モデル化合物を用いたトリハロメタン生成反応機構の解析(パネルディスカッショントリハロメタンの生成機構をめぐって)(第8回環境汚染物質とそのトキシコロジーシンポジウム)

概要

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Since 1,3-diketones and 1,3-dihydroxybenzenes readily produce chloroform by aqueous chlorination, these compounds are suitable as model compounds for the elucidation of the reaction mechanism of trihalomethane formation in drinking water. When 1,3-diketones such as acetylacetone and 1,3-cyclohexanedione were treated with chlorine in phosphate buffer (pH 7.0), chlorine was almost exclusively consumed for the production of chloroform and nonchlorinated carboxylic acids. This results indicated that chlorination of 1,3-diketones proceeds via a haloform-type reaction. On the other hand, chlorination of 1,3-dihydroxybenzenes such as resorcinol and quercetin proceeded via complex pathways, and various chlorinated compounds were found in the reaction mixture. In order to elucidate this reaction mechanism in detail, we used naphthoresorcinol as a model compound, because all of the chlorination products could be detected by ultraviolet light absorption. The following compounds were identified as the products ; phthalic acid, homophthalic acid, phthalide, 3-chloro-1,2-indanedione, 3,3-dichloro-1,2-indanedione, 2,3-dichloroindenone, and 2,2-dichloronaphthoresorcinol. Yields of these products varied by the changes of pH, temperature, and the amount of chlorine added.
社団法人日本薬学会の論文
1982-02-28