최루성 2-Chlorobenzylidene malononitrile 분자의 미셀촉매 가수분해 반응
Micellar Catalytic Hydrolysis of Lachrymal 2-Chlorobenzylidene malononitrile Molecule
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초록
최루성 2-Chlorobenzylidene malononitrile (CS) 분자의 가수분해 반응에 따른 무독화 수단을 탐색하기 위하여 3종류의 계면활성제, Sodium laurylsulfate (NaLS; 음 이온성), Cetylammonium bromide (CTABr;양 이온성) 및 Triton X-100(비 이온성)가 존재하는 중성(pH 7.0) 수용액에서 측정된 가수분해 반응속도 상수(k1 sec.−1)로부터 미셀촉매 효과를 검토하였다. 그 결과 CTABr에 의한 양 이온성 미셀 촉매효과가 확인되었으며 2차 반응속도 상수로서 촉매상수는 kcat. = 9.42 × 10−1 M−1sec.−1 이었다. 이는 CS분자 중 2개의 Cyano group과 CTABr 미셀분자 중 ammonium ion 사이의 상호작용에 따른 정전기적인 안정화에 기인한 결과로 설명되며 CS분자와 CTABr 미셀 분자의 두 분자 간 회합으로부터 결합상수는 kψ= 2.20 ×10−1M−1이었다. 그러므로 CTABr 미셀 분자에 의한 무독화는 CS 분자의 빠른 가수분해 속도와 가수분해생성물의 운동성을 현저하게 제한함으로서 가능할 것이다.
Abstract
To search for detoxification methods from the hydrolysis of lachrymal 2-chlorobenzylidene malononitrile (CS), the catalytic effects of micelles from the hydrolysis rate constant (k1 sec.−1) measured atpH 7.0 in the presence of 3 surfactants, sodium laurylsulfate (NaLS; Anionic), cetylammonium bromide (CTABr;Cationic) and Triton X-100 (None ionic) were examined. As a result, the cationic cataysis effect of CTABr micelles was detected and their catalysis constant was kcat. = 9.42 × 10−1M−1sec.−1 as 2nd order rate constant.It can be explained from the electrostatic stabilization effect within the CS molecule by the interaction between an ammonium ion of a CTABr micelle and two cyano groups of the CS molecule. Also, the association binding constant of the CTABr micelle and CS was kψ = 2.20 × 10−1 M−1. Therefore, the findings of a fast hydrolysis rate of CS and restrictions on the motility of by-products (malononitrile and cyanide) by CTABr can explain how the detoxification of the CS molecule would be possible.
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