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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.

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]

Related compounds

Cyanuric acid

References

^ ^a ^b 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.
^ ^a ^b ^c ^d ^e Scifinder, version 2007.1; Chemical Abstracts Service: Columbus, OH; RN 108-19-0 (accessed June 15, 2012)
^ ^a ^b Meessen, J. H.; Petersen, H., "Urea", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a27_333
^ E. W. Hughes, H. Yakel, H. C. Freeman (1961). "The Crystal Structure of Biuret Hydrate". Acta Crystallogr. 14: 345–352. doi:10.1107/S0365110X61001194.CS1 maint: Uses authors parameter (link)
^ Beef cattle feed, Encyclopædia Britannica Online
^ Kunkle, B.; Fletcher, J.; Mayo, D. (2013). "Florida Cow-Calf Management, 2nd Edition - Feeding the Cow Herd". IFAS Extension, University of Florida. Publication #AN117.
^ ^a ^b 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.
^ 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.
^ 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.
^ 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"
^ 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.
^ 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.

English Journal

Deactivation of Cu-SAPO-34 by urea-related deposits at low temperatures and the regeneration.

Ma Y, Wu X, Zhang J, Ran R, Si Z, Weng D.
Journal of environmental sciences (China). 2019 Jul;81()43-51.
Selective catalytic reduction (SCR) with urea catalyzed by Cu-SAPO-34 is an effective method to eliminate NO from diesel exhaust. However, urea-related deposits may form during cold-start and urban driving due to low exhaust temperatures. The activity of Cu-SAPO-34 at 175°C is significantly degrade
PMID 30975329

Morphological, transcriptional, and metabolic analyses of osmotic-adapted mechanisms of the halophilic Aspergillus montevidensis ZYD4 under hypersaline conditions.

Ding X, Liu K, Lu Y, Gong G.
Applied microbiology and biotechnology. 2019 May;103(9)3829-3846.
Halophilic fungi in hypersaline habitats require multiple cellular responses for high-salinity adaptation. However, the exact mechanisms behind these adaptation processes remain to be slightly known. The current study is aimed at elucidating the morphological, transcriptomic, and metabolomic changes
PMID 30859256

Characterization of bovine serum albumin hydrolysates prepared by subcritical water processing.

Koh BB, Lee EJ, Ramachandraiah K, Hong GP.
Food chemistry. 2019 Apr;278()203-207.
The impact of subcritical water processing (SWP), in a temperature range of 240-300 °C, on the formation of hydrolysates from bovine serum albumin (BSA) was investigated in this study. SDS-PAGE analysis of the samples treated at all temperatures did not reveal any bands. Yield, as evaluated by th
PMID 30583363

「ビウレット」

Biuret
Names
	Preferred IUPAC name 2-Imidodicarbonic diamide
	Other names Biuret; Allophanamide; Carbamylurea; Allophanic acid amide; Allophanimidic acid; N-Carbamoylaminomethanamide[citation needed]; Ureidoformamide; Imidodicarbonic diamide[citation needed]; Diurea[citation needed]
Identifiers
CAS Number	108-19-0 ;
3D model (JSmol)	Interactive image;
3DMet	B00969
Beilstein Reference	1703510
ChEBI	CHEBI:18138 ;
ChemSpider	7625 ;
ECHA InfoCard	100.003.236
EC Number	203-559-0
Gmelin Reference	49702
KEGG	C06555 ;
MeSH	Biuret
PubChem CID	7913;
UNII	89LJ369D1H ;
CompTox Dashboard (EPA)	DTXSID2026783 ;
	InChI InChI=1S/C2H5N3O2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7) Key: OHJMTUPIZMNBFR-UHFFFAOYSA-N ;
	SMILES NC(=O)NC(N)=O;
Properties
Chemical formula	C2H5N3O2
Molar mass	103.081 g·mol−1
Appearance	White crystals
Odor	Odourless
Density	1.467 g/cm3
Melting point	190 °C (decomposes)
Thermochemistry
Heat capacity (C)	131.3 J K−1 mol−1
Std molar; entropy (So298)	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
GHS precautionary statements	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

　　[★]

英: biuret
同: アロファンアミド allophanamide、カルボミルウレア carbomylurea、ジカルボミルアミン dicarbomylamine

「アロファンアミド」

　　[★]

英: allophanamide
関: ビウレット

[iupac2013-1] 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.

[SciFinder-2] Scifinder, version 2007.1; Chemical Abstracts Service: Columbus, OH; RN 108-19-0 (accessed June 15, 2012)

[Ullmann-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: 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.

[oltjen-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. 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.

[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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案内

allophanamide