Conversion of CS (tear gas) to o-chlorostyrene and ammonium sulf

Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing

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423545, 423549, 562495, C07C 2500

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active

042848326

ABSTRACT:
Tear gas or CS (o-Chlorobenzalmalononitrile) has two nitrile functional gps which, when removed, effects the chemical conversion of bulk CS to o-chlorostyrene. This involves a first step, an acid or base catalyzed hydrolysis of CS to o-chlorocinnamic acid. Thereafter a second reaction is the decarboxylation of the intermediate product to give o-chlorostyrene.
CS is reacted with 70% sulfuric acid at 120.degree. C., producing ammonium sulfate and orth-ochlorocinnamic acid (the intermediate product). This intermediate product is separated and thermally decarboxylated at 270.degree. C. (with a catalytic amount of soda lime and copper powder) to ortho-chlorostyrene.

REFERENCES:
patent: 2824144 (1958-02-01), Beets et al.
patent: 3898292 (1975-08-01), Diamond
patent: 3912784 (1975-10-01), Suzuki
patent: 4012454 (1977-03-01), Fields

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