Difference between revisions of "Ethylene glycol dinitrate"

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Ethylene Glycol Dinitrate, IUPAC name 1,2-dinitroxyethane, also known as Nitroglycol or EGDN, is a pale yellow, syrupy, explosive liquid. In the series of [[alkyl nitrates]] it is among those which have a 1:1 rato of nitroxy groups per carbon atom, and also exhibits a perfect [[oxygen balance]].
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| Name = Ethylene glycol dinitrate
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| Reference =
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| IUPACName = 1,2-dinitroxyethane
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| PIN =
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| SystematicName =
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| OtherNames = 1,2-Bis(nitrooxy)ethane<br>1,2-Ethanediol dinitrate<br>Dinitroglycol<br>EGDN<br>Ethylene dinitrate<br>Ethylene glycol dinitrate<br>Ethylene nitrate<br>Ethane-1,2-diyl dinitrate<br>Glycol dinitrate<br>Nitroglycol
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| ImageFile = EGDN structure.png
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless to yellow liquid
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| BoilingPt =
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| BoilingPtC = 197.5
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 1.4918 g/cm<sup>3</sup> (20 °C)
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| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>2</sub>O<sub>6</sub>
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| HenryConstant =
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| MolarMass = 152.1 g/mol
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| MeltingPt =
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| MeltingPtC = −22.3
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| Odor = Odorless
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| pKa =
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| Solubility = 0.5 g/100 ml
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| SolubleOther = Miscibile with glacial [[acetic acid]], [[acetone]], [[benzene]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[chloroform]], [[diethyl ether]], [[methanol]], [[toluene]]
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| Solvent =
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| VaporPressure = 0.05 mmHg (20 °C)
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| DeltaHc = 265.9 kcal/mol
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| Section5 = {{Chembox Explosive
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| ShockSens = Medium
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| FrictionSens = Medium
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| DetonationV = 8300 m/s
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| ExternalMSDS = [http://www.cpcb.nic.in/divisionsofheadoffice/pci-ssi/MATERIAL_SAFETY-DATABASE/MSDS2008/268.pdf cpcb]
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| FlashPt = 215 °C (419 °F, 488 K)
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| MainHazards = Explosive
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| OtherCompounds = [[Methyl nitrate]]<br>[[Nitroglycerin]]
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'''Ethylene glycol dinitrate''', IUPAC name '''1,2-dinitroxyethane''', also known as '''nitroglycol''' or '''EGDN''', is a pale yellow, syrupy, explosive liquid. In the series of [[alkyl nitrate]]s it is among those which have a 1:1 ratio of nitroxy groups per carbon atom, and also exhibits a perfect [[oxygen balance]].
  
 
==Properties==
 
==Properties==
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==Preparation==
 
==Preparation==
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EGDN can be prepared by nitrating [[ethylene glycol]] under careful monitoring.
  
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==Safety==
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Another route is the reaction between [[ethylene oxide]] and [[dinitrogen pentoxide]], in the presence of [[ozone]]. Reaction takes place in [[dichloromethane]] for 5 min, at temperatures between 10-15 °C. Yield is 96%.<ref>[http://www.sciencedirect.com/science/article/pii/0040403988852729 Golding, P.; Millar, R. W.; Paul, N. C.; Richards, D. H.; Tetrahedron Letters; vol. 29; nb. 22; (1988); p. 2731 - 2734]</ref><ref>[http://www.sciencedirect.com/science/article/pii/S0040402001879783 Golding, Peter; Millar, Ross W.; Paul, Norman C.; Richards, David H.; Tetrahedron; vol. 49; nb. 32; (1993); p. 7037-7050]</ref>
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==Handling==
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===Safety===
 
Like nitroglycerin, EGDN is highly explosive, although somewhat less sensitive to impact. One disadvantage EGDN has against NG is that EGDN is more volatile. This makes a person working with it more susceptible to its [[wikipedia:Nitrovasodilator|vasodilation]] effects, which is where the nitro group in the nitrated alcohol causes the body to widen blood vessels, resulting in phenomenal headaches.
 
Like nitroglycerin, EGDN is highly explosive, although somewhat less sensitive to impact. One disadvantage EGDN has against NG is that EGDN is more volatile. This makes a person working with it more susceptible to its [[wikipedia:Nitrovasodilator|vasodilation]] effects, which is where the nitro group in the nitrated alcohol causes the body to widen blood vessels, resulting in phenomenal headaches.
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===Storage===
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Never store EGDN! Use it as soon as possible.
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===Disposal===
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EGDN can be neutralized by strongly dilute it in an organic solvent, then carefully burning the extremely diluted solution.
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Diluted cold sodium hydroxide solution can also be used to neutralize diluted EGDN.
  
 
==References==
 
==References==
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Chemistry and Technology of Explosives - Volume II, first edition, 1965.
 
Chemistry and Technology of Explosives - Volume II, first edition, 1965.
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=5057 Playing with EGDN]
  
 
[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
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[[Category:Energetic materials]]
 
 
[[Category:Nitrates]]
 
[[Category:Nitrates]]
 
[[Category:Nitrated organic compounds]]
 
[[Category:Nitrated organic compounds]]
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[[Category:Energetic materials]]
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[[Category:High explosives]]
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[[Category:Liquids]]

Latest revision as of 20:03, 25 October 2020

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Ethylene glycol dinitrate
EGDN structure.png
Names
IUPAC name
1,2-dinitroxyethane
Other names
1,2-Bis(nitrooxy)ethane
1,2-Ethanediol dinitrate
Dinitroglycol
EGDN
Ethylene dinitrate
Ethylene glycol dinitrate
Ethylene nitrate
Ethane-1,2-diyl dinitrate
Glycol dinitrate
Nitroglycol
Properties
C2H4N2O6
Molar mass 152.1 g/mol
Appearance Colorless to yellow liquid
Odor Odorless
Density 1.4918 g/cm3 (20 °C)
Melting point −22.3 °C (−8.1 °F; 250.8 K)
Boiling point 197.5 °C (387.5 °F; 470.6 K)
0.5 g/100 ml
Solubility Miscibile with glacial acetic acid, acetone, benzene, CCl4, chloroform, diethyl ether, methanol, toluene
Vapor pressure 0.05 mmHg (20 °C)
Thermochemistry
Hazards
Safety data sheet cpcb
Flash point 215 °C (419 °F, 488 K)
Related compounds
Related compounds
 Methyl nitrate
Nitroglycerin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ethylene glycol dinitrate, IUPAC name 1,2-dinitroxyethane, also known as nitroglycol or EGDN, is a pale yellow, syrupy, explosive liquid. In the series of alkyl nitrates it is among those which have a 1:1 ratio of nitroxy groups per carbon atom, and also exhibits a perfect oxygen balance.

Properties

Explosive

Thanks to its perfect oxygen balance, EGDN is one of the strongest explosives known, with a lead block test value of 650 cm3 (10% higher than NG). It is more sensitive to initiation but can also detonate incompletely with low velocity. The reported detonation velocity is around 7800 m/s.

Physical

Its properties are very similar to nitroglycerin. It is however less viscous, less dense and more volatile. The freezing point is -22 °C, and it has therefore been used for dynamites in cold climates.

Preparation

EGDN can be prepared by nitrating ethylene glycol under careful monitoring.

Another route is the reaction between ethylene oxide and dinitrogen pentoxide, in the presence of ozone. Reaction takes place in dichloromethane for 5 min, at temperatures between 10-15 °C. Yield is 96%.[1][2]

Handling

Safety

Like nitroglycerin, EGDN is highly explosive, although somewhat less sensitive to impact. One disadvantage EGDN has against NG is that EGDN is more volatile. This makes a person working with it more susceptible to its vasodilation effects, which is where the nitro group in the nitrated alcohol causes the body to widen blood vessels, resulting in phenomenal headaches.

Storage

Never store EGDN! Use it as soon as possible.

Disposal

EGDN can be neutralized by strongly dilute it in an organic solvent, then carefully burning the extremely diluted solution.

Diluted cold sodium hydroxide solution can also be used to neutralize diluted EGDN.

References

  1. ↑ Golding, P.; Millar, R. W.; Paul, N. C.; Richards, D. H.; Tetrahedron Letters; vol. 29; nb. 22; (1988); p. 2731 - 2734
  2. ↑ Golding, Peter; Millar, Ross W.; Paul, Norman C.; Richards, David H.; Tetrahedron; vol. 49; nb. 32; (1993); p. 7037-7050

Chemistry and Technology of Explosives - Volume II, first edition, 1965.

Relevant Sciencemadness threads

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