Nitroglycerin (NG), (US spelling) also known as nitroglycerine, (UK Spelling), trinitroglycerin, trinitroglycerine, 1,2,3-trinitroxypropane and glyceryl trinitrate, is a heavy, colorless, oily, explosive liquid obtained by nitrating glycerol. The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to UN numbers or UN IDs are four-digit numbers that identify Hazardous substances, and articles (such as explosives flammable liquids toxic substances etc List of UN Numbers UN 0101 to UN 0200 List of UN Numbers UN 1201 to UN 1300 List of UN Numbers UN 3001 to UN 3100 PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The United States of America —commonly referred to as the The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located Nitration is a general Chemical process for the introduction of a nitro group into a Chemical compound. Since the 1860s, it has been used as an active ingredient in the manufacture of explosives, specifically dynamite, and as such is employed in the construction and demolition industries. An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied Dynamite is an explosive based on the explosive potential of Nitroglycerin, initially using Diatomaceous earth (kieselgur US Spelling kieselguhr In the fields of Architecture and Civil engineering, construction is a process that consists of the Building or assembling of Infrastructure Demolition is the opposite of Construction: the tearing-down of Buildings and other Structures It contrasts with deconstruction Similarly, since the 1880s, it has been used by the military as an active ingredient, and a gellatinizer for nitrocellulose, in some solid propellants, such as Cordite and Ballistite. Nitrocellulose (also cellulose nitrate, flash paper) is a highly flammable compound formed by Nitrating Cellulose through exposure to A propellant is a material that is used to move ("propel" an object Cordite is a family of smokeless propellants developed and produced in the United Kingdom from 1889 to replace Gunpowder as a military propellant Ballistite is a smokeless propellant made from two High explosives Nitrocellulose and nitroglycerine (UK spelling nitroglycerin (US spelling Nitroglycerin is also used medically as a vasodilator to treat heart conditions, such as angina and chronic heart failure. Glyceryl trinitrate (GTN has been used to treat angina and Heart failure since at least 1870 The heart is a muscular organ in all Vertebrates responsible for pumping Blood through the Blood vessels by repeated rhythmic Angina pectoris, commonly known as angina, is severe Chest pain due to Ischemia (a lack of blood and hence Oxygen supply of the heart Heart failure is a Cardiac condition that occurs when a problem with the structure or function of the Heart impairs its ability to supply

History

Nitroglycerin was discovered by chemist Ascanio Sobrero in 1846, working under TJ Pelouze at the University of Turin. Ascanio Sobrero ( October 12 1812 &ndash May 26 1888) was the Italian Chemist, born in Casale Monferrato, who Théophile-Jules Pelouze (also known as Jules Pelouze, Théophile Pelouze, Theo Pelouze, or TJ Pelouze, February 26, 1807 The University of Turin ( Italian Università degli Studi di Torino, UNITO is a University in the city of Turin in the Piedmont region The best manufacturing process was developed by Alfred Nobel in the 1860s. (21 October 1833 Stockholm, Sweden – 10 December 1896 Sanremo, Italy) was a Swedish chemist engineer innovator armaments manufacturer 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. Gunpowder is a an explosive mixture of Sulfur, Charcoal and Potassium nitrate (also known as saltpetre/saltpeter that burns rapidly producing volumes Wells Fargo & Co ( is a diversified Financial services company headquartered in San Francisco California, United States with operations around the The City and County of San Francisco is the fourth most populous city

Liquid nitroglycerin was widely banned, and this led to the development of dynamite (and similar mixtures, such as blasting gelatine, dualine and lithofracteur), made by mixing the nitroglycerin with inert absorbents; for example, Nobel used kieselguhr. Dynamite is an explosive based on the explosive potential of Nitroglycerin, initially using Diatomaceous earth (kieselgur US Spelling kieselguhr Gelignite, also known as blasting gelatin, is an Explosive material consisting of Collodion - Cotton (a type of Nitrocellulose Diatomaceous earth (ˌdaɪətəˈmeɪʃəs ˈɝθ also known as DE, TSS, diatomite, diahydro, kieselguhr, kieselgur and Other nitrated materials, such as nitrocellulose gel, were also used. Nitrocellulose (also cellulose nitrate, flash paper) is a highly flammable compound formed by Nitrating Cellulose through exposure to Dynamites containing nitrocellulose, which increase the viscosity of the mix, are commonly known as "gelatins. "

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. Contact explosive generally refers to any substance that will explode when relatively small quantities of Energy are applied to the substance, whether that This makes it highly dangerous to transport or use. In this undiluted form, it is one of the more powerful explosives, comparable to the more recently developed RDX and PETN, as well as the plastic explosive C-4—which contains over 90% RDX as its active ingredient. Cyclotrimethylenetrinitramine, also known as RDX, cyclonite, hexogen, and T4, is an Explosive Nitroamine widely used Pentaerythritol tetranitrate ( PETN, also known as pentrite, or rarely and primarily in German as nitropenta) is one of the most powerful high explosives Plastic explosive (or the obsolete term plastique) is a specialised form of Explosive material. 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. The Celsius Temperature scale was previously known as the centigrade scale. Fahrenheit is a temperature scale named after Daniel Gabriel Fahrenheit (1686–1736 a German Physicist who proposed it in 1724 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). An explosive material is a material that either is chemically or otherwise Energetically unstable or produces a sudden expansion of the material usually accompanied Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Dinitrotoluene ( DNT) or Dinitro is an Explosive with the formula C6H3(CH3(NO22 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 °C (55 °F). The Celsius Temperature scale was previously known as the centigrade scale. Fahrenheit is a temperature scale named after Daniel Gabriel Fahrenheit (1686–1736 a German Physicist who proposed it in 1724 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). Ethylene glycol dinitrate ( EGDN) also known as nitroglycol, is a Chemical compound a yellowish oily explosive liquid obtained by nitrating The Celsius Temperature scale was previously known as the centigrade scale. Fahrenheit is a temperature scale named after Daniel Gabriel Fahrenheit (1686–1736 a German Physicist who proposed it in 1724 ^[1]

Detonation

Nitroglycerin and any or all of the dilutents used can certainly deflagrate or burn. Deflagration (Lat de + flagrare, "to burn down" is a technical term describing subsonic Combustion that usually propagates through Thermal conductivity However, the explosive power of nitroglycerin is derived from detonation: energy from the initial decomposition causes a pressure gradient that detonates the surrounding fuel. 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 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. Sound is a vibration that travels through an elastic medium as a Wave. This is quite unlike deflagration, which depends solely upon available fuel, regardless of pressure or shock.

Manufacturing

The industrial manufacturing process often uses a nearly 50:50 mixture of sulfuric acid and nitric acid. Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and 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, also known as oleum, (sulfuric acid containing excess sulfur trioxide) and azeotropic nitric acid (consisting of around 70% nitric acid, the rest being water). Sulfur trioxide (also spelled sulphur trioxide) is the chemical compound with the formula SO3 An azeotrope (pronounced

The sulfuric acid produces protonated nitric acid species, which are attacked by glycerin's nucleophilic oxygen atoms. In Chemistry, a nucleophile (literally nucleus lover as in nucleus and phile) is a Reagent that forms a Chemical bond to Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The nitro group is thus added as an ester C-O-NO₂ and water is produced. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions 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. The nitronium ion (improperly called nitryl ion, because it is not a radical 2+ is a generally unstable Cation created by the removal of an

The addition of glycerin results in an exothermic reaction (i. A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called 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. Nitrogen dioxide is the Chemical compound with the formula N[[Oxygen O]]2 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.

Use as an explosive and a propellant

Main articles: Dynamite, Ballistite, Cordite, smokeless powder, and Gelignite

Alfred Nobel's patent application from 1864. Dynamite is an explosive based on the explosive potential of Nitroglycerin, initially using Diatomaceous earth (kieselgur US Spelling kieselguhr Ballistite is a smokeless propellant made from two High explosives Nitrocellulose and nitroglycerine (UK spelling nitroglycerin (US spelling Cordite is a family of smokeless propellants developed and produced in the United Kingdom from 1889 to replace Gunpowder as a military propellant Smokeless powder is the name given to a number of Propellants used in Firearms and Artillery which produce negligible smoke when fired unlike the older Gelignite, also known as blasting gelatin, is an Explosive material consisting of Collodion - Cotton (a type of Nitrocellulose (21 October 1833 Stockholm, Sweden – 10 December 1896 Sanremo, Italy) was a Swedish chemist engineer innovator armaments manufacturer A patent application is a request pending at a Patent office for the grant of a Patent for the Invention described and claimed by that application Year 1864 ( MDCCCLXIV) was a Leap year starting on Friday (link will display the full calendar of the Gregorian Calendar (or a Leap year

The main use of nitroglycerin, by tonnage, is in explosives such as dynamite and in propellants.

Alfred Nobel developed the use of nitroglycerin as a blasting explosive by mixing the nitroglycerine with inert absorbents particularly kieselgur. (21 October 1833 Stockholm, Sweden – 10 December 1896 Sanremo, Italy) was a Swedish chemist engineer innovator armaments manufacturer Chemistry (from Egyptian kēme (chem meaning "earth") is the Science concerned with the composition structure and properties Diatomaceous earth (ˌdaɪətəˈmeɪʃəs ˈɝθ also known as DE, TSS, diatomite, diahydro, kieselguhr, kieselgur and He named this explosive dynamite and patented it in 1867. Dynamite is an explosive based on the explosive potential of Nitroglycerin, initially using Diatomaceous earth (kieselgur US Spelling kieselguhr A patent is a set of Exclusive rights granted by a State to an inventor or his assignee for a fixed period of time in exchange for a disclosure of an It was supplied ready for use in the form of sticks, individually wrapped in grease proof paper. Dynamite and similar explosives were widely adopted for civil engineering tasks, such as building railway tunnels and cuttings; and for quarrying.

Nitroglycerin was also adapted as a military propellant, for use in guns and rifles. Poudre B, invented in France in 1886, was one of the first military propellants to replace gunpowder; but it was based on nitrocellulose, not nitroglycerin. Poudre B (from French: Poudre Blanche, meaning "white powder" or Vieille powder, was the first smokeless Gunpowder. This article is about the country For a topic outline on this subject see List of basic France topics. Gunpowder is a an explosive mixture of Sulfur, Charcoal and Potassium nitrate (also known as saltpetre/saltpeter that burns rapidly producing volumes It was later found to be unstable.

Alfred Nobel then developed ballistite, by combining nitroglycerin and guncotton. Ballistite is a smokeless propellant made from two High explosives Nitrocellulose and nitroglycerine (UK spelling nitroglycerin (US spelling Nitrocellulose (also cellulose nitrate, flash paper) is a highly flammable compound formed by Nitrating Cellulose through exposure to He patented it in 1887. Ballistite was adopted by a number of European governments, as a military propellant. Italy was the first to adopt it. Italy (Italia officially the Italian Republic, (Repubblica Italiana is located on the Italian Peninsula in Southern Europe, and on the two largest However, it was not adopted by the British Government. They, together with the British Commonwealth countries, adopted cordite, which had been developed by Sir Frederick Abel and Sir James Dewar, in 1889. Cordite is a family of smokeless propellants developed and produced in the United Kingdom from 1889 to replace Gunpowder as a military propellant Sir Frederick Augustus Abel 1st Baronet FRS ( 17 July 1827 &ndash 6 September 1902) was an English Chemist. Sir James Dewar FRS ( September 20, 1842 &ndash March 27, 1923) was a Scottish Chemist and Physicist The original Cordite Mk I consisted of 58% nitroglycerine, 37% guncotton and 5% petroleum jelly. Petroleum jelly, petrolatum or soft paraffin is a Semi-solid mixture of Hydrocarbons (with Carbon numbers mainly higher than 25 Ballistite and cordite were both manufactured in the forms of cords.

Smokeless powders were originally developed using nitrocellulose as the sole explosive ingredient; and were therefore known as single base propellants. Smokeless powder is the name given to a number of Propellants used in Firearms and Artillery which produce negligible smoke when fired unlike the older A range of smokeless powders that contain both nitrocellulose and nitroglycerin, known as double base propellants, were also developed. Smokeless powders were originally supplied only for military use; however they were also soon developed for civilian use and were quickly adopted for sport. Some are known as sporting powders.

Blasting gelatin, also known as gelignite, was invented by Nobel in 1875, using nitroglycerine, wood pulp, and sodium or potassium nitrates. Gelignite, also known as blasting gelatin, is an Explosive material consisting of Collodion - Cotton (a type of Nitrocellulose This was an early low-cost, flexible explosive.

War time production rates

Large quantities of nitroglycerin were manufactured in both World Wars for use in military propellants.

World War I

In World War I HM Factory, Gretna, the largest propellant factory in the United Kingdom was producing 800 tons (812 tonne) of Cordite RDB per week. World War I (abbreviated WWI; also known as the First World War, the Great War, and the War to End All His Majesty's Factory Gretna, or HM Factory Gretna as it was usually known was a UK government World War I Cordite factory adjacent to Units of mass There are three similar units of Mass called the ton: Long ton (simply ton in countries such as the United This article is about the tonne or metric ton For other tons see Ton. This required 336 tons of nitroglycerin per week (assuming no losses in production). The Royal Navy had its own factory at Royal Navy Cordite Factory, Holton Heath. The Royal Navy of the United Kingdom is the oldest of the British armed services (and is therefore known as the Senior Service) The Royal Navy Cordite Factory Holton Heath, ( RNCF) was set up at Holton Heath, Dorset in World War I to manufacture Cordite for

A large cordite factory was also built in Canada in World War I. Country to "Dominion of Canada" or "Canadian Federation" or anything else please read the Talk Page The Canadian Explosives Limited Cordite factory at Nobel, Ontario was designed to produce 1,500,000 lb (681 tonne) of Cordite per month. Canadian Industries Limited, also known as C-I-L is a Canadian Chemicals manufacturer Nobel is a village located on the picturesque shores of Parry Sound. It required 286 tonnes of nitroglycerin per month.

Medical implications

Main article: Glyceryl trinitrate (pharmacology)

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). Glyceryl trinitrate (GTN has been used to treat angina and Heart failure since at least 1870 Medicine is the art and science of healing It encompasses a range of Health care practices evolved to maintain and restore Human Health by the The heart is a muscular organ in all Vertebrates responsible for pumping Blood through the Blood vessels by repeated rhythmic 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). Angina pectoris, commonly known as angina, is severe Chest pain due to Ischemia (a lack of blood and hence Oxygen supply of the heart Coronary disease (or coronary heart disease) refers to the failure of Coronary circulation to supply adequate circulation to Cardiac muscle and surrounding The principal action of nitroglycerin is vasodilation—widening of the blood vessels. The blood vessels are part of the Circulatory system and function to transport Blood throughout the body 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. Angina pectoris, commonly known as angina, is severe Chest pain due to Ischemia (a lack of blood and hence Oxygen supply of the heart Blood pressure is also the title of a short story by Damon Runyan in Guys and Dolls and Other Stories
• 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. Orthostatic hypotension (also known as postural hypotension, and colloquially as head rush or a dizzy spell) is a form of Hypotension in which Nitric oxide or nitrogen monoxide is a Chemical compound with Chemical formula N[[Oxygen O]] Recently, it has also become popular in an off-label use at reduced (0. Off-label use is the practice of prescribing drugs for a purpose outside the scope of the drug's approved label most often concerning the drug's indication. 2%) concentration in ointment form as an effective treatment for anal fissure. An anal fissure is an unnatural crack or tear in the Anus skin

Industrial exposure

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 (NTG) manufacturing facilities, this can result in a "Monday morning headache" phenomenon for those who experience regular nitroglycerin exposure in the workplace leading to the development of NTG tolerance for the vasodilating effects. Over the weekend the workers lose the tolerance to NTG and when they are reexposed on Monday the prominent vasodilation produces tachycardia, dizziness, and a headache.

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.

See also

• Mannitol hexanitrate
• Xylitol pentanitrate
• Erythritol tetranitrate
• Nitroglycerine, most properly Gycerol trinitrate
• Ethylene glycol dinitrate
• Nitromethane

External links

• WebBook page for C3H5N3O9
• Computational Chemistry Wiki
• The Tallini Tales of Destruction Detailed and horrific stories of the historical use of nitroglycerin-filled torpedoes to restart petroleum wells. Mannitol hexanitrate is a powerful Explosive. Physically it is a powdery solid at normal temperature ranges with density 1 Xylitol pentanitrate is a rarely-used liquid explosive compound with extremely high viscosity formed by completely nitrating Xylitol, a Sugar alcohol Erythritol tetranitrate (ETN is an explosive compound chemically similar to PETN. Nitroglycerin ( NG) ( US spelling also known as nitroglycerine, ( UK Spelling trinitroglycerin, trinitroglycerine Ethylene glycol dinitrate ( EGDN) also known as nitroglycol, is a Chemical compound a yellowish oily explosive liquid obtained by nitrating Nitromethane is an Organic compound with the chemical formula CH3NO2