Synthesis and Characterization of New Azido Esters Derived from Malonic Acid

Classen, Moritz J.; Heimsch, Stefanie B.; Klapötke, Thomas M.

doi:10.1002/prep.201900285

Cited by 14 publications

(9 citation statements)

References 21 publications

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“…Organic azides have been well investigated during the past decades, as they are widely used in various different fields of application ranging from pharmaceutical and medical science [1,2] over precursors for click chemistry [3] to chemical biology [4] and the agricultural sector. [5] The azido moiety is also commonly found in the area of energetic materials, [6] with many materials like plasticizers, hypergolic ionic liquids and binders containing at least one functional azido group. [7,8] Figure 1 shows a selection of commonly used organic azides in exemplary fields of application, as well as an example for the importance of geminal diazides in cyclisation reactions towards tetrazoles.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Geminal Diazido Derivatives Based on Diethyl Malonate

et al. 2021

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New geminal diazide derivatives based on diethyl 2,2-diazidomalonate (1) are presented. 2,2-Diazidomalonic acid (2) as well as four alkaline and nitrogen rich salts of 2,2-diazidomalonate (3-6) were synthesized and extensively characterized e. g. by low temperature X-ray diffraction. All compounds, which represent promising starting materials for further nitrogen-rich materials, were analyzed by 1 H and 13 C NMR spectroscopy, elemental analysis, differential thermal analysis (DTA) and regarding their sensitivity towards impact, friction, and electrostatic discharge according to BAM standard techniques. In addition, all synthesized compounds were evaluated regarding their energetic behavior using the EXPLO5 code and compared to TNT in order to provide a comparison to a well-known energetic material. In addition, two selected compounds were investigated towards their aquatic toxicity, using the bioluminescent bacteria vibrio fischeri.

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Section: Introductionmentioning

confidence: 99%

“…Figure 9. Molecular unit of guanidinium 2,2-diazidoacetate(6). Thermal ellipsoids of non-hydrogen atoms are drawn at the 50 % probability level and hydrogen atoms are shown as small spheres of arbitrary radius.…”

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Synthesis and Characterization of Geminal Diazido Derivatives Based on Diethyl Malonate

et al. 2021

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“…The five most common explosives tested, and the number of observations per explosive, are given in Table . Unless otherwise noted, we use log E 50 to represent sensitivity, where “log” is the base-10 logarithm, as in Kamlet, Nefati et al, and Wang et al The main source of data was legacy LANL tests; however, many of the data were obtained from the published scientific literature. ,− …”

Section: Datamentioning

confidence: 99%

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Marrs

Davis

Burch

et al. 2023

J. Chem. Inf. Model.

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The drop-weight impact test is an experiment that has been used for nearly 80 years to evaluate handling sensitivity of high explosives. Although the results of this test are known to have large statistical uncertainties, it is one of the most common tests due to its accessibility and modest material requirements. In this paper, we compile a large data set of drop-weight impact sensitivity test results (mainly performed at Los Alamos National Laboratory), along with a compendium of molecular and chemical descriptors for the explosives under test. These data consist of over 500 unique explosives, over 1000 repeat tests, and over 100 descriptors, for a total of about 1500 observations. We use random forest methods to estimate a model of explosive handling sensitivity as a function of chemical and molecular properties of the explosives under test. Our model predicts well across a wide range of explosive types, spanning a broad range of explosive performance and sensitivity. We find that properties related to explosive performance, such as heat of explosion, oxygen balance, and functional group, are highly predictive of explosive handling sensitivity. Yet, models that omit many of these properties still perform well. Our results suggest that there is not one or even several factors that explain explosive handling sensitivity, but that there are many complex, interrelated effects at play.

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“…Addition of the fuel component increases the performance of the propellant blend by reducing the high adiabatic temperature of the ionic liquid binary aqueous solution and further stabilizing the combustion process. Typically, methanol is used to control the burning rate of the monopropellant while the ammonium nitrate (AN) is used as a stabilizer [10] beside other stabilizing additives; a new article by M. Claßen et al [11] introduced novel additive promoters of new azido esters and suggested it would improve the total energy and performance of ionic liquid propellants. As an example, the maximum specific impulse of 78 wt% ADN in water mixture (Ionic Liquid) is 192 s when used as monopropellant, while the specific impulse rises to 252 s when methanol (molecular fuel) is added to the mixture, as in the case of LMP-103S (63.4 wt% ADN, 25.4 wt% water and 11.2 wt% methanol) at a nozzle area expansion ratio of 50 [12] as cited in [3].…”

Section: Energetic Ionic Liquids (Eils)mentioning

confidence: 99%

Review of State-of-the-Art Green Monopropellants: For Propulsion Systems Analysts and Designers

2021

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Current research trends have advanced the use of “green propellants” on a wide scale for spacecraft in various space missions; mainly for environmental sustainability and safety concerns. Small satellites, particularly micro and nanosatellites, evolved from passive planetary-orbiting to being able to perform active orbital operations that may require high-thrust impulsive capabilities. Thus, onboard primary and auxiliary propulsion systems capable of performing such orbital operations are required. Novelty in primary propulsion systems design calls for specific attention to miniaturization, which can be achieved, along the above-mentioned orbital transfer capabilities, by utilizing green monopropellants due to their relative high performance together with simplicity, and better storability when compared to gaseous and bi-propellants, especially for miniaturized systems. Owing to the ongoing rapid research activities in the green-propulsion field, it was necessary to extensively study and collect various data of green monopropellants properties and performance that would further assist analysts and designers in the research and development of liquid propulsion systems. This review traces the history and origins of green monopropellants and after intensive study of physicochemical properties of such propellants it was possible to classify green monopropellants to three main classes: Energetic Ionic Liquids (EILs), Liquid NOx Monopropellants, and Hydrogen Peroxide Aqueous Solutions (HPAS). Further, the tabulated data and performance comparisons will provide substantial assistance in using analysis tools—such as: Rocket Propulsion Analysis (RPA) and NASA CEA—for engineers and scientists dealing with chemical propulsion systems analysis and design. Some applications of green monopropellants were discussed through different propulsion systems configurations such as: multi-mode, dual mode, and combined chemical–electric propulsion. Although the in-space demonstrated EILs (i.e., AF-M315E and LMP-103S) are widely proposed and utilized in many space applications, the investigation transpired that NOx fuel blends possess the highest performance, while HPAS yield the lowest performance even compared to hydrazine.

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Synthesis and Characterization of New Azido Esters Derived from Malonic Acid

Cited by 14 publications

References 21 publications

Synthesis and Characterization of Geminal Diazido Derivatives Based on Diethyl Malonate

Synthesis and Characterization of Geminal Diazido Derivatives Based on Diethyl Malonate

Chemical Descriptors for a Large-Scale Study on Drop-Weight Impact Sensitivity of High Explosives

Review of State-of-the-Art Green Monopropellants: For Propulsion Systems Analysts and Designers

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