20600-96-8

Usage

InChI:InChI=1/C6H10N4O13/c11-7(12)20-3-5(22-9(15)16)1-19-2-6(23-10(17)18)4-21-8(13)14/h5-6H,1-4H2

Upstream product

• 2238-07-5 Diglycidyl ether 
• 627-82-7 diglycerol 

Relevant academic research and scientific papers

METHODS OF PRODUCING NITRATE ESTERS

Methods of forming a nitrate ester include combining at least one nitrate salt and sulfuric acid to form a nitrating solution and adding an aliphatic polyol to the nitrating solution. Nitrate esters formed by this method may be, for example, triethylene glycol dinitrate (TEGDN), pentaerythritol tetranitrate (PETN), diglycerol tetranitrate (DGTN), 1,1,1-tris(methylol)ethane trinitrate (TMETN), 1,2,4-butanetriol trinitrate (BTTN), nitroglycerin (NG), diethylene glycol dinitrate (DEGDN), ethylene glycol dinitrate (EGDN), metriol trinitrate (MTN), nitrocellulose (NC), or 1,2-propanediol dinitrate (PDDN).

Method of synthesizing diglycerol tetranitrate, and solid rocket motor propellant containing the same

Diglyercol tetranitrate is an energetic nitrate ester plasticizer having no freezing point, making the nitrate ester plasticizer especially suited for use in solid rocket motor propellants that are subjected to low temperature storage and operational environments, which can reach as low as -54°C in temperature. In order to avoid problems associated with fume-off that characterize the conventional synthesis method of making diglycerol tetranitrate, synthesis is performed in a medium including a mixed acid phase and an inert organic phase. The mixed acid phase contains, as ingredients, at least one nitronium ion source and at least one acid having sufficient strength to generate nitronium ions from the nitronium ion source. The nitronium ions in the mixed acid nitrated diglycerol to form diglycerol tetranitrate, which is then received into the organic liquid. The organic liquid, which preferably is a chlorocarbon such as dichloromethane, is insoluble with diglycerol but soluble with diglycerol tetranitrate. The inert organic phase is then treated to neutralize any acid contained in the inert organic phase, and the diglycerol tetranitrate is separated from the inert organic phase.

Preparation of Di- and polynitrates by ring-opening nitration of epoxides by dinitrogen pentoxide (N2O5)

Eighteen epoxides of various kinds were reacted with N2O5 in chlorinated hydrocarbon solvents (principally CH2Cl2) to give vicinal nitrate ester products by a novel ring-opening nitration reaction. The procedure offers easier temperature control and simpler isolation procedures compared with conventional mixed acid nitrations; it also enables selective nitration reactions to be carried out on polyfunctional substrates. The scope and limitations of the reaction, as well as those of an alternative route utilising N2O4 with in situ oxidation of an intermediate nitrite-nitrate, are discussed.