Biuret is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

. 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 Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...

, organyl or other groups. Also known as carbamylurea, it results from the condensation of two equivalents of

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

. 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

at 150 °C for ~6 hours until it gets slightly cloudy, then recrystallizing from

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...

. 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 al ...

solution and water to finally get base-free crystalline needles of the monohydrate which are free of

cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleach ...

. While heating, a lot of

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

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 ...

. In general, organic biurets (those with alkyl or aryl groups in place of one or more H atoms) are prepared by

trimerization In chemistry, a trimer (; ) is a molecule or polyatomic anion formed by combination or association of three molecules or ions of the same substance. In technical jargon, a trimer is a kind of oligomer derived from three identical precursors ofte ...

isocyanate In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyan ...

s. 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 Ruminants (suborder Ruminantia) are hoofed herbivorous grazing or browsing mammals that are able to acquire nutrients from plant-based food by fermenting it in a specialized stomach prior to digestion, principally through microbial actions. The ...

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 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 ...

is a

chemical test In chemistry, a chemical test is a qualitative or quantitative procedure designed to identify, quantify, or characterise a chemical compound or chemical group. Purposes Chemical testing might have a variety of purposes, such as to: * Determine ...

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 Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. A p ...

. 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 , wher ...

, 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 Gustav Heinrich Wiedemann (; 2 October 1826 – 24 March 1899) was a German physicist and scientific author. Life Wiedemann was born in Berlin the son of a merchant who died two years later. Following the death of his mother in 1842 he lived w ...

(1826 – 1899) for his doctoral dissertation, which was submitted in 1847. His findings were reported in several articles.

Related compounds

Cyanuric acid Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a component of bleach ...

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 Biuret is a chemical compound with the chemical formula . It is a white solid that is soluble in hot wa ...

, the carboxylic acid derivative of biuret

References

{{reflist Ureas Functional groups