Polynitro-substituted pyrazoles and triazoles as potential energetic materials and oxidizers

Yin, Ping; Zhang, Jiaheng; He, Chunlin; Parrish, Damon A.; Shreeve, Jean’ne M.

doi:10.1039/c3ta15057g

Cited by 110 publications

(46 citation statements)

References 42 publications

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“…Herve and co-workers [83] reported the synthesis of 3amino-4,5-dinitropyrazole (3-ADNP)a sa ni ntermediate to the synthesis of 3,4,5-trinitropyrazole (TNP). 3-ADNP was synthesized by allowing 1,3,4-trinitropyrazole (1,3,4-TNP) [84]t or eactw ith sodium azide to yield 2-azido-3,4-dinitropyrazole.T his wasa llowedt or eact with triphenylphosphine and hydrolyzed to yield 3-ADNP.Therei sl imited data on the sensitivity of this compound but Shreeve and coworkers [85] repeated the synthesis and used it as asynthon for several new energetic compounds. They reported the synthesis of 1,5-diamino-3,4-dinitropyrazole (1,5-DADNP) by the amination of 3-ADNP with O-tosylhydroxylamine.…”

Section: Small-ring Heterocyclic Insensitive Energetic Compoundsmentioning

confidence: 99%

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Pagoria

2016

Propellants Explo Pyrotec

109

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1IntroductionIn general, highe xplosivesa re categorized as primary,s econdary,a nd tertiary explosives, basedo nt heir sensitivity to mechanical insults. Primarye xplosivesa re very sensitive to mechanical and electricali nitiation and are used as initiating explosives in an explosivet rain. Secondary explosives are less sensitivet om echanical stimuli, although in many cases can still be somewhat sensitive materials. Te rtiary explosives are generallyv ery insensitivee xplosivesv ery often consistingo fa no xidizer and af uel, and are generallyu sed in mining. Subsets of secondary explosives are insensitive energetic compoundso rm aterials. Insensitive energetic compounds are defined as compoundst hat have relatively benign responses to externali nsults such as impact, shock, spark, friction, and heat. Understandingt he various factors that affectt he sensitivity of energetic compoundst ov arious mechanical insults plays an important role in the design of new,i nsensitive, and thermally stable higher-performance energetic materials. While there have been several excellent reviewsa nd books on new energetic compounds in the past 15 years [1-7],t his review will concentrate on insensitivee nergetic compounds. Also this paper will concentrate on insensitive energeticc ompounds and not discuss insensitivee nergetic formulationso rm ixtures or engineering methods to decrease sensitivity.Althoughs park and friction sensitivity are important, impact, shock, and thermal stabilitya re the most commonly used measurements to determine the relatives ensitivity of ag iven compoundc ompared to knowns tandards. In this paper the term insensitivity will refer mainly to impact and thermal sensitivity.I mpact sensitivity is generally measured by using a" drop hammer" impact machine, in which an anvil of ag iven weight (generally 5kg) is allowed to impact as mall sample (ca. 35 mg) of an explosive and the responsei sr ecorded. Historically,d rop hammer results (Dh 50 or H 50 )w ere reported as the height, at which there is a5 0% probabilityo fi gnition. In recenty ears, some authors are convertingt he recorded drop hammer heights to Joules and are reporting the energy required at which there is a5 0% probability of ignition. Thermal stabilitym ay be measured using several methods including differential scanning calorimetry (DSC), differential thermala nalysis (DTA), chemical reactivity test (CRT), vacuum stability test (VTS), slow cook-off test, and fast cook-off test.The industry standardf or an insensitive energetic compound is 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), ar easonably powerful explosive, whose response to shock, thermal, impact and friction insultsi ss ignificantly more benign than that of any other knownm aterial of comparable energy [8,9].T his "enhanced" insensitivity of TATB has led to as ignificant amount of studies on how various physical properties including molecular structure,c rystal structure, and crystal packing of TATB contributes to its "enhanced" insensitivity,a nd how these physical properties c...

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Section: Small-ring Heterocyclic Insensitive Energetic Compoundsmentioning

confidence: 99%

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

Pagoria

2016

Propellants Explo Pyrotec

109

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“…1,1′‐Methylenebis[3‐(2,2,2‐trinitroethyl)urea] (5): H‐FOX, 4 (0.200 g, 1.22 mmol) was placed in a 100 mL round‐bottomed flask in 10 mL of distilled water. 2,2,2‐Trinitroethanol (0.66 g, 3.68 mmol) was added slowly to the reaction mixture over a period of 10 minutes. After complete addition, the reaction mixture was stirred overnight at room temperature.…”

Section: Methodsmentioning

confidence: 99%

A Halogen‐Free Green High Energy Density Oxidizer from H‐FOX

Dharavath

Tang

Kumar³

et al. 2019

Eur J Org Chem

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Reaction of H‐FOX (1‐hydrazinyl‐2,2‐dinitroethenamine) with 2,2,2‐trinitroethanol resulted in an unexpected compound, 1,1′‐methylenebis[3‐(2,2,2‐trinitroethyl)urea] (5), which when treated with acetic anhydride and 100 % nitric acid gave an N‐NO2 derivative, 1,1′‐methylenebis[1‐nitro‐3‐(2,2,2‐trinitroethyl)urea] (6) in good yield. Compound 6 exhibits a good oxygen balance (+20.4 %), density (d = 1.87 g/cm3) and excellent detonation performance (vD = 8910 m/s; P = 35.8 GPa) as well as acceptable stability and sensitivity, which suggests it as an attractive replacement for ammonium perchlorate (AP).

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Section: Introductionmentioning

confidence: 99%

“…Polynitro derivatives of pyrazole have gained considerable attention becauseo ft heir high density, high heat of formation combined with high thermal stability,a nd low impact sensitivity [1][2][3][4][5].E .g.,p yrazole with two nitro groups, viz. 3,4-dinitropyrazole, is considered as as ubstitute for TNT in melt-casted compositions due to increased performance [6].…”

Section: Introductionmentioning

confidence: 99%

“…

1IntroductionPolynitro derivatives of pyrazole have gained considerable attention becauseo ft heir high density, high heat of formation combined with high thermal stability,a nd low impact sensitivity [1][2][3][4][5].E .g.,p yrazole with two nitro groups, viz. 3,4-dinitropyrazole, is considered as as ubstitute for TNT in melt-casted compositions due to increased performance [6].The main problemi nd evelopingn ew energetic materials is to combine various( in particular cases, mutually exclusive) properties in as ame moiety.F or example, guanidinium 4-amino-3,5-dinitropyrazolate, being highly insensitive and remarkably thermalstabile (up to 303 8C), has an unsatisfactory detonation velocity of 7.7 km s À1 becauseo fi ts low density (1.63 gcm À3 ) [ 3].O ther promisingp yrazole species with fully-nitrated Ca toms, viz.

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confidence: 99%

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5‐Amino‐3,4‐dinitropyrazole as a Promising Energetic Material

Muravyev

Bragin

Моногаров

et al. 2016

Propellants Explo Pyrotec

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The nitrogen‐rich energetic compound 5‐amino‐3,4‐dinitropyrazole (5‐ADP) was investigated using complementary experimental techniques. X‐ray diffraction indicates the strong intermolecular hydrogen bonding in 5‐ADP crystals. Compound exhibits low impact sensitivity (23 J) and insensitivity to friction. The activation energy of thermolysis determined to be 230±5 kJ mol−1 from DSC measurements. Accelerating rate calorimetry indicates the lower thermal stability (173 °C) of 5‐ADP than that of RDX, which is probably the main concern about using this compound. 5‐ADP also exhibits good compatibility with common energetic materials (viz. TNT, RDX, ammonium perchlorate), including an active binder. The burning rate of 5‐ADP monopropellant is higher than that of benchmark HMX, while the pressure exponent 0.51±0.04 is surprisingly low. Addition of ammonium perchlorate does not affect the pressure exponent of 5‐ADP, while the burning rate increases. The 5‐amino‐3,4‐dinitropyrazole exhibits a notable combination of combustion performance, low sensitivity, and good compatibility, which renders it as a promising energetic material.

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Polynitro-substituted pyrazoles and triazoles as potential energetic materials and oxidizers

Cited by 110 publications

References 42 publications

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

A Comparison of the Structure, Synthesis, and Properties of Insensitive Energetic Compounds

A Halogen‐Free Green High Energy Density Oxidizer from H‐FOX

5‐Amino‐3,4‐dinitropyrazole as a Promising Energetic Material

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