Triethylene glycol dinitrate

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Triethylene glycol dinitrate
TEGDN.png
Names
IUPAC name
2,2'-(Ethane-1,2-diylbis(oxy))bisethyl dinitrate ]
Other names
TEGDN
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.498 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H12N2O8/c9-7(10)15-5-3-13-1-2-14-4-6-16-8(11)12/h1-6H2
    Key: AGCQZYRSTIRJFM-UHFFFAOYSA-N
  • C(CO[N+](=O)[O-])OCCOCCO[N+](=O)[O-]
Properties
C6H12N2O8
Molar mass 240.168 g·mol−1
Appearancepale yellow oily liquid
Density 1.33 g/cm3
Melting point −19 °C (−2 °F; 254 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethylene glycol dinitrate (TEGDN) is a nitrated alcohol ester of triethylene glycol. It is used as an energetic plasticizer in explosives and propellants. Its chemical formula is O2N-O-CH2CH2-O-CH2CH2-O-CH2CH2-O-NO2. It is a pale yellow oily liquid. [1] It is somewhat similar to nitroglycerin.

TEGDN is often used together with trimethylolethane trinitrate (TMETN).

Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate are being considered as replacements for nitroglycerin in propellants. [2]

Related Research Articles

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Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, 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 an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Invented in 1847 by Ascanio Sobrero, nitroglycerin has been used ever since as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by the military as an active ingredient and gelatinizer for nitrocellulose in some solid propellants such as cordite and ballistite. It is a major component in double-based smokeless propellants used by reloaders. Combined with nitrocellulose, hundreds of powder combinations are used by rifle, pistol, and shotgun reloaders.

<span class="mw-page-title-main">Pentaerythritol tetranitrate</span> Explosive chemical compound

Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, TEN, corpent, or penthrite, is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66. When mixed with a plasticizer, PETN forms a plastic explosive. Along with RDX it is the main ingredient of Semtex.

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A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.

<span class="mw-page-title-main">Smokeless powder</span> Type of propellant

Smokeless powder is a type of propellant used in firearms and artillery that produces less smoke and less fouling when fired compared to gunpowder. The combustion products are mainly gaseous, compared to around 55% solid products for black powder. In addition, smokeless powder does not leave the thick, heavy fouling of hygroscopic material associated with black powder that causes rusting of the barrel. Despite its name, smokeless powder is not completely free of smoke; while there may be little noticeable smoke from small-arms ammunition, smoke from artillery fire can be substantial.

<span class="mw-page-title-main">Otto fuel II</span> Torpedo fuel

Otto fuel II is a monopropellant used to drive torpedoes and other weapon systems. It is not related to the Otto cycle. Otto fuel II was developed by US Navy in the 1960s for use as fuel in torpedoes. Otto fuel II was invented by Otto Reitlinger in 1963 ; it is named after Reitlinger and for being the second iteration of the fuel. The first torpedo to use it was the Mark 48 torpedo in the 1960s.

<span class="mw-page-title-main">Mannitol hexanitrate</span> Chemical compound

Mannitol hexanitrate is a powerful explosive. Physically, it is a powdery solid at normal temperature ranges, with density of 1.73 g/cm3. The chemical name is hexanitromannitol and it is also known as nitromannite, MHN, and nitromannitol, and by the trademarks Nitranitol and Mannitrin. It is more stable than nitroglycerin, and it is used in detonators.

Triethylene glycol, TEG, or triglycol is a colorless odorless viscous liquid with molecular formula HOCH2CH2OCH2CH2OCH2CH2OH. It is used as a plasticizer for vinyl polymers. It is also used in air sanitizer products, such as "Oust" or "Clean and Pure". When aerosolized it acts as a disinfectant. Glycols are also used as liquid desiccants for natural gas and in air conditioning systems. It is an additive for hydraulic fluids and brake fluids and is used as a base for "smoke machine" fluid in the entertainment industry.

<span class="mw-page-title-main">Ethylene glycol dinitrate</span> Chemical compound

Ethylene Glycol Dinitrate, abbreviated EGDN and NGC, also known as Nitroglycol, is a chemical compound a colorless, oily explosive liquid obtained by nitrating Ethylene Glycol. It is similar to Nitroglycerin in both manufacture and properties, though it is more volatile and less viscous. Unlike Nitroglycerine, the chemical has a perfect (0) Oxygen balance, meaning that its ideal exothermic decomposition would completely convert it to low energy CO2, H2O, and N2, with no excess unreacted O2, H2, C, or other substances, without needing to react with anything else.

<span class="mw-page-title-main">Triacetin</span> Chemical compound

Triacetin, is the organic compound with the formula C3H5(OCOCH3)3. It is classified as a triglyceride, i.e., the triester of glycerol. It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations. It is one of the glycerine acetate compounds.

<span class="mw-page-title-main">Nitroglycerin (medication)</span> Medication

Nitroglycerin, also known as glyceryl trinitrate (GTN), is a medication used for heart failure, high blood pressure, anal fissures, painful periods, and to treat and prevent chest pain caused by decreased blood flow to the heart (angina) or due to the recreational use of cocaine. This includes chest pain from a heart attack. It is taken by mouth, under the tongue, applied to the skin, or by injection into a vein.

<span class="mw-page-title-main">Propylene glycol dinitrate</span> Chemical compound

Propylene glycol dinitrate (PGDN, ttup 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrate group. It is a characteristically and unpleasantly smelling colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive and burns with a clean flame producing water vapor, carbon monoxide, and nitrogen gas.

<span class="mw-page-title-main">2-Nitrodiphenylamine</span> Chemical compound

2-Nitrodiphenylamine, also called NDPA, 2-NDPA, 2NO2DPA, Sudan Yellow 1339, C.I. 10335, CI 10335, phenyl 2-nitrophenylamine, 2-nitro-N-phenylaniline, or N-phenyl-o-nitroaniline, is an organic chemical, a nitrated aromatic amine, a derivate of diphenylamine. Its chemical formula is C12H10N2O2, or C6H5NHC6H4NO2. It is a red crystalline solid, usually in form of flakes or powder, with melting point of 74-76 °C and boiling point of 346 °C. It is polar but hydrophobic.

A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic chemical reactions. Pyrotechnic substances do not rely on oxygen from external sources to sustain the reaction.

<span class="mw-page-title-main">1,2,4-Butanetriol trinitrate</span> Chemical compound

1,2,4-Butanetriol trinitrate (BTTN), also called butanetriol trinitrate, is an important military propellant. It is a colorless to brown explosive liquid.

<span class="mw-page-title-main">Diethylene glycol dinitrate</span> Chemical compound

Diethylene glycol dinitrate is a nitrated alcohol ester produced by the action of concentrated nitric acid on diethylene glycol, normally with an excess of strong sulfuric acid as a dehydrating agent.

<span class="mw-page-title-main">Nitrovasodilator</span>

A nitrovasodilator is a pharmaceutical agent that causes vasodilation by donation of nitric oxide (NO), and is mostly used for the treatment and prevention of angina pectoris.

<span class="mw-page-title-main">Trimethylolethane trinitrate</span> Chemical compound

Trimethylolethane trinitrate (TMETN), also known as metriol trinitrate or nitropentaglycerin, is a nitrate ester. It is a high explosive similar to nitroglycerin. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some solid propellants and smokeless powders as a plasticizer. Its chemical formula is CH3−C(CH2−O−NO2)3.

<span class="mw-page-title-main">Trimethylolethane</span> Chemical compound

Trimethylolethane (TME) is the organic compound with the formula CH3C(CH2OH)3. This colorless solid is a triol, as it contains three hydroxy functional groups. More specifically, it features three primary alcohol groups in a compact neopentyl structure. Its esters are known for their resistance to heat, light, hydrolysis, and oxidation. More important than TME and closely related is trimethylolpropane (TMP).

<span class="mw-page-title-main">Nitrate ester</span> Chemical group (–ONO2)

In organic chemistry, a nitrate ester is an organic functional group with the formula R−ONO2, where R stands for any organic residue. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a nitro compound, despite its name.

References

  1. Triethylene glycol dinitrate at ChemYQ
  2. Pentagon reports Archived 2012-09-03 at the Wayback Machine at stormingmedia.us