TETRAACETYLGLYCOLURIL AND ITS DERIVATIVES: SYNTHESIS, PROPERTIES AND APPLICATION

Abstract

Due to high multi-functionality, bicyclic ureas of octoic type (also known as glycolurils) are used in many applications, including the manufacturing of slow-release nitrogen fertilizers, additives for paints and coatings, polymer stabilizers, psychoactive drugs, intermediates for synthesize supramolecular compounds such as cucurbiturils and bambusurils and other practically important products. Among the glycoluril derivatives, N,N,N,N-tetraacetic derivative named as tetraacetylglycoluril occupies a special place and is produced as a fine chemical and used as a bleaching activator (as an example for perborates) in detergents. Tetraacetylglycoluril as a parent compound of acylated glycolurils finds its application as a bleaching activator in detergents and successfully competes with its counterpart tetraacetylethylenediamine. The chemistry of tetraacetylglycoluril presented in the literature is fragmentary and unsystematized, and does not allow receiving a deep understanding on the chemical properties and fields of application of this available compound. We suppose that the availability and multi-functionality of the tetraacetylglycoluril makes it possible to realize its synthetic potential. In the present article the main processes to produce tetraacetylglycoluril, its chemical properties and application fields are discussed in details. Chemical properties of tetraacetylglycoluril are described in details for reactions of hydrolysis, nucleophilic substitution, N- and O-acylation of amines and alcohols. It is noteworthy that tetraacetylglycoluril can be successfully used as a soft acylating agent for biogenic organic substrates and as a building block to synthesize new supramolecular compounds.