6659-62-7

Usage

Uses

Used in Aerospace Industry:
2,3-epoxypropyl nitrate is used as a stabilizer in rocket propellants for its ability to enhance the performance and safety of the propellant system.
Used in Explosive Industry:
2,3-epoxypropyl nitrate is used as a plasticizer in explosive compositions to improve the flexibility and handling characteristics of the explosives.

InChI:InChI=1/C3H5NO4/c5-4(6)8-2-3-1-7-3/h3H,1-2H2

Upstream product

• 624-57-7 epiiodohydrin 
• 56-81-5 glycerol 
• 106-89-8 epichlorohydrin 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 623-87-0 1,3-bis(nitrooxy)propan-2-ol 
• 50333-23-8 nitric acid-(3-chloro-2-hydroxy-propyl ester) 
• 621-65-8 glyceryl 1,2-dinitrate 

Relevant academic research and scientific papers

Methods of producing glycidyl nitrate

Methods of producing glycidyl nitrate. The method comprises reacting glycerol and nitric acid in a microfluidic reactor to form a nitrated glycerol compound. The microfluidic reactor comprises a reaction volume of the microfluidic reactor of less than about 20 ml and an inner diameter of a reaction channel of the microfluidic reactor of less than or equal to about 1000 μm. The nitrated glycerol compound is reacted with a base in the microfluidic reactor to form glycidyl nitrate. Additional methods of producing glycidyl nitrate are also disclosed.

Probing the compatibility of energetic binder poly-glycidyl nitrate with energetic plasticizers: Thermal, rheological and DFT studies

The essential idea of developing energetic binders and plasticizers is to enhance the thermal stability and energy content, improve the oxygen balance and burning behaviour of moulds, reduce the glass transition temperature and improve other mechanical properties of propellant and explosives formulations. The compatibility of energetic binder poly-glycidyl nitrate (PGN) with some energetic plasticizers of solid propellants was studied using differential scanning calorimetry (DSC), rheology and DFT methods in relation to the effect of the addition of five different energetic plasticizers, i.e. bis(2,2-dinitro propyl) acetal (BDNPA), dinitro-diaza-alkanes (DNDA-57), 1,2,4-butanetriol trinitrate (BTTN), N-N-butyl-N′(2-nitroxy-ethyl) nitramine (BuNENA) and diethyleneglycol dinitrate (DEGDN), on the rheological and thermal properties of the energetic binder PGN. The results obtained for the mixture of plasticizer and binder with respect to decomposition temperature (Tmax) and the format of the peak are compared with the results obtained for the pure binder, indicating the compatibility of these plasticizers with PGN. The glass transition temperatures (Tg) of all these mixes were determined by low-temperature DSC, which showed a lowering of Tg with a single peak. Rheological evaluation revealed that the viscosity of the binder is sufficiently lowered with an increase in flow behaviour on addition of 20% (w/w) plasticizer. The addition of 20% DEGDN has the maximum effect on the lowering of the viscosity of PGN. Quantum chemically derived molecular electrostatic potential (MESP) shows the possible sites of interaction of plasticizers and binder with the estimated lowest Vmin values and their magnitudes provide an insight into their mutual interactions. The relative trend in interaction energies between plasticizer and binder, PGN, is well correlated with a corresponding trend in the ability of plasticizers towards reducing the viscosity of PGN. The information gathered in the present study would in general be valuable with respect to designing new plasticizers.

A safe two-step process for manufacturing glycidyl nitrate from glycidol involving solid-liquid phase-transfer catalysis

A new and safer two-step process for manufacturing glycidyl nitrate from glycidol is reported. In the first step glycidyl tosylate is obtained by reacting glycidol with p-tosyl chloride in the presence of triethylamine according to any one of the well-known procedures for obtaining tosyl esters described in the literature. In the second step, glycidyl tosylate is reacted with NaNO3 in refluxing acetonitrile under solid-liquid phase-transfer catalysis conditions using tetrabutylammonium nitrate as catalyst. Acetonitrile and the phase-transfer catalyst were recycled 12 times without deactivation, yielding 99% pure glycidyl nitrate in a cumulative isolated yield of 81.5% with a catalyst turnover number of 85.7 mol substrate per mol phase-transfer catalyst. This procedure avoids the use of the dangerous reactants used in the current manufacturing processes of glycidyl nitrate and could be useful as a safe and general method for obtaining nitrate esters.

Process for making stable cured poly(glycidyl nitrate) and energetic compositions comprising same

A process is provided in which at least one multi-functional alcohol having a hydroxyl functionality of at least two serves as a polymerization initiator. The multi-functional alcohol initiator is optionally, although preferably, reacted with a catalyst to form a catalyst-initiator complex, which is then used in the polymerization of glycidyl nitrate. The resulting poly(glycidyl nitrate) has a functionality substantially equivalent in number to the hydroxyl functionality of the multi-functional alcohol initiator. The poly(glycidyl nitrate) is cross-linked with at least one aromatic polyisocyanate having at least one aromatic ring and, on average, more than two isocyanate moieties bonded directly to the aromatic ring.

Continuous process and system for production of glycidyl nitrate from glycerin, nitric acid and caustic and conversion of glycidyl nitrate to poly(glycidyl nitrate)

A continuous and scalable process for producing glycidyl nitrate, or glyn, from glycerin, nitric acid, and caustic wherein the process includes the reaction of glycerin and nitric acid to form dinitroglycerin and the reaction of dinitroglycerin with caustic, such as sodium hydroxide, to produce glycidyl nitrate. A system for producing the inventive material is also disclosed. The system includes a first reaction vessel, a second reaction vessel, and a separation apparatus.

Isotactic poly(glycidyl nitrate) and synthesis thereof

Isotactic poly(glycidyl nitrate) useful in solid propellants is produced by polymerizing chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate. Chiral (R) glycidyl nitrate or its enantiomer is prepared by sequential treatment of chiral (S) glycidyl tosylate or its enantiomer with nitric acid and sodium hydroxide. Chiral (S) glycidyl tosylate or its enantiomer, (R) glycidyl tosylate, can be produced by Sharpless epoxidation of allyl alcohol or by direct tosylation or commercially available chiral glycidol. Likewise, chiral (R) glycidyl nitrate or its enantiomer, (S) glycidyl nitrate, can be prepared directly via nitration of (S) or (R) glycidol, respectively.