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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 from shale formations the technique involves displacing and detonating nitroglycerin in natural or hydraulically induced fracture systems or displacing and detonating nitroglycerin in hydraulically induced fractures followed by wellbore shots using pelletized tnt 33 nitroglycerin has an advantage over some other high explosives in that on detonation it produces practically no visible smoke therefore it is useful as an ingredient in the formulation of various kinds of smokeless powder 34 alfred nobel then developed ballistite by combining nitroglycerin and guncotton he patented it in 1887 ballistite was adopted by several european governments as a military propellant italy was the first to adopt it the british government and the commonwealth governments adopted cordite instead which had been developed by sir frederick abel and sir james dewar of the united kingdom in 1889 the original cordite mk i consisted of 58 nitroglycerin 37 guncotton and 5 0 petroleum jelly ballistite and cordite were both manufactured in the form of cords smokeless powders were originally developed using nitrocellulose as the sole explosive ingredient therefore they were known as single base propellants a range of smokeless powders that contain both nitrocellulose and nitroglycerin known as double base propellants was also developed smokeless powders were originally supplied only for military use but they were also soon developed for civilian use and were quickly adopted for sports some are known as sporting powders triple base propellants contain nitrocellulose nitroglycerin and nitroguanidine but are reserved mainly for extremely high caliber ammunition rounds such as those used in tank cannons and naval artillery blasting gelatin also known as gelignite was invented by nobel in 1875 using nitroglycerin wood pulp and sodium or potassium nitrate this was an early low cost flexible explosive medical use edit main article medical use of nitroglycerin nitroglycerin in three different forms intravenous sublingual spray and the nitroglycerin patch nitroglycerin belongs to a group of drugs called nitrates which includes many other nitrates like isosorbide dinitrate isordil and isosorbide mononitrate imdur ismo monoket 35 these agents all exert their effect by being converted to nitric oxide in the body by mitochondrial aldehyde dehydrogenase aldh2 8 and nitric oxide is a potent natural vasodilator in medicine nitroglycerin is probably most commonly prescribed for angina pectoris a painful symptom of ischemic heart disease caused by inadequate flow of blood and oxygen to the heart and as a potent antihypertensive agent nitroglycerin corrects the imbalance between the flow of oxygen and blood to the heart and the heart s energy demand 35 there are many formulations on the market at different doses at low doses nitroglycerin dilates veins more than arteries thereby reducing preload volume of blood in the heart after filling this is thought to be its primary mechanism of action by decreasing preload the heart has less blood to pump which decreases oxygen requirement since the heart does not have to work as hard additionally having a smaller preload reduces the ventricular transmural pressure pressure exerted on the walls of the heart which decreases the compression of heart arteries to allow more blood to flow through the heart at higher doses it also dilates arteries thereby reducing afterload decreasing the pressure against which the heart must pump 35 an improved ratio of myocardial oxygen demand to supply leads to the following therapeutic effects during episodes of angina pectoris subsiding of chest pain decrease of blood pressure increase of heart rate and orthostatic hypotension patients experiencing angina when doing certain physical activities can often prevent symptoms by taking nitroglycerin 5 to 10 minutes before the activity overdoses may generate methemoglobinemia 36 37 nitroglycerin is available in tablets ointment solution for intravenous use transdermal patches or sprays administered sublingually some forms of nitroglycerin last much longer in the body than others nitroglycerin as well as the onset and duration of action of each form is different the sublingual or tablet spray of nitroglycerin has a two minute onset and a twenty five minute duration of action the oral formulation of nitroglycerin has a thirty five minute onset and a duration of action of 4 8 hours the transdermal patch has an onset of thirty minutes and a duration of action of ten to twelve hours continuous exposure to nitrates has been shown to cause the body to stop responding normally to this medicine experts recommend that the patches be removed at night allowing the body a few hours to restore its responsiveness to nitrates shorter acting preparations of nitroglycerin can be used several times a day with less risk of developing tolerance 38 nitroglycerin was first used by william murrell to treat angina attacks in 1878 with the discovery published that same year 18 39 industrial exposure edit infrequent exposure to high doses of nitroglycerin can cause severe headaches known as ng head or bang head these headaches can be severe enough to incapacitate some people however humans develop a tolerance to and dependence on nitroglycerin after long term exposure although rare withdrawal can be fatal 40 symptoms include chest pain and other heart problems these symptoms may be relieved with re exposure to nitroglycerin or other suitable organic nitrates 41 for workers in nitroglycerin ntg manufacturing facilities the effects of withdrawal sometimes include sunday heart attacks in those experiencing regular nitroglycerin exposure in the workplace leading to the development of tolerance for the venodilating effects over the weekend the workers lost their tolerance and when they were re exposed on monday the drastic vasodilation produced a fast heart rate dizziness and a headache this is referred to as monday disease 42 43 people can be exposed to nitroglycerin in the workplace by breathing it in skin absorption swallowing it or eye contact the occupational safety and health administration has set the legal limit permissible exposure limit for nitroglycerin exposure in the workplace as 0 2 ppm 2 mg m 3 skin exposure over an 8 hour workday the national institute for occupational safety and health has set a recommended exposure limit of 0 1 mg m 3 skin exposure over an 8 hour workday at levels of 75 mg m 3 nitroglycerin is immediately dangerous to life and health 44 see also edit erythritol tetranitrate ethylene glycol dinitrate mannitol hexanitrate methyl nitrate relative effectiveness factor tetranitratoxycarbon xylitol pentanitrate references edit 1 2 occupational safety and health guideline for nitroglycerin archived from the original on 16 may 2013 retrieved 19 october 2016 niosh pocket guide to chemical hazards 0456 national institute for occupational safety and health niosh hazard rating information for nfpa fire diamonds archived from the original on 17 february 2015 ascanio sobrero oxford reference retrieved 16 july 2024 1 2 3 occupational safety and health guideline for nitroglycerin 16 may 2013 archived from the original on 16 may 2013 retrieved 9 july 2024 haynes w m crc handbook of chemistry and physics 97th ed crc press pp 3 540 nitroglycerin desensitized liquid cameo chemicals noaa archived from the original on 26 august 2023 retrieved 9 july 2024 1 2 chen z foster m w zhang j mao l rockman h a kawamoto t kitagawa k nakayama k i hess d t stamler j s 2005 an essential role for mitochondrial aldehyde dehydrogenase in nitroglycerin bioactivation proceedings of the national academy of sciences 102 34 12159 12164 bibcode 2005pnas 10212159c doi 10 1073 pnas 0503723102 pmc 1189320 pmid 16103363 unknown behind paywall archived archived from the original on 10 may 2017 retrieved 14 april 2018 sobrero ascagne 1847 sur plusieur composés détonants produits avec l acide nitrique et le sucre la dextrine la lactine la mannite et la glycérine on several detonating compounds produced with nitric acid and sugar dextrin lactose mannitol and glycerin comptes rendus 24 247 248 whose translation sobrero ascanio 1849 sopra alcuni nuovi composti fulminanti ottenuti col mezzo dell azione dell acido nitrico sulle sostante organiche vegetali on some new explosive products obtained by the action of nitric acid on some vegetable organic substances memorie della reale accademia delle scienze di torino 2nd series 10 195 2...
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