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Diethylene glycol dinitrate

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Name

Diethylene glycol dinitrate

EINECS N/A
CAS No. 693-21-0 Density 1.8145 (rough estimate)
PSA 119.33000 LogP 0.46600
Solubility 3.9g/L at 25℃ Melting Point -11.2°C
Formula C4H8 N2 O7 Boiling Point 332.98°C (rough estimate)
Molecular Weight 196.117 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Moderately toxic by ingestion. Ingestion of this compound can cause a drop in blood pressure and cardiac disturbances. A dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing or reducing materials. A dangerous explosive sensitive to heat, shock, and vibration. Used in low-freezing dynamites and some permissible explosives. Upon decomposition it emits toxic fumes of NOx. See also GLYCOL ETHERS, NITRATES, and EXPLOSIVES, HIGH. Risk Codes R3; R26/27/28; R33; R52/53
Molecular Structure Molecular Structure of 693-21-0 (DEGN) Hazard Symbols Severe explosion hazard when shocked or heated. Toxic by ingestion.
Synonyms

Diethyleneglycol, dinitrate (6CI,7CI,8CI); Ethanol, 2,2'-oxybis-, dinitrate (9CI);2,2'-Oxydiethanol dinitrate; DEGDN; DEGN; Diglycol dinitrate; Dinitrodiglycol;Oxydiethylene nitrate

Article Data 24

Diethylene glycol dinitrate Synthetic route

111-46-6

diethylene glycol

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
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
5414-19-7

1,1'-oxybis(2-bromo-ethane)

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
With silver nitrate In acetonitrile at 70℃; for 16h; Darkness;93.4%
74-85-1

ethene

A

628-96-6

1,2-ethyl dinitrate

B

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
With nitric acid Electrolysis.an Platinanode;
With nitric acid; acetic acid Electrolysis.an Platinanode;
With sodium nitrate; acetic acid Electrolysis.an Platinanode;
34270-90-1

2,2'-diiodoethyl ether

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
With nitric acid
75-21-8

oxirane

A

16051-48-2

2-(nitrooxy)ethan-1-ol

B

628-96-6

1,2-ethyl dinitrate

C

111-22-8

triethylene glycol dinitrate

D

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
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.
75-21-8

oxirane

A

20633-16-3

2-(2-hydroxyethoxy)ethyl nitrate

B

628-96-6

1,2-ethyl dinitrate

C

111-22-8

triethylene glycol dinitrate

D

693-21-0

diethylene glycol dinitrate

E

71038-55-6

tetraethyleneglycol dinitrate

F

82205-21-8

2,2'-dinitratediethylsulphate

Conditions
ConditionsYield
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.
75-21-8

oxirane

A

628-96-6

1,2-ethyl dinitrate

B

111-22-8

triethylene glycol dinitrate

C

693-21-0

diethylene glycol dinitrate

D

82205-21-8

2,2'-dinitratediethylsulphate

Conditions
ConditionsYield
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.
75-21-8

oxirane

A

628-96-6

1,2-ethyl dinitrate

B

693-21-0

diethylene glycol dinitrate

C

71038-55-6

tetraethyleneglycol dinitrate

D

82205-21-8

2,2'-dinitratediethylsulphate

Conditions
ConditionsYield
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.
111-46-6

diethylene glycol

HNO3+H2SO4

HNO3+H2SO4

693-21-0

diethylene glycol dinitrate

74-85-1

ethene

7697-37-2

nitric acid

platinum

platinum

A

628-96-6

1,2-ethyl dinitrate

B

693-21-0

diethylene glycol dinitrate

Conditions
ConditionsYield
Electrolysis;
Electrolysis;

Diethylene glycol dinitrate Chemical Properties

Chemical Name: DEGN
IUPAC NAME: 2-(2-Nitrooxyethoxy)ethyl nitrate
CAS No.: 693-21-0
EINECS: 211-745-8
Molecular Formula: C4H8N2O7
Molecular Weight: 196.12 g/mol
Density: 1.408 g/cm3 
Flash Point: 132.5 °C
Boiling Point: 273.6 °C at 760 mmHg 
Following is the structure of Diethylene glycol dinitrate (693-21-0):


The chemical synonymous of Diethylene glycol dinitrate (693-21-0) are 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

Diethylene glycol dinitrate Toxicity Data With Reference

1.    

orl-rat LD50:753 mg/kg

    JACTDZ    Journal of the American College of Toxicology. 12 (1993),602.
2.    

orl-mus LD50:1250 mg/kg

    JOHYAY    Journal of Hygiene. 17 (1973),114.

Diethylene glycol dinitrate Consensus Reports

Reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.

Diethylene glycol dinitrate Safety Profile

Moderately toxic by ingestion. Ingestion of this compound can cause a drop in blood pressure and cardiac disturbances. A dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing or reducing materials. A dangerous explosive sensitive to heat, shock, and vibration. Used in low-freezing dynamites and some permissible explosives. Upon decomposition it emits toxic fumes of NOx. See also GLYCOL ETHERS, NITRATES, and EXPLOSIVES, HIGH.
Hazard Codes:
E: Explosive
T+: Very toxic 
Risk Statements about Diethylene glycol dinitrate (693-21-0):
R3 Extreme risk of explosion by shock, friction, fire or other sources of ignition.
R33 Danger of cumulative effects.
R26/27/28: Very toxic by inhalation, in contact with skin and if swallowed.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements about Diethylene glycol dinitrate (693-21-0):
S33 Take precautionary measures against static discharges. 
S35 This material and its container must be disposed of in a safe way.
S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61 Avoid release to the environment. Refer to special instructions / safety data sheets.
S36/37: Wear suitable protective clothing and gloves.

Diethylene glycol dinitrate Standards and Recommendations

DOT Classification:  Forbidden; DOT Class: EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D (UN 0075)

Diethylene glycol dinitrate Specification

 Diethylene glycol dinitrate (693-21-0) is a 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.It is a colorless, odorless, viscous, oily liquid, specific gravity 1.4092 at 0 °C and 1.3846 at 20 °C ;  freezing point -11.5 °C under a standard atmosphere, the theoretical boiling point of approximately 197 °C difficult to confirm as the compound begins to decompose and spontaneously inflames at or slightly below this temperature. Partial pressure is reported as 0.007 mmHg (930 mPa) at 22.4 °C and 760 mmHg (101 kPa). It is readly miscible in most non-polar solvents, methanol, and cold acetic acid. Solubility in water (4.1 gm/L at 24 °C) and ethanol is very low. While chemically similar to a number of powerful high explosives, 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.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 amterials.If ingested, it, like nitroglycerine, produces rapid vasodialation through the release of nitrogen monoxide, NO, a physiological signaling molecule that acts to relax smooth muscle. As such it has occasionally been used medically to relieve angina, substernal chest pain associated with impaired cardiac circulation, since the concurrent headache it induces is somewhat less severe than other nitro compounds.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.

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