Diethylene glycol dinitrate

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Diethylene glycol dinitrate
Diethylene glycol dinitrate.png
DEGDN.JPG
Names
Preferred IUPAC name
Oxydi(ethane-2,1-diyl) dinitrate
Other names
Diethyleneglycol dinitrate
Diethyl glycol dinitrate
Oxydiethylene dinitrate
DEGDN
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.679 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
UN number 0075
  • InChI=1S/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 Yes check.svgY
    Key: LYAGTVMJGHTIDH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2
    Key: LYAGTVMJGHTIDH-UHFFFAOYAD
  • C(CO[N+](=O)[O-])OCCO[N+](=O)[O-]
Properties
C4H8N2O7
Molar mass 196.115 g·mol−1
AppearanceColorless oily liquid
Odor Odorless
Density 1.4092 g/mL (0 °C)
1.3846 g/mL (20 °C)
Melting point −11.5 °C (11.3 °F; 261.6 K)
Boiling point 197 °C (387 °F; 470 K) (decomposes)
4.1 g/L (24 °C)
Solubility Soluble in methanol, acetic acid
Vapor pressure 0.007 mmHg (22.4 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite or detonate. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized.

Contents

Preparation and uses

Diethylene glycol dinitrate can be made by nitration of diethylene glycol with nitric acid in presence of a dehydrating agent like concentrated sulfuric acid.

DEGDN can be mixed with nitrocellulose or nitroglycol to form a colloid, which is used in smokeless powder for artillery and rocket propellant. During World War II, the Kriegsmarine frequently used this mixture in their artillery. [1] It has also found use as desensitizing plasticizer because it contributes to the power of the mixture while stabilizing the explosives.

Toxicity

If ingested, like nitroglycerine, it rapidly causes vasodilation through the release of nitric oxide, a physiological signaling molecule that relaxes smooth muscle.[ clarification needed ] Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve angina, which is substernal chest pain associated with impaired cardiac circulation.[ citation needed ] The rationale is that the concurrent headache it induces is somewhat less severe than other nitro compounds.

Uses

At present, interest in the chemical seems to be mostly historical retaining only a few specialist uses. The medical application was never widespread, the standard nitroglycerine being faster acting and very inexpensive; oral nitrates in any case being only palliative, not an effective treatment.

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

See also

Related Research Articles

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

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. Discovered in 1847 by Ascanio Sobrero, 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, which has been used as a propellant in artillery and firearms since the 1880s.

<span class="mw-page-title-main">Nitric acid</span> Highly corrosive mineral acid

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

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<span class="mw-page-title-main">Ethylene glycol</span> Organic compound ethane-1,2-diol

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

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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.

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

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<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 colorless, oily, explosive liquid obtained by nitrating ethylene glycol. It is similar to nitroglycerine in both manufacture and properties, though it is more volatile and less viscous. Unlike nitroglycerine, the chemical has a perfect oxygen balance, meaning that its ideal exothermic decomposition would completely convert it to low energy carbon dioxide, water, and nitrogen gas, with no excess unreacted substances, without needing to react with anything else.

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

Propylene glycol dinitrate (PGDN, 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.

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<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.

Triethylene glycol dinitrate (TEGDN) is an, ether, nitrated alcohol ester of triethylene glycol. It is used as an energetic plasticizer in explosives and propellants. It is a pale yellow oily liquid. It is somewhat similar to nitroglycerin.

Bulk loaded liquid propellants are an artillery technology that was pursued at the U.S. Army Research Laboratory and U.S. Naval Weapons Center from the 1950s through the 1990s. The advantages would be simpler guns and a wider range of tactical and logistic options. Better accuracy and tactical flexibility would theoretically come from standard shells with varying propellant loads, and logistic simplification by eliminating varying powder loads.

References

  1. Tony DiGiulian. "History and Technology - Naval Propellants - A Brief Overview". NavWeaps. Retrieved 2022-08-20.
  2. "Guns and Ordnance: Ammunition and Explosives - Storming Media". Stormingmedia.us. Archived from the original on 2012-09-03. Retrieved 2011-12-23.