塩化シアヌールの加水分解

概要

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Hydrolysis of cyanuric chloride (1) in NaHCO3, Na2CO3, etc. gives a sodium salt of 2, 4-dichloro-6-hydroxy-s-triazine (2), while its hydrolysis with NaOH at low temperature-gives the sodium salt of (2) and that with an excess of NaOH at room temperature gives a sodium salt of 2-chloro-4, 6-dihydroxy-s-triazine (3); the Na salt of (2) and (3), respectively, can be obtained in a crystalline form, and crystalline (3) as a free acid is obtained. (2) and (3) are stable in alkaline reaction but unstable in acidic reaction and easily decomposed to give cyanuric acid.(2) and (3) react with aniline and give their corresponding anilino derivatives.By application of their differenceof solubilities in alkali, separation and determination of them are possible. Also, treating of (2) with methanolic-NaOH gives 0-dimethylcyanuric acid. Contrary to this stepwise proceeding of the whole reaction system by alkali hydrolysis, the acid hydrolysis of (1) is slow and it does not proceed stepwise as a whole reaction system due to rapid decompositon of intermediates (2) and (3). Stability of (2) and (3) in alkaline reaction may be attributed to the formation of their salts which can be present as anions and this may have the great deactivation effect on the residual chlorine atom.
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