Isoclast Active Manufacture: In Situ Spectroscopic Investigation of the Unstable Products of Cyanamide and Sodium Hypochlorite Reactions

Isoclast Active is a new insecticide manufactured by Dow AgroSciences LLC. In an effort to lower the cost of manufacture of Isoclast Active, we have studied the reaction which produces <i>N</i>-cyano sulfilimine, which is the precursor to Isoclast Active. The reaction involves the oxidative coupling of cyanamide with the sulfide intermediate using sodium hypochlorite. In this study, we demonstrated that a transient intermediate species is produced by the reaction between bleach and cyanamide. On the basis of in situ Raman, IR, and NMR spectroscopic evidence we propose that the intermediate is the anionic form of <i>N</i>-chlorocyanamide: ClN^––CN. The degradation of this intermediate species was found to be highly sensitive to its environment and leads to a complicated mixture of products. This work also demonstrates that in situ Raman and IR spectroscopy are powerful and invaluable tools for monitoring reactions/processes involving unstable reaction intermediates for kinetic modeling and process R&D