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Biuret is a chemical compound with the chemical formula . It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula , where are hydrogen, organyl or other groups. 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. As biuret is toxic to plants, its percentage in fertilizers must be kept low.


Preparation and structure

The parent compound can be prepared by heating urea at 150 °C for ~6 hours until it gets slightly cloudy, then recrystallizing from water. After that, it can be recrystallized repeatedly from 2%
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
solution and water to finally get base-free crystalline needles of the monohydrate which are free of cyanuric acid. While heating, a lot of ammonia is expelled: : Under related conditions, pyrolysis of urea affords
triuret 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 p ...
. 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 form, 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 monohydrate. 220 px, left, 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, where it is converted into protein by gut microorganisms. It is less favored than urea, due to its higher cost and lower digestibility but the latter characteristic also slows down its digestion and so decreases the risk of ammonia toxicity.


Biuret test

The biuret test is a chemical test for
proteins Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...
and polypeptides. It is based on the
biuret reagent Biuret is a chemical compound with the chemical formula . It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula , where ...
, a blue solution that turns violet upon contact with proteins, or any substance with
peptide bond In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 (carbon number one) of one alpha-amino acid and N2 (nitrogen number two) of another, along a peptide or protein cha ...
s. 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.


Related compounds

* Cyanuric acid *
Allophanic acid Allophanic acid is the organic compound with the formula H2NC(O)NHCO2H. It is a carbamic acid, the carboxylated derivative of urea. Biuret can be viewed as the amide of allophanic acid. The compound can be prepared by treating urea with sodium ...
, the carboxylic acid derivative of biuret


References

{{reflist Ureas Functional groups