Studies on n‐Butyl Nitroxyethylnitramine (n‐BuNENA): Synthesis, Characterization and Propellant Evaluations

Rao, K. Poornachandra; Sikder, A. K.; Kulkarni, Mahadev A.; Bhalerao, M. M.; Gandhe, B.R.

doi:10.1002/prep.200400035

Cited by 33 publications

(16 citation statements)

References 3 publications

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“…The energetic binder polyNIMMOw as synthesized and characterizeda sr eported in the literature [ 8,[10][11][12].E nergetic plasticizers viz. bis(2,2-dinitro propyl) acetal (BDNPA) [27,28],d initro-diaza-alkanes (DNDA-57) [29],1 ,2,4-butanetriol trinitrate (BTTN) [ 30], N-N-butyl-N'(2-nitroxy-ethyl) nitramine (BuNENA) [ 31] and diethylene-glycol dinitrate (DEGDN) [30] were also synthesized and characterized in lab by reported methods. Otherc hemicalsa nd reagents used in this study were purchased and used as such.…”

Section: Methodsmentioning

confidence: 99%

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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Section: Methodsmentioning

confidence: 99%

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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“…2-[Butyl(nitro)amino] ethyl nitrate (n-BuNENA) is currently being combined with hydroxyterminated polyethers (HTPEs) to develop propellant formulations that meet insensitive munitions (IM) requirements. This compound is currently prepared by nitration of N-butylethanolamine [9][10][11] and involves a zinc chloride-catalyzed, secondary amine nitration using acetic anhydride/nitric acid [12,13]. The replacement of amino and hydroxyl hydrogens with a nitro group via direct nitration is an important route to N-and O-nitro derivatives.…”

Section: Introductionmentioning

confidence: 99%

N-Nitropyridinium Nitrate: An Efficient Nitrating Agent for the Synthesis of 2-[Butyl(nitro)amino]ethyl Nitrate (n-BuNENA)

Bayat

Esmailmarandi

2016

Cent. Eur. J. Energ. Mater.

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Abstract:The present investigation focused on the synthesis of 2-[butyl(nitro) amino]ethyl nitrate (n-BuNENA), by the nitration of N-butylethanolamine. For this purpose, various nitrating agents were studied and N-nitropyridinium nitrate was found to be a good nitrating agent. Short reaction time, ease of handling, performance of the reaction in one step and good yield are the main aspects of the present method. It also lead to 75% yield, which is a higher yield than by other methods. The purity of the product was evaluated by HPLC analysis, and its identity was confirmed by IR and 1 H NMR spectroscopy.

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“…Due to their importance, it is not surprising that the synthesis of n-BuNENAd erivatives is in the focuso fc urrentr esearch. These compounds are prepared by nitration of n-butylethanolamine [8][9][10] involving az inc chloride-catalyzed secondary amine nitration using acetic anhydride/HNO 3 [11,12].…”

Section: Introductionmentioning

confidence: 99%

Thionyl Nitrate as Nitrating Agent for the Synthesis of 2‐[Butyl(nitro)amino]ethyl Nitrate (n‐BuNENA)

Bayat

Esmailmarandi

2016

Propellants Explo Pyrotec

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The synthesis of n‐BuNENA by reaction of N‐butylethanolamine and thionyl nitrate is reported herein. Various nitrating agents were studied and thionyl nitrate was found to be a promising nitrating agent. The reaction conditions for the nitration with thionyl nitrate were optimized and the best results were obtained with one equivalent of thionyl nitrate at 0 °C for 3 h. This method has a number of advantages such as performing the reaction in one step, easy handling and work‐up, and good yield. The reaction progress was monitored by HPLC and the product was characterized by IR and 1H NMR spectroscopy.

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Studies on n‐Butyl Nitroxyethylnitramine (n‐BuNENA): Synthesis, Characterization and Propellant Evaluations

Cited by 33 publications

References 3 publications

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

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

N-Nitropyridinium Nitrate: An Efficient Nitrating Agent for the Synthesis of 2-[Butyl(nitro)amino]ethyl Nitrate (n-BuNENA)

Thionyl Nitrate as Nitrating Agent for the Synthesis of 2‐[Butyl(nitro)amino]ethyl Nitrate (n‐BuNENA)

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