Names | |||
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IUPAC name Methyl nitrate | |||
Other names nitric acid methyl ester, nitrooxymethane | |||
Identifiers | |||
3D model (JSmol) | |||
ChemSpider | |||
ECHA InfoCard | 100.009.039 | ||
PubChem CID | |||
UNII | |||
CompTox Dashboard (EPA) | |||
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Properties | |||
CH3NO3 | |||
Molar mass | 77.04 g/mol | ||
Appearance | Liquid | ||
Density | 1.203 g/cm3, liquid | ||
Melting point | −82.3 °C (−116.1 °F; 190.8 K) [1] | ||
Boiling point | 64.6 °C (148.3 °F; 337.8 K) (explodes) [1] | ||
Explosive data | |||
Shock sensitivity | High [2] | ||
Friction sensitivity | High [2] | ||
Detonation velocity | 6300 m s−1 at ρ=1.217 g cm−3 [2] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Toxic, High Explosive | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Methyl nitrate is the methyl ester of nitric acid and has the chemical formula CH3NO3. It is a colourless explosive volatile liquid.
It can be produced by the condensation of nitric acid and methanol: [3]
A newer method uses methyl iodide and silver nitrate: [4]
Methyl nitrate can be produced on a laboratory or industrial scale either through the distillation of a mixture of methanol and nitric acid, or by the nitration of methanol by a mixture of sulfuric and nitric acids. The first procedure is not preferred due to the great explosion danger presented by the methyl nitrate vapour. The second procedure is essentially identical to that of making nitroglycerin. However, the process is usually run at a slightly higher temperature and the mixture is stirred mechanically on an industrial scale instead of with compressed air.
Methyl nitrate is a sensitive explosive. When ignited it burns extremely fiercely with a gray-blue flame. Methyl nitrate is a very strong explosive, like nitroglycerin, ethylene glycol dinitrate, and other nitrate esters. The sensitivity of methyl nitrate to initiation by detonation is among the greatest known, with even a number one blasting cap, the lowest power available, producing a near full detonation of the explosive.[ citation needed ]
Despite the superior explosive properties of methyl nitrate, it has not received application as an explosive due mostly to its high volatility, which prevents it from being stored or handled safely.
As well as being an explosive, methyl nitrate is toxic and causes headaches when inhaled.
Methyl nitrate has not received much attention as an explosive, but as a mixture containing 25% methanol it was used as rocket fuel and volumetric explosive under the name Myrol in Nazi Germany during World War II. This mixture would evaporate at a constant rate and so its composition would not change over time. It presents a slight explosive danger (it is somewhat difficult to detonate) and does not detonate easily via shock. [5] [6]
According to A. Stettbacher, the substance was used as a combustible during the Reichstag fire in 1933. [7] Gartz shows in a recent work that only methyl nitrate with its production and explosion potential can represent the famous and mysterious "shooting water" from the German Feuerwerkbuch ("fireworks book") of about 1420 [8] (the oldest technical text in German language, handwritten in Dresden and later printed in Augsburg). [9]
An extract of the text from the 1420 Feuerwerkbuch is as follows (written in Early New High German):
"Wildu mit wasser schyessen // daß du kein pulfer prauch // est vnd sterker und waiter // mit schewst dann als du daß aller // pest pulfer hast das yemann gehab // en mag und ye gemacht wurd so ny // salpeter und distillier den mit wasser // vnd nym oleo benedicto dazu auch … // … vnd zunt sie an mit sinnen das du davon kommen magst … // …mit disem wasser schewst du dreytousent schrit weit … // … es ist gar köstlich…"
Translated:
"Do you want to shoot with water // so that you don't need powder // and stronger and further // you shoot than the very // best powder somebody might have had ever // and was made ever // so take salpetre and distill it with water // and also take oleo benedicto (the oil of Benedicus) // and ignite it with the intention that you may get off ... with this water you will shoot threethousand foot // it is so delicious"
The structure of methyl nitrate has been studied experimentally in the gas phase (combined gas-electron diffraction and microwave spectroscopy, GED/MW) and in the crystalline state (X-ray diffraction, XRD) (see Table 1). [4]
In the solid state there are weak interactions between the O and N atoms of different molecules (see figure).
Parameter | ||
XRD | GED/MW | |
C–O | 1.451(1) | 1.425(3) |
N–OC | 1.388(1) | 1.403(2) |
N–Oterminal | 1.204(1) | 1.205(1) |
C–O–N | 113.3(1) | 113.6(3) |
Oterminal-N-Oterminal | 128.6(1) | 131.4(4) |
RDX (abbreviation of "Research Department 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.
Dynamite is an explosive made of nitroglycerin, sorbents, and stabilizers. It was invented by the Swedish chemist and engineer Alfred Nobel in Geesthacht, Northern Germany, and was patented in 1867. It rapidly gained wide-scale use as a more robust alternative to the traditional black powder explosives. It allows the use of nitroglycerine's favorable explosive properties while greatly reducing its risk of accidental detonation.
In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.
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. Discovered in 1847 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, which has been used as a propellant in artillery and firearms since the 1880s.
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, 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 and C4.
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.
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.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.
Smokeless powder, also referred to as gunpowder, is a type of propellant used in firearms and artillery that produces less smoke and less fouling when fired compared to black powder. 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.
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.
Nital is a solution of nitric acid and alcohol commonly used for etching of metals. It is especially suitable for revealing the microstructure of carbon steels. The alcohol can be methanol or ethanol.
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.
Tovex is a water-gel explosive composed of ammonium nitrate and methylammonium nitrate that has several advantages over traditional dynamite, including lower toxicity and safer manufacture, transport, and storage. It has thus almost entirely replaced dynamite. There are numerous versions ranging from shearing charges to aluminized common blasting agents. Tovex is used by 80% of international oil companies for seismic exploration.
Erythritol tetranitrate (ETN) is an explosive compound chemically similar to PETN, though it is thought to be slightly more sensitive to friction and impact.
Methylammonium nitrate is an explosive chemical with the molecular formula CH6N2O3, alternately CH3NH3+NO3−. It is the salt formed by the neutralization of methylamine with nitric acid. This substance is also known as methylamine nitrate and monomethylamine nitrate, not to be confused with methyl nitramine or monomethyl nitramine.
Methyl chloroformate is a chemical compound with the chemical formula Cl−C(=O)−O−CH3. It is the methyl ester of chloroformic acid. It is an oily colorless liquid, although aged samples appear yellow. It is also known for its pungent odor.
Trinitroanisole is a chemical compound that exists as pale yellow crystals with a melting point of 68 °C. It is highly toxic. It is an explosive with a detonation velocity of 7200 meters per second. The compound's primary hazard is a blast of an instantaneous explosion, not flying projectiles or fragments.
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.
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