diethylene glycol dinitrate
{{chembox
| Watchedfields = changed
| verifiedrevid = 445844227
| Name = Diethylene glycol dinitrate
| ImageFile1 = Diethylene glycol dinitrate.png
| ImageSize1 =
| PIN = Oxydi(ethane-2,1-diyl) dinitrate
| OtherNames = Diethyleneglycol dinitrate
Diethyl glycol dinitrate
Oxydiethylene dinitrate
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
| InChIKey = LYAGTVMJGHTIDH-UHFFFAOYAD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H8N2O7/c7-5(8)12-3-1-11-2-4-13-6(9)10/h1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LYAGTVMJGHTIDH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=693-21-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 77W50O99G1
| PubChem=61198
| UNNumber = 0075
| SMILES=C(CO[N+](=O)[O-])OCCO[N+](=O)[O-]
}}
| Section2 = {{Chembox Properties
| C=4 | H=8 | N=2 | O=7
| Appearance= Colorless oily liquid
| Odor = Odorless
| Density=1.4092 g/mL (0 °C)
1.3846 g/mL (20 °C)
| MeltingPtC=-11.5
| BoilingPtC=197
| BoilingPt_notes = (decomposes)
| Solubility=4.1 g/L (24 °C)
| VaporPressure = 0.007 mmHg (22.4 °C)
| SolubleOther = Soluble in methanol, acetic acid
}}
| Section3 = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}
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Diethylene glycol dinitrate (DEGDN) is an explosive nitrated alcohol ester with the formula C4H8N2O7. It is commonly used as a plasticizer in propellant or explosive formulations.{{Cite book |last=Kubota |first=Naminosuke |title=Propellants and explosives: thermochemical aspects of combustion |date=2015 |publisher=Wiley-VCH |isbn=978-3-527-69348-1 |edition=3 |location=Weinheim}} While chemically similar to numerous other high explosives, pure diethylene glycol dinitrate is difficult to ignite. Ignition typically requires localized heating to the decomposition point unless the DEGDN is first atomized. It is sensitive to detonation by impact but not due to friction.{{Cite journal |last=Hoque |first=Ehtasimul |last2=Pant |first2=Chandra Shekhar |last3=Das |first3=Sushanta |date=2020-03-09 |title=Study on Friction Sensitivity of Passive and Active Binder based Composite Solid Propellants and Correlation with Burning Rate |url=https://publications.drdo.gov.in/ojs/index.php/dsj/article/view/14802 |journal=Defence Science Journal |volume=70 |issue=2 |pages=159–165 |doi=10.14429/dsj.70.14802 |issn=0976-464X|doi-access=free }}
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.{{Cite journal |last=Rinkenbach |first=Wm. H. |last2=Aaronson |first2=H. A. |date=1931 |title=Nitration of Diethylene Glycol |url=https://pubs.acs.org/doi/abs/10.1021/ie50254a014 |journal=Industrial & Engineering Chemistry |language=en |volume=23 |issue=2 |pages=160–163 |doi=10.1021/ie50254a014 |issn=0019-7866|url-access=subscription }}
Toxicity
If ingested, like nitroglycerine, it rapidly causes vasodilation through the release of nitric oxide, a physiological signaling molecule that relaxes vascular smooth muscle which leads to a rapid loss in blood pressure. Other acute effects include convulsions and loss of consciousness.{{Cite web |title=ICSC 1473 - DIETHYLENE GLYCOL DINITRATE |url=https://chemicalsafety.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=1473 |access-date=2025-03-08 |website=chemicalsafety.ilo.org}} Its median lethal dose (LD50) is 650 mg/kg in guinea pigs.{{Cite web |last=PubChem |title=Diethylene glycol dinitrate |url=https://pubchem.ncbi.nlm.nih.gov/compound/Diethylene-glycol-dinitrate#section=Acute-Effects |access-date=2025-03-08 |website=pubchem.ncbi.nlm.nih.gov |language=en}}
Uses
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.{{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}}
Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate can be used as less-sensitive as replacements for nitroglycerin in propellants.{{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 }}
See also
References
{{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}}
{{Nitric oxide signaling}}