Explosive Properties of Erythritol Tetranitrate

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The physical and explosive properties of erythritol tetranitrate (ETN) are described herein. Although the chemical structure of ETN is simple and its preparation is undemanding, this explosive is only briefly described in the literature. Nowadays, it is widely prepared by amateur chemists and by criminals as well. Therefore, it is necessary to describe its physical and explosive properties for pre-explosion and post-explosion forensic analyses. However, as a nitric acid ester, it can also be potentially useful for some industrial applications. ETN was prepared in 83 % yield by the reaction of nitric acid/sulfuric acid with erythritol. The molecular structure of ETN was characterized by single-crystal X-ray diffraction. The structure of the ETN molecule is composed of a central carbohydrate chain and two pairs of facing coplanar ONO2 groups. The crystal density of ETN is 1.827 g cm−3. It is a non-hygroscopic compound, which is slightly soluble in water (the solubility in water was determined in a temperature range from 5 °C to 80 °C; the solubility at 20 °C is similar to that of PETN). The sensitivity of melt cast ETN to friction significantly differs from powdered ETN. Melt cast ETN is more sensitive to friction than PETN, whereas powdered ETN is less sensitive than RDX. The sensitivity of powdered ETN to impact is slightly lower than for melt cast ETN that is on the level of PETN. The detonation velocity of melt cast ETN is 7940 m s−1 at a density of 1.69 g cm−3, which is slightly below the PETN level. The relative explosive strength was measured using the ballistic mortar method and value of 143 % TNT was found, which is similar to that of PETN (145 % TNT is reported in the literature). Additionally, the relative brisance was determined using the Hess test.

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... The basic analytical data, physical and explosive properties of ETN were published by Oxley et al. [9] the other properties of ETN are under reviewing process [10]. The blast wave parameters of ETN were not published yet. ...
... Product was purified by recrystallization. The details of this procedure are described are described in [9,10]. ...
Conference Paper
The knowledge of blast wave parameters of detonating explosive is important for evaluation of protective measures, modeling and post blast analysis. The relevant data are quite common for military explosives, but much less common for the improvised ones. In this contribution we present experimental blast wave parameters of small scale bare charges of erythritol tetranitrate (low density charges were powdered and taped – d = 0.80, high density charges were cast – d = 1.70, their comparison to small scale charges of TNT and calculation of TNT equivalency based on maximum overpressure and impulse of positive phase of the blast wave. The maximum incident overpressure and incident impulse of the positive phase were not influenced by the density of the charges. Average TNT equivalency from incident overpressures was 160%, and from the impulse of the positive phase of the blast wave was 171%.
Encapsulation is proposed as a safer way of handling energetic materials. Different encapsulation methods for explosives, such as solvent evaporation, spray coating and supercritical carbon dioxide assisted encapsulation, were explored. Explosive training aids, where energetic materials, such as triacetone triperoxide (TATP), erythritol tetranitrate (ETN) and trinitrotoluene (TNT), are encapsulated in a polymer matrix were developed, followed by comprehensive quality control testing, including differential scanning calorimetry (DSC), thermogravimetric analysis-infrared spectroscopy (TGA-IR), gas chromatography-mass spectrometry (GC-MS), high-resolution mass spectrometry (HRMS) and sensitivity testing, and finally field approved by canine units trained on the pure explosive.
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Publisher Summary X-ray data can be collected with zero-, one-, and two-dimensional detectors, zero-dimensional (single counter) being the simplest and two-dimensional the most efficient in terms of measuring diffracted X-rays in all directions. To analyze the single-crystal diffraction data collected with these detectors, several computer programs have been developed. Two-dimensional detectors and related software are now predominantly used to measure and integrate diffraction from single crystals of biological macromolecules. Macromolecular crystallography is an iterative process. To monitor the progress, the HKL package provides two tools: (1) statistics, both weighted (χ 2 ) and unweighted (R-merge), where the Bayesian reasoning and multicomponent error model helps obtain proper error estimates and (2) visualization of the process, which helps an operator to confirm that the process of data reduction, including the resulting statistics, is correct and allows the evaluation of the problems for which there are no good statistical criteria. Visualization also provides confidence that the point of diminishing returns in data collection and reduction has been reached. At that point, the effort should be directed to solving the structure. The methods presented in the chapter have been applied to solve a large variety of problems, from inorganic molecules with 5 A unit cell to rotavirus of 700 A diameters crystallized in 700 × 1000 × 1400 A cell.
This monograph contains 25 chapters on the chemistry and production of explosive chemicals. Topics presented include explosives properties, detonation, sensitivity, high temperature effects, and strength; nitration and nitrating agents; nitration of aromatic systems; structures and physico-chemical properties of nitro compounds; reactivity of aromatic nitro compounds; photochemistry of nitro compounds; nitro derivatives of benzene, toluene, and other aromatics; heat resistant explosives; aliphatic nitro compounds; esters; difluoroamino compounds; production of nitrate esters; carbohydrates nitrates; N-nitro compounds; explosive polymers; recovery of spent acids; salts of nitric acid and of oxy-acids of chlorine; primary explosives: initiators, initiating explosives; black powder (gunpowder); commercial and mining explosives; manufacture of commercial and mixing explosives; liquid explosives; smokeless powder; composite propellants; safety in the manufacture and handling of explosives; and toxicity of explosives. Refs.
This paper focuses on ammonium nitrate based explosives sensitized with erythritol tetranitrate. Erythritol tetranitrate (ETN) is an ester of nitric acid and erythritol. It is a low melting crystalline solid with explosive properties similar to those of pentaerythritol tetranitrate. Experiments were conducted in order to determine any sensitizing effect this compound might have on three basic types of ammonium nitrate based mixtures – powdered, slurry and emulsion explosives. According to the results obtained, erythritol tetranitrate acts as a sensitizer giving detonator sensitivity to ammonium nitrate based explosives when incorporated therein in quantities from 10 to 20 percent.
4,6-Diazido-N-nitro-1,3,5-triazine-2-amine (DANT) was prepared with a 35 % yield from cyanuric chloride in a three step process. DANT was characterized by IR and NMR spectroscopy (1H, 13C, 15N), single-crystal X-ray diffraction, and DTA. The crystal density of DANT is 1.849 g cm−3. The cyclization of one azido group and one nitrogen atom of the triazine group giving tetrazole was observed for DANT in a dimethyl sulfoxide solution using NMR spectroscopy. An equilibrium exists between the original DANT molecule and its cyclic form at a ratio of 7 : 3. The sensitivity of DANT to impact is between that for PETN and RDX, sensitivity to friction is between that for lead azide and PETN, and sensitivity to electric discharge is about the same as for PETN. DANT′s heat of combustion is 2060 kJ mol−1.
Thermal behaviors, vapor pressures, densities, and drop weight impact results, as well as analytical protocols, are reported for three tetranitrate esters: erythritol tetranitrate (ETN), 1,4-dinitrato-2,3-dinitro-2,3bis(nitratomethylene) butane (DNTN), and pentaerythritol tetranitrate (PETN). ETN and DNTN both melt below 100 °C and have ambient vapor pressures comparable to TNT. While LC/MS was shown to be a viable technique for analysis of all three tetranitrate esters, only ETN was successfully analyzed by GC/MS. Performance of these nitrate esters as evaluated in lab using the small-scale explosivity device (SSED) suggested RDX≫DNTN>PETN>ETN. Detonation velocities were calculated using Cheetah 6.0. Since the starting material is now widely available, it is likely that law enforcement will find ETN in future improvised explosive devices. This paper with its analytical schemes should prove useful in identification of this homemade explosive.
Pattern decomposition programs are able to derive, from the measured powder diffraction patterns, estimates of the square moduli of the structure factors. A method is described that, by statistical analysis of the normalized structure-factor moduli, is able to obtain information about the possible presence of preferred orientation. Cylindrical symmetry of the specimen is necessary. The method proves to be efficient and quite useful for the application of direct methods to powder data.
Erythritol tetranitrate (butane-1,2,3,4-tetrayl tetranitrate, ETN) has become one of the most synthesized improvised explosives nowadays as it can be found on public internet discussion boards. However the low melting point, nitrocellulose gelling ability, high energy content and easy availability of precursor make the substance potentially useful in industry as an energetic component or additive in certain gun propellants. Mixtures of ETN with other high explosives are also frequently discussed on web pages deals with improvised explosives. This article deals with thermal behavior and decomposition kinetics of pure ETN and its mixtures with pentaerythritol tetranitrate (PETN) and hexogen (1,3,5-trinitro-1,3,5-triazinane, RDX). The thermal behavior and decomposition kinetics of such mixtures are described using nonisothermal DSC and TG techniques. Kissinger method, Soviet manometric method and modified Kissinger-Akahira-Sunose method were used for data evaluation.
This volume contains entries for U through Z; Errata; and Index for Encyclopedia Volumes 1 through 10.
Erythritol, a four-carbon polyol, is a biological sweetener with applications in food and pharmaceutical industries. It is also used as a functional sugar substitute in special foods for people with diabetes and obesity because of its unique nutritional properties. Erythritol is produced by microbial methods using mostly osmophilic yeasts and has been produced commercially using mutant strains of Aureobasidium sp. and Pseudozyma tsukubaensis. Due to the high yield and productivity in the industrial scale of production, erythritol serves as an inexpensive starting material for the production of other sugars. This review focuses on the approaches for the efficient erythritol production, strategies used to enhance erythritol productivity in microbes, and the potential biotechnological applications of erythritol.
Nitrate esters have been known as useful energetic materials since the discovery of nitroglycerin by Ascanio Sobrero in 1846. The development of methods to increase the safety and utility of nitroglycerin by Alfred Nobel led to the revolutionary improvement in the utility of nitroglycerin in explosive applications in the form of dynamite. Since then, many nitrate esters have been prepared and incorporated into military applications such as double-based propellants, detonators and as energetic plasticizers. Nitrate esters have also been shown to have vasodilatory effects in humans and thus have been studied and used for treatments of ailments such as angina. The mechanism of the biological response towards nitrate esters has been elucidated recently. Interestingly, many of the nitrate esters used for military purposes are liquids (ethylene glycol dinitrate, propylene glycol dinitrate, etc). Pentaerythritol tetranitrate (PETN) is one of the only solid nitrate esters, besides nitrocellulose, that is used in any application. Unfortunately, PETN melting point is above 100 {sup o}C, and thus must be pressed as a solid for detonator applications. A more practical material would be a melt-castable explosive, for potential simplification of manufacturing processes. Herein we describe the synthesis of a new energetic nitrate ester (1) that is a solid at ambient temperatures, has a melting point of 85-86 {sup o}C and has the highest density of any known nitrate ester composed only of carbon, hydrogen, nitrogen and oxygen. We also describe the chemical, thermal and sensitivity properties of 1 as well as some preliminary explosive performance data.
Chemical bonding in the pentaerythritol tetranitrate crystal based on the experimental electron density obtained from X-ray diffraction data at 100 K and theoretical calculations at the experimental molecular geometry have been analyzed in terms of the Quantum Theory of Atoms in Molecules. Features of the intra- and intermolecular bond critical points and the oxygen atom lone-pair locations are discussed. Numerous intermolecular bonding interactions, including O...H and O...O, have been found and characterized. Atomic charges and atomic energies were integrated and compared with those for similar compounds. The N-O topological bond orders have been calculated for the first time, and the PETN atomic valences have been estimated.
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