エチレンイミン

エチレンイミン
エチレンイミンの構造式エチレンイミンの分子モデル
IUPAC名アジリジン（系統名）
別名アザシクロプロパン
分子式C2H5N
分子量43.07
CAS登録番号151-56-4
形状無色液体
密度と相0.83 g/cm3,
融点-71 °C
沸点55 °C
SMILESN1CC1

エチレンイミン (ethyleneimine) とは含窒素有機化合物の一種で、炭素2個と窒素1個からなる三員環構造を持つ脂肪族アミン。エチレンイミンの構造を持つ一連の化合物群をアジリジン、アジリジン類と呼ぶが、その母化合物にあたる。アジリジンはエチレンイミンのIUPAC系統名でもある。アンモニア臭を示す無色の液体。

製造

エタノールアミンと硫酸から硫酸エステルを作り、塩基と作用させて分子内環化生成物であるエチレンイミンを得る[1]。

H2NCH2CH2OH + H2SO4 → H2NCH2CH2OSO3H → ethyleneimine

反応

三員環の立体的ひずみのために反応性は高い。求核剤を作用させると容易に開環し、アミノエチル化した生成物を与える。

Nu + ethyleneimine → Nu-CH2CH2NH2　（Nu は求核剤）

用途

合成中間体や、エポキシ樹脂の硬化剤として利用される[2]。

安全性

労働安全衛生法の特定第2類物質に指定されている。

強い皮膚および眼、気管支への刺激性・腐食性に加え、いわゆる直接発がん物質として遺伝子障害作用を有しており、取り扱いには細心の注意を要する。

参考文献

  1. ^ 園田、亀岡『有機工業化学』第2版、1993年、化学同人
  2. ^ 岩波理化学辞典「エチレンイミン」


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