Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Isocyanurates. I. A Novel Method of Synthesizing Trialkyl Isocyanurates
Kenichi FukuiFumio TanimotoHisao Kitano
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1965 Volume 38 Issue 10 Pages 1586-1589


Reactions of alkyl halides with potassium cyanate have been carried out in several aprotic solvents. Dimethylformamide and dimethyl sulfoxide have been proved to play a superior role as aprotic solvents in the displacement reaction and also in the subsequent trimerization of the isocyanates. Several trialkyl isocyanurates have been obtained in yields better than those of the other known methods.
From 2-alkoxyethyl halides and 2-vinyloxyethyl chloride respectively, tris-(2-alkoxyethyl) isocyanurates and tris-(2-vinyloxyethyl) isocyanurate have been synthesized.
The presence of water in the reaction mixture results in the formation of 1,3-dialkyl ureas, consequently decreasing the yield of isocyanurates.

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