Diethylene glycol dinitrate: Difference between revisions

Diethylene glycol dinitrate
Names
	Preferred IUPAC name Oxydi(ethane-2,1-diyl) dinitrate
	Other names Diethyleneglycol dinitrate; Diethyl glycol dinitrate; Oxydiethylene dinitrate; DEGDN
Identifiers
CAS Number	693-21-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	55142 ;
ECHA InfoCard	100.010.679
PubChem CID	61198;
UNII	77W50O99G1 ;
UN number	0075
CompTox Dashboard (EPA)	DTXSID1024047 ;
	InChI InChI=1S/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 Key: LYAGTVMJGHTIDH-UHFFFAOYSA-N ; InChI=1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2 Key: LYAGTVMJGHTIDH-UHFFFAOYAD;
	SMILES C(CO[N+](=O)[O-])OCCO[N+](=O)[O-];
Properties
Chemical formula	C4H8N2O7
Molar mass	196.115 g·mol−1
Appearance	Colorless 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)
Solubility in water	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). verify (what is ?) Infobox references

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

Inline

Latest revision as of 17:55, 3 June 2024

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.

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]

References

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

W. H. Rinkenbach, Industrial Engineering Chemistry v19 p925 (1927) Note: the present author has transliterated some terminology and notation in line with modern practice.
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

[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.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{More citations needed|date=October 2022}}
 {{chembox
-| Watchedfields = changed
+| Watchedfields  = changed
-| verifiedrevid = 445844227
+| verifiedrevid  = 445844227
-|ImageFile=Diethylene glycol dinitrate.png
+| Name           = Diethylene glycol dinitrate
+| ImageFile1     = Diethylene glycol dinitrate.png
-|ImageSize=200px
+| ImageSize1     =
-|IUPACName=Nitric acid 2-(2-nitrooxyethoxy)ethyl ester
+| ImageFile2     = DEGDN.JPG
-|OtherNames=Diethyleneglycol dinitrate<br>Diethyl glycol dinitrate<br>Oxydiethylene dinitrate
+| ImageSize2     = 150px
-|Section1= {{Chembox Identifiers
+| PIN            = Oxydi(ethane-2,1-diyl) dinitrate
-|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| OtherNames     = Diethyleneglycol dinitrate<br>Diethyl glycol dinitrate<br>Oxydiethylene dinitrate<br>DEGDN
+| Section1       = {{Chembox Identifiers
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 55142
 | InChI = 1/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2
@@ Line 17: / Line 22: @@
 | CASNo_Ref = {{cascite|correct|??}}
 | CASNo=693-21-0
+| UNII_Ref = {{fdacite|correct|FDA}}
-|  PubChem=61198
+| UNII = 77W50O99G1
-|  UNNumber = [[List of UN Numbers 0001 to 0100|0075]]
+| PubChem=61198
-|  SMILES=C(CO[N+](=O)[O-])OCCO[N+](=O)[O-]
+| UNNumber = [[List of UN Numbers 0001 to 0100|0075]]
-  }}
+| SMILES=C(CO[N+](=O)[O-])OCCO[N+](=O)[O-]
-|Section2= {{Chembox Properties
+}}
-|  C=4|H=8|N=2|O=7
+| Section2       = {{Chembox Properties
-|  Appearance=
+| C=4 | H=8 | N=2 | O=7
-|  Density=1.4092 g/mL (0&nbsp;°C)<br/>1.3846 g/mL (20&nbsp;°C)
+| Appearance= Colorless oily liquid
-|  MeltingPtC=-11.5
+| Odor = Odorless
-|  BoilingPtC=197
+| Density=1.4092 g/mL (0&nbsp;°C)<br/>1.3846 g/mL (20&nbsp;°C)
-|  Boiling_notes = decomposes
+| MeltingPtC=-11.5
-|  Solubility=4.1&nbsp;g/L (24&nbsp;°C)
+| BoilingPtC=197
-  }}
+| BoilingPt_notes = (decomposes)
-|Section3= {{Chembox Hazards
+| Solubility=4.1&nbsp;g/L (24&nbsp;°C)
-|  MainHazards=
+| VaporPressure = 0.007&nbsp;mmHg (22.4&nbsp;°C)
-|  FlashPt=
+| SolubleOther   = Soluble in [[methanol]], [[acetic acid]]
-|  Autoignition=
-  }}
+}}
+| Section3       = {{Chembox Hazards
+| MainHazards=
+| FlashPt=
+| AutoignitionPt =
+}}
 }}
-'''Diethylene glycol dinitrate''' is a [[nitration|nitrated]] [[alcohol]] [[ester]] produced by the action of concentrated [[nitric acid]], normally admixed with an excess of strong [[sulfuric acid]] as a dehydrating agent, upon [[diethylene glycol]].
+'''Diethylene glycol dinitrate''' ('''DEGDN''') is an explosive [[nitration|nitrated]] [[Alcohol (chemistry)|alcohol]] [[ester]] 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 [[high explosive]]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.
+== Preparation and uses ==
-Diethylene glycol dinitrate is a colorless, odorless, viscous, oily liquid, with [[specific gravity]] 1.4092 at 0&nbsp;°C and 1.3846 at 20&nbsp;°C; freezing point −11.5&nbsp;°C under a standard atmosphere; the theoretical boiling point of approximately 197&nbsp;°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&nbsp;°C and {{convert|760|mmHg|abbr=on}}. It is readily miscible in most non-polar solvents, [[methanol]], and cold [[acetic acid]]. Solubility in water (4.1&nbsp;g/L at 24&nbsp;°C) and [[ethanol]] is very low. While chemically similar to a number of powerful [[high explosive]]s, pure diethylene glycol dinitrate is extremely hard to initiate and will not propagate a [[detonation wave]]. It inflames only with difficulty (requiring localized heating to decomposition point) unless first atomized, and burns placidly even in quantity.
+Diethylene glycol dinitrate can be made by [[nitration]] of [[diethylene glycol]] with [[nitric acid]] in presence of a [[Dehydration reaction|dehydrating agent]] like concentrated [[sulfuric acid]].
+DEGDN can be mixed with [[nitrocellulose]] or [[Ethylene glycol dinitrate|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.<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 [[plasticizer]] because it contributes to the power of the mixture while stabilizing the explosives.
-Mixed with [[nitrocellulose]] and [[extruded]] under pressure, diethylene glycol dinitrate forms a tough [[colloid]] whose characteristics (good [[specific impulse]], moderate burn rate and temperature, great resistance to accidental ignition and casual handling) make it well suited as a [[solid propellant]] 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 [[nitroglycerine]] and [[nitroglycol]]-based explosives such as [[dynamite]] and [[blasting gelatin]]. It is also used as [[plasticizer]] for [[energetic material]]s.
+== Toxicity ==
-If ingested, like nitroglycerine, it produces rapid [[vasodilation]] through the release of [[nitrogen monoxide]], NO.  Popularly-termed [[nitric oxide]], NO is a physiological signaling molecule that relaxes smooth muscle.  Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve [[Angina pectoris|angina]], substernal [[chest pain]] associated with impaired [[cardiac]] circulation.   The rationale is that the concurrent headache it induces is somewhat less severe than other [[nitro compound]]s.
+{{Unreferenced section|date=November 2023}}
+If ingested, like [[Nitroglycerin|nitroglycerine]], it rapidly causes [[vasodilation]] through the release of [[nitric oxide]], 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 [[Angina pectoris|angina]], which is substernal [[chest pain]] associated with impaired [[cardiac]] circulation.{{Citation needed|date=October 2022}} The rationale is that the concurrent headache it induces is somewhat less severe than other [[nitro compound]]s.
+== Uses ==
-At present, interest in the chemical seems to be mostly historical: more potent [[perchlorate]]–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 [[palliative]], not an effective treatment.
+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.<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 |date= |accessdate=2011-12-23}}</ref>
+[[Triethylene glycol dinitrate]], diethylene glycol dinitrate, and [[trimethylolethane trinitrate]] 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>
 ==See also==
+*[[Triethylene glycol dinitrate]]
 * [[TNT equivalent]]
 * [[RE factor]]
@@ Line 56: / Line 71: @@
 {{reflist}}
 *W. H. Rinkenbach, ''Industrial Engineering Chemistry'' v19 p925 (1927) Note: the present author has transliterated some terminology and notation in line with modern practice.
-*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
+*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}}
+{{Nitric oxide signaling}}
-[[Category:Alkyl nitrates]]
+[[Category:Nitrate esters]]
 [[Category:Propellants]]
 [[Category:Monopropellants]]