PdFe bimetallic catalysts for debenzylation of hexabenzylhexaazaisowurtzitane (HBIW) and tetraacetyldibenzylhexaazaisowurtzitane (TADBIW)

Lou, Deyuan; Wang, Huishu; Liu, Shuang; Li, Li; Zhao, Wei; Xin-han, Chen; Wang, Junlan; Li, Xiaoqiang; Wu, Pingfan; Yang, Jeong-Mo

doi:10.1016/j.catcom.2018.02.008

Cited by 19 publications

(20 citation statements)

References 27 publications

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“…It is obliged to first convert part or all of the benzyl group into other functional groups that must have good stability to this cage structure and that are easy to be converted by the nitro group. Thus, the key step in HNIW synthesis is the debenzylation of HBIW; therefore, the current work introduces the debenzylation process of HBIW in detail [12].…”

Section: Typical Synthesis Methodsmentioning

confidence: 99%

“…As can be seen from Table 1, compared with HMX, the "king" of explosives, CL-20 has the advantages of higher energy density, lower oxygen balance, and higher enthalpy of formation [3,7,11]. Therefore, CL-20 has greater potential in applications [12]. For example, it can be used as the most powerful futuristic propellants or explosives due to the higher detonation velocity and detonation pressure.…”

Section: The Development and Performances Of The Explosivesmentioning

confidence: 99%

“…In order to maintain the cage structure, it is essential to launch the debenzylation and to transform it in a short time at a low temperature (generally 15-23 • C). It has been proved by plenty of optimization experiments that the better starting temperature falls in the range of 17-19 • C. Thus, in the above-mentioned reaction process, the catalysts play an important role when providing high efficiency at around room temperature [12]. Catalyst development.…”

Section: Synthesis Of Tadbiwmentioning

confidence: 99%

“…However, the catalysts in the acid solvents can be etched by the solution, resulting in poor cycle catalytic properties, which has been reported. There is a declining trend in the catalytic performances for the hydrogenation of N,N-dibenzyl-3-phenylindolizin-1-amine when it is in the acetic acid solution with cycles over recycled PtO 2 and Pt/C [12]. According to the report, the catalysts must be stable so that they can resist the acid corrosion.…”

Section: Synthesis Of Taiwmentioning

confidence: 99%

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Research Progress and Key Issues of Hydrodebenzylation of Hexabenzylhexaazaisowurtzitane (HBIW) in the Synthesis of High Energy Density Material Hexanitrohexaazaisowurtzitane (HNIW)

Tang¹,

Zhu

Shi

et al. 2022

Materials

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High energy density materials (HEDM) are the subject of an extensive research effort in relation to the use of these compounds as components of rocket propellants, powders, and formulations of high-performance explosives. Hexanitrohexaazaisowurtzitane (HNIW, i.e., CL-20) has received much attention in these research fields for its specific impulse, burning rate, ballistics, and detonation velocity. In this paper, the development and performances of the explosives from the first to the fourth generation are briefly summarized, and the synthesis status of the fourth-generation explosive, HNIW, is reviewed. The key issues that restrict the development of industrial amplification synthesis of HNIW are analyzed, and the potential directions of development are proposed. It is pointed out that to synthesize new and efficient catalysts is the key to making the cost-effective manufacturing of CL-20 a reality.

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Section: Typical Synthesis Methodsmentioning

confidence: 99%

Section: The Development and Performances Of The Explosivesmentioning

confidence: 99%

Section: Synthesis Of Tadbiwmentioning

confidence: 99%

Section: Synthesis Of Taiwmentioning

confidence: 99%

See 2 more Smart Citations

Research Progress and Key Issues of Hydrodebenzylation of Hexabenzylhexaazaisowurtzitane (HBIW) in the Synthesis of High Energy Density Material Hexanitrohexaazaisowurtzitane (HNIW)

Tang¹,

Zhu

Shi

et al. 2022

Materials

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“…Extensive research focused on upgrading the existing synthetic technologies for CL-20 and on finding alternative methods for obtaining the same has been pursued, dating back decades. The most promising direction is to develop a synthetic method for hexaazaisowurtzitane derivatives by direct condensation, which are nitratable to CL-20 [ 16 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 ].…”

Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed Condensation of Benzamide with Glyoxal, and Reaction Features

et al. 2022

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Scholars from around the world have been attempting to simplify and cheapen the synthetic method for the promising high-energy compound CL-20 for decades. The lack of understanding of the formation mechanisms of hexaazaisowurtzitane derivatives―CL-20 precursors―is a barrier to solving the said problems. Here, we report the results from an in-depth study into the acid-catalyzed condensation between benzamide and glyoxal in a molar ratio of 2:1 in polar protic and aprotic solvents. Sixteen compounds were isolated and identified, of which eight were synthesized for the first time. A geminal diol, N,N’-(2,2-dihydroxyethane-1,1-diyl)dibenzamide, was synthesized. Two isomers of 1,2-bis(benzoylamino)-1,2-ethanediol were isolated and identified. N,N’-(1-oxoethane-1,2-diyl)dibenzamide and 2-oxo-2-[(phenylcarbonyl)amino]ethyl benzoate were produced that were likely formed due to the 1,2-hydride shift. N-polysubstituted 1,4-dioxane-2,3,5,6-tetramine was synthesized for the first time, whose structure may be of interest as a scaffold for new explosives. DMSO, THF and HCOOH were found to be able to engage in a reaction with benzamide, or condensation products thereof, and glyoxal under acid-catalyzed conditions.

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Synthesis of Oxaazaisowurtzitane Derivatives Via Condensation of p‐Toluenesulfonamide With Glyoxal

Paromov,

Kubasova,

Sysolyatin

2024

Journal of Heterocyclic Chem

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This work presents the study results on the acid‐catalyzed cascade condensation of p‐toluenesulfonamide with glyoxal in H2SO4 in order to synthesize aza‐ and oxaazaisowurtzitanes—a platform for promising high‐energy‐density compounds—and explore their formation processes. The effects of the ratio of starting reactants, acidity, reaction medium concentration, and temperature on this process were studied in detail. Five novel compounds were derived, including four oxaazaisowurtzitanes comprising one to three aza groups, and one condensation intermediate. The most favorable conditions for the formation of the resultant caged compounds were established and some new regularities of the process were revealed. For instance, the reaction medium concentration was discovered for the first time to influence the generation process of oxaazaisowurtzitanes via direct condensation. The limiting stage of the cage formation process of oxaazaisowurtzitanes was identified. The formation rate of the oxaazaisowurtzitanes was shown to be dependent on their structure. The factor dramatically reducing the yield of the oxaazaisowurtzitanes at elevated synthesis temperature was also revealed.

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PdFe bimetallic catalysts for debenzylation of hexabenzylhexaazaisowurtzitane (HBIW) and tetraacetyldibenzylhexaazaisowurtzitane (TADBIW)

Cited by 19 publications

References 27 publications

Research Progress and Key Issues of Hydrodebenzylation of Hexabenzylhexaazaisowurtzitane (HBIW) in the Synthesis of High Energy Density Material Hexanitrohexaazaisowurtzitane (HNIW)

Research Progress and Key Issues of Hydrodebenzylation of Hexabenzylhexaazaisowurtzitane (HBIW) in the Synthesis of High Energy Density Material Hexanitrohexaazaisowurtzitane (HNIW)

Acid-Catalyzed Condensation of Benzamide with Glyoxal, and Reaction Features

Synthesis of Oxaazaisowurtzitane Derivatives Via Condensation of p‐Toluenesulfonamide With Glyoxal

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