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| CAS No.: | 693-21-0 |
|---|---|
| Name: | DEGN |
| Article Data: | 24 |
| Molecular Structure: | |
|
|
|
| Formula: | C4H8 N2 O7 |
| Molecular Weight: | 196.117 |
| Synonyms: | Diethyleneglycol, dinitrate (6CI,7CI,8CI); Ethanol, 2,2'-oxybis-, dinitrate (9CI);2,2'-Oxydiethanol dinitrate; DEGDN; DEGN; Diglycol dinitrate; Dinitrodiglycol;Oxydiethylene nitrate |
| Density: | 1.8145 (rough estimate) |
| Melting Point: | -11.2°C |
| Boiling Point: | 332.98°C (rough estimate) |
| Solubility: | 3.9g/L at 25℃ |
| Hazard Symbols: | Severe explosion hazard when shocked or heated. Toxic by ingestion. |
| Risk Codes: | R3; R26/27/28; R33; R52/53 |
| 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. |
| PSA: | 119.33000 |
| LogP: | 0.46600 |
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| 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 |
| Conditions | Yield |
|---|---|
| With silver nitrate In acetonitrile at 70℃; for 16h; Darkness; | 93.4% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | 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. |
- 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 | 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. |
- 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 | 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. |
- 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 | 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. |
- Total:15 Page 1 of 1 1
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Chemistry
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
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. |
Consensus Reports
Reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.
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:
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T+: Very toxic .gif){kind=small}
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.
Standards and Recommendations
DOT Classification: Forbidden; DOT Class: EXPLOSIVE 1.1D; Label: EXPLOSIVE 1.1D (UN 0075)
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.