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Encyclopedia > Nitroglycerin

Nitroglycerin chemical structure
Nitroglycerin Image File history File links Download high-resolution version (1100x1043, 48 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Nitroglycerin Glyceryl trinitrate (pharmacology) ...

propane-1,2,3-triyl trinitrate
IUPAC name
Chemical formula C3H5(NO3)3
Molar mass 227.0872 g/mol
Shock sensitivity Very High
Friction sensitivity Very high
Density 1.6 g/cm³ at 15 °C
Explosive velocity 7700 m/s
RE factor 1.50
Melting point 13.2 °C (55.76 °F)
Autoignition temperature Decomposes at 50 to 60 °C (122 to 140 °F)
Appearance Clear yellow/colorless oily liquid
CAS number 55-63-0
PubChem 4510
SMILES C(C(CO[N+](=O)[O-])O
[N+](=O)[O-])O[N+](=O)[O-]

Nitroglycerin (NG), also known as nitroglycerine, trinitroglycerin, and glyceryl trinitrate, is a chemical compound. It is a heavy, colorless, oily, explosive liquid obtained by nitrating glycerol. It is used in the manufacture of explosives, specifically dynamite, and as such is employed in the construction and demolition industries, and as a plasticizer in some solid propellants. Nitroglycerin is also used medically as a vasodilator to treat heart conditions; it is a venous dilator that decreases waste production. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... BIC pen cap, about 1 gram. ... The mole (symbol: mol) is the SI base unit that measures an amount of substance. ... Shock sensitivity is a comparative measure of the sensitivity to sudden movement of a chemical compound, usually of an explosive. ... Friction Sensitivity This is an approximation of the amount of friction or rubbing a compound can withstand before prematurely exploding. ... For other uses, see Density (disambiguation). ... BIC pen cap, about 1 gram. ... A cubic centimetre (cm3) is an SI derived unit of volume, equal to the volume of a cube with side length of 1 centimetre. ... Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... djbdasjkhfohasoiflkasdfioalkjsfoijaoislkna wu9832u09q1b oai iu3y hq oi23u89q This page meets Wikipedias criteria for speedy deletion. ... Metre per second (U.S. spelling: meter per second) is an SI derived unit of both speed (scalar) and velocity (vector), defined by distance in metres divided by time in seconds. ... Relative effectiveness factor () is a measurement of an explosives power for military demolitions purposes. ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... This article does not cite any references or sources. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Nitration is a general chemical process for the introduction of a nitro group in a chemical compound by means of a chemical reaction. ... Glycerine, Glycerin redirects here. ... This article is concerned solely with chemical explosives. ... Dynamite is an explosive based on the explosive potential of nitroglycerin, initially using diatomaceous earth (kieselguhr) as an adsorbent. ... This article does not cite any references or sources. ... For other uses, see Demolition (disambiguation). ... Plasticizers are additives that soften the materials (usually a plastic or a concrete mix) they are added to. ... A propellant is a material that is used to move an object by applying a motive force. ... Glyceryl trinitrate (GTN) has been used to treat angina and heart failure since at least 1880. ... Vasodilation is where blood vessels in the body become wider following the relaxation of the smooth muscle in the vessel wall. ... The heart and lungs, from an older edition of Grays Anatomy. ...

Contents

History

Nitroglycerin was discovered by chemist Ascanio Sobrero in 1847, working under TJ Pelouze at the University of Turin. The best manufacturing process was developed by Alfred Nobel in the 1860s. His company exported a liquid combination of nitroglycerin and gunpowder as 'Swedish Blasting Oil', but it was extremely dangerous as a result of its extreme instability, as shown in numerous "appalling catastrophes," such as the explosion that destroyed a Wells Fargo office in San Francisco in 1866. The liquid was widely banned, and this led to the development of dynamite (and similar mixtures such as dualine and lithofracteur), by mixing the nitroglycerine with inert absorbents (e.g., nitrocellulose gel, blasting gelatine) (Nobel used kieselguhr.) Ascanio Sobrero (1812-1888) was an Italian chemist who discovered nitroglycerin in 1847 while working under Théophile-Jules Pelouze at the University of Torino, who had worked with the explosive material guncotton. ... 1847 was a common year starting on Friday (see link for calendar). ... Théophile-Jules Pelouze (also known as Jules Pelouze, Théophile Pelouze, Theo Pelouze, or TJ Pelouze) was a French chemist. ... The University of Turin (Italian Università degli Studi di Torino, UNITO) is the university of Turin in the Piedmont region of north-western Italy. ...   (October 21, 1833, Stockholm, Sweden—December 10, 1896, Sanremo, Italy) was a Swedish chemist, engineer, innovator, armaments manufacturer and the inventor of dynamite. ... Smokeless powder Gunpowder is a pyrotechnic composition, an explosive mixture of sulfur, charcoal and potassium nitrate that burns rapidly, producing volumes of hot gas which can be used as a propellant in firearms and fireworks. ... An older Wells Fargo branch, located in Berkeley, California Wells Fargos corporate headquarters and main branch Wells Fargo & Co. ... This page is a candidate for speedy deletion. ... Dynamite is an explosive based on the explosive potential of nitroglycerin, initially using diatomaceous earth (kieselguhr) as an adsorbent. ... For other uses, see Chemistry (disambiguation). ... Skeletal formula of nitrocellulose Ball-and-stick model of a section of nitrocellulose Nitrocellulose (also: cellulose nitrate, flash paper) is a highly flammable compound formed by nitrating cellulose through, for example, exposure to nitric acid or another powerful nitrating agent. ... Blasting gelatine is an explosive invented by Alfred Nobel. ... Diatomaceous earth (also known as diatomite, DE or kieselguhr) is a naturally occurring, light-colored, solid material that is easily crumbled into a fine dust. ...


Instability and desensitization

In its pure form, it is a contact explosive (physical shock can cause it to explode) and degrades over time to even more unstable forms. This makes it highly dangerous to transport or use. In this undiluted form it is one of the most powerful high explosives, comparable to the military explosives RDX and PETN (which are not used in munitions at full concentration because of their sensitivity) as well as the plastic explosive C-4. Contact explosives explode when energy is applied to the substance, whether that be heat, light, sound, or physical pressure. ... RDX redirects here. ... PETN (Pentaerythritol Tetranitrate, also known as Penthrite) is one of the strongest known high explosives, with a relative effectiveness factor (R.E. factor) of 1. ... A C-4 plastic explosive. ... Preparing C-4 explosive C-4 or Composition C-4 is a common variety of military plastic explosive. ...


Early in the history of this explosive it was discovered that liquid nitroglycerin can be "desensitized" by cooling to 5 to 10 °C (40 to 50 °F), at which temperature it freezes, contracting upon solidification. However, later thawing can be extremely sensitizing, especially if impurities are present or if warming is too rapid. It is possible to chemically "desensitize" nitroglycerin to a point where it can be considered approximately as "safe" as modern high explosive formulations, by the addition of approximately 10-30% ethanol, acetone, or dinitrotoluene (percentage varies with the desensitizing agent used). Desensitization requires extra effort to reconstitute the "pure" product. Failing this, it must be assumed that desensitized nitroglycerin is substantially more difficult to detonate, possibly rendering it useless as an explosive for practical application. Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... For other uses, see Fahrenheit (disambiguation). ... Preparing C-4 explosive This article is concerned solely with chemical explosives. ... Grain alcohol redirects here. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Dinitrotoluene or Dinitro C6H3(CH3)(NO2)2. ...


A serious problem in the use of nitroglycerin results from its high freezing point 13 °C (55 °F). Solid nitroglycerin is much less sensitive to shock than the liquid, a feature common in explosives; in the past it was often shipped in the frozen state, but this resulted in a high number of accidents during the thawing process by the end user just prior to use. This disadvantage is overcome by using mixtures of nitroglycerin with other polynitrates; for example, a mixture of nitroglycerin and ethylene glycol dinitrate freezes at -29 °C (-20 °F).[1] Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... For other uses, see Fahrenheit (disambiguation). ... Ethylene glycol dinitrate (EGDN) is a chemical compound an yellowish, oily explosive liquid obtained by nitrating ethylene glycol. ... Celsius is, or relates to, the Celsius temperature scale (previously known as the centigrade scale). ... For other uses, see Fahrenheit (disambiguation). ...


Detonation

Nitroglycerin and any or all of the dilutents used can certainly deflagrate or burn. However, the explosive power of nitroglycerin is derived from detonation: energy from the initial decomposition causes a pressure gradient that detonates the surrounding fuel. This can generate a self-sustained shock-wave that propagates through the fuel-rich medium at or above the speed of sound as a cascade of near-instantaneous pressure-induced decomposition of the fuel into gas. This is quite unlike deflagration, which depends solely upon available fuel, regardless of pressure or shock. A log in a fire place. ... A weapons cache is detonated at the East River Range on Bagram Airfield, Afghanistan Detonation is a process of supersonic combustion in which a shock wave is propagated forward due to energy release in a reaction zone behind it. ... This page is about the physical speed of sound waves in a medium. ...


Manufacturing

The industrial manufacturing process often uses a nearly 50:50 mixture of sulfuric acid and nitric acid. This can be produced by mixing white fuming nitric acid (quite costly pure nitric acid in which oxides of nitrogen have been removed, as opposed to red fuming nitric acid) and concentrated sulfuric acid. More often, this mixture is attained by the cheaper method of mixing fuming sulfuric acid (sulfuric acid containing excess sulfur trioxide) and azeotropic nitric acid (consisting of around 70% nitric acid, the rest being water). R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ... The chemical compound nitric acid (HNO3), also known as aqua fortis and spirit of nitre, is an aqueous solution of hydrogen nitrate (anhydrous nitric acid). ... “SO3” redirects here. ...


The sulfuric acid produces protonated nitric acid species, which are attacked by glycerin's nucleophilic oxygen atoms. The nitro group is thus added as an ester C-O-NO2 and water is produced. This is different from an aromatic nitration reaction in which nitronium ions are the active species in an electrophilic attack of the molecules ring system. In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... Nitro may refer to: Nitroglycerin, an extremely explosive chemical compound Nitrous, a type of fuel additive for race cars Nitromethane, another type of fuel additive for race cars [[GlyceryBold textl trinitrate (pharmacology)]], a medical compound used for the treatment of angina pectoris Nitrogen, especially when used in draught beer Nitrocellulose... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... The nitronium ion, NO2+, is not stable enough to exist in normal conditions, but it is used extensively in the nitration of other substances. ...


The addition of glycerin results in an exothermic reaction (i.e., heat is produced), as usual for mixed acid nitrations. However, if the mixture becomes too hot, it results in runaway, a state of accelerated nitration accompanied by the destructive oxidizing of organic materials of nitric acid and the release of very poisonous brown nitrogen dioxide gas at high risk of an explosion. Thus, the glycerin mixture is added slowly to the reaction vessel containing the mixed acid (not acid to glycerin). The nitrator is cooled with cold water or some other coolant mixture and maintained throughout the glycerin addition at about 22 °C, much below which the esterification occurs too slowly to be useful. The nitrator vessel, often constructed of iron or lead and generally stirred with compressed air, has an emergency trap door at its base, which hangs over a large pool of very cold water and into which the whole reaction mixture (called the charge) can be dumped to prevent an explosion, a process referred to as drowning. If the temperature of the charge exceeds about 10 °C (actual value varying by country) or brown fumes are seen in the nitrators vent, then it is immediately drowned. For other uses, see Chemical reaction (disambiguation). ... [1] R-phrases , S-phrases , , , , , Supplementary data page Structure and properties n, εr, etc. ...


Because of the great dangers associated with its production, most nitroglycerin production facilities are in offshore rigs or very remote locations.


Medical use

Nitroglycerin in medicine, where it is generally called glyceryl trinitrate, is used as a heart medication (under the trade names Nitrospan®, Nitrostat®, and Tridil®, amongst others). It is used as a medicine for angina pectoris (ischaemic heart disease) in tablets, ointment, solution for intravenous use, transdermal patches (Transderm Nitro®, Nitro-Dur®), or sprays administered sublingually (Nitrolingual Pump Spray®, Natispray®). The principal action of nitroglycerin is vasodilation—widening of the blood vessels. Nitroglycerin will dilate veins more than arteries, decreasing cardiac preload and leading to the following therapeutic effects during episodes of angina pectoris: Glyceryl trinitrate (GTN) has been used to treat angina and heart failure since at least 1880. ... For the chemical substances known as medicines, see medication. ... The heart and lungs, from an older edition of Grays Anatomy. ... This article does not cite any references or sources. ... Sublingual, literally under the tongue, from Latin, refers to a pharmacological route of administration in which certain drugs are entered directly into the bloodstream via absorption under the tongue. ... The blood vessels are part of the circulatory system and function to transport blood throughout the body. ... f you all The blood vessels are part of the circulatory system and function to transport blood throughout the body. ...

These effects arise because nitroglycerin is converted to nitric oxide in the body (by a mechanism that is not completely understood), and nitric oxide is a natural vasodilator. Recently, it has also become popular in an off-label use at reduced (0.2%) concentration in ointment form as an effective treatment for anal fissure. A sphygmomanometer, a device used for measuring arterial pressure. ... Orthostatic hypotension (also known as postural hypotension, orthostatic intolerance and, colloquially, as head rush or a dizzy spell) is a sudden fall in blood pressure, typically greater than 20/10 mm Hg, that occurs when a person assumes a standing position, usually after a prolonged period of rest. ... R-phrases , , , , S-phrases , , , Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Nitric oxide or Nitrogen monoxide is a chemical compound with chemical formula NO. This gas is an important signaling molecule in the body of... The term off-label refers to the use of a drug for a medical condition other than for which it was officially approved and marketed. ... An anal fissure is an unnatural crack or tear in the anus skin. ...


A recent medical development will include a small amount of nitroglycerin in the tip of a new Durex condom to stimulate erection during intercourse. "The CSD500 condom contains a chemical in its teat, called glyceryl trinitrate (GTN), which is absorbed by the skin and causes blood vessels to dilate." According to anecdotal evidence, Nitroglycerin patches have also found use as treatment for the bite of the Brown recluse spider, which has a vasoconstricting venom. However, research has suggested that nitroglycerin has negligible benefits and might even increase inflammation of the bite wound. The brand Durex is used for a number of unrelated products around the world. ... This article is about the male contraceptive device. ... Anecdotal evidence is an informal account of evidence in the form of an anecdote, or hearsay. ... Glyceryl trinitrate (GTN) has been used to treat angina and heart failure since at least 1880. ... Binomial name Gertsch & Mulaik, 1940 The brown recluse spider, Loxosceles reclusa, of the family Sicariidae (formerly of the family Loxoscelidae). ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ...


Infrequent exposure to high doses of nitroglycerin can cause severe headaches known as "NG head". These headaches can be severe enough to incapacitate some people; however, humans develop a tolerance and dependence to nitroglycerin after long-term exposure. Withdrawal can (rarely) be fatal; withdrawal symptoms include headaches and heart problems; with re-exposure to nitroglycerin, these symptoms may disappear. For workers in nitroglycerin manufacturing facilities, this can result in a "Monday Morning Headache" phenomenon for those who experience regular nitroglycerin exposure in the workplace; over the weekend they develop symptoms of withdrawal, which are then countered by reexposure on the next work day.


References

  • Nitroglycerine! Terrible Explosion and Loss of Lives in San Francisco. Central Pacific Railroad Photographic History Museum. Retrieved on 23 March, 2005. - 1866 Newspaper article
  1. ^ nitroglycerin. Britannica. Retrieved on 23 March, 2005.

External links

  • Computational Chemistry Wiki
  • The Tallini Tales of Destruction Detailed and horrific stories of the historical use of nitroglycerin-filled torpedoes to restart petroleum wells.

  Results from FactBites:
 
Nitrostat (Nitroglycerin) drug description - prescription drugs and medications at RxList (525 words)
Nitroglycerin injection is a clear, practically colorless additive solution for intravenous infusion after dilution.
Nitroglycerin sublingual tablets contain 0.15 mg (1/400 grain), 0.3 mg (1/200 grain), 0.4 mg (1/150 grain) and 0.6 (1/100 grain) nitroglycerin.
The remainder of nitroglycerin in each system serves as a reservoir and is not delivered in normal use.
RxMed: Pharmaceutical Information - NITROGLYCERIN (2154 words)
Nitroglycerin is rapidly metabolized in the liver by hepatic enzymes to dinitrates and mononitrates.
Nitroglycerin is approximately 60% protein bound while the metabolites 1,2 dinitroglycerol and 1,3 dinitroglycerol are 60 and 30% protein bound, respectively.
Nitroglycerin is excreted by the renal route, primarily as the 2 dinitrometabolites, which have an excretion half-life of approximately 3 to 4 hours.
  More results at FactBites »

 
 

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