Reliable prediction of the condensed (solid or liquid) phase enthalpy of formation of organic energetic materials at 298 K through their molecular structures

Abadi

2018

ChemistrySelect

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This work introduces eight novel cyclic nitramine derivatives of energetic compounds as high performance energetic compounds. Assessments of physicothermal, detonation and combustion properties as well as sensitivities with respect to external stimuli impact, friction and shock are done for these compounds. The method of density functional theory (DFT) at B3LYP/6‐31G (d,p) as well as the best available predictive methods are used for prediction of 20 different parameters including crystal density, solid phase heat formation, Gibbs free energy of formation, activation energy, heat of sublimation, melting point, enthalpy of fusion, entropy of fusion, heat of combustion, heat of detonation, temperature of detonation, specific impulse, velocity of detonation, detonation pressure, Gurney velocity, power, brisance, heat sensitivity, impact sensitivity, friction sensitivity and shock sensitivity. These properties are compared with corresponding measured or calculated data of octahydro‐1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocine (HMX) and 2,4,6,8‐tetranitro‐1H,5H‐2,4,6,8‐tetraazabicyclo [3.3.0] octane (BCHMX) as two high performance nitramines. Among the introduced cyclic nitramines, it shown that N,N‐bis(1,3,4,6‐tetranitrooctahydroimidazo[4, 5‐d]imidazol‐2‐yl) nitramide is a good candidate of high performance nitramine where its sensitivity with respect to impact, friction and shock is close to BCHMX.

“…The solid phase heat of formation (Δ f H θ (s)) shows the energy content of an energetic material. A reliable model is used here for evaluation of the condensed phase heat of formation as :

true Δ_{f} H^{θ} (s) = - 111.4 + 333.11 a - 28.84 b + 86.80 c - 62.03 d 79.25 (Δ_{f} H^{θ}_{add, D H C} + Δ_{f} H^{θ}_{non - add, D H C}) + 153.3 (Δ_{f} H^{θ}_{add, I H C} + Δ_{f} H^{θ}_{non - add, I H C})

…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Novel Organic Compounds Containing Nitramine Groups Suitable as High‐Energy Cyclic Nitramine Compounds

Abadi

2018

ChemistrySelect

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“…Three different experimental values of standard liquid phase heat of formation (D f H q liquid ) for phenylhydrazine are reported in literature, i. e. 141.0, 142.2 and 179.0 kJ/mol [44]. Meanwhile, the calculated standard solid phase heat of formation (D f H q solid ) of 4-nitrophenylhydrazine and 2,4-dinitrophenylhydrazine are 21.7 and 13.3 kJ/mol, respectively [45]. Thus, the attachment of nitro groups can decrease the values of D f H q solid in nitro derivatives of phenylhydrazine.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Investigation of the New Derivatives of Poly(Epichlorohydrin) Containing Energetic Groups

Atabaki

Propellants Explo Pyrotec

Bastam

2017

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In this research, poly(epichlorohydrin)(PECH) is modified by phenylhydrazine as well as 4-nitrophenylhydrazine and 2,4-dinitro phenylhydrazine. The chemical structures of the new derivatives of PECH are analyzed by Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR) and ultraviolet-visible (UV) techniques as well as carbon-hydrogen-nitrogen (CHN) ultimate analysis. Thermal characteristics of reaction products are studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). Moreover, glass transition temperature (T g ) of these new polymers are determined. The results indicate that modifications of the poly(epichlorohydrin) are carried out successfully. The new energetic derivatives of PECH are good candidates for chemical industries, which may be considered as a novel class of energetic binders.Keywords: PECH · phenyl hydrazine · 4-nitrophenylhydrazine · 2,4-dinitrophenylhydrazine · energetic poly(epichlorohydrin) 2 Experimental MaterialsAll the chemicals used in this work were of analytical grade. Epichlorohydrin and N,N-dimethylacetamide (DMAc) were purchased from sigma-Aldrich. Tin tetrachloride (SnCl 4 ), phenylhydrazine, 4-nitrophenylhydrazine, 2,4-dinitrophenylhydrazine, ethylene glycol and dichloromethane were obtained from [a] F.

“…Because of attractive properties of different types of ILs such as EILs in recent years, some models have been developed to predict their physicochemical and thermophysical properties, e.g. density, ignition delay of hypergolic ILs, heats of combustion, and glass transition temperature . The study of decomposition temperature of imidazolium based EILs has shown that it is possible to introduce a new correlation based on the number of some atoms in cations and anions as well as some specific cations or anions.…”

Section: Methodsmentioning

confidence: 99%

A New Method for Predicting Decomposition Temperature of Imidazolium‐based Energetic Ionic Liquids

Zeitschrift anorg allge chemie

Pouretedal

Saberi

2016

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Two novel correlations are introduced to predict decomposition temperatures of imidazolium-based energetic ionic liquids. The first simple model is based only on the number of some of atoms in cationic and anionic structures. Meanwhile, a suitable correction term was added in the second correlation to adjust the predicted results for the presence of some specific cation/anion moieties. The measured data of 164 different types of imidazolium-based energetic ionic liquids were used to derive the new correlations. The calculated mean absolute percent errors (MAPEs) of the first and second models are 6 * Dr. M. H. Keshavarz 171and 4, respectively. The predicted results have confirmed that insertion of correcting function in the second correlation can provide better estimations. These models were also tested and compared with one of the best available group contribution methods, where group contribution method can be applied, for 17 further imidazolium-based energetic ionic liquids containing complex molecular structures. Furthermore, the predicted values of MAPEs of the new models are close to that of obtained by group contribution method.