Hydantoin

• Imidazolidine -2 ,4- dione
• 2.4 Dioxotetrahydroimidazol
• Glykolylharnstoff
• 2,4 - (3H, 5H)- imidazoledione

Colorless solid

Fixed

219-222 ° C

Sparingly soluble in water

Template: Infobox chemical / molecular formula search available

Hydantoin is a saturated heterocyclic compound and a derivative of imidazole. The lactam ( cyclic amide ) hydantoin can be regarded as a derivative of urea or the amino acid glycine. It crystallizes easily and forms colorless crystals with a weak sweet taste.

History and Occurrence

As part of its work on the degradation products of uric acid Adolf von Baeyer received in 1861 by reduction of allantoin (primary degradation product of uric acid ) with hydrogen iodide is a white crystalline powder, which he hydantoin (IUPAC: imidazolidine -2 ,4- dione) called.

Production and representation

Hydantoin can be determined by F. Urech (1873 ) by reacting glycine with an isocyanate obtained ( see also Friedrich Wohler, urea synthesis). This glycine is condensed with isocyanate to hydantoic that splits off when heated in acidic water.

Properties

Under normal conditions hydantoin is stable. In water it is hydrolyzed under acid catalysis as dilactam to hydantoic.

Use

Hydantoin is used, inter alia, for the synthesis of amino acids, and as softeners for textiles and as sizing agents. In a basic medium, the methyl group can be deprotonated in the 5-position so that a condensation reaction proceeds with aldehydes or ketones. Hydrogenation and hydrolysis of the condensation products gave a racemic 2 -amino acids.

Use of the derivatives

N- halogenated derivatives of hydantoin to be used as a disinfectant.

• Dichlorodimethylhydantoin ( DCDMH )
• Bromochlorodimethylhydantoin ( BCDMH )
• Dibromodimethylhydantoin ( DBDMH )

Some derivatives are important as anticonvulsants ( antiepileptics ).

• Ethotoin
• Phenytoin
• Mephenytoin
• Fosphenytoin

Polyhydantoins have become known as heat-resistant plastics.