Glycoluril
Chemical compound
From Wikipedia, the free encyclopedia
Glycoluril is an organic compound with the formula (HC)2(HNC(O)NH)2. It is classified as diurea, consisting of two cyclic urea groups sharing a two-carbon linker. It is a white powder that has been extensively examined as a precursor to macrocyclic compounds and as a precursor to amino resins used in paints and coatings.[1] Many other applications have been considered.
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| Names | |
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| IUPAC name
Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione | |
| Other names
Acetylenediurea; Acetyleneurea; Acetylenediureine; Acetylene carbamide; Glyoxalbiuret; Glyoxaldiureine; Glyoxaldiurene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 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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Production
Glycoluril can be synthesized by the reaction two equivalents of urea with glyoxal. The reaction is catalyzed by sulfuric acid:[2]
- 2 OC(NH2)2 + (CHO)2 → (HC)2(HNC(O)NH)2 + 2 H2O
Likewise, using other vicinal carbonyl (or carbonyl hydrate) reactants give derivatives having various functional groups in place of the hydrogen atoms on the carbon chain.[3]
Reactions
The four amide-like hydrogen atoms of glycoluril undergo a variety of reactions. Substitution with halogen atoms gives the tetrachloride and tetrabromide:[2]
- (HC)2(HNC(O)NH)2 + 4 Cl2 → (HC)2(ClNC(O)NCl)2 + 4 HCl
Tetrachloromoglycoluril and tetrabromoglycoluril are halogenating agents and potential disinfectants.[4]
Condensation reactions with aldehydes results initially in hydroxyalkylation, but is often pushed to give macrocycles or polymers. One large family of rings are formed from formaldehyde:
- (HC)2(HNC(O)NH)2 + 4 CH2O → (HC)2(HOCH2NC(O)NHCH2OH)2
This tetramethylol glycoluril has use as a biocide in water-based paints, in liquid detergents and in care and cleaning agents (in concentrations of 0.1%).[5] It also finds utility as a crosslinker for hydroxyl-containing polymers, as an industrial fungicide and as an accelerator in cements.
- 6 (HC)2(HOCH2NC(O)NHCH2OH)2 → [(HC)2(CH2NC(O)NHCH2)2]6
These cucurbituril-like chains, rings, and polymers serve as hosts to bind to various neutral and cationic species.[6][7]
Use
Glycoluril has been assessed as a controlled-release fertilizer, but the economic factors are not favorable.[8]
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.[9] [10]
The reaction with nitrating acid (concentrated nitric acid and concentrated sulfuric acid) leads to the explosives dinitroglycoluril and tetranitroglycoluril.[11]