An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound
The exploration of energetic derivatives of 1,1-diamino-2,2-dinitroethylene (FOX-7) is a feasible strategy for attaining high-performance energetic materials. Of all the extant types of energetic derivatives, hydrazino-substituted FOX-7 derivatives have received the most extensive attention because...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
KeAi Communications Co. Ltd.
2022-09-01
|
| Series: | Energetic Materials Frontiers |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666647222000343 |
| _version_ | 1797936318753275904 |
|---|---|
| author | Zhao-yang Yin Wei Huang Ya-qun Dong Yu-ji Liu Yong-xing Tang |
| author_facet | Zhao-yang Yin Wei Huang Ya-qun Dong Yu-ji Liu Yong-xing Tang |
| author_sort | Zhao-yang Yin |
| collection | DOAJ |
| description | The exploration of energetic derivatives of 1,1-diamino-2,2-dinitroethylene (FOX-7) is a feasible strategy for attaining high-performance energetic materials. Of all the extant types of energetic derivatives, hydrazino-substituted FOX-7 derivatives have received the most extensive attention because of their excellent detonation performance. However, the applications of these derivatives are restricted by their relatively high mechanical sensitivities. In this study, the exploration of the reaction between 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene (Tri-FOX) and hydrazine monohydrate resulted in the development of an unexpected dihydrotetrazine bridged energetic compound: 3,6-bis((E)-hydrazono(1H-1,2,4-triazol-5-yl)methyl)-1,4-dihydro-1,2,4,5-tetrazine (BHDT). BHDT exhibits high onset decomposition temperature (Td = 240 °C), low impact sensitivity (IS = 30 J), and low friction sensitivity (FS = 270 N). These features are more advantageous than those of H-FOX (Td = 125 °C, IS = 6 J) and HTz-FOX (Td = 237 °C, IS = 10 J, FS = 240 N). |
| first_indexed | 2024-04-10T18:28:57Z |
| format | Article |
| id | doaj.art-86eecf8aac6f4514a4f04cef9788581f |
| institution | Directory Open Access Journal |
| issn | 2666-6472 |
| language | English |
| last_indexed | 2024-04-10T18:28:57Z |
| publishDate | 2022-09-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Energetic Materials Frontiers |
| spelling | doaj.art-86eecf8aac6f4514a4f04cef9788581f2023-02-02T04:50:16ZengKeAi Communications Co. Ltd.Energetic Materials Frontiers2666-64722022-09-0133172176An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compoundZhao-yang Yin0Wei Huang1Ya-qun Dong2Yu-ji Liu3Yong-xing Tang4School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, ChinaSchool of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, ChinaSchool of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, ChinaSchool of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, ChinaCorresponding author.; School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094, ChinaThe exploration of energetic derivatives of 1,1-diamino-2,2-dinitroethylene (FOX-7) is a feasible strategy for attaining high-performance energetic materials. Of all the extant types of energetic derivatives, hydrazino-substituted FOX-7 derivatives have received the most extensive attention because of their excellent detonation performance. However, the applications of these derivatives are restricted by their relatively high mechanical sensitivities. In this study, the exploration of the reaction between 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene (Tri-FOX) and hydrazine monohydrate resulted in the development of an unexpected dihydrotetrazine bridged energetic compound: 3,6-bis((E)-hydrazono(1H-1,2,4-triazol-5-yl)methyl)-1,4-dihydro-1,2,4,5-tetrazine (BHDT). BHDT exhibits high onset decomposition temperature (Td = 240 °C), low impact sensitivity (IS = 30 J), and low friction sensitivity (FS = 270 N). These features are more advantageous than those of H-FOX (Td = 125 °C, IS = 6 J) and HTz-FOX (Td = 237 °C, IS = 10 J, FS = 240 N).http://www.sciencedirect.com/science/article/pii/S2666647222000343Energetic compoundDihyrotetrazineHydrazine1,2,4-Triazole |
| spellingShingle | Zhao-yang Yin Wei Huang Ya-qun Dong Yu-ji Liu Yong-xing Tang An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound Energetic Materials Frontiers Energetic compound Dihyrotetrazine Hydrazine 1,2,4-Triazole |
| title | An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound |
| title_full | An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound |
| title_fullStr | An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound |
| title_full_unstemmed | An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound |
| title_short | An unusual reaction of 1,1-diamino-2-nitro-2-(1H-triazol-5-yl)ethene and hydrazine: The synthesis of a dihydrotetrazine bridged energetic compound |
| title_sort | unusual reaction of 1 1 diamino 2 nitro 2 1h triazol 5 yl ethene and hydrazine the synthesis of a dihydrotetrazine bridged energetic compound |
| topic | Energetic compound Dihyrotetrazine Hydrazine 1,2,4-Triazole |
| url | http://www.sciencedirect.com/science/article/pii/S2666647222000343 |
| work_keys_str_mv | AT zhaoyangyin anunusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT weihuang anunusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yaqundong anunusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yujiliu anunusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yongxingtang anunusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT zhaoyangyin unusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT weihuang unusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yaqundong unusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yujiliu unusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound AT yongxingtang unusualreactionof11diamino2nitro21htriazol5yletheneandhydrazinethesynthesisofadihydrotetrazinebridgedenergeticcompound |