Difference between revisions of "Nitroglycerin" - New World Encyclopedia

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{{Images OK}}{{Submitted}}{{Approved}}{{Paid}}{{Copyedited}}
 
{{explosivebox |
 
{{explosivebox |
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|IUPAC_name =       propane-1,2,3-triyl trinitrate
+
|IUPAC_name = propane-1,2,3-triyl trinitrate
 
|image=Nitroglycerin-2D-skeletal.png
 
|image=Nitroglycerin-2D-skeletal.png
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|chemical_formula = [[Carbon|C]]<sub>3</sub>[[Hydrogen|H]]<sub>5</sub>[[Nitrogen|N]]<sub>3</sub>[[Oxygen|O]]<sub>9</sub>
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|chemical_formula = C<sub>3</sub>H<sub>5</sub>(NO<sub>3</sub>)<sub>3</sub>
 
|molecular_weight = 227.0872 [[gram|g]]/[[mole (unit)|mol]]
 
|molecular_weight = 227.0872 [[gram|g]]/[[mole (unit)|mol]]
−
|shock_sensitivity = Very high
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|shock_sensitivity = Very High
 
|friction_sensitivity = Very high
 
|friction_sensitivity = Very high
 
|density = 1.13 [[kilogram|kg]]/[[cubic metre|dm³]] at 15 [[Celsius|°C]]
 
|density = 1.13 [[kilogram|kg]]/[[cubic metre|dm³]] at 15 [[Celsius|°C]]
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|CAS_number = 55-63-0
 
|CAS_number = 55-63-0
 
|PubChem = 4510
 
|PubChem = 4510
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|SMILES = C(C(CO[N+](=O)[O-])O<br>[N+](=O)[O-])O[N+](=O)[O-]
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|SMILES = C(C(CO[N+](=O)[O-])O<br/>[N+](=O)[O-])O[N+](=O)[O-]
 
}}
 
}}
  
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'''Nitroglycerin''' ('''NG'''), also known as '''nitroglycerine''', '''trinitroglycerin''', and '''glyceryl trinitrate''', is a [[chemical compound]]. It is a heavy, colorless, oily, explosive liquid obtained by [[nitration|nitrating]] [[glycerol]]. It is used in the manufacture of [[explosive]]s, specifically [[dynamite]], and as such is employed in the [[construction]] and [[demolition]] industries, and as a [[plasticizer]] in some solid [[propellant]]s. It is also used [[Glyceryl trinitrate (pharmacology)|medically]] as a [[vasodilator]] to treat [[heart]] conditions.
+
'''Nitroglycerin''' ('''NG''')—also known as '''nitroglycerine''', '''trinitroglycerin''', and '''glyceryl trinitrate'''—is a heavy, colorless, oily liquid obtained by [[nitration|nitrating]] [[glycerol]]. It is a powerful [[explosive]] and is used in the manufacture of [[dynamite]], which in turn is employed in the [[construction]] and [[demolition]] industries. It is also a [[plasticizer]] in some solid [[propellant]]s for [[rocket]]s. In medicine, nitroglycerin serves as a [[vasodilator]] (an agent that dilates blood vessels) and is therefore used to treat [[heart]] conditions.
−
 
+
{{toc}}
 
== History ==
 
== History ==
  
−
Nitroglycerin was discovered by chemist [[Ascanio Sobrero]] in [[1847]], working under [[TJ Pelouze]] at the [[University of Torino]]. 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 a number of "appalling catastrophes," such as the expolosion 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 (Nobel used ''[[kieselguhr]]'') or combustible [[absorption (chemistry)|absorbents]] (e.g., [[nitrocellulose]] to produce the yellow [[gel]], [[blasting gelatine]]).
+
Nitroglycerin was discovered by chemist [[Ascanio Sobrero]] in 1847, working under [[T.J. Pelouze]] at the [[University of Torino]]. 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 unstable and dangerous, resulting in numerous catastrophes, including an explosion that destroyed a [[Wells Fargo]] office in [[San Francisco]] in 1866.<ref>[http://CPRR.org/Museum/Newspapers/Nitroglycerine.html Nitroglycerine! Terrible Explosion and Loss of Lives in San Francisco.] ''Central Pacific Railroad Photographic History Museum.'' (1866 newspaper article). Retrieved September 20, 2007.</ref> The liquid was widely banned, and Nobel developed [[dynamite]], a less sensitive explosive, by mixing nitroglycerin with the inert [[absorbent]] ''[[kieselguhr]]'' ([[diatomaceous earth]]). Other similar mixtures, such as ''dualine'' and ''lithofracteur,'' were also prepared by mixing nitroglycerin with inert materials such as [[nitrocellulose|nitrocellulose gel]] or [[blasting gelatin]].
  
 
== Instability and desensitization ==
 
== Instability and desensitization ==
−
In its pure form, it is a [[contact explosive]] (i.e., 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 (explosive)|C-4]].
 
−
 
−
Early in the history of this explosive it was discovered that liquid nitroglycerin can be "desensitized" by cooling to 5 to 10&nbsp;[[Celsius|°C]]&nbsp;(40 to 50&nbsp;[[Fahrenheit|°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 [[Explosive material|High Explosive]] formulations, by the addition of approximately 10 to 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.
 
−
 
−
A serious problem in the use of nitroglycerin results from its high freezing point (13&nbsp;°C&nbsp;[55&nbsp;°F]). Solid nitroglycerin is much less sensitive to shock than the liquid, a feature common in explosives and in the past it has often been shipped in the frozen state, but this has 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&nbsp;°C&nbsp;(-20&nbsp;°F).<ref name="fn_1">{{cite web|url=http://www.britannica.com/nobel/micro/426_77.html | work=Britannica | title=nitroglycerin | accessmonthday=23 March | accessyear=2005 }}</ref>
 
  
−
== Detonation ==
+
In its pure form, nitroglycerin is a [[contact explosive]]—that is, physical shock can cause it to explode. It degrades over time to even more unstable forms, making it highly dangerous to transport or use. In its 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 (explosive)|C-4]].
  
−
Nitroglycerin and any or all of the dilutents mentioned above can certainly [[deflagration|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.
+
Early in the history of this explosive it was discovered that liquid nitroglycerin can be "desensitized" by cooling to 5 to 10&nbsp;[[Celsius|°C]] (40 to 50&nbsp;[[Fahrenheit|°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.
  
−
== Preparation ==
+
It is possible to chemically "desensitize" nitroglycerin to a point where it can be considered approximately as "safe" as modern [[Explosive material|high explosive]] formulations, by the addition of approximately 10-30 percent [[ethanol]], [[acetone]], or [[dinitrotoluene]]. (The 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 applications.
  
−
{{wikibooks|Chemical synthesis|Nitroglycerine|Nitroglycerin synthesis}}
+
A serious problem in the use of nitroglycerin is associated with its high freezing point 13&nbsp;[[Celsius|°C]]&nbsp;(55&nbsp;[[Fahrenheit|°F]]). Solid nitroglycerin is much less sensitive to shock than the liquid form, a feature common in explosives. In the past, it was often shipped in the frozen state, but this resulted in many accidents during the thawing process by the end user, just prior to use. This disadvantage can be overcome by using mixtures of nitroglycerin with other polynitrates; for example, a mixture of nitroglycerin and [[ethylene glycol dinitrate]] freezes at -29&nbsp;°C&nbsp;(-20&nbsp;°F).
−
Nitroglycerin is prepared by [[nitration]] of [[glycerol]] (also known as [[glycerin]]). In the process, glycerin is slowly tipped into a mix of full concentration [[nitric acid]] and [[sulfuric acid]] (about 50% sulfuric acid, 40% nitric acid, and 5-10% glycerin). The mixed acid must be cooled to approximately room temperature before the glycerin is added because they exotherm (heat up) greatly when combined. The solution is slowly stirred. A few seconds after mixing, the vessel must be immersed in a jacket of ice water to prevent the exothermic reaction from overheating it, causing nitric acid decomposition or even explosion. The temperature should never exceed 10 °C (50 °F), but the chemicals must not be cooled by the ice water before mixing, or the nitrating reaction will not take place.
 
  
−
If the reaction is successful, the nitroglycerin will form a slightly yellow or straw colored liquid which will float to the top of the acid mix. The mix is then carefully poured into a large container of water. The nitroglycerin will settle to the bottom (it is water insoluble) and should be neutralized with sodium carbonate and water mix until its pH becomes neutral.
+
== Detonation versus deflagration ==
  
−
Another method of producing nitroglycerin is to mix the glycerin and sulfuric acid first, which produces heat, but at this stage is not dangerous. After cooling, the Nitric acid can be added reasonably quickly to the mix, but it can still cause uncontrolled nitration. It can also cause the acid to spurt back at you. Therefore it should be avoided and the nitration mixture should be added very slowly to the glycerol. The then nitrated glycerin and acid solution has to be left for the nitroglycerin to float to the top, as this method can sometimes produce the nitroglycerin in fine quantities. The waiting period is a day or less, but the prolonged exposure to the acids may cause the decomposition or even the explosion of the nitroglycerin, although the latter will only occur in large batches. If a milky colour is seen, it is only because of water in the mix, and not to be worried about. From this point, continue as above. This method was used in the time of Nobel, although it was not his own.
+
Nitroglycerin and any or all of the diluents used can certainly [[deflagration|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 differences or shock.
  
−
=== Manufacturing ===
+
== Manufacture ==
  
−
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).
+
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 (pure nitric acid from which oxides of nitrogen have been removed, as opposed to red fuming nitric acid) and concentrated sulfuric acid. This mixture is often attained by the cheaper method of mixing fuming sulfuric acid (sulfuric acid containing excess [[sulfur trioxide]]) and azeotropic nitric acid (consisting of around 70 percent nitric acid, the rest being water).
  
−
The sulfuric acid produces protonated nitric acid species, which are attacked by glycerin's [[Nucleophile|nucleophilic]] [[oxygen]] atoms. The [[nitro]] [[functional group|group]] is thus added as an ester C-O-NO<sub>2</sub> and water is produced. This is different from an aromatic nitration reaction in which [[nitronium ion]]s are the active species in an electrophilic attack of the molecules ring system.
+
The sulfuric acid produces protonated nitric acid species, which are attacked by glycerin's [[Nucleophile|nucleophilic]] [[oxygen]] atoms. The [[nitro]] [[functional group|group]] is thus added as an ester (C-O-NO<sub>2</sub>), and water is produced.<ref>This is different from an aromatic nitration reaction in which [[nitronium ion]]s are the active species in an electrophilic attack of the molecule's ring system.</ref>
  
−
The addition of glycerin results in an [[chemical reaction|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 as one might expect). 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.
+
The addition of glycerin results in an [[chemical reaction|exothermic reaction]] (that is, heat is released). However, if the mixture becomes too hot, it results in runaway reaction—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 [[Container|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. 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 varies by country), or brown fumes are seen in the nitrators vent, then it is immediately drowned.
  
−
Due to the great dangers associated with its production, most nitroglycerin production facilities are in offshore rigs or very remote locations.
+
Because of the great dangers associated with its production, most nitroglycerin production facilities are in offshore rigs or remote locations.
  
−
== Medical use ==
+
== Medical uses ==
 
{{main|Glyceryl trinitrate (pharmacology)}}
 
{{main|Glyceryl trinitrate (pharmacology)}}
  
−
In [[medicine]], nitroglycerin (sometimes called [[Glyceryl trinitrate (pharmacology)|Glyceryl trinitrate]], presumably to avoid alarming people) is used as a [[heart]] medication (under the trade names '''Nitrospan®''' and '''Nitrostat®'''). It is used as a medicine for [[angina pectoris]] ([[coronary heart disease|ischaemic heart disease]]) in tablets, ointment, solution for intravenous use, transdermal patches ('''Transderm Nitro®''', '''Nitro-Dur®'''), or sprays administered [[sublingual|sublingually]] ('''Nitrolingual Pump Spray®''', '''Natispray®''').  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 [[Glyceryl trinitrate (pharmacology)#Uses|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.
+
In [[medicine]], nitroglycerin is generally called glyceryl trinitrate and is used as a [[heart]] medication (under the trade names '''Nitrospan®''', '''Nitrostat®''', and '''Tridil®''', amongst others). Used as a treatment for [[angina pectoris]] ([[coronary heart disease|ischemic heart disease]]), it is available in the form of tablets, ointment, solution (for intravenous use), transdermal patches ('''Transderm Nitro®''', '''Nitro-Dur®'''), or sprays administered [[sublingual]]ly ('''Nitrolingual Pump Spray®''', '''Natispray®''').
  
−
The principal action of nitroglycerin is [[vasodilation]] — that is, widening of the [[blood vessel]]s. The main effects of nitroglycerin in episodes of [[angina pectoris]] are
+
The principal action of nitroglycerin is [[vasodilation]]&mdash;widening of the [[blood vessel]]s. Nitroglycerin will dilate veins more than arteries, decreasing cardiac preload and leading to the following therapeutic effects during episodes of [[angina pectoris]]:
 
* subsiding of chest pain
 
* subsiding of chest pain
 
* decrease of [[blood pressure]]
 
* decrease of [[blood pressure]]
 
* increase of heart rate.
 
* increase of heart rate.
 +
* [[orthostatic hypotension]]
 +
 +
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 percent) concentration in ointment form, as an effective treatment for [[anal fissure]].
  
 +
== Adverse health effects ==
  
−
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]].
+
Infrequent exposure to high doses of nitroglycerin can cause severe headaches—a condition known as "NG head." The headaches can be severe enough to incapacitate some people. It appears, however, that many people develop a tolerance for and dependence on nitroglycerin after long-term exposure. Withdrawal symptoms include headaches and heart problems. These symptoms may disappear with re-exposure to nitroglycerin. For workers regularly exposed to this substance in the workplace (such as in nitroglycerin manufacturing facilities), this can result in a "Monday Morning Headache"—they develop they develop symptoms of withdrawal over the weekend, which are countered by reexposure on the next working day. In rare cases, withdrawal has been found to be fatal.
  
−
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 addiction to nitroglycerin after long-term exposure. Withdrawal can 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.
+
== See also ==
 +
 
 +
* [[Alfred Nobel]]
 +
* [[Dynamite]]
 +
* [[Explosive]]
 +
* [[Glycerol]]
 +
 
 +
== Notes ==
 +
<references />
  
 
== References ==
 
== References ==
  
−
* {{cite web|url=http://CPRR.org/Museum/Newspapers/Nitroglycerine.html | work=Central Pacific Railroad Photographic History Museum | title=Nitroglycerine! Terrible Explosion and Loss of Lives in San Francisco | accessmonthday=23 March | accessyear=2005 }} - 1866 Newspaper article
+
* Akhavan, Jacqueline. 2004. ''The Chemistry of Explosives.'' RSC Paperbacks. Cambridge, UK: Royal Society of Chemistry. ISBN 0854046402.
−
<references />
+
 
 +
* Davis, Tenney Lombard. 1984. ''The Chemistry of Powder and Explosives.'' Hollywood, CA: Angriff Press. ISBN 0913022004.
 +
 
 +
* Meyer, Edith Patterson. 1958. ''Dynamite and Peace; the Story of Alfred Nobel.'' Boston: Little, Brown. OCLC 1252824.
 +
 
 +
* Meyer, Rudolf, Josef Köhler, and Axel Homburg. 2007. ''Explosives.'' Weinheim: Wiley-VCH. ISBN 978-3527316564.
  
 
==External links==
 
==External links==
−
* [http://www.roguesci.org/megalomania/explo/nitroglycerin.html Nitroglycerin]. Detailed synthesis information.
+
All links retrieved November 15, 2022.
−
* [http://www.compchemwiki.org/index.php?title=Nitroglycerin Computational Chemistry Wiki]
+
* [http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4510 PubChem: Nitroglycerin.] ''NCBI''.  
−
* [http://www.logwell.com/tales/menu/index.html The Tallini Tales of Destruction] Detailed and horrific stories of the historical use of nitroglycerin-filled torpedoes to restart petroleum wells.  
+
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C55630 1,2,3-Propanetriol, trinitrate (Nitroglycerin)] ''NIST''.
−
{{ChemicalSources}}
+
* [http://www.logwell.com/tales/menu/index.html The Tallini Tales of Destruction.] ''logwell.com''. (Detailed and horrific stories of the historical use of nitroglycerin-filled torpedoes to restart petroleum wells.)
  
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[[Category:Alkyl nitrates]]
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[[Category:Physical sciences]]
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[[Category:Antianginals]]
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[[Category:Chemistry]]
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[[Category:Explosive chemicals]]
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[[Category:Organic chemistry]]
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[[Category:Liquid explosives]]
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[[Category:Construction technology]]
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[[Category:Military technology]]
  
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[[ar:نيتروجلسرين]]
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[[bg:Нитроглицерин]]
 
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[[eo:Nitroglicerino]]
 
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[[fr:Nitroglycérine]]
 
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[[ko:나이트로글리세린]]
 
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[[id:Nitrogliserin]]
 
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Latest revision as of 02:27, 16 November 2022

Nitroglycerin chemical structure
Nitroglycerin

propane-1,2,3-triyl trinitrate
IUPAC name
Chemical formula C3H5(NO3)3
Molecular mass 227.0872 g/mol
Shock sensitivity Very High
Friction sensitivity Very high
Density 1.13 kg/dm³ 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 heavy, colorless, oily liquid obtained by nitrating glycerol. It is a powerful explosive and is used in the manufacture of dynamite, which in turn is employed in the construction and demolition industries. It is also a plasticizer in some solid propellants for rockets. In medicine, nitroglycerin serves as a vasodilator (an agent that dilates blood vessels) and is therefore used to treat heart conditions.

History

Nitroglycerin was discovered by chemist Ascanio Sobrero in 1847, working under T.J. Pelouze at the University of Torino. 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 unstable and dangerous, resulting in numerous catastrophes, including an explosion that destroyed a Wells Fargo office in San Francisco in 1866.[1] The liquid was widely banned, and Nobel developed dynamite, a less sensitive explosive, by mixing nitroglycerin with the inert absorbent kieselguhr (diatomaceous earth). Other similar mixtures, such as dualine and lithofracteur, were also prepared by mixing nitroglycerin with inert materials such as nitrocellulose gel or blasting gelatin.

Instability and desensitization

In its pure form, nitroglycerin is a contact explosive—that is, physical shock can cause it to explode. It degrades over time to even more unstable forms, making it highly dangerous to transport or use. In its 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.

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 percent ethanol, acetone, or dinitrotoluene. (The 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 applications.

A serious problem in the use of nitroglycerin is associated with its high freezing point 13 °C (55 °F). Solid nitroglycerin is much less sensitive to shock than the liquid form, a feature common in explosives. In the past, it was often shipped in the frozen state, but this resulted in many accidents during the thawing process by the end user, just prior to use. This disadvantage can be 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).

Detonation versus deflagration

Nitroglycerin and any or all of the diluents 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 differences or shock.

Manufacture

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 (pure nitric acid from which oxides of nitrogen have been removed, as opposed to red fuming nitric acid) and concentrated sulfuric acid. This mixture is often attained by the cheaper method of mixing fuming sulfuric acid (sulfuric acid containing excess sulfur trioxide) and azeotropic nitric acid (consisting of around 70 percent nitric acid, the rest being water).

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.[2]

The addition of glycerin results in an exothermic reaction (that is, heat is released). However, if the mixture becomes too hot, it results in runaway reaction—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. 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 varies by country), or brown fumes are seen in the nitrators vent, then it is immediately drowned.

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

Medical uses

In medicine, nitroglycerin is generally called glyceryl trinitrate and is used as a heart medication (under the trade names Nitrospan®, Nitrostat®, and Tridil®, amongst others). Used as a treatment for angina pectoris (ischemic heart disease), it is available in the form of 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:

  • subsiding of chest pain
  • decrease of blood pressure
  • increase of heart rate.
  • orthostatic hypotension

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 percent) concentration in ointment form, as an effective treatment for anal fissure.

Adverse health effects

Infrequent exposure to high doses of nitroglycerin can cause severe headaches—a condition known as "NG head." The headaches can be severe enough to incapacitate some people. It appears, however, that many people develop a tolerance for and dependence on nitroglycerin after long-term exposure. Withdrawal symptoms include headaches and heart problems. These symptoms may disappear with re-exposure to nitroglycerin. For workers regularly exposed to this substance in the workplace (such as in nitroglycerin manufacturing facilities), this can result in a "Monday Morning Headache"—they develop they develop symptoms of withdrawal over the weekend, which are countered by reexposure on the next working day. In rare cases, withdrawal has been found to be fatal.

See also

Notes

  1. ↑ Nitroglycerine! Terrible Explosion and Loss of Lives in San Francisco. Central Pacific Railroad Photographic History Museum. (1866 newspaper article). Retrieved September 20, 2007.
  2. ↑ This is different from an aromatic nitration reaction in which nitronium ions are the active species in an electrophilic attack of the molecule's ring system.

References
ISBN links support NWE through referral fees

  • Akhavan, Jacqueline. 2004. The Chemistry of Explosives. RSC Paperbacks. Cambridge, UK: Royal Society of Chemistry. ISBN 0854046402.
  • Davis, Tenney Lombard. 1984. The Chemistry of Powder and Explosives. Hollywood, CA: Angriff Press. ISBN 0913022004.
  • Meyer, Edith Patterson. 1958. Dynamite and Peace; the Story of Alfred Nobel. Boston: Little, Brown. OCLC 1252824.
  • Meyer, Rudolf, Josef Köhler, and Axel Homburg. 2007. Explosives. Weinheim: Wiley-VCH. ISBN 978-3527316564.

External links

All links retrieved November 15, 2022.

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