Synthesis and Characterization of Two Potential Energetic Azido Esters

Pant, Chandra Shekhar; Wagh, R. M.; Nair, J. K.; Gore, G. M.; Venugopalan, S.

doi:10.1002/prep.200600065

Cited by 22 publications

(15 citation statements)

References 4 publications

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“…Then, it could be concluded that ABAMPA is much insensitive than TAP‐Ac, which was also confirmed by the friction sensitivity (FS) results of ABAMPA (324 N) and TAP‐Ac (54 N) . Besides, the impact and friction sensitivities of ABAMPA were comparable if not less than some previously reported azido ester plasticizers, such as BAEM, BAEG and 1,5‐diazido‐3‐nitrazapentane (DIANP) ,,. Therefore, the insensitivities toward impact and friction of ABAMPA is proved experimentally.…”

Section: Resultssupporting

confidence: 68%

“…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 57 were comparable if not less than some previously reported azido ester plasticizers, such as BAEM, BAEG and 1,5-diazido-3-nitrazapentane (DIANP). [4,12,[21][22][23][24] Therefore, the insensitivities toward impact and friction of ABAMPA is proved experimentally.…”

Section: Thermal Decomposition and Sensitivity Analysismentioning

confidence: 99%

“…Compared with general organic azido compounds, energetic azido ester plasticizers provided with better lubricant effect and thermal stability, lower sensitivity and glass transition temperature . Previous work have reported the synthesis and properties of some energetic azido ester plasticizers such as bis(2‐azido‐1‐(azidomethyl)ethyl) malonate (BAEM), bis(2‐azido‐1‐(azidomethyl)ethyl) glutarate (BAEG), 1,3‐bis(azidoacetoxy)‐2,2‐bis(azidomethyl)propane (BABAMP) and triazidopentaerythrite acetate (TAP‐Ac) (Scheme ) ,,. However, the most conspicuous drawback of these azido ester plasticizers is their low level of nitrogen content, oxygen balance, density and energy.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

et al. 2019

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This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ⋅ cm−3, 16 J, 324 N, 235.9 °C and −50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ⋅ cm−3)0.5, and the glass transition temperature of GAP was reduced from −35 °C to −43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.

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Section: Resultssupporting

confidence: 68%

Section: Thermal Decomposition and Sensitivity Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

et al. 2019

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“…The experimental data of the heat of formation of 40 organic azido compounds [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] were used for construction and validation of the proposed models. Table 2 illustrates the experimental data of 33 different azido compounds with various molecular structures, which were used as training set.…”

Section: Methodsmentioning

confidence: 99%

Heat of Formation Assessment of Organic Azido Compounds Used as Green Energetic Plasticizers by QSPR Approaches

Sheibani

2019

Propellants Explo Pyrotec

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Quantitative structure‐property relationship (QSPR) approaches were applied as a tool for assessment of the standard enthalpy of formation of 40 organic azido compounds with different molecular structure which are used as energetic plasticizers in energetic material formulations. Chemical structures of these compounds were encoded into several sets of molecular descriptors, which represent various physical and chemical properties of these molecules. A total number of 1475 molecular descriptors of 22 different types were selected and calculated. Then a stepwise regression method was applied to determine the most relevant molecular descriptors which have significant effects on the ΔH°f of azido compounds. Finally, the best subsets regression method and also the response plot of PLS regression is used to evaluate the predictive power of the selected molecular descriptors and find out the possibility to reduce the dimension of the initially developed model. The finally derived models displayed a good predictive ability arising from the determination coefficient corresponding to the leave one out (LOO) cross validation technique (R2=0.9821, 0.9962 and QnormalLnormalOnormalO2 =0.9907, 0.9851 respectively). Moreover, the obtained results of this investigation are compared with results which have been calculated using “Energetic Materials Designing Bench (EMDB), Version 1.0” software package.

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“…The glass transition temperature (T g )o fs ome mixtures of polymer and plasticizer for the effect of monomer mixture on the T g 's of copolymers systemsh ave been studied in the literature [12,[46][47][48][49][50][51].S ince, the molecular flexibility of the plasticizer is an importantm echanism for altering the brittleness of polymers via plasticization, the implication of this observation can be obtainedf rom the deviations of T g .I n the presented study,t he effect of adding plasticizer was observedi nt ermso fT g of polyNIMMO, which again indicates the compatibility of plasticizers with polyNIMMO. Maximum lowering of T g (À52 8C) was observed in the cases of BuNENA and DEGDN, where as BDNPAh as shown minimum lowering of T g at À38.85 8C ( Figure 2).…”

Section: Thermal Studiesmentioning

confidence: 98%

Understanding the Compatibility of the Energetic Binder PolyNIMMO with Energetic Plasticizers: Experimental and DFT Studies

Shee

Shah

Athar

et al. 2016

Propellants Explo Pyrotec

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The development of energetic binders with suitable energetic plasticizers is required to enhance the mechanical properties and to reduce the glass transition temperature of propellant and explosive formulations. The compatibility of the energetic binder poly(3‐nitratomethyl‐3‐methyloxetane) (polyNIMMO) with five different energetic plasticizers viz. bis(2,2‐dinitro propyl)acetal (BDNPA), dinitro‐diaza‐alkanes (DNDA‐57), 1,2,4‐butanetriol trinitrate (BTTN), N‐N‐butyl‐N‘(2‐nitroxy‐ethyl) nitramine (BuNENA) and diethyleneglycoldinitrate (DEGDN) was studied by differential scanning calorimetry (DSC), rheology, and DFT methods. The results obtained for the pure binder were compared with the results obtained for the binder/plasticizer blend in regard of the decomposition temperature and the format of the peak indicated the compatibility of polyNIMMO with the plasticizers. The glass transition temperatures of the blends were determined by low temperature DSC and showed desirable lowering of glass transition temperature with single peak. The rheological evaluation revealed that the viscosity of the binder is considerably lowered by means of flow behavior upon addition of 20 % (w/w) plasticizer. The addition of BuNENA and DEGDN has maximum effect on the lowering of viscosity of polyNIMMO. The predicted relative trend of interaction energies between plasticizer and binder is well correlated with the corresponding trend of viscosity of binder/plasticizer blends. These experimental studies verified by theoretical methods are valuable to design practical blends of new plasticizers and binders.

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Synthesis and Characterization of Two Potential Energetic Azido Esters

Cited by 22 publications

References 4 publications

Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer

Heat of Formation Assessment of Organic Azido Compounds Used as Green Energetic Plasticizers by QSPR Approaches

Understanding the Compatibility of the Energetic Binder PolyNIMMO with Energetic Plasticizers: Experimental and DFT Studies

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