Ammeline (4,6-diamino-2-hydroxy-1,3,5-triazine) is a triazine

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

. It is the hydrolysis product of

melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67% nitrogen by mass, and its derivatives have fire retardant properties due t ...

Synthesis

Ammeline can be synthesized by the

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...

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 r ...

or the

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

among 2 moles of

dicyandiamide 2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents. Production ...

and 1 mole of

biuret 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 ...

. : 2 C₂H₄N₄ + C₂H₅N₃O₂ → 2C₃H₅N₅O + NH₃

Chemical properties

Ammeline is weakly acidic with pKa ~9. It can form

nitrate Nitrate is a polyatomic ion A polyatomic ion, also known as a molecular ion, is a covalent bonded set of two or more atoms, or of a metal complex, that can be considered to behave as a single unit and that has a net charge that is not zer ...

sulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ar ...

, chromate, and

oxalate Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl o ...

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

. Ammeline reacts with boiling dilute

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

to form

melem In chemistry, melem is a compound with formula ; specifically, 2,5,8-triamino-heptazine or 2,5,8-triamino-tri-''s''-triazine, whose molecule can be described as that of heptazine with the three hydrogen atoms replaced by amino groups. It is a whit ...

and

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 was ...

. Ammeline is the first step in melamine hydrolysis. Further hydrolysis (e.g. boiling ammeline with dilute alkali) yields

ammelide , Section2={{Chembox Properties , Formula = C3H4N4O2 , MolarMass = 128.09 g/mol , Appearance = white powder , Density = , MeltingPt = , MeltingPt_notes = , BoilingPt = , BoilingPt_notes = , Solubility = insoluble , SolubleOther = sol ...

References

* {{cite journal , author = B. Bann and S.A. Miller , title = Melamines and derivatives of melamine , journal =

Chemical Reviews ''Chemical Reviews'' is peer-reviewed scientific journal published twice per month by the American Chemical Society. It publishes review articles on all aspects of chemistry. It was established in 1924 by William Albert Noyes (University of Illinoi ...

, doi = 10.1021/cr50019a004 , volume = 58 , pages = 131–172 , date = 1958 Triazines Aromatic amines