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Diethylene glycol dinitrate

Diethylene glycol dinitrate structure

Diethylene glycol dinitrate 

structure
  • CAS No:

    693-21-0

  • Formula:

    C4H8N2O7

  • Chemical Name:

    Diethylene glycol dinitrate

  • Synonyms:

    Ethanol,2,2′-oxybis-,1,1′-dinitrate;Diethylene glycol,dinitrate;Ethanol,2,2′-oxybis-,dinitrate;Diglycol dinitrate;Dinitrodiglycol;Oxydiethylene nitrate;2,2′-Oxydiethanol dinitrate;DEGDN;DEGN;Diethylene glycol dinitrate;2-(2-Nitrooxyethoxy)ethyl Nitrate;66492-77-1

  • Categories:

    Organic Chemistry  >  Inorganic Acid Esters

Description

LIQUID.


Diethylene glycol dinitrate appears as a liquid. Extremely sensitive explosive if not properly desensitized with a phlegmatizer. Slightly soluble in alcohol and soluble in ether. 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.|LIQUID.


Diethylene glycol dinitrate appears as a liquid. Extremely sensitive explosive if not properly desensitized with a phlegmatizer. Slightly soluble in alcohol and soluble in ether. 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.

Diethylene glycol dinitrate Basic Attributes

196.12

196.12

211-745-8

77W50O99G1

1473

0075

DTXSID1024047

Liquid|Yellow oil|Colorless or yellowish liquid of low volatility

2920909090

Characteristics

119

0.98

Diethylene glycol dinitrate appears as a liquid. Extremely sensitive explosive if not properly desensitized with a phlegmatizer. Slightly soluble in alcohol and soluble in ether. 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.

1.3890 g/cm3 @ Temp: 16 °C

2 °C

139 °C @ Press: 7 Torr

1.51

Slightly soluble in alcohol; soluble in ether

Fireproof. Store in separate building. Separated from acids, food and feedstuffs . Cool. Well closed.

Vapour pressure, Pa at 20°C: 0.5

6.76 (Air = 1)

Diethyleneglycol dinitrate ... is a liquid which is an extremely sensitive explosive if not properly desensitized with a phlegmatizer ... Under prolonged exposure to heat or fire or from sudden shock /it/ can explode. /Diethylenegylcol dinitrate, desensitized/

Depending on the purity of the product, it gives water a bitter-astringent taste at concentrations of 130 mg/L

Henry's Law constant = 3.90X10-7 atm cu m/mol at 25 °C (est)

Conversion factors (25 °C, 760 mm Hg): 1 ppm approximates 8.02 mg/cu m; 1 mg/L approximates 124.7 ppm|Upon decomposition it emits toxic fumes of NOx.|Hydroxyl radical reaction rate constant = 3.26X10-12 cu cm/molec-sec at 25 °C (est)

Slightly soluble in water.

Ethers

Explosive

Nitroorganics, such as DIETHYLENE GLYCOL DINITRATE, 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.

As a result of flow, agitation, etc., electrostatic charges can be generated.

Safety Information

1.1A

0473

3-26/27/28-33-52/53

33-35-36/37-45-61

ID6825000

E,T+

Fireproof. Store in a separate building. Separated from acids and food and feedstuffs. Cool. Well closed.

P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P372, P373, P380, P401, P403+P233, P405, P501

H200

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Can react vigorously with oxidizing or reducing materials.|Heating may cause violent combustion or explosion producing toxic fumes of nitrogen oxides. May decompose explosively on shock, friction, or concussion. Reacts with acids .

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: MAY EXPLODE AND THROW FRAGMENTS 1600 METERS (1 MILE) OR MORE IF FIRE REACHES CARGO. For information on "Compatibility Group" letters, refer to Glossary section. (ERG, 2016)|Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion. Explosive.|Flammable - 4th degree, Reactive - 4th degree

|Danger|H200: Unstable Explosive [Danger Explosives]|P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P372, P373, P380, P401, P403+P233, P405, and P501|H201: Explosive; mass explosion hazard [Danger Explosives]|P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P370+P380, P372, P373, P401, P403+P233, P405, and P501|H200 (50%): Unstable Explosive [Danger Explosives]|P201, P202, P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P370+P380, P372, P373, P380, P401, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Isolate spill or leak area immediately for at least 500 meters (1/3 mile) in all directions. LARGE SPILL: Consider initial evacuation for 800 meters (1/2 mile) in all directions. FIRE: If rail car or trailer is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, initiate evacuation including emergency responders for 1600 meters (1 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. DO NOT OPERATE RADIO TRANSMITTERS WITHIN 100 METERS (330 FEET) OF ELECTRIC DETONATORS. DO NOT CLEAN-UP OR DISPOSE OF, EXCEPT UNDER SUPERVISION OF A SPECIALIST. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Protective gloves. Protective clothing. Face shield, or eye protection in combination with breathing protection.

A dangerous fire hazard when exposed to heat or flame.

A dangerous explosive sensitive to heat, shock, and vibration.|Diethyleneglycol dinitrate ... is a liquid which is an extremely sensitive explosive if not properly desensitized with a phlegmatizer ... Under prolonged exposure to heat or fire or from sudden shock /it/ can explode. /Diethylenegylcol dinitrate, desensitized/

Powder, water spray, foam, carbon dioxide. Note: Evacuate area, fight fires only from an explosion-resistant location ... Cool drums, etc., by spraying with water but avoid contact of the substance with water.|If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Diethylenegylcol dinitrate, desensitized/|Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Diethylenegylcol dinitrate, desensitized/|Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Diethylenegylcol dinitrate, desensitized/

The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments. /Diethylenegylcol dinitrate, desensitized/

Evacuate danger area! Consult an expert! Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT let this chemical enter the environment. (Extra personal protection: complete protective clothing including self-contained breathing apparatus.)

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material wet. /Diethylenegylcol dinitrate, desensitized/|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.|Ventilation, local exhaust.

Evacuate danger area! Consult an expert! Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: complete protective clothing including self-contained breathing apparatus.

Fireproof. Store in a separate building. Separated from acids and food and feedstuffs. Cool. Well closed.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.

The substance may cause effects on the cardiovascular system, central nervous system and blood. This may result in impaired functions and the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

The substance may have effects on the cardiovascular system. This may result in cardiac disorders.

NO open flames, NO sparks and NO smoking. Prevent build-up of electrostatic charges (e.g., by grounding). Use non-sparking handtools. Do NOT expose to friction or shock.

STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

LD50 Rat male oral gavage 990 mg/kg|LD50 Rat female oral gavage 753 mg/kg|LD50 Mouse oral 1250 mg/kg|LD50 Mouse male oral gavage 1394 mg/kg|For more Non-Human Toxicity Values (Complete) data for Diethylene glycol dinitrate (6 total), please visit the HSDB record page.

Diethylene glycol dinitrate's production and use as plasticizer in solid rocket propellants(1), in low-freezing dynamites and some permissible explosives(2), and in low sensitivity gun propellants(3) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a log Kow of 0.98(2) and a regression-derived equation(3), indicates that diethylene glycol dinitrate is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol dinitrate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 5.9X10-3 mm Hg(2), and water solubility, 3.9X10+3 mg/L(2). Diethylene glycol dinitrate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). 24% Degradation in dry soil after 5 weeks following the addition of 20 ppm diethylene glycol dinitrate(4) indicates biodegradation in soil is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a log Kow of 0.98(2) and a regression-derived equation(3), indicates that diethylene glycol dinitrate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 5.9X10-3 mm Hg(2), and water solubility, 3.9X10+3 mg/L(2). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis of diethylene glycol dinitrate will be very slow in the environment; at 25 °C and pH 7, 9 and 10, hydrolysis half-lives were greater than 400 days(2). Photolysis half-lives ranging from 15 to 59 days were measured in surface waters at 40 deg N latitude(7). Nearly complete degradation in less than 35 days when incubated in diethylene glycol dinitrate-contaminated water enhanced with the addition of yeast and glucose(8) suggests that biodegradation in acclimated aquatic environments may occur(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol dinitrate, which has a vapor pressure of 5.9X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol dinitrate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4.9 days(SRC), calculated from its rate constant of 3.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethylene glycol dinitrate contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). Photolysis half-lives ranging from 15 to 59 days were measured in surface waters at 40 deg N latitude(2).

The rate constant for the vapor-phase reaction of diethylene glycol dinitrate with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis of diethylene glycol dinitrate will be very slow in the environment; at 25 °C and pH 7, 9 and 10, hydrolysis rate constants were less than 2X10-8/s, corresponding to half-lives greater than 400 days(2). A base-catalyzed hydrolysis rate constant of 7X10-7 L/mole-sec was measured at pH 12.8(2). Diethylene glycol dinitrate contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).|The photolysis half-lives of diethylene glycol dinitrate in surface waters under cloudless conditions at 40 deg N latitude for spring, summer, fall and winter were 19, 15, 33 and 59 days, respectively; average photolysis rates will decrease at depths below the surface. Photolysis products include nitrite, nitrate, and 2-hydroxyethyl nitratoacetate, with nitrate being the major inorganic degradation product of diethylene glycol dinitrate photolysis(1).

An estimated BCF of 3.2 was calculated in fish for diethylene glycol dinitrate(SRC), using a log Kow of 0.98(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of diethylene glycol dinitrate is estimated as 32(SRC), using a log Kow of 0.98(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol dinitrate is expected to have very high mobility in soil. The sorption partition coefficients, Kp, were calculated as 2.3 and 0.8 g/mL for EPA-5 sediment (33.6% sand, 31.0% clay, and 35.4% silt at pH 7.44) and EPA-18 sediment (34.6% sand, 39.5% clay, and 25.8% silt at pH 7.76), respectively; these correspond to Koc values of 100 and 120 g/mL, respectively(1).

The Henry's Law constant for diethylene glycol dinitrate is estimated as 3.9X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 5.9X10-3 mm Hg(1), and water solubility, 3.9X10+3 mg/L(1). This Henry's Law constant indicates that diethylene glycol dinitrate is expected to be essentially nonvolatile from water surfaces(2). No loss (less than 5%) of diethylene glycol dinitrate from the aqueous phase was observed after 10 days of purging, indicating that volatilization will be extremely slow in the environment(1). Diethylene glycol dinitrate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to diethylene glycol dinitrate may occur through dermal contact with this compound at workplaces where diethylene glycol dinitrate is produced or used. Limited exposure to general population to diethylene glycol dinitrate may occur via inhalation. (SRC)

Drug Information

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Fire may produce irritating, corrosive and/or toxic gases. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ethylene glycol, glycols, and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ethylene glycol, glycols, and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethylene glycol, glycols, and related compounds/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Nitrates, nitrites, and related compounds/|For more Antidote and Emergency Treatment (Complete) data for Diethylene glycol dinitrate (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ The main effects /of diethylene glycol dinitrate/ seem to be those of CNS injury and hypotension, but unlike the other dinitrates, it seems to be low in its ability to cause methemoglobinemia, especially at small doses. The hypotensive effect was not accompanied by changes in electrocardiograph readings, suggesting that this material influences vascular tonus without impairing the activity of the myocardium.|/SIGNS AND SYMPTOMS/ The main adverse effects are those of CNS injury and hypotension. Although it apparently does cause the production of methemoglobinemia, it does so only at fairly high doses. Chronic exposure has been shown to cause a drop in blood pressure.|/SIGNS AND SYMPTOMS/ The neurotoxic effects of dinitroglycol and dinitrodiglycol were investigated in 38 explosives production workers. Headaches were the most commonly reported symptom. Hyperemia of the face and ligaments occurred suddenly among some workers, and was accompanied by cephalalgia. One worker complained of depression and sleep interruption. Loss of consciousness was reported by some of the workers.|/SIGNS AND SYMPTOMS/ Short term exposure: the substance may cause effects on the cardiovascular system, central nervous system and blood, resulting in impaired functions and the formation of methemoglobin. The effects may be delayed. Long term or repeated exposure: The substance may have effects on the cardiovascular system, resulting in cardiac disorders .|For more Human Toxicity Excerpts (Complete) data for Diethylene glycol dinitrate (6 total), please visit the HSDB record page.

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Flushing of the face. Fall in blood pressure. Dizziness. Headache. Nausea. Weakness. Blue lips, fingernails and skin. Confusion. Convulsions. Unconsciousness.


MAY BE ABSORBED! See Inhalation.

Diethylene glycol dinitrate Use and Manufacturing

Production

Ethanol, 2,2'-oxybis-, dinitrate is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7548]

Ethanol, 2,2'-oxybis-, 1,1'-dinitrate: ACTIVE

Fire Hazards -> Flammable - 4th degree, Reactive - 4th degree

Computed Properties

Molecular Weight:196.12
XLogP3:0.6
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:6
Exact Mass:196.03315060
Monoisotopic Mass:196.03315060
Topological Polar Surface Area:119
Heavy Atom Count:13
Complexity:143
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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