Glycoluril
Names | |
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IUPAC name
Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
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Other names
Acetylenediurea; Acetyleneurea; Acetylenediureine; Acetylene carbamide; Glyoxalbiuret; Glyoxaldiureine; Glyoxaldiurene
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.007.111 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C4H6N4O2 | |
Molar mass | 142.118 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glycoluril is an
Production
Glycoluril can be synthesized by reacting two equivalents of urea with
Properties
The four amide-like and therefore acidic 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 cucurbiturils 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.[1][2]
Glycoluril is used as the starting material for tetrachloromoglycoluril[3] and tetrabromoglycoluril, which are used as biocides 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,[4] but it has not been widely used because of its high cost.
Glycoluril can be converted with excess
Tetraacetylglycoluril (TAGU) can be prepared from glycoluril by reaction with acetic anhydride. Tetraacetylglycoluril can be used, but it not very common as a bleach activator for sodium percarbonate in solid detergent formulations because of its slow biodegradability.[6] [7]
The reaction with nitrating acid (concentrated nitric acid and concentrated sulfuric acid) leads to the explosives dinitroglycoluril and tetranitroglycoluril.[8]
References
- S2CID 96246662.
- .
- doi:10.1021/jo01053a069)
{{citation}}
: CS1 maint: multiple names: authors list (link - ISSN 0038-0768
- ^ Verwendung von Formaldehyd oder Formaldehyd-Abspaltern in Pflege- und Reinigungsmitteln in Privathaushalten (PDF; 53 kB), Vortrag auf der BfR-Fachveranstaltung „Neubewertung von Formaldehyd – Beitrag des BfR zum Verb raucherschutz"
- ISBN 978-3527306732.
- ISBN 978-1-4200-1816-5
- ISBN 978-0-470-02967-1