.334 Å are shorter than the internal C-N distances of 1.379 and 1.391 Å. The C=O bond distances 1.247 and 1.237 Å. It crystallizes from water as the hydrate.[4]

Structure of biuret in the solid state (blue = N, red = O, gray = C, cyan = H).

Applications

Biuret is also used as a non-protein nitrogen source in ruminant feed,[5] where it is converted into protein by gut microorganisms.[6] It is less favored than urea, due to its higher cost and lower digestibility[7] but the latter characteristic also slows down its digestion and so decreases the risk of ammonia toxicity.[7][8]

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.

History

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.[9][10][11][12]

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References
  1. 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. Scifinder, version 2007.1; Chemical Abstracts Service: Columbus, OH; RN 108-19-0 (accessed June 15, 2012)
  3. Meessen, J. H.; Petersen, H. "Urea". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_333.
  4. E. W. Hughes, H. Yakel, H. C. Freeman (1961). "The Crystal Structure of Biuret Hydrate". Acta Crystallogr. 14 (4): 345–352. doi:10.1107/S0365110X61001194.CS1 maint: uses authors parameter (link)
  5. Beef cattle feed, Encyclopædia Britannica Online
  6. Kunkle, B.; Fletcher, J.; Mayo, D. (2013). "Florida Cow-Calf Management, 2nd Edition - Feeding the Cow Herd". IFAS Extension, University of Florida. Publication #AN117.
  7. 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. doi:10.2527/jas1969.295816x. PMID 5391979.
  8. 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. doi:10.2527/jas1975.4061150x.
  9. 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.
  10. 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"
  11. 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.
  12. 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.
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