Glycoluril is an

organic chemical In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The st ...

composed of two cyclic

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 ...

groups joined across the same two-carbon chain. It is a white powder that has been used in water treatment, in paints and coatings, and occasionally as a slow-release fertilizer.

Production

Glycoluril can be synthesized by reacting two equivalents of urea with

glyoxal Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of ...

. Likewise, using other vicinal

carbonyl In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a ...

(or carbonyl hydrate) reactants give derivatives having various

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

s in place of the hydrogen atoms on the carbon chain.

Properties

The four amide-like and therefore

acid In computer science, ACID ( atomicity, consistency, isolation, durability) is a set of properties of database transactions intended to guarantee data validity despite errors, power failures, and other mishaps. In the context of databases, a sequ ...

ic hydrogen atoms of glycoluril are amenable to a variety of chemical reactions, such as substitution with halogen atoms or a reaction with formaldehyde.

Use

Glycouril itself and derivatives of it are used as monomers for producing the macrocyclic

cucurbituril In host-guest chemistry, cucurbiturils are macrocyclic molecules made of glycoluril () monomers linked by methylene bridges (). The oxygen atoms are located along the edges of the band and are tilted inwards, forming a partly enclosed cavity ( ...

s polymers, which serve as hosts to bind to various neutral and cationic species. They are also used in several classes of non-cyclic structures that also bind a variety of structures. Glycoluril is used as the starting material for tetrachloromoglycoluril and tetrabromoglycoluril, which are used as

biocide A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slig ...

s in water treatment, swimming pool disinfection, and as sludge control agents in papermaking. The use of glycoluril as a sustained-release nitrogen fertilizer has been discussed, but it has not been widely used because of its high cost. Glycoluril can be converted with excess

methanal Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...

into tetramethylol glycoluril, which releases methanal with delay and is therefore used as a biocide in water-based paints, in liquid detergents and in care and cleaning agents (in concentrations of 0.1%). It also finds utility as a crosslinker for hydroxyl-containing polymers, as an industrial

fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

and as an accelerator in cements. Tetraacetylglycoluril (TAGU) can be prepared from glycoluril by reaction with

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a col ...

. Tetraacetylglycoluril can be used, but it not very common as a bleach activator for

sodium percarbonate Sodium percarbonate is a chemical substance with formula . It is an adduct of sodium carbonate ("soda ash" or "washing soda") and hydrogen peroxide (that is, a perhydrate) whose formula is more properly written as 2 · 3 . I ...

in solid detergent formulations because of its slow biodegradability. The reaction with nitrating acid (concentrated nitric acid and concentrated sulfuric acid) leads to the explosives dinitroglycoluril and tetranitroglycoluril.

References

{{reflist Nitrogen heterocycles Monomers