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n8 and n9 explosive data shock sensitivity high friction sensitivity high detonation velocity 7 820 m s re factor 1 50 thermochemistry std enthalpy of formation δ f h 298 370 kj mol 1 std enthalpy of combustion δ c h 298 1 529 mj mol 1 pharmacology atc code c01da02 who c05ae01 who routes of administration intravenous by mouth under the tongue topical pharmacokinetics bioavailability 1 metabolism liver biological half life 3 min legal status au s3 pharmacist only hazards occupational safety and health ohs osh main hazards explosive toxic ghs labelling pictograms signal word danger hazard statements h202 h205 h241 h301 h311 h331 h370 precautionary statements p210 p243 p250 p260 p264 p270 p271 p280 p302 p352 p410 nfpa 704 fire diamond 3 2 4 niosh us health exposure limits pel permissible c 0 2 ppm 2 mg m 3 skin 2 except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound nitroglycerin ng alternative spelling nitroglycerine 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 a nitrate ester rather than a nitro compound but the traditional name is retained discovered in 1846 by ascanio sobrero 4 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 as is the case for many other explosives nitroglycerin becomes more and more prone to exploding i e spontaneous decomposition as the temperature is increased upon exposure to heat above 218 c at sea level atmospheric pressure nitroglycerin becomes extremely unstable and tends to explode when placed in vacuum it has an autoignition temperature of 270 c instead 5 with a melting point of 12 8 c the chemical is almost always encountered as a thick and viscous fluid changing to a crystalline solid when frozen 5 6 although the pure compound itself is colorless in practice the presence of nitric oxide impurities left over during production tends to give it a slight yellowish tint due to its high boiling point and consequently low vapor pressure 0 00026 mmhg at 20 c 5 pure nitroglycerin has practically no odor at room temperature with a sweet and burning taste when ingested unintentional detonation may ensue when dropped shaken lit on fire rapidly heated exposed to sunlight and ozone subjected to sparks and electrical discharges or roughly handled 7 its sensitivity to exploding is responsible for numerous devastating industrial accidents throughout its history the chemical s characteristic reactivity may be reduced through the addition of desensitizing agents which makes it less likely to explode clay diatomaceous earth is an example of such an agent forming dynamite a much more easily handled composition the addition of other desensitizing agents gives birth to the various formulations of dynamite nitroglycerin as a medication has been used since 1878 as a potent vasodilator causing dilation of the vascular system to treat heart conditions such as angina pectoris and chronic heart failure though it was previously known that these beneficial effects are due to nitroglycerin being converted to nitric oxide a potent vasodilator the enzyme for this conversion was only discovered to be mitochondrial aldehyde dehydrogenase aldh2 in 2002 8 nitroglycerin is available in sublingual tablets sprays ointments and patches 9 history edit alfred nobel s patent application from 1864 nitroglycerin was the first practical explosive produced that was stronger than black powder it was synthesized by the italian chemist ascanio sobrero in 1846 working under théophile jules pelouze at the university of turin 10 sobrero initially called his discovery pyroglycerin and warned vigorously against its use as an explosive 11 nitroglycerin was adopted as a commercially useful explosive by alfred nobel who experimented with safer ways to handle the dangerous compound after his younger brother emil oskar nobel and several factory workers were killed in an explosion at the nobels armaments factory in 1864 in heleneborg sweden 12 one year later nobel founded alfred nobel and company in germany and built an isolated factory in the krümmel hills of geesthacht near hamburg this business exported a liquid combination of nitroglycerin and gunpowder called blasting oil but this was extremely unstable and difficult to handle as evidenced in numerous catastrophes 13 the buildings of the krümmel factory were destroyed twice 14 in april 1866 several crates of nitroglycerin were shipped to california three of which were destined for the central pacific railroad which planned to experiment with it as a blasting explosive to expedite the construction of the 1 659 foot long 506 m summit tunnel through the sierra nevada mountains one of the remaining crates exploded destroying a wells fargo company office in san francisco and killing 15 people this led to a complete ban on the transportation of liquid nitroglycerin in california the on site manufacture of nitroglycerin was thus required for the remaining hard rock drilling and blasting required for the completion of the first transcontinental railroad in north america 15 on christmas day 1867 an attempt to dispose of nine canisters of blasting oil that had been illegally stored at the white swan inn in the centre of newcastle upon tyne resulted in an explosion on the town moor that killed eight people in june 1869 two one ton wagons loaded with nitroglycerin then known locally as powder oil exploded during transport while passing through the village of cwm y glo in north wales 16 the explosion led to the loss of six lives many injuries and much damage to the village little trace was found of the two horses the uk government was so alarmed at the damage caused and what could have happened in a city location these two tons were part of a larger load coming from germany via liverpool that they soon passed the nitro glycerine act 1869 32 33 vict c 113 16 liquid nitroglycerin was widely banned elsewhere as well and these legal restrictions led to alfred nobel and his company developing dynamite in 1867 this was made by mixing nitroglycerin with diatomaceous earth kieselguhr in german found in the krümmel hills similar mixtures such as dualine 1867 lithofracteur 1869 and gelignite 1875 were formed by mixing nitroglycerin with other inert absorbents and many combinations were tried by other companies in attempts to get around nobel s tightly held patents for dynamite dynamite mixtures containing nitrocellulose which increases the viscosity of the mix are commonly known as gelatins following the discovery that amyl nitrite helped alleviate chest pain the physician william murrell experimented with the use of nitroglycerin to alleviate angina pectoris and to reduce the blood pressure he began treating his patients with small diluted doses of nitroglycerin in 1878 and this treatment was soon adopted into widespread use after murrell published his results in the lancet in 1879 17 18 a few months before he died in 1896 alfred nobel was prescribed nitroglycerin for this heart condition writing to a friend isn t it the irony of fate that i have been prescribed nitro glycerin to be taken internally they call it trinitrin so as not to scare the chemist and the public 19 the medical establishment also used the name glyceryl trinitrate for the same reason wartime production rates edit large quantities of nitroglycerin were manufactured during world war i and world war ii for use as military propellants and in military engineering work during world war i hm factory gretna the largest propellant factory in the united kingdom produced about 800 tonnes of cordite rdb per week this amount required at least 336 tonnes of nitroglycerin per week assuming no losses in production the royal navy had its own factory at the royal navy cordite factory holton heath in dorset england a large cordite factory was also built in canada during world war i the canadian explosives limited cordite factory at nobel ontario was designed to produce 1 500 000 lb 680 t of cordite per month requiring about 286 tonnes of nitroglycerin per month instability and desensitization edit in its undiluted form nitroglycerin is a contact explosive meaning physical shock causes it to explode if it has not been adequately purified during manufacture it can degrade over time to even more unstable forms this makes nitroglycerin highly dangerous to transport or use in its undiluted form it is one of the world s most powerful explosives comparable to the more recently developed rdx and petn early in its history liquid nitroglycerin was found to be desensitized by freezing it at a temperature below 45 to 55 f 7 to 13 c depending on its purity 20 its sensitivity to shock while frozen is somewhat unpredictable it is more insensitive to the shock from a fulminate cap or a rifle ball when in that condition but on the other hand it appears to be more liable to explode on breaking crushing tamping etc 21 frozen nitroglycerin is much less energetic than liquid and so must be thawed before use 22 thawing it out can be extremely sensitizing especially if impurities are present or the warming is too rapid 23 ethylene glycol dinitrate or another polynitrate may be added to lower the melting point and thereby avoid the necessity of thawing frozen explosive 24 chemically desensitizing nitroglycerin is possible to a point where it can be considered about as safe as modern high explosives such as by the addition of ethanol acetone or dinitrotoluene 25 the nitroglycerin may have to be extracted from the desensitizer chemical to restore its effectiveness before use such as by adding water to draw off ethanol used as a desensitizer 25 detonation edit when nitroglycerin explodes the products after cooling are given by 4 c 3 h 5 n 3 o 9 12 co 2 10 h 2 o 6 n 2 o 2 the heat released can be calculated from the heats of formation using 371 kj mol for the heat of formation of condensed phase nitroglycerin 26 gives 1414 kj mol released if forming water vapor and 1524 if forming liquid water the detonation velocity of nitroglycerin is 7820 meters per second which is about 113 the speed of tnt accordingly nitroglycerin is considered to be a high brisance explosive which is to say it has excellent shattering ability the heat liberated during detonation raises the temperature of the gaseous byproducts to about 5 000 c 9 000 f 24 with a standard enthalpy of explosive decomposition of 1414 kj mol and a molecular weight of 227 0865 g mol nitroglycerin has a specific explosive energy density of 1 488 kilocalories per gram or 6 23 kj g making nitroglycerin 49 more energetic on a mass basis than the standard definitional value assigned to tnt precisely 1 kcal g manufacturing edit this article needs more citations please help improve this article by adding citations to reliable sources unsourced material may be challenged and removed find sources nitroglycerin news newspapers books scholar jstor august 2024 learn how and when to remove this message nitroglycerin synthesis 27 28 29 nitroglycerin can be produced by acid catalyzed nitration of glycerol glycerin 30 the industrial manufacturing process often reacts glycerol with a nearly 1 1 mixture of concentrated sulfuric acid and concentrated nitric acid this can be produced by mixing white fuming nitric acid a quite expensive pure nitric acid in which the oxides of nitrogen have been removed as opposed to red fuming nitric acid which contains nitrogen oxides and concentrated sulfuric acid more often this mixture is attained by the cheaper method of mixing fuming sulfuric acid also known as oleum sulfuric acid containing excess sulfur trioxide and azeotropic nitric acid consisting of about 70 nitric acid with the rest being water 31 the sulfuric acid produces protonated nitric acid species which are attacked by glycerol s nucleophilic oxygen atoms the nitro group is thus added as an ester c o no 2 and water is produced this is different from an electrophilic aromatic substitution reaction in which nitronium ions are the electrophile the addition of glycerol results in an exothermic reaction i e heat is produced as usual for mixed acid nitrations if the mixture becomes too hot it results in a runaway reaction a state of accelerated nitration accompanied by the destructive oxidation of organic materials by the hot nitric acid and the release of poisonous 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 72 f hot enough for esterification to occur at a fast rate but cold enough to avoid runaway reaction 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 30 c 86 f actual value varying by country or brown fumes are seen in the nitrator s vent then it is immediately drowned use as an explosive and a propellant edit main articles dynamite ballistite cordite smokeless powder and gelignite nitroglycerin is an oily liquid that explodes when subjected to heat shock or flame the main use of nitroglycerin by tonnage is in explosives such as dynamite and in propellants as an ingredient however its sensitivity has limited the usefulness of nitroglycerin as a military explosive less sensitive explosives such as tnt rdx and hmx have largely replaced it in munitions alfred nobel developed the use of nitroglycerin as a blasting explosive by mixing nitroglycerin with inert absorbents particularly kieselguhr or diatomaceous earth he named this explosive dynamite and patented it in 1867 32 it was supplied ready for use in the form of sticks individually wrapped in greased waterproof paper dynamite and similar explosives were widely adopted for civil engineering tasks such as in drilling highway and railroad tunnels for mining for clearing farmland of stumps in quarrying and in demolition work likewise military engineers have used dynamite for construction and demolition work nitroglycerin has been used in conjunction with hydraulic fracturing a process used to recover oil and gas f...
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