Basic hydrolysis of glyceryl nitrate esters. II. 1,2‐glyceryl and 1, 3‐glyceryl dinitrate esters

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Abstract
Kinetics of the basic hydrolysis of 1,2‐glyceryl dinitrate (1,2‐DNG) and 1,3‐glyceryl dinitrate (1,3‐DNG) esters were investigated in CO2‐free aqueous calcium hydroxide solutions. The hydrolysis reactions were carried out in a temperature controlled reactor vessel with provision for continuous N2 sparging of the reaction mixture. Both glyceryl dinitrate esters hydrolyzed via second‐order reaction at 25°C. 1,2‐DNG in basic solutions isomerized to 1,3‐DNG which subsequently hydrolyzed to yield products. The main hydrolysis product of 1,3‐DNG was identified as glycidyl nitrate. Other products formed during the basic hydrolysis of DNGs were nitrites and nitrates.