628-96-6

Basic information

• Product Name: EGDN
• Synonyms: DINITROETHYLENE GLYCOL;Dinitroglycol;EGDN;ETHYLENEGLYCOLDINITRATE;1,2-ethanediol,dinitrate;1,2-ethanedioldinitrate;dinitrated’ethyleneglycol;dinitrated’ethyleneglycol(french)
• CAS NO: 628-96-6
• Molecular Formula: C₂H₄N₂O₆
• Molecular Weight: 152.06
• EINECS: 211-063-0
• Product Categories: Organics
• Mol File: 628-96-6.mol

Chemical Properties

• Melting Point: -22.8°
• Boiling Point: 274.48°C (rough estimate)
• Flash Point: 2℃
• Appearance: /
• Density: 1.490 g/cm3
• Vapor Pressure: 0.481mmHg at 25°C
• Refractive Index: nD20 1.395
• Storage Temp.: ?20°C
• Water Solubility: 5.2g/L at 25℃
• CAS DataBase Reference: EGDN(CAS DataBase Reference)
• NIST Chemistry Reference: EGDN(628-96-6)
• EPA Substance Registry System: EGDN(628-96-6)

Safety Data

• Hazard Codes: E,T+,Xn
• Statements: 2-26/27/28-33-36-20/21/22-11-3
• Safety Statements: 33-35-36/37-45-26-16
• RIDADR: 0473
• WGK Germany: 2
• HazardClass: 1.1A
• Hazardous Substances Data: 628-96-6(Hazardous Substances Data)

Usage

Uses

Used in Mining and Fuel Industries:
EGDN is used as an explosive ingredient in the mining and fuel industries, where it is mixed with nitroglycerine to create dynamite. This mixture provides a powerful explosive for various applications within these industries.
Used in Military and Security Applications:
EGDN is used as an additive to dynamite in military applications, enhancing its explosive capabilities. Additionally, it is utilized in the detection of hidden bombs by analyzing ambient air for the presence of EGDN, which can indicate the presence of explosives.
Used in Chemical Industry:
As a freezing-point depressant for nitroglycerine, EGDN is used in the chemical industry to lower the freezing point of nitroglycerine, making it more stable and easier to handle in various applications.

Reactivity Profile

EGDN is explosive. Acts as a strong oxidizing agent. Heating to 114°C or above may cause a violent combustion or explosion producing toxic fumes (nitrogen oxides). May also decompose explosively from shock, friction or from a build-up of electrostatic charge that sparks suddenly to ground. Can begin a vigorous reaction that culminates in an explosion if mixed with reducing agents including hydrides, sulfides, and nitrides and numerous ordinary combustible materials. Reacts violently with Al, BP, cyanides, esters, PN2H, P, NaCN, SnCl2, sodium hypophosphite, and thiocyanates. Reacts with acids and with alkalis, including ammonia and amines. Must be stored in a cool, ventilated place, away from acute fire hazards and easily oxidized materials (Sax and Lewis, 1987 p.664).

Hazard

Toxic by skin absorption.

Health Hazard

EGDN causes vasodilation and cardiac effects.

Safety Profile

Can cause lowered blood pressure leading to headache, dizziness, and weakness. Used as an explosive. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES.

Potential Exposure

An explosive ingredient (60%
80%) in dynamite along with nitroglycerine (40%
20%). Although ethylene glycol dinitrate is an explosive in itself, it is primarily used to lower the freezing/melting point of nitroglycerin; together these compounds are the major constituents of commercial dynamite, cordite, and blastine gelatin. Occupational exposure generally involves a mixture of the two compounds. Ethylene glycol dinitrate is 160 times more volatile than nitroglycerin.

Shipping

UN0473 Substances, explosive, n.o.s., Hazard Class: 1.1 A; Labels:1.1A-Explosive (with a mass explosion, hazard); A-Substances which are expected to mass detonate very soon after fire reaches them, Technical Name Required

Incompatibilities

Unstable; highly explosive. Heating may cause violent combustion or explosion producing toxic fumes (nitrogen oxides). May explosively detonate violently from heat above 200℃, mechanical shock, friction, impact or concussion. Not compatible with strong acids and alkalies

InChI:InChI=1/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2

Synthetic route

ethylene glycol (107-21-1) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With carbon dioxide; dinitrogen pentoxide at 0℃; under 45004.5 - 60006 Torr; for 0.5h; Autoclave;	96%
With potassium fluoride; nitrylfluoride In acetonitrile at -30 - -20℃;	94.3%
With nitric acid; urea; europium(III) trifluoromethanesulfonate In cyclohexane at 70℃; for 24h; Schlenk technique;	60%

oxirane (75-21-8) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With dinitrogen pentoxide In dichloromethane at 10 - 15℃; for 0.0833333h; in armoured cupboards;	96%
With dinitrogen tetraoxide; ozone

ethene (74-85-1) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With sulfuric acid; nitric acid und Behandeln des Reaktionsprodukts mit Ammoniumdicarbonat oder Ammoniumdicarbonat-Loesung;
With sulfur trioxide; nitric acid; acetic acid
With dinitrogen pentoxide
technische Darstellung;

ethene (74-85-1) → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With nitric acid Electrolysis.an Platinanode;
With nitric acid; acetic acid Electrolysis.an Platinanode;
With sodium nitrate; acetic acid Electrolysis.an Platinanode;

sodium proprionate (137-40-6) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With sodium nitrate; water Electrolysis.an Platinanode;

methacrylic acid methyl ester (80-62-6) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
at 25 - 90℃; Kinetics;

Iodoethanol (624-76-0) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With nitric acid

N,N'-dinitro-ethane-1,2-diamine; diammonium salt (3315-89-7, 6579-37-9, 10448-93-8) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With nitrylfluoride In acetonitrile

oxirane (75-21-8) → 2-(nitrooxy)ethan-1-ol (16051-48-2) + 1,2-ethyl dinitrate (628-96-6) + triethylene glycol dinitrate (111-22-8) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With nitric acid at 14.9 - 19.9℃; for 0.333333h; density HNO3 1.485 g/cm-3; Further byproducts given;	A 29 % Turnov. B 62.7 % Turnov. C 0.8 % Turnov. D 5.8 % Turnov.
With sulfuric acid; nitric acid at 14.9 - 19.9℃; for 0.333333h; Further byproducts given;	A 3 % Turnov. B 73.7 % Turnov. C 6.7 % Turnov. D 11.4 % Turnov.

oxirane (75-21-8) → 2-(2-hydroxyethoxy)ethyl nitrate (20633-16-3) + 1,2-ethyl dinitrate (628-96-6) + triethylene glycol dinitrate (111-22-8) + diethylene glycol dinitrate (693-21-0) + tetraethyleneglycol dinitrate (71038-55-6) + 2,2'-dinitratediethylsulphate (82205-21-8)

Conditions	Yield
With sulfuric acid; nitric acid at 14.9 - 19.9℃; Product distribution; variation of concentration;	A 0.5 % Turnov. B 56.7 % Turnov. C 8 % Turnov. D 13.8 % Turnov. E 3.4 % Turnov. F 15 % Turnov.

oxirane (75-21-8) → 1,2-ethyl dinitrate (628-96-6) + triethylene glycol dinitrate (111-22-8) + diethylene glycol dinitrate (693-21-0) + 2,2'-dinitratediethylsulphate (82205-21-8)

Conditions	Yield
With sulfuric acid; nitric acid at 14.9 - 19.9℃; for 0.333333h; Further byproducts given;	A 56.7 % Turnov. B 8 % Turnov. C 13.8 % Turnov. D 15 % Turnov.

oxirane (75-21-8) → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0) + tetraethyleneglycol dinitrate (71038-55-6) + 2,2'-dinitratediethylsulphate (82205-21-8)

Conditions	Yield
With sulfuric acid; nitric acid at 14.9 - 19.9℃; for 0.333333h; Further byproducts given;	A 56.7 % Turnov. B 13.8 % Turnov. C 3.4 % Turnov. D 15 % Turnov.

1-nitritoethan-2-ol nitrate (66329-10-0) → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With oxygen; ozone In dichloromethane Yield given;

dipotassium malonate → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With water; potassium nitrate Electrolysis.an Platinanode;

dipotassium succinate → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With water; potassium nitrate Electrolysis.an Platinanode;

sodium levulinate → 1,2-ethyl dinitrate (628-96-6)

Conditions	Yield
With sodium nitrate; water Electrolysis.an Platinanode;

ethene (74-85-1) + nitric acid (7697-37-2) + platinum → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;
Electrolysis;

ethene (74-85-1) + nitric acid (7697-37-2) + acetic acid (64-19-7) + platinum → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;
Electrolysis;

ethene (74-85-1) + acetone (67-64-1) + Ca(NO3)2 + platinum → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;
Electrolysis;

ethene (74-85-1) + acetic acid (64-19-7) + NaNO3 + platinum → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;
Electrolysis;

ethene (74-85-1) + water (7732-18-5) + acetone (67-64-1) + NaNO3 + platinum → 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;
Electrolysis;

ethene (74-85-1) + nitric acid (7697-37-2) + platinum → ethyl nitrate (625-58-1) + butyl nitrate (928-45-0) + 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;

ethene (74-85-1) + nitric acid (7697-37-2) + acetic acid (64-19-7) + platinum → ethyl nitrate (625-58-1) + butyl nitrate (928-45-0) + 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;

ethene (74-85-1) + acetone (67-64-1) + Ca(NO3)2 + platinum → ethyl nitrate (625-58-1) + butyl nitrate (928-45-0) + 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;

ethene (74-85-1) + acetic acid (64-19-7) + NaNO3 + platinum → ethyl nitrate (625-58-1) + butyl nitrate (928-45-0) + 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;

ethene (74-85-1) + water (7732-18-5) + acetone (67-64-1) + NaNO3 + platinum → ethyl nitrate (625-58-1) + butyl nitrate (928-45-0) + 1,2-ethyl dinitrate (628-96-6) + diethylene glycol dinitrate (693-21-0)

Conditions	Yield
Electrolysis;

...Expand

ethene (74-85-1) → 1,2-ethyl dinitrate (628-96-6) + 2-iodo-ethyl nitrate

Conditions	Yield
With diethyl ether; iodine; mercury(II) nitrate

tetrachloromethane (56-23-5) + ethene (74-85-1) + iodine (7553-56-2) + mercury(II) nitrate → 1,2-ethyl dinitrate (628-96-6) + 2-iodo-ethyl nitrate

diethyl ether (60-29-7) + ethene (74-85-1) + iodine (7553-56-2) + mercury(II) nitrate → 1,2-ethyl dinitrate (628-96-6) + 2-iodo-ethyl nitrate

methyl magnesium iodide (917-64-6) + diethyl ether (60-29-7) + 1,2-ethyl dinitrate (628-96-6) → N,N-dimethylhydroxylamine (5725-96-2)

Conditions	Yield
und Zersetzen des Reaktionsprodukts mit Wasser;reagiert analog mit Aethylmagnesiumbromid;

methyl magnesium iodide (917-64-6) + 1,2-ethyl dinitrate (628-96-6) → N,N-dimethylhydroxylamine (5725-96-2)

Conditions	Yield
With diethyl ether erst in der Kaelte,dann bei Zimmertemperatur und Zersetzen des Reaktionsprodukts mit Wasser;

diethyl ether (60-29-7) + 1,2-ethyl dinitrate (628-96-6) + methylmagnesium iodide → N,N-dimethylhydroxylamine (5725-96-2)

diethyl ether (60-29-7) + 1,2-ethyl dinitrate (628-96-6) + ethylmagnesium bromide → N-ethyl-N-hydroxy-ethanamine (3710-84-7)

1,2-ethyl dinitrate (628-96-6) + ethylmagnesium bromide (925-90-6) → N-ethyl-N-hydroxy-ethanamine (3710-84-7)

Conditions	Yield
With diethyl ether

1,2-ethyl dinitrate (628-96-6) + benzyl alcohol (100-51-6) + oxygen → benzaldehyde (100-52-7)

Conditions	Yield
at 135 - 145℃;

Upstream product

• 7697-37-2 nitric acid 
• 107-21-1 ethylene glycol 
• 74-85-1 ethene 
• 137-40-6 sodium proprionate 
• 60-29-7 diethyl ether 
• 7553-56-2 iodine 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 67-64-1 acetone 
• 64-19-7 acetic acid 
• 66329-10-0 1-nitritoethan-2-ol nitrate 
• 75-21-8 oxirane 
• 3315-89-7 N,N'-dinitro-ethane-1,2-diamine; diammonium salt 
• 624-76-0 Iodoethanol 

Downstream Products

• 5725-96-2 N,N-dimethylhydroxylamine 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 
• 119-61-9 benzophenone 
• 91-01-0 1,1-Diphenylmethanol 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Practical catalytic nitration directly with commercial nitric acid for the preparation of aliphatic nitroesters

To pursue a sustainable and efficient approach for aliphatic nitroester preparation from alcohol, europium-triflate-catalyzed nitration, which directly uses commercial nitric acid, has been successfully developed. Gram scalability with operational ease showed its practicability.

Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system

Organic nitric acid esters have been prepared in 89-98% yield by the nitration of the corresponding alcohols and polyols with N2O5 in liquid CO2.

Nitration of alcohols by nitryl fluoride

A general method for the preparation of nitrates by treatment of alcohols with nitryl fluoride (FNO2) in MeCN in the presence of KF has been developed.

Separation of Diastereomeric and Enantiomeric Alkyl Nitrates - Systematic Approach to Chiral Discrimination on Cyclodextrin LIPODEX-D

High-resolution gas chromatographic separation of all diastereomeric monomethyl-substituted cyclohexyl nitrates is shown on a nonpolar methylpolysiloxane stationary phase, and the first application of this procedure to the environmental diastereomeric analysis of alkyl nitrates is presented.Two characteristic signals in the achiral analysis of atmospheric samples could be assigned to the smallest alkyl nitrate containing two asymmetric carbon atoms, 3-methyl-2-pentyl nitrate.Retention indices in the temperature-programmed separation based on the n-alkanes were determined.The homologous series of 1-alkyl nitrates were found to be useful as ECD-visible n-alkanes.Enantiomeric separation of alkyl nitrates was achieved on heptakis(3-O-acetyl,-2,6-di-O-pentyl)-β-cyclodextrin (LIPODEX-D).The influence of the nitrooxy group and the alkyl chain length on the chiral discrimination on LIPODEX-D is discussed for 25 chiral alkyl nitrates.The absolute configurations of some alkyl nitrates were assigned by asymmetric synthesis of enantiomerically pure references.The complexity of the alkyl nitrate mixtures present in air samoles does not allow a direct chiral separation as the alkyl nitrates partly coelute on the LIPODEX-D column.Column coupling of LIPODEX-D with a polar achiral stationary phase like polyalkylenglocol (PAG) was successfully applied to solve this problem, and the chiral alkyl nitrates present in a typical air sample were separated.A systematic nomenclature for alkyl nitrates is introduced to handle the steadily growing number of branched and long-chain nitrates detected in environmental analysis. - Keywords: analytical methods; alkyl nitrates; chiral resolution; cyclodextrins; gas chromatography

Preparation of Di- and polynitrates by ring-opening nitration of epoxides by dinitrogen pentoxide (N2O5)

Eighteen epoxides of various kinds were reacted with N2O5 in chlorinated hydrocarbon solvents (principally CH2Cl2) to give vicinal nitrate ester products by a novel ring-opening nitration reaction. The procedure offers easier temperature control and simpler isolation procedures compared with conventional mixed acid nitrations; it also enables selective nitration reactions to be carried out on polyfunctional substrates. The scope and limitations of the reaction, as well as those of an alternative route utilising N2O4 with in situ oxidation of an intermediate nitrite-nitrate, are discussed.

NITRATION BY OXIDES OF NITROGEN, PART 1: PREPARATION OF NITRATE ESTERS BY REACTION OF STRAINED-RING OXYGEN HETEROCYCLES WITH DINITROGEN PENTOXIDE

Epoxides and oxetanes react with dinitrogen pentoxide to give the corresponding dinitrates in high to near quantitative yields.The scope and limitations of the method are briefly discussed.

About the Nitration of Ethylene Oxide

Nitration of ethylene oxide with pure nitric acid of different concentrations as well as in presence of sulphuric acid was carried out.The products, ethyleneglycol dinitrate 1, diethyleneglycol dinitrate 2, triethyleneglycol dinitrate 3, tetraethyleneglycol dinitrate 4, ethyleneglycol mononitrate 5, diethyleneglycol mononitrate 6, and 2,2'-dinitratediethylsulphate 7 were structurally determined by i.r.- and 1H-n.m.r.-spectroscopy.