Nitric esters. Part I. Characterisation of the isomeric glycerol dinitrates

Glycerol 1,2- and 1,3-dinitrate, prepared from the corresponding dibromohydrins of glycerol, are characterized by reaction with aromatic acid chlorides. The 1,2-dinitrate is also obtained by the action of iodine-silver nitrate on allyl alcohol; derivatives of the dinitrate are prepared similarly from allyl esters and by nitration of 1-glycerides. Partial nitration of glycerol gives glycerol 1,3-dinitrate, also obtained by mild nitration of glycidol (2,3-epoxypropan-1-ol) nitrate. Denitration of glycerol trinitrate by sodium nitrite or potassium hydroxide in aqueous ethanol and by sulphuric acid confirms that the secondary nitric ester group is displaced more readily. (Author)