Glycoluril is an

organic chemical Some chemical authorities define an organic compound as a chemical compound that contains a Carbon–hydrogen bond, carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. F ...

composed of two cyclic

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

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 with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

. Likewise, using other vicinal

carbonyl In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...

(or carbonyl hydrate) reactants give derivatives having various

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

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

Properties

The four amide-like and therefore

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

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 sli ...

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 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 pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

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 chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

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

bleach activator Bleach activators are compounds that allow a lower washing temperature than would be required otherwise to achieve the full activity of bleaching agents in the wash liquor. Bleaching agents, usually peroxides, are usually sufficiently active only ...

for

sodium percarbonate Sodium percarbonate or sodium carbonate peroxide is an inorganic compound with the formula . It is an adduct of sodium carbonate ("soda ash" or "washing soda") and hydrogen peroxide (that is, a perhydrate). It is a colorless, crystalline, hygros ...

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