An overview on importance, synthetic strategies and studies of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW)

Viswanath, J. Venkata; Venugopal, Krishnaveni; Rao, N. Venkateswara; Venkataraman, A.

doi:10.1016/j.dt.2016.05.002

Cited by 50 publications

(26 citation statements)

References 48 publications

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“…In the course of this study, 1,3-dinitroimidazolidine-2-carboxylic acid (1) has been synthesized for the first time (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

“…The design of new high-energy materials superior in detonation performance to the existing ones, as well as the development of their synthetic methods, is still a topical research area worldwide. [1] Among the effective ways to improve energetic characteristics of explosive compounds is incorporating strained moieties such as five-membered rings or complex 2D or 3D molecules (cages) thereto. Predictions demonstrate that caged nitramines are much more attractive in seeking high-energy materials because they exhibit enhanced energetic characteristics and reduced sensitivity.…”

Section: Introductionmentioning

confidence: 99%

“…At first, the isowurtzitane cage is built by condensation between glyoxal and primary amine or amide. [1] The next step is to convert the organic group of amine derivatives into the nitro group to obtain the energetic compound. Despite the promising outlook of CL-20, its application is limited due to the high synthesis cost.…”

Section: Introductionmentioning

confidence: 99%

“…Despite the promising outlook of CL-20, its application is limited due to the high synthesis cost. [1] Scheme 1. Structural formulas of RDX, HMX and CL-20.…”

Section: Introductionmentioning

confidence: 99%

“…In most cases, the isowurtzitane cage originates from condensation of primary amines that comprise an aromatic moiety or multiple bond linked to the amine group via a methylene bridge. [1] It has more recently been found that compounds similar to oxaazaisowurtzitane derivatives can be synthesized by condensation between sulfonamides and glyoxal. [16,17] The development of synthetic methods for high-energy compounds bearing strained moieties and capable of being further transformed into more complex high-energy…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

Sysolyatin¹,

Paromov²

2019

Preprint

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Three new functional 2-substituted 1,3-dinitroImidazolidines were synthesized herein. A synthetic strategy is suggested for structurally different α,α-dinitraminocarboxylic acids via condensation of glyoxylic acid ethyl ester with amine or amide derivatives. Alkali- and acid-catalyzed hydrolyses of ethyl 1,3-dinitro-1,3-diazacyclopentane-2-carboxylate were studied. A series of hydrolysis products were isolated. The Curtius rearrangement of 1,3-dinitroimidazolidine-2-carboxylic acid to 2-isocyanato-1,3-dinitroimidazolidine was carried out. Hydrolyses of 1,3-dinitroimidazolidine-2-carbonyl azide and 2-isocyanato-1,3-dinitroimidazolidine were studied. 1,3-Dinitroimidazolidine-2-amine was captured as 1,3-bis(1,3-dinitroimidazolidin-2-yl)urea.

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“…In the course of this study, 1,3-dinitroimidazolidine-2-carboxylic acid (1) has been synthesized for the first time (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Despite the promising outlook of CL-20, its application is limited due to the high synthesis cost. [1] Scheme 1. Structural formulas of RDX, HMX and CL-20.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

Sysolyatin¹,

Paromov²

2019

Preprint

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CFD Simulation of a Drowning‐out Crystallizer for Hexanitrohexaazaisowurtzitane

Jung

Jun

et al. 2018

Chem Eng & Technol

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Hexanitrohexaazaisowurtzitane (HNIW) is widely used for explosives, filling warheads, and solid propellants due to its high energy density and no halogen content. A pilot‐scale drowning‐out crystallizer is suggested to produce ε‐form HNIW and computational fluid dynamics simulation (CFD) was carried out. Acetone and isopropyl alcohols served as solvent and antisolvent, respectively. Population balance with quadratic method of moment was employed for the prediction of crystal size distribution and the results were compared with experimental data. The driving force of antisolvent crystallization includes impeller speed, ratio of antisolvent to solvent, and feed flow rate. A case study with various operating conditions was performed to identify the influence of such driving forces on crystal mean diameter. The aim was a scale‐up of the antisolvent crystallization process based on experimental results and CFD simulation.

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Synthesis, Characterization and Energetic Properties of Hydroxymethyl‐Bishomocubanone Derivatives

Lal,

Rao Cheekatla,

Suresh

et al. 2024

Chemistry A European J

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The present work reports synthesis, characterization and theoretical insights on novel hydroxymethyl‐bishomocubanone derivatives. Twelve new bishomocubanes (BHCs) were synthesized and fully characterized by various spectroscopic techniques and single crystal X‐ray analysis. The densities of the title compounds were found in the range of 1.34‐1.59 g/cm3. Density‐functional theory (DFT) based calculations at B3LYP/6‐311++G(d,p) level of theory were performed on ten selected BHC based cage compounds. Propulsive and ballistic properties of newly synthesized hydroxymethyl‐bishomocubanone derivatives in solid and liquid propulsion systems were calculated, and the results suggested that these compounds are superior to conventional fuel RP1 and binder HTPB. The detonation parameters revealed that these compounds are not explosive in nature and safe to use as solid propellants. Furthermore, kinetic and thermal stabilities of the title compounds were determined by HOMO‐LUMO energy gap, ESP maps, impact sensitivity (h50) and bond dissociation energies (BDEs) followed by thermogravimetric analysis (TGA) and differential thermogravimetry analysis (DTA). Three compounds, a dinitroazide (Isp,vac= 310.98s), a dinitrate (Isp,vac = 309.51s), and a dinitronitrate (Isp,vac= 309.20s) were found to be excellent candidates for volume limited applications.

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An overview on importance, synthetic strategies and studies of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (HNIW)

Cited by 50 publications

References 48 publications

Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

CFD Simulation of a Drowning‐out Crystallizer for Hexanitrohexaazaisowurtzitane

Synthesis, Characterization and Energetic Properties of Hydroxymethyl‐Bishomocubanone Derivatives

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