693-21-0

Basic information

• Product Name: DEGN
• Synonyms: DEGN;DINITRODIGLYCOL;DIGLYCOLDINITRATE;DIETHYLENEGLYCOL DINITRATE;1-nitrooxy-2-(2-nitrooxy-ethoxy)-ethane;2,2’-oxybis-ethanodinitrate;2,2'-Oxydiethanol dinitrate;2-[2-(Nitrooxy)ethoxy]ethyl nitrate
• CAS NO: 693-21-0
• Molecular Formula: C₄H₈N₂O₇
• Molecular Weight: 196.12
• EINECS: 211-745-8
• Mol File: 693-21-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: -11.2°C
• Boiling Point: 332.98°C (rough estimate)
• Appearance: /
• Density: 1.8145 (rough estimate)
• Vapor Pressure: 0.79Pa at 25℃
• Refractive Index: 1.4520 (estimate)
• Water Solubility: 3.9g/L at 25℃
• CAS DataBase Reference: DEGN(CAS DataBase Reference)
• NIST Chemistry Reference: DEGN(693-21-0)
• EPA Substance Registry System: DEGN(693-21-0)

Safety Data

• Hazard Codes: E,T+
• Statements: 3-26/27/28-33-52/53
• Safety Statements: 33-35-36/37-45-61
• RIDADR: 0473
• HazardClass: 1.1A
• Hazardous Substances Data: 693-21-0(Hazardous Substances Data)

Usage

General Description

A liquid. Extremely sensitive explosive if not properly desensitized with a phlegmatizer. Slightly soluble in alcohol and soluble in ether. Specific gravity 1.38. Slightly toxic by ingestion. May explode under prolonged exposure to heat or fire or from sudden shock. The primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments . Used as a rocket propellant.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Nitroorganics, such as DEGN, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive.

Health Hazard

Fire may produce irritating, corrosive and/or toxic gases.

Fire Hazard

MAY EXPLODE AND THROW FRAGMENTS 1600 meters (1 MILE) OR MORE IF FIRE REACHES CARGO.

InChI:InChI=1/C4H6N4O13/c9-5(10)17-1-3(20-7(13)14)19-4(21-8(15)16)2-18-6(11)12/h3-4H,1-2H2

Synthetic route

diethylene glycol (111-46-6) → diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With carbon dioxide; dinitrogen pentoxide at 0℃; under 45004.5 - 60006 Torr; for 0.5h; Autoclave;	98%
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid

1,1'-oxybis(2-bromo-ethane) (5414-19-7) → diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With silver nitrate In acetonitrile at 70℃; for 16h; Darkness;	93.4%

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;

2,2'-diiodoethyl ether (34270-90-1) → diethylene glycol dinitrate (693-21-0)

Conditions	Yield
With nitric acid

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.

diethylene glycol (111-46-6) + HNO3+H2SO4 → diethylene glycol dinitrate (693-21-0)

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

pyridine (110-86-1) + diethylene glycol dinitrate (693-21-0) → 1,1'-(3-oxa-pentanediyl)-bis-pyridinium; dinitrate

Upstream product

• 74-85-1 ethene 
• 111-46-6 diethylene glycol 
• 75-21-8 oxirane 
• 5414-19-7 1,1'-oxybis(2-bromo-ethane) 
• 7732-18-5 water 
• 67-64-1 acetone 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 34270-90-1 2,2'-diiodoethyl ether 

Relevant articles and documents

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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.