CYCLOHEXYL NITRATE PRODUCTION PROCESS Russian patent published in 2006 - IPC C07C201/02 C07C201/10 

FIELD: industrial organic synthesis.

SUBSTANCE: invention relates to production of nitric acid esters and, in particular, to production of cyclohexyl nitrate via nitration of cyclohexanol with nitric acid/acetic anhydride mixture followed by separation of resulting reaction mass, diluting it with water, and separating organic layer, which is then washed with water and soda solution. More specifically, when carrying out nitration with nitric acid/acetic anhydride mixture prepared at 1:1 molar ratio, 1.80-1.84 wt parts such mixture is taken per 1 wt part cyclohexanol, reaction mass is held for 60 min at 18-20°C, after which is diluted with water taken in amount 0.48-0.55 wt parts per 1 wt part reaction mass and separated cyclohexyl nitrate layer is washed by any of known techniques, whereas nitric acid contained in spent liquid is neutralized with some stoichiometric excess of sodium hydroxide or carbonate. Neutralized spent liquid is distilled to obtain first fraction boiling at 99-102°C and second fraction boiling at 102-105°C. From the first fraction is separated precipitated condensate of cyclohexyl nitrate, which is washed, and a part of the rest of the first fraction id combined with above-mentioned second fraction of the spent liquid. Resulting mixture is neutralized with sodium hydroxide or carbonate and sodium acetate formed therein is isolated using any of known techniques, while remaining solution is returned into process to be used in subsequent cycles.

EFFECT: improved technology, expanded operational possibilities due to enabled conditions for stable high yield of cyclohexyl nitrate, excluded possibility of decomposition of reaction mass after nitration, and ensured reuse of spent acids resulting in production of sodium acetate suitable as second commercial product.

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