水中含窒素化合物の塩素化反応によるクロロピクリンの生成

概要

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In order to clarify a mechanism of chloropicrin formation, chloropicrin and chloroform formation potential by aqueous chlorination of organic nitrogen compounds were investigated from viewpoints of structural correlation and stoichiometry. The results obtained were as follws. 1) Chloropicrin formation potential by aqueous chlorination of alanine related compounds, phenols and resorcinols containing nitrogen depended on oxidation state of nitrogen in functional group, the potential being in the decreasing order of -NO_2>-NO>-NH_2. 2) By the reaction of chloropicrin formation by aqueous chlorination of alanine, it was considered that oxidation of amino group to nitro group was rate-determining step and this reaction was antagonized reaction of chloroform formation. 3) Mechanism of chloropicrin formation by aqueons chlorination of aminophenol was proposed as follows ; Amino group was oxidized (-NH_2→-NO→-NO_2) and consequently chlorinated to chloropicrin by way of cleavage of aromatic ring. It was recognized that oxidation of nitrosophenol to nitrophenol was rate-determining step. 4) By the reaction of chloropicrin formation by aqueous chlorination of aminoresorcinol, it was recognized that two steps of oxidation (-NH_2→NO→-NO_2) were rate-determining steps and this reaction was not antagonize reaction of chloroform formation.
公益社団法人日本薬学会の論文
1984-10-31