Glycoluril

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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.

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

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

  1. Budavari, S., ed. (1996) The Merck Index, 12th ed., Whitehouse Station, NJ, Merck & Co., Inc.
  2. Lide, D.R., ed. (1995) CRC Handbook of Chemistry and Physics, 76th ed., Boca Raton, FL, CRC Press, Inc., p. 3-197
  3. Hoechst Celanese Corp. (1997) Material Safety Data Sheet: Glycoluril, Charlotte, NC
  4. Shimizu, T. (1987) Glycoluril as a slow release nitrogen fertilizer. Soil. Sci. Plant Nutr., 33(2), 291- 298

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