Names | |
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IUPAC name [(2R,3R)-1,3,4-Trinitrooxybutan-2-yl] nitrate | |
Other names Erythrityl tetranitrate (INN) | |
Identifiers | |
3D model (JSmol) | |
1730082 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.027.940 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H6N4O12 | |
Molar mass | 302.108 g·mol−1 |
Density | 1.7219 (±0.0025) g/cm3 |
Melting point | 61 °C (142 °F; 334 K) |
Boiling point | Decomposes at 160 °C |
0.00302 g/100 mL | |
Hazards | |
GHS labelling: | |
NFPA 704 (fire diamond) | |
Explosive data | |
Shock sensitivity | Medium (2.0 Nm) |
Friction sensitivity | Medium |
Detonation velocity | 8200 m/s |
RE factor | 1.60 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, [1] though it is thought to be slightly more sensitive to friction and impact.
Like many nitrate esters, ETN acts as a vasodilator, and was the active ingredient in the original "sustained release" tablets, made under a process patent in the early 1950s, called "nitroglyn".[ citation needed ] Ingesting ETN or prolonged skin contact can lead to absorption and what is known as a "nitro headache".
It was discovered by John Stenhouse in 1849 by nitrating erithrytol he recently discovered. [2] He described its explosive properties but suggested an incorrect formula due to atomic weights not yet being accurately determined.
Its vasodilator properties have been researched since 1895. [3]
DuPont researched the explosive after the war, getting a patent in 1928, [4] but it was never commercialized due to the difficulty of erythritol synthesis. Only in the 1990s genetically-engineered yeasts made the carbohydrate widely available.
ETN has a relatively high velocity of detonation of 8206 m/s at a density of 1.7219 (±0.0025) g/cm3. [5] It is white in color and odorless. ETN is commonly cast into mixtures with other high explosives. It is somewhat sensitive to shock and friction, so care needs to be taken while handling. ETN dissolves readily in acetone and other ketone solvents. The impact and friction sensitivity is slightly higher than the sensitivity of pentaerythritol tetranitrate (PETN). The sensitivity of melt cast and pressed ETN is comparable. Lower nitrates of erythritol, such as erythritol trinitrate, are soluble in water, so they do not contaminate most ETN samples.
Much like PETN, ETN is known for having a very long shelf life. Studies that directly observed the crystalline structure saw no signs of decomposition after four years of storage at room temperature. ETN has a melting point of 61 °C, compared to PETN which has a melting point of 141.3 °C. Recent studies of ETN decomposition suggested a unimolecular rate-limiting step in which the O−NO2 bond is cleaved and begins the decomposition sequence. [6]
ETN can and should be recrystallized, as to remove the trapped acids from synthesis. Warm ethanol or methanol is a viable solvent (close to 10 g of ETN/100 ml EtOH). ETN will precipitate as big platelets with bulk density of about 0.3 g/cm3 (fluffy material) when the ETN/ethanol solution is quickly poured into several liters of cold water. Smaller, fine crystals are produced by slow addition of water in said ETN/ethanol solution with intense mixing. Very fine crystals can be prepared by shock cooling of warm ETN/ethanol solution in a below −20 °C cooling bath. ETN can be easily hand pressed to about 1.2 g/cm3 (with a slight risk of accidental detonation).
Even small samples of ETN on the order of 20 mg can cause relatively powerful explosions verging on detonation when heated without confinement, e.g. when placed on a layer of aluminium foil and heated with flame from below.
ETN can be melt-cast in warm (about 65 °C) water. Slight decomposition is possible (often displayed by change in color from white to very light yellow). Nonetheless, no reports of runaway reactions leading to explosion have been confirmed (when melt-casting using only a bucket of warm water and recrystallized ETN). Melt-cast ETN, if cooled down slowly over a period of 10–30 minutes, has density of 1.70 g/cm3, detonation velocity of 8040 m/s, and Pcj detonation pressure of about 300 kbar. Its brisance is far higher than that of Semtex (about 220 kbar, depending on brand) [5] [7] [8] Mixtures of melt-cast ETN with PETN (about 50:50% by weight) are about the most brisant explosives that can be produced by moderately equipped amateurs. These mixtures have Pcj slightly above 300 kbar and detonation velocity above 8 km/s. This is close to the maximum of fielded military explosives like LX-10 or EDC-29 (about 370 kbar and close to 9 km/s). [9]
ETN is often plasticized using PIB/synthethic oil binders (very comparable to the binder system in C4) or using liquid nitric esters. The PIB-based plastic explosives are nontoxic and completely comparable to C4 or Semtex with Pcj of 200–250 kbar, depending on density (influenced by crystal size, binder amount, and amount of final rolling). EGDN/ETN/NC systems are toxic to touch, quite sensitive to friction and impact, but generally slightly more powerful than C4 (Pcj of about 250 kbar and Edet of 5.3 MJ/kg) and more powerful than Semtex (Pcj of about 220 kbar and Edet below 5 MJ/kg) with Pcj of about 250–270 kbar and Edet of about 6 MJ/kg.[ citation needed ] Note that different explosive software[ clarification needed ] and different experimental tests will yield absolute detonation pressures that can vary by 5% or more with the relative proportions being maintained.
Melt-cast ETN gives invalid results in the Hess test, i.e. the deformation is greater than 26 mm, with the lead cylinder being completely destroyed. Semtex 1A gives only 21 mm in the same test, i.e. melt-cast ETN is at least 20% more brisant than Semtex 1A. [10]
Melt-cast ETN or high density/low inert content ETN plastic explosives are one of the materials on "watch-lists" for terrorism.
One quality this explosive has, that PETN does not, is a positive oxygen balance, which means that ETN possesses more than enough oxygen in its structure to fully oxidize all of its carbon and hydrogen upon detonation. This can be seen in the schematic chemical equation below.
Whereas PETN decomposes to:
The carbon monoxide (CO) still requires oxygen to complete oxidation to carbon dioxide (CO2). A detailed study of the decomposition chemistry of ETN has been recently elucidated. [6]
Thus, for every two moles of ETN that decompose, one free mole of O2 is released. This oxygen could be used to oxidize an added metal dust, or an oxygen-deficient explosive, such as TNT or PETN. A chemical equation of how the oxygen from ETN with oxidizes PETN is shown below. The extra oxygen from the ETN oxidizes the carbon monoxide (CO) to carbon dioxide (CO2).
Like other nitrated polyols, ETN is made by nitrating erythritol either through the mixing of concentrated sulfuric acid and a nitrate salt, or by using a mixture of sulfuric and nitric acid.
RDX (abbreviation of "Research Department eXplosive" or Royal Demolition eXplosive) or hexogen, among other names, is an organic compound with the formula (CH2N2O2)3. It is white, odorless, and tasteless, widely used as an explosive. Chemically, it is classified as a nitroamine alongside HMX, which is a more energetic explosive than TNT. It was used widely in World War II and remains common in military applications.
An explosive is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An explosive charge is a measured quantity of explosive material, which may either be composed solely of one ingredient or be a mixture containing at least two substances.
Nitroglycerin (NG), also known as trinitroglycerol (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless or pale yellow, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Discovered in 1846 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, used as a propellant in artillery and firearms since the 1880s.
Nitric acid is an inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.
Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA, TEN, corpent, or penthrite, is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex.
Ammonium nitrate is a chemical compound with the formula NH4NO3. It is a white crystalline salt consisting of ions of ammonium and nitrate. It is highly soluble in water and hygroscopic as a solid, although it does not form hydrates. It is predominantly used in agriculture as a high-nitrogen fertilizer.
ANFO ( AN-foh) (or AN/FO, for ammonium nitrate/fuel oil) is a widely used bulk industrial high explosive. It consists of 94% porous prilled ammonium nitrate (NH4NO3) (AN), which acts as the oxidizing agent and absorbent for the fuel, and 6% number 2 fuel oil (FO). The use of ANFO originated in the 1950s.
Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula CH
3NO
2. It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent. As an intermediate in organic synthesis, it is used widely in the manufacture of pesticides, explosives, fibers, and coatings. Nitromethane is used as a fuel additive in various motorsports and hobbies, e.g. Top Fuel drag racing and miniature internal combustion engines in radio control, control line and free flight model aircraft.
A triggering sequence, also called an explosive train or a firing train, is a sequence of events that culminates in the detonation of explosives. For safety reasons, most widely used high explosives are difficult to detonate. A primary explosive of higher sensitivity is used to trigger a uniform and predictable detonation of the main body of the explosive. Although the primary explosive itself is generally a more sensitive and expensive compound, it is only used in small quantities and in relatively safely packaged forms. By design there are low explosives and high explosives made such that the low explosives are highly sensitive and high explosives are comparatively insensitive. This not only affords inherent safety to the usage of explosives during handling and transport, but also necessitates an explosive triggering sequence or explosive train. The explosive triggering sequence or the explosive train essentially consists of an 'initiator', an 'intermediary' and the 'high explosive'.
An entropic explosion is an explosion in which the reactants undergo a large change in volume without releasing a large amount of heat. The chemical decomposition of triacetone triperoxide (TATP) may be an example of an entropic explosion. It is not a thermochemically highly favored event because little energy is generated in chemical bond formation in reaction products, but rather involves an entropy burst, which is the result of formation of one ozone and three acetone gas phase molecules from every molecule of TATP in the solid state.
Mannitol hexanitrate is a powerful explosive. Physically, it is a powdery solid at normal temperature ranges, with density of 1.73 g/cm3. The chemical name is hexanitromannitol and it is also known as nitromannite, MHN, and nitromannitol, and by the trademarks Nitranitol and Mannitrin. It is more stable than nitroglycerin, and it is used in detonators.
Ethylene glycol dinitrate, abbreviated EGDN and NGC, also known as Nitroglycol, is a colorless, oily, explosive liquid obtained by nitrating ethylene glycol. It is similar to nitroglycerine in both manufacture and properties, though it is more volatile and less viscous. Unlike nitroglycerine, the chemical has a perfect oxygen balance, meaning that its ideal exothermic decomposition would completely convert it to low energy carbon dioxide, water, and nitrogen gas, with no excess unreacted substances, without needing to react with anything else.
Rocket candy, or R-Candy, is a type of rocket propellant for model rockets made with a form of sugar as a fuel, and containing an oxidizer. The propellant can be divided into three groups of components: the fuel, the oxidizer, and the (optional) additive(s). In the past, sucrose was most commonly used as fuel. Modern formulations most commonly use sorbitol for its ease of production. The most common oxidizer is potassium nitrate (KNO3). Potassium nitrate is most commonly found in tree stump remover. Additives can be many different substances, and either act as catalysts or enhance the aesthetics of the liftoff or flight. A traditional sugar propellant formulation is typically prepared in a 65:35 (13:7) oxidizer to fuel ratio. This ratio can vary from fuel to fuel based on the rate of burn, timing and use.
Pentolite is a composite high explosive used for military and civilian purposes, e.g., warheads and booster charges. It is made of pentaerythritol tetranitrate (PETN) phlegmatized with trinitrotoluene (TNT) by melt casting.
Xylitol pentanitrate (XPN) is a nitrated ester primary explosive first synthesized in 1891 by Gabriel Bertrand. Law enforcement has taken an interest in XPN along with erythritol tetranitrate (ETN) and pentaerythritol tetranitrate (PETN) due to their ease of synthesis, which makes them accessible to amateur chemists and terrorists.
Explosive materials are produced in numerous physical forms for their use in mining, engineering, or military applications. The different physical forms and fabrication methods are grouped together in several use forms of explosives.
Tetranitratoxycarbon, systematic name tetra(nitrato-O,O,O-methyl)methane, is a hypothetical molecule that was proposed by Clara Lazen, a fifth-grader in Kansas City, Missouri, who conceived of its structure and built a model in 2012. She is credited as co-author of a scientific paper on the molecule, which uses computational chemistry to predict that the molecule could actually exist.
In organic chemistry, a nitrate ester is an organic functional group with the formula R−ONO2, where R stands for any organyl group. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a nitro compound, despite its name.
Nickel hydrazine nitrate (NHN), (chemical formula: [Ni(N2H4)3](NO3)2 is an energetic material having explosive properties in between that of primary explosive and a secondary explosive. It is a salt of a coordination compound of nickel with a reaction equation of 3N2H4·H2O + Ni(NO3)2 →〔Ni(N2H4)3〕(NO3)2 + 3H2O
Guanylurea dinitramide is a novel insensitive high explosive.