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{{More citations needed|date=October 2022}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 399897398 |
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| verifiedrevid = 445844227 |
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|ImageFile=Diethylene glycol dinitrate.png |
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| Name = Diethylene glycol dinitrate |
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|ImageSize=200px |
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| ImageFile1 = Diethylene glycol dinitrate.png |
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|IUPACName=Nitric acid 2-(2-nitrooxyethoxy)ethyl ester |
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| ImageSize1 = |
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|OtherNames=Diethyleneglycol dinitrate<br>Diethyl glycol dinitrate<br>Oxydiethylene dinitrate |
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| ImageFile2 = DEGDN.JPG |
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|Section1= {{Chembox Identifiers |
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| ImageSize2 = 150px |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PIN = Oxydi(ethane-2,1-diyl) dinitrate |
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| OtherNames = Diethyleneglycol dinitrate<br>Diethyl glycol dinitrate<br>Oxydiethylene dinitrate<br>DEGDN |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 55142 |
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| ChemSpiderID = 55142 |
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| InChI = 1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 |
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| InChI = 1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LYAGTVMJGHTIDH-UHFFFAOYSA-N |
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| StdInChIKey = LYAGTVMJGHTIDH-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=693-21-0 |
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| CASNo=693-21-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=61198 |
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| UNII = 77W50O99G1 |
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| UNNumber = ] |
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| PubChem=61198 |
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| SMILES=C(CO(=O))OCCO(=O) |
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| UNNumber = ] |
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}} |
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| SMILES=C(CO(=O))OCCO(=O) |
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|Section2= {{Chembox Properties |
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}} |
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| Formula=C<sub>4</sub>H<sub>8</sub>N<sub>2</sub>O<sub>7</sub> |
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| Section2 = {{Chembox Properties |
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| MolarMass=196.12 g/mol |
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| C=4 | H=8 | N=2 | O=7 |
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| Appearance= |
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| Appearance= Colorless oily liquid |
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| Density=1.4092 (0 °C)<br/>1.3846 (20 °C) |
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| Odor = Odorless |
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| MeltingPtC=-11.5 |
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| Density=1.4092 g/mL (0 °C)<br/>1.3846 g/mL (20 °C) |
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| BoilingPt=197 °C (decomposes) |
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| MeltingPtC=-11.5 |
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| Solubility=4.1 g/L (24 °C) |
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| BoilingPtC=197 |
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}} |
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| BoilingPt_notes = (decomposes) |
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|Section3= {{Chembox Hazards |
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| Solubility=4.1 g/L (24 °C) |
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| MainHazards= |
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| VaporPressure = 0.007 mmHg (22.4 °C) |
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| FlashPt= |
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| SolubleOther = Soluble in ], ] |
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| Section3 = {{Chembox Hazards |
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'''Diethylene glycol dinitrate''' is a ] ] ] produced by the action of concentrated ], normally admixed with an excess of strong ] as a dehydrating agent, upon ]. |
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'''Diethylene glycol dinitrate''' ('''DEGDN''') is an explosive ] ] ] with the formula C<sub>4</sub>H<sub>8</sub>N<sub>2</sub>O<sub>7</sub>. While chemically similar to numerous other ]s, 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. |
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== Preparation and uses == |
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Diethylene glycol dinitrate is a colorless, odorless, viscous, oily liquid, ] 1.4092 at 0 °C and 1.3846 at 20 °C; freezing point −11.5 °C under a standard atmosphere, the theoretical boiling point of approximately 197 °C difficult to confirm as the compound begins to decompose and spontaneously inflames at or slightly below this temperature. Partial pressure is reported as {{convert|0.007|mmHg|mPa|abbr=on}} at 22.4 °C and {{convert|760|mmHg|abbr=on}}. It is readily miscible in most non-polar solvents, ], and cold ]. Solubility in water (4.1 gm/L at 24 °C) and ] is very low. While chemically similar to a number of powerful ]s, pure diethylene glycol dinitrate is extremely hard to initiate and will not propagate a ]. It inflames only with difficulty (requiring localized heating to decomposition point) unless first atomized, and burns placidly even in quantity. |
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Diethylene glycol dinitrate can be made by ] of ] with ] in presence of a ] like concentrated ]. |
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DEGDN can be mixed with ] or ] to form a ], which is used in smokeless powder for ] and ]. During ], the ] frequently used this mixture in their artillery.<ref>{{cite web |author=Tony DiGiulian |date= |title=History and Technology - Naval Propellants - A Brief Overview |url=http://www.navweaps.com/index_tech/tech-100.htm |accessdate=2022-08-20 |publisher=NavWeaps}}</ref> It has also found use as desensitizing ] because it contributes to the power of the mixture while stabilizing the explosives. |
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Mixed with ] and ] under pressure, diethylene glycol dinitrate forms a tough ] whose characteristics (good ], moderate burn rate and temperature, great resistance to accidental ignition and casual handling) make it well suited as a ] for rocketry. It was widely used in this capacity, by both sides, during World War II. It also found use as a "productive" desensitizer (one that contributes to the overall power of the explosion rather than having a neutral or negative effect) in ] and ] based explosives such as ] and ]. It is also used as ] for ]s. |
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== Toxicity == |
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If ingested, like nitroglycerine, it produces rapid ] through the release of ], NO. Popularly-termed ], NO is a physiological signaling molecule that relaxes smooth muscle. Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve ], substernal ] associated with impaired ] circulation. The rational is that the concurrent headache it induces is somewhat less severe than other ]s. |
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{{Unreferenced section|date=November 2023}} |
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If ingested, like ], it rapidly causes ] through the release of ], a physiological signaling molecule that relaxes smooth muscle.{{Clarify|date=October 2022|reason=what is meant by "relaxes smooth muscle"}} Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve ], which is substernal ] associated with impaired ] circulation.{{Citation needed|date=October 2022}} The rationale is that the concurrent headache it induces is somewhat less severe than other ]s. |
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== Uses == |
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At present, interest in the chemical seems to be mostly historical: more potent ]–metal mixtures have long since supplanted it as a solid propellant; safer explosives have replaced nitroglycerine, true dynamites (the term is often used generically, even by experienced field technicians, to refer to almost any explosive supplied in small, discrete packages) retaining only a few specialist uses. The medical application was never widespread, the standard nitroglycerine being faster acting and almost literally dirt cheap; oral nitrates in any case being only ], not an effective treatment. |
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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 ], not an effective treatment. |
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], diethylene glycol dinitrate, and ] are being considered as replacements for nitroglycerin in propellants. |
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], diethylene glycol dinitrate, and ] are being considered as replacements for nitroglycerin in propellants.<ref>{{cite web |url=http://www.stormingmedia.us/cat/sub/subcat20-57.html |title=Guns and Ordnance: Ammunition and Explosives - Storming Media |publisher=Stormingmedia.us |access-date=2011-12-23 |archive-date=2012-09-03 |archive-url=https://web.archive.org/web/20120903212929/http://www.stormingmedia.us/cat/sub/subcat20-57.html |url-status=dead }}</ref> |
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==See also== |
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*] |
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* ] |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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*W. H. Rinkenbach, ''Industrial Engineering Chemistry'' v19 p925 (1927) Note: the present author has transliterated some terminology and notation in line with modern practice. |
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*W. H. Rinkenbach, ''Industrial Engineering Chemistry'' v19 p925 (1927) Note: the present author has transliterated some terminology and notation in line with modern practice. |
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*Military applications referenced in ''Encyclopedia of Weapons of World War 2''; Gen. Ed. Chris Bishop, c.2003 Friedman/Fairfax NYNY, ISBN 1-58663-762-2 |
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*Military applications referenced in ''Encyclopedia of Weapons of World War 2''; Gen. Ed. Chris Bishop, c.2003 Friedman/Fairfax NYNY, {{ISBN|1-58663-762-2}} |
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{{Nitric oxide signaling}} |
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