Glycoluril
| Names | |
|---|---|
| IUPAC name
Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione
| |
| Other names
Acetylene carbamide
Acetylenediurea Acetylenediureine Acetyleneurea Glyoxalbiuret Glyoxaldiureine Glyoxaldiurene | |
| Properties | |
| C4H6N4O2 | |
| Molar mass | 142.118 g/mol |
| Appearance | White solid |
| Odor | Odorless |
| Melting point | 272–300 °C (522–572 °F; 545–573 K) |
| Boiling point | Decomposes |
| 0.2 g/100 ml (20 °C) 1.5 g/100 ml (100 °C) | |
| Solubility | Soluble in aq. ammonia, diethyl ether, aq. HCl Insoluble in acetic acid, ethanol[1][2][3] |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Glycoluril (C4H6N4O2) is an organic chemical composed of two cyclic urea groups joined across the same two-carbon chain.
Contents
Properties
Chemical
Glycoluril can be converted with excess aq. formaldehyde (methanal) into tetramethylol glycoluril. The compound is not very stable, and will slowly release formaldehyde. As such the compound is used in slow-acting biocides in water-based paints, in liquid detergents and in care and cleaning agents (in concentrations of 0.1%).
Reaction of glycoluril with acetic anhydride produces tetraacetylglycoluril (TAGU).
Nitration of glycoluril with a mixture of conc. nitric and sulfuric acids yields tetranitroglycoluril (TNGU), a potent explosive.
Physical
Glycoluril is a white solid, slightly soluble in cold water and a few organic solvents, like ether. It is odorless.
Availability
Glycoluril is sold by chemical suppliers.
Preparation
Glycoluril can be synthesized by reacting two equivalents of urea with glyoxal. Yield of this reaction is 90 %.[4]
Another route involves the reduction of allantoin using sodium amalgam.
Projects
- Preparation of tetranitroglycoluril (TNGU)
Handling
Safety
There is little data available about its toxicity.
Storage
In closed bottles.
Disposal
Maybe diluted and poured down the drain or in soil, as it has been shown to be useful as fertilizer.
References
- ↑ Budavari, S., ed. (1996) The Merck Index, 12th ed., Whitehouse Station, NJ, Merck & Co., Inc.
- ↑ Lide, D.R., ed. (1995) CRC Handbook of Chemistry and Physics, 76th ed., Boca Raton, FL, CRC Press, Inc., p. 3-197
- ↑ Hoechst Celanese Corp. (1997) Material Safety Data Sheet: Glycoluril, Charlotte, NC
- ↑ Shimizu, T. (1987) Glycoluril as a slow release nitrogen fertilizer. Soil. Sci. Plant Nutr., 33(2), 291- 298
