Oxalyl Chloride and Hydrazide Based Energetic Polynitro Derivatives

Klapötke, Thomas M.; Krumm, Burkhard; Scharf, Regina

doi:10.1002/ejic.201600357

Cited by 28 publications

(27 citation statements)

References 44 publications

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“…Then OFW equation can be written as: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 moiety in 1H NMR spectra was appeared as a singlet d = 6.12 (s, 4H, CH 2 ) ppm. In the spectra of 13 [12] and were found to be identical. By recrystallization from chloroform, single crystals for Xray diffraction measurements were obtained for the oxidizer (BTNEOx).…”

Section: Calculation Of the Activation Energymentioning

confidence: 88%

“…By filtration and washing by cold water, solid crystals are obtained. By recrystallization from chloroform yielded (BTNEOx) as a colorless crystals (27 % yield) [12].…”

Section: Preparation Of Bis(222-trinitroethyl)-oxalatementioning

confidence: 99%

“…BTNEOx is an interesting new HEDO which has been prepared by Klapö tke group et al [12] by one step method, it has oxygen balance of + 7.7, impact sensitivity of 10 J and friction sensitivity higher than 360 N. BTNEOx has much lower sensitivities than NG and has not been studied in any propellant formulation yet. Also the investigation of the thermal behavior of the energetic materials is necessary and important for the research and development to find a suit- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 able new materials.…”

Section: Introductionmentioning

confidence: 99%

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Thermal Behavior and Decomposition Kinetics of Bis(2,2,2‐trinitroethyl)‐oxalate as a High Energy Dense Oxidizer and its Mixture with Nitrocellulose

Abd‐Elghany

Klapötke

Elbeih

2017

Propellants Explo Pyrotec

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A new propellant formulation (NC‐BTNEOx) based on bis(2,2,2‐trinitroethyl)oxalate (BTNEOx) as a high energy dense oxidizer (HEDO) mixed with nitrocellulose (NC) matrix was prepared and studied. BTNEOx was prepared and characterized by nuclear magnetic resonance (NMR) and X‐ray diffraction (XRD). Photos of the prepared formulation obtained by scanning electron microscope (SEM) clarified a good mixing of the nitrocellulose (NC) matrix with BTNEOx. A smokeless burning was observed and recorded for the prepared NC‐BTNEOx by a high speed camera. The thermal behavior and decomposition kinetics of the NC matrix, BTNEOx and their mixture have been investigated nonisothermally by using thermogravimetric analysis (TGA) and Differential scanning calorimetry (DSC). Isoconversional (model‐free) methods; Kissinger, Ozawa and Flynn−Wall (OFW) and Kissinger−Akahira−Sunose (KAS), were used to determine the kinetic parameters of the studied samples. The results proved that BTNEOx has melting temperature at 104.1 °C and maximum peak temperature at 200.6 °C, also it has effective activation energy in the range of 107–110 kJ/mol. The prepared NC‐BTNEOx has no endothermic peak and has exothermic peak at 201.7 °C which means that a composite might be formed due to the mixing of BTNEOx with NC. The prepared NC‐BTNEOx has effective activation energy in the range of 172–180 kJ/mol. BTNEOx required more study to proof the possibility of replacing the nitroglycerine in a smokeless double base propellant.

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Section: Calculation Of the Activation Energymentioning

confidence: 88%

“…By filtration and washing by cold water, solid crystals are obtained. By recrystallization from chloroform yielded (BTNEOx) as a colorless crystals (27 % yield) [12].…”

Section: Preparation Of Bis(222-trinitroethyl)-oxalatementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermal Behavior and Decomposition Kinetics of Bis(2,2,2‐trinitroethyl)‐oxalate as a High Energy Dense Oxidizer and its Mixture with Nitrocellulose

Abd‐Elghany

Klapötke

Elbeih

2017

Propellants Explo Pyrotec

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“…hasbeen studied. [8] 2,2,2-Trinitroethyl formate (TNEF) is an interesting HEDO, which was first prepared in 1967, [9] and more recently it has been synthesized by other methods. [6] 2,2,, which is easily synthesized through aH enry reaction, [7] is one of the interesting starting materials forp reparation of large number of compounds.…”

mentioning

confidence: 99%

“…Figure 1d shows the clear homogeneityo ft he NC matrix with TNEF in the prepared propellant sample. TG/DTG thermograms of NC-TNEF recorded at four different heatingr ates (2,4,8, and 16 8Cmin À1 )a re presentedi n Figure 3. This result is in line with the homogeneous and smokeless burning process of the propellant recorded by ah igh-speed camera ( Figure 2).…”

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confidence: 99%

Higher Performance and Safer Handling: Formulation Based on 2,2,2‐Trinitroethyl Formate and Nitrocellulose

et al. 2018

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on theoccasiono fhis 65th birthday An ew,g reen propellant formulation based on the high-energy dense oxidizer (HEDO) 2,2,2-trinitroethyl formate(TNEF) and nitrocellulose (NC) was prepared and thermally investigated using non-isothermal thermogravimetric analysis (TGA) and differentials canning calorimetry (DSC).S canning electronm icroscopy (SEM) was used to check the crystals of the oxidizer and the homogeneity of the new propellant formulation (NC-TNEF). The burning behavior of NC-TNEFw as recorded by high-speed camerat oo bserve the smoke produced. Ah igh specific impulse (I s = 257.4 s) waso btained from the characteristics calculation of the new propellant formulation by using EXPLO5_ V6.03 software.T he NC-TNEF mixture did not show any endothermicp eak and its exothermic peak wasa t2 04.6 8C, which means that ac omposite might be formed. The activation energy of the NC-TNEF was in the range of 184-190 kJ mol À1 . NC-TNEFh as ah igherp erformance and al ower hazard compared with the double-base propellant.

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Synthesis, Characterization and Energetic Performance of Oxalyl Diazide, Carbamoyl Azide, and N,N’‐Bis(azidocarbonyl)hydrazine

et al. 2021

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As pure compounds, small carbonyl azides enjoy a bad reputation, due to the high explosive sensitivity and instability they demonstrate. Consequently, most reported examples have only been poorly characterized. The compounds oxalyl diazide (1), carbamoyl azide (2), as well as N,N’‐bis(azidocarbonyl)hydrazine (3) were obtained by performing a diazotation reaction on the corresponding hydrazo precursor. Carbamoyl azide (2) could also be obtained from oxalyl diazide via Curtius rearrangement to the reactive isocyanate, followed by reaction with water. Further, different trapping reactions of the isocyanate with hydroxyl (methanol, oxetan‐3‐ol) and amino (2‐amino‐5H‐tetrazole) functions are described. All products were extensively analyzed using IR, EA, DTA and multinuclear NMR spectroscopy, and the crystal structures elucidated using single crystal X‐ray diffraction. In addition, the sensitivities toward friction and impact were determined and the energetic performances of the carbonyl azides were calculated using the EXPLO5 code.

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Oxalyl Chloride and Hydrazide Based Energetic Polynitro Derivatives

Cited by 28 publications

References 44 publications

Thermal Behavior and Decomposition Kinetics of Bis(2,2,2‐trinitroethyl)‐oxalate as a High Energy Dense Oxidizer and its Mixture with Nitrocellulose

Thermal Behavior and Decomposition Kinetics of Bis(2,2,2‐trinitroethyl)‐oxalate as a High Energy Dense Oxidizer and its Mixture with Nitrocellulose

Higher Performance and Safer Handling: Formulation Based on 2,2,2‐Trinitroethyl Formate and Nitrocellulose

Synthesis, Characterization and Energetic Performance of Oxalyl Diazide, Carbamoyl Azide, and N,N’‐Bis(azidocarbonyl)hydrazine

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