Isomerism of nitratoalkylazoles DOI Creative Commons

Lukas Bauer,

Maximilian Benz,

Thomas M. Klapötke

и другие.

FirePhysChem, Год журнала: 2023, Номер 4(3), С. 201 - 210

Опубликована: Ноя. 23, 2023

In the field of energetic materials, traditional materials with high toxicity or other disadvantages are mostly used. There is an urgent need for trinitrotoluene replacements (TNT), which itself toxic and its production problematic due to red wastewater. New should be safe handle, have good performance, inexpensive synthesize. Nitratoalkylazoles known low melting points properties compared TNT. this paper, seven compounds synthesized starting from 5-methyltetrazole, 5-hydroxymethyltetrazole 4,5-bishydroxymethyltriazole. The nitrates characterized in terms their physical, chemical, properties. Of those compounds, five solid, between 27 110°C, two liquid. Methylation hydroxyalkylation were performed discussed extensively. organic nitrate introduced last step so that synthesis remains scalable. Correlations molecular geometry explained. Calculations indicate detonation velocities 6-11% higher than A discussion effect isomerism on leads surprising insights help focus accelerate research replacement

Язык: Английский

Di- and polyazides. Synthesis, chemical transformations and practical applications DOI

Biligma D. Tsyrenova,

Pavel S. Lemport, Valentine G. Nenajdenko

и другие.

Russian Chemical Reviews, Год журнала: 2023, Номер 92(1), С. RCR5066 - RCR5066

Опубликована: Янв. 1, 2023

The chemistry of organic di- and polyazides has been extensively developed in recent years. Methods for the synthesis 1,1- 1,2-diazides are diverse include stoichiometric, catalytic, photochemical electrochemical approaches. These compounds highly reactive involved a wide range reactions, from thermal transformations to click chemistry. Of particular attention transformations, which one azido group undergoes intramolecular cyclization, while another remains intact can participate further chemical transformations. Tri- investigated as precursors production high-energy materials high-molecular-weight compounds. This review addresses methods containing two or more groups their Aliphatic, aromatic heteroaromatic diazides considered. Specific characteristic geminal vicinal diazides, differ reactions monoazides, described. Examples practical application di-, tri- highlighted.<br> bibliography includes 355 references

Язык: Английский

Процитировано

6

N‐Azidoethyl azoles through N‐alkylation under highly harmonized reaction conditions: Synthesis, characterization, and complexation as energetic coordination compounds DOI Creative Commons

Lukas Bauer,

Simon M. J. Endraß,

Thomas M. Klapötke

и другие.

Journal of Heterocyclic Chemistry, Год журнала: 2024, Номер 61(6), С. 839 - 851

Опубликована: Март 22, 2024

Abstract Organic azides are universally important in many areas of chemistry, particularly organic synthesis. The availability these often depends on specific transfer reagents and reaction conditions, or only work with certain substrates. Customizable offer a safe direct pathway to desired compounds, thereby increasing the N ‐alkyl‐azides. In an effort streamline synthesis broaden scope ‐azidoethyl‐containing molecules, three different versatile azidoethyl were synthesized uniform protocol azoles as substrates, including imidazole, pyrazole, 1,2,3‐triazole, 1,2,4‐triazole, tetrazole was established. resulting azidoethyl‐azoles further used ligands for energetic coordination compounds create new lead‐free primary explosives. A comprehensive characterization reagents, azidoethyl‐containing products, conducted using multinuclear nuclear magnetic resonance (NMR), elemental analysis, mass spectrometry, infrared spectroscopy (IR). Furthermore, their thermal stability sensitivity toward friction impact determined well detonation properties calculated by EXPLO5 code.

Язык: Английский

Процитировано

2

Design, synthesis, and properties of melt-cast explosive carriers: a review DOI
Cong Li, Qiyao Yu,

Jian-guo Zhang

и другие.

Journal of Materials Science, Год журнала: 2024, Номер 59(31), С. 14172 - 14184

Опубликована: Июль 28, 2024

Язык: Английский

Процитировано

2

Crystal Structures of the Commonly Used Plasticizers Ethylene Glycol Dinitrate, Diethylene Glycol Dinitrate, and Triethylene Glycol Dinitrate─Characterization and Discussion of Their Structural Behavior DOI
Jasmin T. Lechner, Andreas Neuer,

Valentin Bockmair

и другие.

Crystal Growth & Design, Год журнала: 2022, Номер 22(10), С. 6215 - 6223

Опубликована: Сен. 7, 2022

Ethylene glycol dinitrate (EGDN), diethylene (DEGDN), and triethylene (TEGDN) are used as plasticizers in propellant mixtures have been known for more than 100 years. Despite the industrial application long history of these compounds, crystal structures all three which liquids at room temperature, not determined. Therefore, this work, were examined by low-temperature X-ray diffraction, thus, bonding properties packing solid state could be compared discussed first time. Furthermore, compounds characterized nuclear magnetic resonance spectroscopy infrared spectroscopy. The thermal investigated DTA (differential analysis) measurements, experimental vapor pressures measured with chromatography-assisted transpiration method. densities temperature (for liquids) gas pycnometry, energetic calculated using EXPLO5 code. Moreover, a in-depth analysis different sensitivities through discussion Hirshfeld surfaces, created based on their structures, was performed to compare state.

Язык: Английский

Процитировано

9

Dinitrophenyl-oxadiazole compounds: Design strategy, synthesis, and properties of a series of new melt-cast explosives DOI Creative Commons

Baolong Kuang,

Tingwei Wang, Cong Li

и другие.

Defence Technology, Год журнала: 2023, Номер 35, С. 100 - 107

Опубликована: Дек. 21, 2023

Melt-cast explosives are the most widely used energetic materials in military composite explosives, researchers have been unremittingly exploring high-energy and insensitive melt-cast explosives. In this work, a series of dinitrophenyl-oxadiazole compounds were designed prepared. These an ideal low melting point (80–97 °C), good detonation performance (detonation velocity D = 6455–6971 m/s, pressure P 18–19 GPa) extreme nature (impact sensitivity ≥60 J, friction >360 N). All these well characterized by nuclear magnetic resonance, fourier transform infrared spectroscopy, elemental analysis. Compounds 2, 3 unambiguously confirmed X-ray single crystal diffraction As result, their overall properties superior to traditional trinitrotoluene (TNT) dinitroanisole (DNAN) which may excellent potential applications

Язык: Английский

Процитировано

5

Synthesis and Characterization of Azido- and Nitratoalkyl Nitropyrazoles as Potential Melt-Cast Explosives DOI Creative Commons
Elena Reinhardt, Tobias Lenz,

Lukas Bauer

и другие.

Molecules, Год журнала: 2023, Номер 28(18), С. 6489 - 6489

Опубликована: Сен. 7, 2023

Desirable advancements in the field of explosive materials include development novel melt-castable compounds with melting points ranging from 80 to 110 °C. This is particularly important due limited performance and high toxicity associated TNT (trinitrotoluene). In this study, a series innovative explosives featuring nitratoalkyl azidoalkyl functionalities attached 3-nitro-, 4-nitro-, 3,4-dinitropyrazole, or 3-azido-4-nitropyrazole scaffold are introduced. These were synthesized using straightforward methods thoroughly characterized various analytical techniques, including single-crystal X-ray diffraction, IR spectroscopy, multinuclear nuclear magnetic resonance (NMR) mass spectrometry, elemental analysis, DTA. Furthermore, energetic properties such as (theoretical) data, sensitivities, compatibilities evaluated compared among different structures.

Язык: Английский

Процитировано

4

Azidomethyl-bisoxadiazol-linked-1,2,3-triazole-(ABT)-based potential liquid propellant and energetic plasticizer DOI Creative Commons
Sohan Lal, Richard J. Staples, Jean’ne M. Shreeve

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(16), С. 7100 - 7104

Опубликована: Янв. 1, 2024

A scalable synthesis of azidomethyl bisoxadiazol linked-1,2,3-triazole-(ABT) based potential liquid propellant and energetic plasticizer is obtained from commercially available diaminomaleonitrile in excellent yield. Newly synthesized compounds were fully characterized by various spectroscopic techniques. These materials exhibit good densities (1.77 g cm

Язык: Английский

Процитировано

1

A rocky road toward a suitable TNT replacement – A closer look at three promising azoles DOI Creative Commons
Maximilian Benz,

A. Delage,

Thomas M. Klapötke

и другие.

Propellants Explosives Pyrotechnics, Год журнала: 2023, Номер 48(8)

Опубликована: Май 19, 2023

Abstract The goal of this research project was to establish a literature known explosive, which can be used as future melt‐cast explosive. substance should not only theoretically suitable substitute but also meet all industrially relevant requirements. Therefore, intensive executed filter appropriate candidates. three most promising substances were re‐synthesized verify their key properties. If criteria the requirements, synthesis optimization and preindustrial upscaling carried out.

Язык: Английский

Процитировано

3

Design and Synthesis of Energetic Melt‐Castable Materials by Substituent‐Specific Modification DOI
Fang Chen, Yi Wang, Siwei Song

и другие.

ChemPlusChem, Год журнала: 2023, Номер 88(9)

Опубликована: Сен. 1, 2023

With the increase in demand for high-performance composite explosives, search advanced energetic melt-castable compounds has attracted increasing attention field of materials. Herein, two new materials with nitromethyl and azidomethyl substituents (1-(nitromethyl)-3,4-dinitro-1H-pyrazole (NMDNP) 1-(azidomethyl)-3,4-dinitro-1H-pyrazole (AMDNP) were prepared by substituent modification a potential molecule ((3,4-dinitro-1H-pyrazol-1-yl) methyl nitrate, MC-4), respectively. NMDNP exhibited suitable melting point (90 °C), good thermal stability (Td : 185 °C) excellent detonation performance (8484 m s-1 ) impact sensitivity (25 J), thereby demonstrating promise as an material. Simultaneously, compared nitrato-methyl substituents, greater advantages regulating performance.

Язык: Английский

Процитировано

3

Synthesis of heterocyclic (triazole, furoxan, furazan) fused pyridazine di-N-oxides via hypervalent iodine oxidation DOI
Qi Zhang, Chunlin He, Siping Pang

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(30), С. 14324 - 14327

Опубликована: Янв. 1, 2022

Use of a mild PIDA oxidation strategy to access heterocyclic (triazole, furoxan, furazan) fused pyridazine di- N -oxides.

Язык: Английский

Процитировано

5