Studies on CL-20/HMX (2:1) Cocrystal: A New Preparation Method and Structural and Thermokinetic Analysis

Ghosh, M. K.; Sikder, A. K.; Banerjee, Shaibal; Gonnade, Rajesh G.

doi:10.1021/acs.cgd.8b00015

Cited by 61 publications

(52 citation statements)

References 72 publications

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“…Encouraged by the great success of pharmaceutical co-crystallization, the development of new functional materials by co-crystallization techniques in other fields is attracting more and more interest. Nowadays, energetic cocrystallization has become very promising as an alternative method of tuning explosive structures and properties by rearranging existing molecules, instead of synthesizing new compounds (Ghosh et al, 2018;Sun et al, 2019). Another application of co-crystals is organic nonlinear optical materials with high second-order nonlinear susceptibilities.…”

Section: Introductionmentioning

confidence: 99%

Melting points of one- and two-component molecular crystals as effective characteristics for rational design of pharmaceutical systems

Perlovich

2020

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Based on the review of the literature results the database of the fusion temperatures of two-component molecular crystals (1947 co-crystals) and individual components thereof was built up. To improve the design of co-crystals with predictable melting temperatures, the correlation equations connecting co-crystals and individual components melting points were deduced. These correlations were discovered for 18 co-crystals of different stoichiometric compositions. The correlation coefficients were analysed, and the conclusions about the main/determinative and slave components of a co-crystal were made. The comparative analysis of the melting points of co-crystals composed from the same components but with different stoichiometry showed a co-crystal melting temperature growth when increasing the content of a high-melting component. The differences in the melting temperatures were determined and discussed for the following: (a) monotropic polymorphic forms, (b) two-component crystals with the same composition and different stoichiometry, and (c) two-component crystals based on racemates and enantiomers. The database analysis revealed the active pharmaceutical ingredients (APIs) and co-formers (CFs) more particularly used for co-crystal design. The approach based on an efficacy parameter allowing the prediction of co-crystals with melting points lower than those of individual compounds was developed.

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Section: Introductionmentioning

confidence: 99%

Melting points of one- and two-component molecular crystals as effective characteristics for rational design of pharmaceutical systems

Perlovich

2020

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…In recent report, Mirnal Ghosh et al. reported the synthesis of EECC with CL‐20 and HMX having stoichiometric mixture 2 : 1 through solvent evaporation in presence of high boiling anti solvent and the authors observed better thermokinetic parameters with improved velocity of detonation and reduced sensitivity than CL‐20 . Zongwei Yang et al.…”

Section: Introductionmentioning

confidence: 99%

Studies and Theoretical Optimization of CL‐20 : RDX Cocrystal

Viswanath

Shanigaram

Vijayadarshan

et al. 2019

Propellants Explo Pyrotec

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CL-20 among other nitramines is highly energetic along with the high positive heat of formation, and is a green energetic material employed as solid propellant [1][2][3]. However, it suffers basically from mechanical sensitivity and cost of synthesis. Cocrystallization of CL-20 with other suitable HEMs and LEMs is considered as the best crystal engineering technique to reduce its sensitivity [2,[4][5][6] as it masks crystal defects which in turn are responsible for mechanical sensitivity. The present investigation reports on the scale up process for the synthesis of Energy-Energy Cocrystallization (EECC) of ɛ-CL-20 and RDX and focus on the process to optimize the structure and energetics of thus formed cocrystal (CRCC) through DFT study. In our study CL-20 and RDX are taken in 1 : 1 molar ratio as sug-gested by . We claim successful scale up of cocrystallization to the earlier report [4] employing a more user friendly solvent (acetone) in the present study and the cocrystal formed was through ultra centrifugation. During the course of the cocrystal formation a phase transition from ɛto α took place. The Trauzl lead block tests on CRCC support the better performance of the synthesised EECC. Introducing shock tube test as the parameter to claim the strength of HEMs enhances the comparability [8]. The present report envisages and collaborates the synthesised CRCC through the theoretical study in arriving at the spatial conformation leading to optimization in structure and energy of the synthesized EECC.Keywords: Low sensitive High Energy Material (LSHEM) · Cocrystallization · Secondary bonding · Theoretical structure optimization · Gaussian [a] J.

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“…Recently, cocrystallization has attracted interest in the field of energetic materials. Despite the lack of hydrogen bond donors in explosive molecules, some cocrystals of HEDMs were still obtained in a fortunate manner, such as benzotrifuroxan (Zhang, Guo et al, 2013), 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane (Shen et al, 2011;Li et al, 2015;Ghosh et al, 2018) and CL-20 (Bolton et al, 2011(Bolton et al, , 2012Yang et al, 2012;Huang et al, 2018). Cocrystallization yielded considerable improvement in the safety performance of HEDMs without a significant energy loss.…”

Section: Introductionmentioning

confidence: 99%

Design, preparation, characterization and formation mechanism of a novel kinetic CL-20-based cocrystal

Sun

Zhang

et al. 2019

Acta Crystallogr B Struct Sci Cryst Eng Mater

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2,4,6,8,10,-based cocrystals have gained increasing attention as a means of obtaining insensitive high explosives. However, the design of ideal candidates for these cocrystals remains difficult. This work compares the crystal energies of the CL-20-dinitrobenzene (DNB) and CL-20-2,4,6-trinitrotoluene (TNT) cocrystals with those of the respective pure coformers. The results indicate that the cocrystal formation is driven by the differences in the energies of the cocrystals and the coformers. Furthermore, analysis via Hirshfeld surfaces and two-dimensional fingerprint plots confirms that the OÁ Á ÁO, OÁ Á ÁH, OÁ Á ÁN and CÁ Á ÁO interactions were the main force for stabilizing the CL-20-based cocrystal structure. Based on these findings, a novel energetic-energetic cocrystal of CL-20-2,4,6-trinitrophenol (TNP) was designed and prepared by means of a rapid method for solvent removal. The crystal structure was investigated via powder X-ray diffraction methods, solid-state nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy. The results revealed that the O-HÁ Á ÁO hydrogen bonding interaction between the phenolic hydroxyl group of TNP and nitro groups of CL-20, as well as nitroÁ Á Á, nitroÁ Á Ánitro and O NO2 Á Á Á(N) NO2 interactions, based on the benzene ring and nitro groups, are the main interactions occurring in the cocrystal.

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Studies on CL-20/HMX (2:1) Cocrystal: A New Preparation Method and Structural and Thermokinetic Analysis

Cited by 61 publications

References 72 publications

Melting points of one- and two-component molecular crystals as effective characteristics for rational design of pharmaceutical systems

Melting points of one- and two-component molecular crystals as effective characteristics for rational design of pharmaceutical systems

Studies and Theoretical Optimization of CL‐20 : RDX Cocrystal

Design, preparation, characterization and formation mechanism of a novel kinetic CL-20-based cocrystal

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