ChemInform Abstract: Energetic 1,2,4‐Triazoles and Tetrazoles: Synthesis, Structure and Properties

Островский, В. А.; Pevzner, M. S.; Kofman, T. P.; Shcherbinin, Mikhail B.; Целинский, И. В.

doi:10.1002/chin.200050296

Cited by 77 publications

(120 citation statements)

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“…18,19 The explosive is placed in an open ended, flanged steel tube, which is locked up with a closing plate with variable orifice (0 10 mm), through which gaseous decomposition products are Fig. 1 Representation of the solid state molecular structure of TKX 50 at 100 K. Thermal ellipsoids are drawn at the 50% probability level; symmetry codes: (i) 2 x, y, 2 z; (ii) x, 0.5 y, 0.5 + z; and (iii) 1 + x, 0.5 y, 0.5 + z.…”

Section: Energetic Performancementioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

622

553

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The safe preparation and characterization (XRD, NMR and vibrational spectroscopy, DSC, mass spectrometry, sensitivities) of a new explosive dihydroxylammonium 5,5 0 bistetrazole 1,1 0 diolate (TKX 50) that outperforms all other commonly used explosive materials is detailed. While much publicized high performing explosives, such as octanitrocubane and CL 20, have been at the forefront of public awareness, this compound differs in that it is simple and cheap to prepare from commonly available chemicals. TKX 50 expands upon the newly exploited field of tetrazole oxide chemistry to produce a material that not only is easily prepared and exceedingly powerful, but also possesses the required thermal insensitivity, low toxicity, and safety of handling to replace the most commonly used military explosive, RDX (1,3,5 trinitro 1,3,5 triazacyclohexane). In addition, the crystal structures of the intermediates 5,5 0 bistetrazole 1,1 0 diol dihydrate, 5,5 0 bistetrazole 1,1 0 diol dimethanolate and dimethylammonium 5,5 0 bistetrazole 1,1 0 diolate were determined and presented.

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Section: Energetic Performancementioning

confidence: 99%

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Fischer¹,

Fischer²,

Klapötke³

et al. 2012

J. Mater. Chem.

622

553

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“…Due to its cheap and comparatively easy synthesis, 1-amino-3-nitroguanidinium nitrate (3) was investigated reguarding its explosion performance under confinement using a "Koenen test" steel sleeve apparatus [42,43]. The performance of an explosive can be related to the data obtained from the Koenen test.…”

Section: Koenen Test Of 1-amino-3-nitroguanidinium Nitrate (3)mentioning

confidence: 99%

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

Fischer

Klapötke

Stierstorfer

2012

Zeitschrift Für Naturforschung B

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1-Amino-3-nitroguanidine (ANQ, 2) was synthesized via hydrazinolysis of nitroguanidine (1). An appropriate Lewis structure of ANQ is drawn based on VB calculations. Due to its basicity, it can be protonated by strong mineral acids or acidic heterocycles. In order to synthesize new energetic materials the nitrate (3) and perchlorate (4) salts of 1-amino-3-nitroguanidine were synthesized by protonation of 2 with 40 % nitric acid and 60 % perchloric acid, respectively. 5-Nitrimino-1,4H-tetrazole obtained by reacting 5-amino-1H-tetrazole with 100 % HNO 3 was used to synthesize the nitriminotetrazolate salt 5. Furthermore, the dinitramide salt 6 of 1-amino-3-nitroguanidine was synthesized by metathesis reaction of silver dinitramide and 1-amino-3-nitroguanidinium chloride. The dinitroguanidinate salt 7 was synthesized by protonation of 2 with 1,3-dinitroguanidine, which was prepared from nitroguanidine in anhydrous nitric acid/N 2 O 5 . All compounds were fully characterized by singlecrystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and DSC measurements. The heats of formation of 2 -7 were calculated using the atomization method based on CBS-4M enthalpies. With these values and the experimental (X-ray) densities several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. In addition, the sensitivities towards impact, friction and electrical discharge were tested using the BAM drophammer, friction tester as well as a small-scale electrical discharge device. A Koenen test with 1-amino-3-nitroguanidinium nitrate (3) was carried out in order to evaluate its explosive performance and shipping classification.

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“…. 이러한 화합물들은 고에너지, 고질소 함유 물질 로 1,2,4-트리아졸의 생성열은 109 KJ/mol, 1H-1,2,3-트 리아졸은 272 KJ/mol, 테트라졸은 237.2 KJ/mol이다 [2] . 트리아졸 및 테트라졸을 포함한 고분자는 에너지 물질로 잘 알려져 있다 [3] .…”

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Synthesis of Tetrazole-containing Energetic Copolymers

Shin¹

2011

Journal of the Korea Institute of Military Science and Technolo

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Polymers containing tetrazole groups are very attractive as energetic materials. Copolymer having tetrazole groups could be obtained by 3-steps from commercially available epichlorohydrin. These methods provide a new synthetic pathway to construct polymers containing tetrazole groups from non-energetic polynitrile compounds. These polymers are expected to be good candidates for green and high energetic materials. . 이러한 화합물들은 고에너지, 고질소 함유 물질 로 1,2,4-트리아졸의 생성열은 109 KJ/mol, 1H-1,2,3-트 리아졸은 272 KJ/mol, 테트라졸은 237.2 KJ/mol이다 [2] . 트리아졸 및 테트라졸을 포함한 고분자는 에너지 물질로 잘 알려져 있다 [3] . 우리는 에너지 물질을 연구 하는 과정에서 GAP(Glycidyl Azido Polymer)을 대신하 는 새로운 타입의 고분자로 GAP과 다양한 알킨 화합 물간의 클릭반응을 통해 얻어진 트리아졸기를 포함한 에너지 함유 고분자에 관한 보고를 하였다 [4] . 이처럼, 테트라졸과 물리적, 화학적 성질이 유사한 트리아졸의 †2011년 4월 18일 접수～2011년 7월 8일 게재승인 * 국방과학연구소(ADD) 책임저자 : 신정아(zzang0491@gmail.com) 경우는 클릭반응 . 그러나 이 화합물들은 유기용매에 대한 낮은 용해도 때문에 에너지 함유 바인더로 적용하기에는 한계가 있다.

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ChemInform Abstract: Energetic 1,2,4‐Triazoles and Tetrazoles: Synthesis, Structure and Properties

Cited by 77 publications

References 0 publications

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

Pushing the limits of energetic materials – the synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate

1-Amino-3-nitroguanidine (ANQ) in High-performance Ionic Energetic Materials

Synthesis of Tetrazole-containing Energetic Copolymers

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