Other Reactions of Nitrate Esters

In the presence of sodium ethoxide or potassium ethoxide, nitrate esters can be reacted with active methylene compounds to produce isonitro salt compounds (-(HO)ON=). The esters are hydrolyzed in the condition. 

Similar to nitrite esters, alkyl nitrate would react with excessive Grignard reagent to produce A-dialkyl hydroxylamine. 

A remarkable special property of nitrate esters is the ability to catalyze some additional polymerization reactions [42]. In nitroglycerine, both styrene and methyl methacrylate can be self-polymerized. If the amount of nitroglycerine is up to 5-20 portion (weight fraction), equals to 10 % of polymers, the polymerization rate will be fastened. The molecular weight of polymers is less than that obtained through slowly polymerization or in situ anionic polymerization. 

For the typical polymerization between methyl methacrylate and glycol nitrate [43], their molar ratio is in the range of 0.07-5.9. The reaction temperatures are 25, 60, 80, and 90 °C. Glycol nitrate will be partly decomposed to produce radicals for initiating polymerization. 

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