693-21-0 structure, C4H8N2O7

2-(2-nitrooxyethoxy)ethyl nitrate

CAS No.

693-21-0

Formula:

C4H8N2O7

Basic Info

Diethylene glycol dinitrate 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.
Diethylene glycol dinitrate is a colorless, odorless, viscous, oily liquid, with 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 0.007mmHg (930mPa) at 22.4°C and 760mmHg (101kPa). It is readily miscible in most non-polar solvents, methanol, and cold acetic acid. Solubility in water (4.1g/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 smokeless powder for artillery and a solid propellant for rocketry. It was widely used in this capacity during World War II (e.g., by the Kriegsmarine). 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 materials.
If ingested, like nitroglycerine, it produces rapid vasodilation through the release of nitrogen monoxide, NO. Popularly-termed nitric oxide, NO is a physiological signaling molecule that relaxes smooth muscle. Consequently, diethylene glycol dinitrate has occasionally been used medically to relieve angina, substernal chest pain associated with impaired cardiac circulation. The rationale is that 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.
Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethylolethane trinitrate are being considered as replacements for nitroglycerin in propellants.

Formula
C4H8N2O7
Molecular Weight
196.116
Exact Mass
196.033
LogP
0.466
PSA
119.33
Synonyms

O,O'-Dinitro-diaethylenglykol

Oxydiethylene dinitrate

Ethanol, 2,2‘-oxybis-, dinitrate

ETHANOL,2,2'-OXYBIS-,DINITRATE

Diethyleneglycol dinitrate

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Properties

Density
1.38
Melting Point
2(稳定体)ºC
Refractive Index
1.51

Safety Info

Risk Statements
R3; R26/27/28; R33; R52/53
HS Code
2920909090
Hazard Class
1.1A

MSDS

SDS 1.0
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SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2-nitrooxyethoxy)ethyl nitrate

1.2 Other means of identification

Product number -
Other names Oxydiethylene dinitrate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

Company MOLBASE (Shanghai) Biotechnology Co., Ltd.
Address Floor 4 & 5, Building 12, No. 1001 North Qinzhou Road,
Xuhui District, Shanghai, China
Telephone +86(21)64956998
Fax +86(21)54365166

1.5 Emergency phone number

Emergency phone number +86-400-6021-666
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

3.Composition/information on ingredients

3.1 Substances

Chemical name Common names and synonyms CAS number EC number Concentration
2-(2-nitrooxyethoxy)ethyl nitrate 2-(2-nitrooxyethoxy)ethyl nitrate 693-21-0 none 100%

4.First-aid measures

4.1 Description of necessary first-aid measures

General advice

Consult a physician. Show this safety data sheet to the doctor in attendance.

If inhaled

Fresh air, rest. Refer for medical attention.

In case of skin contact

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

In case of eye contact

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

If swallowed

Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

4.2 Most important symptoms/effects, acute and delayed

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)

4.3 Indication of immediate medical attention and special treatment needed, if necessary

/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/

5.Fire-fighting measures

5.1 Extinguishing media

Suitable extinguishing media

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.

5.2 Specific hazards arising from the chemical

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)

5.3 Special protective actions for fire-fighters

Wear self-contained breathing apparatus for firefighting if necessary.

6.Accidental release measures

6.1 Personal precautions, protective equipment and emergency procedures

Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8.

6.2 Environmental precautions

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.

6.3 Methods and materials for containment and cleaning up

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.)

7.Handling and storage

7.1 Precautions for safe handling

Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2.

7.2 Conditions for safe storage, including any incompatibilities

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

8.Exposure controls/personal protection

8.1 Control parameters

Occupational Exposure limit values

no data available

Biological limit values

no data available

8.2 Appropriate engineering controls

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

8.3 Individual protection measures, such as personal protective equipment (PPE)

Eye/face protection

Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection

Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it.

Respiratory protection

Wear dust mask when handling large quantities.

Thermal hazards

no data available

9.Physical and chemical properties

Physical state Diethylene glycol dinitrate is 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.
Colour Liquid
Odour no data available
Melting point/ freezing point 2(稳定体)ºC
Boiling point or initial boiling point and boiling range 161°C
Flammability Gives off irritating or toxic fumes (or gases) in a fire.
Lower and upper explosion limit / flammability limit no data available
Flash point no data available
Auto-ignition temperature no data available
Decomposition temperature no data available
pH no data available
Kinematic viscosity no data available
Solubility In water, 3.9X10+3 mg/L at 25°C
Partition coefficient n-octanol/water (log value) log Kow = 0.98
Vapour pressure 5.9X10-3 mm Hg at 25°C
Density and/or relative density 1.38
Relative vapour density 6.76 (Air = 1)
Particle characteristics no data available

10.Stability and reactivity

10.1 Reactivity

no data available

10.2 Chemical stability

Stable under recommended storage conditions.

10.3 Possibility of hazardous reactions

A dangerous fire hazard when exposed to heat or flame.As a result of flow, agitation, etc., electrostatic charges can be generated.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.

10.4 Conditions to avoid

no data available

10.5 Incompatible materials

Can react vigorously with oxidizing or reducing materials.

10.6 Hazardous decomposition products

Upon decomposition it emits toxic fumes of /nitroxides/.

11.Toxicological information

Acute toxicity

  • Oral: LD50 Rat male oral gavage 990 mg/kg
  • Inhalation: no data available
  • Dermal: no data available

Skin corrosion/irritation

no data available

Serious eye damage/irritation

no data available

Respiratory or skin sensitization

no data available

Germ cell mutagenicity

no data available

Carcinogenicity

Classification - D; not classifiable as to human carcinogenicity Basis - No human or animal carcinogenic studies found in the available literature. /Based on former classification system/

Reproductive toxicity

no data available

STOT-single exposure

no data available

STOT-repeated exposure

no data available

Aspiration hazard

no data available

12.Ecological information

12.1 Toxicity

  • Toxicity to fish: no data available
  • Toxicity to daphnia and other aquatic invertebrates: no data available
  • Toxicity to algae: no data available
  • Toxicity to microorganisms: no data available

12.2 Persistence and degradability

AEROBIC: Aliphatic nitric acid esters undergo aerobic biodegradation readily via successive removal of nitrate groups to isomeric derivatives. Nitrate esters undergo microbial metabolism by cleaving the nitrate ester group(1). An unspecified amount of diethylene glycol dinitrate was nearly completely degraded in less than 35 days when incubated in diethylene glycol dinitrate-contaminated water enhanced with the addition of yeast and glucose. Degradation in pure water was minimal, suggesting that degradation may occur in acclimated environments(SRC). Loss in combinations of sterile, nonsterile, aerobic and anaerobic river and pond sediments was all within 21 days, suggesting abiotic processes. Degradation in dry soil was slow with 16 and 24% loss after 5 weeks in sterile and nonsterile soil, respectively following the addition of 20 ppm test chemical. Using activated sludge enhanced with mineral salts, oxygen, and ethanol, diethylene glycol dinitrate was shown to degrade by hydrolytic cleavage to porducts including diethylene glycol mononitrate and diethyle glycol(2) and to finally carbon dioxide and methane(3).

12.3 Bioaccumulative potential

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).

12.4 Mobility in soil

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).

12.5 Other adverse effects

no data available

13.Disposal considerations

13.1 Disposal methods

Product

The material can be disposed of by removal to a licensed chemical destruction plant or by controlled incineration with flue gas scrubbing. Do not contaminate water, foodstuffs, feed or seed by storage or disposal. Do not discharge to sewer systems.

Contaminated packaging

Containers can be triply rinsed (or equivalent) and offered for recycling or reconditioning. Alternatively, the packaging can be punctured to make it unusable for other purposes and then be disposed of in a sanitary landfill. Controlled incineration with flue gas scrubbing is possible for combustible packaging materials.

14.Transport information

14.1 UN Number

ADR/RID: no data available IMDG: no data available IATA: no data available

14.2 UN Proper Shipping Name

ADR/RID: no data available
IMDG: no data available
IATA: no data available

14.3 Transport hazard class(es)

ADR/RID: no data available IMDG: no data available IATA: no data available

14.4 Packing group, if applicable

ADR/RID: no data available IMDG: no data available IATA: no data available

14.5 Environmental hazards

ADR/RID: no IMDG: no IATA: no

14.6 Special precautions for user

no data available

14.7 Transport in bulk according to Annex II of MARPOL 73/78 and the IBC Code

no data available

15.Regulatory information

15.1 Safety, health and environmental regulations specific for the product in question

Chemical name Common names and synonyms CAS number EC number
2-(2-nitrooxyethoxy)ethyl nitrate 2-(2-nitrooxyethoxy)ethyl nitrate 693-21-0 none
European Inventory of Existing Commercial Chemical Substances (EINECS) Listed.
EC Inventory Listed.
United States Toxic Substances Control Act (TSCA) Inventory Listed.
China Catalog of Hazardous chemicals 2015 Listed.
New Zealand Inventory of Chemicals (NZIoC) Not Listed.
Philippines Inventory of Chemicals and Chemical Substances (PICCS) Not Listed.
Vietnam National Chemical Inventory Not Listed.
Chinese Chemical Inventory of Existing Chemical Substances (China IECSC) Not Listed.

16.Other information

Information on revision

Creation Date Aug 12, 2017
Revision Date Aug 12, 2017

Abbreviations and acronyms

  • CAS: Chemical Abstracts Service
  • ADR: European Agreement concerning the International Carriage of Dangerous Goods by Road
  • RID: Regulation concerning the International Carriage of Dangerous Goods by Rail
  • IMDG: International Maritime Dangerous Goods
  • IATA: International Air Transportation Association
  • TWA: Time Weighted Average
  • STEL: Short term exposure limit
  • LC50: Lethal Concentration 50%
  • LD50: Lethal Dose 50%
  • EC50: Effective Concentration 50%

References

  • IPCS - The International Chemical Safety Cards (ICSC), website: http://www.ilo.org/dyn/icsc/showcard.home
  • HSDB - Hazardous Substances Data Bank, website: https://toxnet.nlm.nih.gov/newtoxnet/hsdb.htm
  • IARC - International Agency for Research on Cancer, website: http://www.iarc.fr/
  • eChemPortal - The Global Portal to Information on Chemical Substances by OECD, website: http://www.echemportal.org/echemportal/index?pageID=0&request_locale=en
  • CAMEO Chemicals, website: http://cameochemicals.noaa.gov/search/simple
  • ChemIDplus, website: http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp
  • ERG - Emergency Response Guidebook by U.S. Department of Transportation, website: http://www.phmsa.dot.gov/hazmat/library/erg
  • Germany GESTIS-database on hazard substance, website: http://www.dguv.de/ifa/gestis/gestis-stoffdatenbank/index-2.jsp
  • ECHA - European Chemicals Agency, website: https://echa.europa.eu/

Disclaimer: The above information is believed to be correct but does not purport to be all inclusive and shall be used only as a guide. The information in this document is based on the present state of our knowledge and is applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee of the properties of the product. We as supplier shall not be held liable for any damage resulting from handling or from contact with the above product.

Spectrum

NMR Spectrum 1H NMR : Predict
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Mass Spectrum Mass spectrum (electron ionization)
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Analysis Methods

Kovats' RI, non-polar column, isothermal
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Column Shape
Capillary
Active Phase(℃)
DB-5
Retention index
1351.13
Temperature Control
140.
Method
isothermal
Comments
30. m/0.25 mm/0.25 μm
Reference
Hobbs, J.R.Conde, E.P.Gas chromatographic retention indices of explosives and nitro-compoundsAdvances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem IsraelJ. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164.
Kovats' RI, non-polar column, isothermal
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Column Shape
Capillary
Active Phase(℃)
DB-5
Retention index
1357.28
Temperature Control
140.
Method
isothermal
Comments
30. m/0.25 mm/0.25 μm
Reference
Hobbs, J.R.Conde, E.P.Gas chromatographic retention indices of explosives and nitro-compoundsAdvances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem IsraelJ. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164.
Van Den Dool and Kratz RI, non-polar column, temperature ramp
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Column Shape
Capillary
Active Phase(℃)
DB-5
Retention index
1332.85
Temperature Control
Method
temperature ramp
Comments
30. m/0.25 mm/0.25 μm, 5. K/min; T<sub>start</sub>: 40. C; T<sub>end</sub>: 300. C
Reference
Hobbs, J.R.Conde, E.P.Gas chromatographic retention indices of explosives and nitro-compoundsAdvances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem IsraelJ. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164.
Van Den Dool and Kratz RI, non-polar column, temperature ramp
expand collapse
Column Shape
Capillary
Active Phase(℃)
DB-5
Retention index
1344.19
Temperature Control
Method
temperature ramp
Comments
30. m/0.25 mm/0.25 μm, 5. K/min; T<sub>start</sub>: 40. C; T<sub>end</sub>: 300. C
Reference
Hobbs, J.R.Conde, E.P.Gas chromatographic retention indices of explosives and nitro-compoundsAdvances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem IsraelJ. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164.

Toxicity

ACUTE TOXICITY DATA
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Type of Test
LD50 - Lethal dose, 50 percent kill
Exposure Route
Oral
Species Observed
Rodent - rat
Dose/Duration
753 mg/kg
Toxic Effects
Behavioral--tremor<br>Behavioral--muscle contraction or spasticity<br>Behavioral--irritability
Reference
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 12,602,1993
ACUTE TOXICITY DATA
expand collapse
Type of Test
LD50 - Lethal dose, 50 percent kill
Exposure Route
Oral
Species Observed
Rodent - mouse
Dose/Duration
1250 mg/kg
Toxic Effects
Behavioral--changes in motor activity (specific assay)<br>Lungs, Thorax, or Respiration--cyanosis
Reference
Journal of Hygiene, Epidemiology, Microbiology, and Immunology. (Avicenum, Malostranske namesti 28, 11802 Prague 1, Czechoslovakia) V.1- 1957- Volume(issue)/page/year: 17,114,1973
ACUTE TOXICITY DATA
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Type of Test
LD - Lethal dose
Exposure Route
Administration onto the skin
Species Observed
Rodent - rabbit
Dose/Duration
>2 gm/kg
Toxic Effects
Behavioral--tremor<br>Behavioral--muscle contraction or spasticity<br>Behavioral--irritability
Reference
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 12,600,1993
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