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Names | |
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Preferred IUPAC name Oxydi(ethane-2,1-diyl) dinitrate | |
Other names Diethyleneglycol dinitrate Diethyl glycol dinitrate Oxydiethylene dinitrate DEGDN | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.010.679 |
PubChem CID | |
UNII | |
UN number | 0075 |
CompTox Dashboard (EPA) | |
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Properties | |
C4H8N2O7 | |
Molar mass | 196.115 g·mol−1 |
Appearance | Colorless oily liquid |
Odor | Odorless |
Density | 1.4092 g/mL (0 °C) 1.3846 g/mL (20 °C) |
Melting point | −11.5 °C (11.3 °F; 261.6 K) |
Boiling point | 197 °C (387 °F; 470 K) (decomposes) |
4.1 g/L (24 °C) | |
Solubility | Soluble in methanol, acetic acid |
Vapor pressure | 0.007 mmHg (22.4 °C) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite or detonate. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized.
Diethylene glycol dinitrate can be made by nitration of diethylene glycol with nitric acid in presence of a dehydrating agent like concentrated sulfuric acid.
DEGDN can be mixed with nitrocellulose or nitroglycol to form a colloid, which is used in smokeless powder for artillery and rocket propellant. During World War II, the Kriegsmarine frequently used this mixture in their artillery. [1] It has also found use as desensitizing plasticizer because it contributes to the power of the mixture while stabilizing the explosives.
If ingested, like nitroglycerine, it rapidly causes vasodilation through the release of nitric oxide, a physiological signaling molecule that relaxes smooth muscle.[ clarification needed ] Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve angina, which is substernal chest pain associated with impaired cardiac circulation.[ citation needed ] The rationale is that the concurrent headache it induces is somewhat less severe than other nitro compounds.
At present, interest in the chemical seems to be mostly historical: more potent perchlorate–metal mixtures have long since supplanted it as a solid propellant; safer explosives have replaced nitroglycerine, true dynamites (the term is often used generically, even by experienced field technicians, to refer to almost any explosive supplied in small, discrete packages) retaining only a few specialist uses. The medical application was never widespread, the standard nitroglycerine being faster acting and very inexpensive; oral nitrates in any case being only palliative, not an effective treatment.
Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate are being considered as replacements for nitroglycerin in propellants. [2]
RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is a white solid without smell or taste, 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 trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, 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. Invented in 1847 by Ascanio Sobrero, nitroglycerin has been used ever since as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by militaries as an active ingredient and gelatinizer for nitrocellulose in some solid propellants such as cordite and ballistite. It is a major component in double-based smokeless propellants used by reloaders. Combined with nitrocellulose, hundreds of powder combinations are used by rifle, pistol, and shotgun reloaders.
Trinitrotoluene, more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.
Pentaerythritol tetranitrate (PETN), also known as PENT, 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.
Nitrocellulose is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and sulfuric acid. One of its first major uses was as guncotton, a replacement for gunpowder as propellant in firearms. It was also used to replace gunpowder as a low-order explosive in mining and other applications. In the form of collodion it was also a critical component in an early photographic emulsion, the use of which revolutionized photography in the 1860s.
Monopropellants are propellants consisting of chemicals that release energy through exothermic chemical decomposition. The molecular bond energy of the monopropellant is released usually through use of a catalyst. This can be contrasted with bipropellants that release energy through the chemical reaction between an oxidizer and a fuel. While stable under defined storage conditions, monopropellants decompose very rapidly under certain other conditions to produce a large volume of its own energetic (hot) gases for the performance of mechanical work. Although solid deflagrants such as nitrocellulose, the most commonly used propellant in firearms, could be thought of as monopropellants, the term is usually reserved for liquids in engineering literature.
Dinitrogen tetroxide, commonly referred to as nitrogen tetroxide (NTO), and occasionally (usually among ex-USSR/Russia rocket engineers) as amyl, is the chemical compound N2O4. It is a useful reagent in chemical synthesis. It forms an equilibrium mixture with nitrogen dioxide. Its molar mass is 92.011 g/mol.
Smokeless powder is a type of propellant used in firearms and artillery that produces less smoke and less fouling when fired compared to gunpowder. The combustion products are mainly gaseous, compared to around 55% solid products for black powder. In addition, smokeless powder does not leave the thick, heavy fouling of hygroscopic material associated with black powder that causes rusting of the barrel. Despite its name, smokeless powder is not completely free of smoke; while there may be little noticeable smoke from small-arms ammunition, smoke from artillery fire can be substantial.
Otto fuel II is a monopropellant used to drive torpedoes and other weapon systems. It is not related to the Otto cycle. Otto fuel II was developed by US Navy in the 1960s for use as fuel in torpedoes. Otto fuel II was invented by Otto Reitlinger in 1963 ; it is named after Reitlinger and for being the second iteration of the fuel. The first torpedo to use it was the Mark 48 torpedo in the 1960s.
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.
Methyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3. It is a colourless explosive volatile liquid.
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.
Propylene glycol dinitrate (PGDN, ttup 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrate group. It is a characteristically and unpleasantly smelling colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive and burns with a clean flame producing water vapor, carbon monoxide, and nitrogen gas.
2-Nitrodiphenylamine, also called NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-o-nitroaniline, is an organic chemical, a nitrated aromatic amine, a derivate of diphenylamine. Its chemical formula is C12H10N2O2, or C6H5NHC6H4NO2. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic.
A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic chemical reactions. Pyrotechnic substances do not rely on oxygen from external sources to sustain the reaction.
Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid.
Trimethylolethane trinitrate (TMETN), also known as metriol trinitrate or nitropentaglycerin, is a nitrate ester. It is a high explosive similar to nitroglycerin. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some solid propellants and smokeless powders as a plasticizer. Its chemical formula is CH3−C(CH2−O−NO2)3.
Triethylene glycol dinitrate (TEGDN) is a nitrated alcohol ester of triethylene glycol. It is used as an energetic plasticizer in explosives and propellants. Its chemical formula is O2N-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-NO2. It is a pale yellow oily liquid. It is somewhat similar to nitroglycerin.
Bulk loaded liquid propellants are an artillery technology that was pursued at the U.S. Army Research Laboratory and U.S. Naval Weapons Center from the 1950s through the 1990s. The advantages would be simpler guns and a wider range of tactical and logistic options. Better accuracy and tactical flexibility would theoretically come from standard shells with varying propellant loads, and logistic simplification by eliminating varying powder loads.