Studies into reactions of N-methylmorpholine-N-oxide (NMMO) and its hydrates with cyanuric chloride

The course of the reaction between N-methylmorpholine-N-oxide (NMMO, ) and cyanuric chloride () is strictly dependent on the hydrate water content of the amine oxide. In solid phase, both substances undergo an explosion-like, extremely exothermic reaction. In solution, this process becomes controllable and leads to a quantitative degradation of NMMO into morpholine and formaldehyde, with only acting as an inducing agent. The reaction can be conducted in a way that a clean deoxygenative demethylation is achieved. The monohydrate of NMMO () is quantitatively converted into N-methylmorpholine and hypochlorous acid by the action of . This conversion can be used in synthesis either to deoxygenate tertiary amine N-oxide monohydrates, or to produce chlorohydrins in non-aqueous, organic media in superior yields. The semisesquihydrate of NMMO () reacts with under consumption of water until non-hydrated NMMO is present, which is then further converted into morpholine and HCHO, as in the case of being directly employed as the starting material.