ニトログリコール

log Kow = 1.16

1.16

1.37

1.49 (NIOSH, 2024) - Denser than water; will sink

1.4918 g/cu cm at 20 °C

Relative density (water = 1): 1.49

1.49

1.483 @ 8°C

1.49

Insoluble (NIOSH, 2024)

Very soluble in ether, ethanol

Soluble in carbon tetrachloride, benzene, toluene, acetone; limited solublity in common alcohols

In water, 0.52%

Soluble in dilute alkali

In water, 6,800 mg/L at 20 °C

419 °F (NIOSH, 2024)

215 °C (closed cup)

419 °F (closed cup)

419 °F

419 °F

387 °F at 760 mmHg (NIOSH, 2024)

198.5 °C

114 °C (explodes)

387 °F

105.5 °C @760 [mm Hg]

387 °F

... Decomposes violently upon heating or impact with a force similar to that of nitroglycerin.

When heated to decomposition it emits toxic fumes of /nitroxides/.

-8 °F (NIOSH, 2024)

-22.3 °C

In the presence of more than slight traces of free acid, ethylene glycol dinitrate is unstable with a melting point of -21 °C.

-22 °C

-8 °F

-22.3 °C

Danger

H200: (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P372, P373, P380, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H200 (19.1%): (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P372, P373, P380, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: 1,2-Ethanediol, dinitrate

1,2-Ethanediol, 1,2-dinitrate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediol, 1,2-dinitrate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Ethylene dinitrate (EC: 211-063-0)

Ethylene glycol dinitrate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/29/2006; Reporting date: 11/28/2006.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Ethanediol, dinitrate is included on this list. Effective date 9/29/2006; Sunset date: 11/28/2006.

Permissible Exposure Limit: Table Z-1 Ceiling value: 0.2 ppm (1 mg/cu m). Skin designation.

Vacated 1989 OSHA PEL STEL 0.1 mg/cu m, skin designation, is still enforced in some states.

ETHYLENE GLYCOL DINITRATE is explosive. Acts as a strong oxidizing agent. Heating to 114 °C or above may cause a violent combustion or explosion producing toxic fumes (nitrogen oxides). May also decompose explosively from shock, friction or from a build-up of electrostatic charge that sparks suddenly to ground. Can begin a vigorous reaction that culminates in an explosion if mixed with reducing agents including hydrides, sulfides, and nitrides and numerous ordinary combustible materials. Reacts violently with Al, BP, cyanides, esters, PN2H, P, NaCN, SnCl2, sodium hypophosphite, and thiocyanates. Reacts with acids and with alkalis, including ammonia and amines. Must be stored in a cool, ventilated place, away from acute fire hazards and easily oxidized materials (Sax and Lewis, 1987 p.664).

Use water spray, powder, foam, carbon dioxide. Evacuate area, fight fires only from an explosion-resistant location. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water. Combat fire from a sheltered position.

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.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

Excerpt from NIOSH Pocket Guide for Ethylene glycol dinitrate:

(General first aid procedures)

Evacuate area of fire ... Fight fires only from a secure, explosion-resistant position ... Use dry chemical, carbon dioxide, water spray, or foam extinguishers. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position.

Buildings used for storage of nitroglycerin or ethylene glycol dinitrate shall be separated by at least the minimum distances required; containers of nitroglycerin or ehylene glycol dinitrate shall be kept tightly closed at all times when not in use and shall be stored in a manner that will minimized the risk of spills; only properly informed, trained, and equipped personnel shall be involved in storing, loading, and unloading, or processing liquid nitroglycerin, ethylene glycol dinitrate, or explosive mixtures containing these compounds. Also, storage areas for nitroglycerin or ethylene glycol dinitrate shall be clean, dry, and well ventilated. Storage areas for explosive forms of nitroglycerin or ethylene glycol dinitrate shall be in a structure that is bullet resistant, weather resistant, and ventilated.

Before entering confined space where EGDN is present, check to make certain that explosive concentrations do not exist. EGDN is highly explosive and can detonate violently upon heating or impact. Store in tightly closed containers in a cool, well ventilated area away from strong acids and alkalies. All sources of ignition are prohibited. Use non-sparking tools and equipment especially when opening or closing containers. Use explosion-proof electrical equipment and fittings in all areas of handling, use, or manufacture. Where possible, automatically pump liquid from drums or other storage containers to process containers.

Spread sodium bisulfate over the area and sprinkle with water. Then flush to sewer with water. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep EGDN out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental protection or your regional office of the federal EPA for specific recommendations.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. 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.

The prime consideration in the prodn and use of ethylene glycol dinitrate is the prevention of explosions: it is consequently necessary to adopt the same safety measures as those employed in the manufacture of nitroglycerin and in the explosives industry as a whole. ... Progress ... has been achieved by /use of/ remote control (by optical, mechanical or electronic means) of the most dangerous operations (in particular, milling) and by the automation of numerous processes such as nitration, mixing, cartridge filling, etc. Arrangements of this type have the advantage of reducing to a minimum both the number of workers exposed to direct contact with ethylene glycol dinitrate and the related exposure times, ... where workers are still exposed to ethylene glycol dinitrate, , ... safety & health measures are necessary. ... the concn of ethylene glycol dinitrate in the explosives mixture should be reduced depending on the ambient temp and in temperate-climate countries it should not exceed 20-25% ethylene glycol dinitrate; during the warm season, it may be appropriate to exclude ethylene glycol dinitrate completely. ... In order to reduce the inhalation hazard, it is necessary to control the atmospheric concn at the workplace by means of general ventilation, and, if necessary, air induction; local exhaust ventilation may entail an explosion hazard. ... Careful control of the temp of ethylene glycol dinitrate is extremely important in view of the product's volatility: it is recommmended that 22 °C should not be exceeded in areas occupied by workers, and 32 °C in premises where processes are remotely controlled.

... Essential that adequate skin protection be provided for each worker: impervious clothing where liquids are likely to contaminate and full body clothing where dust creates the problem. All clothing should be discarded at the end of the shift and clean work clothing provided each day. Showers should be taken at the end of each shift and prior to changing to street clothing. In case of spill or splash that contaminates work clothing, the clothes should be changed at once and the skin area washed thoroughly.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

For more Preventive Measures (Complete) data for Ethylene glycol dinitrate (7 total), please visit the HSDB record page.

Hyperthyroidism increases the acute toxicity of ethylene glycol dinitrate-glyceryl trinitrate (83:17), whereas hypothyroidism reduced it. Rats were treated with thyroxine and triiodothyronine, (100 and 20 ug/animal, respectively, daily for 17 days) and then given an LD50 dose of the nitrate mixture. Half of the control rats died, 93% of those treated with thyroxine, and 100% of those treated with triiodothyronine. All thyroidectomized rats survived a normal LD50 dose.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dinitrate is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol dinitrate from moist soil surfaces is expected to be an important fate process(SRC) given a calculated Henry's Law constant of 2.1X10-6 atm-cu m/mole(SRC), from its vapor pressure, 0.072 mm Hg(3), and water solubility, 6800 mg/L(4). Ethylene glycol dinitrate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Ethylene glycol dinitrate was biodegraded to ethylene glycol mononitrate at a rate of 6.32 umol/hr/mg by Klebsiella oxytoca(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dinitrate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a calculated Henry's Law constant of 2.1X10-6 atm-cu m/mole(SRC), from its vapor pressure, 0.072 mm Hg(4), and water solubility, 6800 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 and 120 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of 1.16(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ethylene glycol dinitrate was biodegraded to ethylene glycol mononitrate at a rate of 6.32 umol/hr/mg by Klebsiella oxytoca(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol dinitrate, which has a vapor pressure of 0.072 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene glycol 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 22 days(SRC), calculated from its rate constant of 7.3X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethylene glycol dinitrate contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Headache. Dizziness. Nausea. Weakness. Flushing of the face. Chest pain. Symptoms may be delayed.

MAY BE ABSORBED! See Inhalation.

See Inhalation.

throbbing headache; dizziness; nausea, vomiting, abdominal pain; hypotension, flush, palpitations, angina; methemoglobinemia; delirium, central nervous system depression; irritation skin; In Animals: anemia; liver, kidney damage

Medical prevention ... includes a pre-employment exam dealing with the general state of health, the cardiovascular system (electrocardiographic exam at rest and during exercise is essential), neurovegetative reactivity, urine & blood exam. ... All workers suffering from cardiac diseases, hypertension, hepatic disorders, especially of the vasomotor system, should not be exposed to nitroglycerin/ethylene glycol dinitrate mixtures. It is also advisable to move to other jobs all workers who have been employed for more than 5 to 6 yr on dangerous work, and to avoid too frequent a change in the intensity of exposure.

In view of the effects of exposure to nitroglycerin and ethylene glycol dinitrate on the cardiovascular system, NIOSH recommends that comprehensive preplacement and periodic examinations be made available to all workers occupationally exposed to these substances. ECG's taken during rest and during exercise should be conducted at last annually, as these tests are indicators of cardiovascular damage. The worker should be informed that symptoms such as headaches, dizziness, or nausea (that can develop during working hours) and chest pains or palpitations (that can develop during periods away from work) may be indicative of nitroglycerin or ethylene glycol dinitrate toxicity /SRP: or withdrawal/ and that these symptoms should be immediately reported to the responsible physician. All pertinent medical records, with supporting documents, must be kept for at least 30 years after termination of employment.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of ethylene glycol dinitrate can be estimated to be 40(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene glycol dinitrate is expected to have very high mobility in soil.

/HUMAN EXPOSURE STUDIES/ ... Humans /were exposed/ to ethylene glycol dinitrate by inhalation and /it caused/ severe cranioencephalic dilation as shown by an increase in systolic blood pressure, in cerebral flow, and in vasoelasticity with a reduction in local capillary resistance. The changes began almost immediately upon exposure and reached a maximum in 4 to 8 min and disappeared in 15 to 20 min. This corresponds with the presence of ethylene glycol dinitrate in the blood.

/HUMAN EXPOSURE STUDIES/ ... Thresholds for lowered blood pressure and headache among volunteers exposed to a mixture of nitroglycerin and EGDN showed an immediate fall in blood pressure and marked headache at 2 mg/cu m. A mean concentration of 0.7 mg/cu m for 25 minutes also produced lowered blood pressure and slight headache.

/HUMAN EXPOSURE STUDIES/ The minimum dose, applied as a 1 percent solution in alcohol, which causes headaches in /humans/, was reported as 18 to 35 mg.

/SIGNS AND SYMPTOMS/ Short Term Exposure: EGDN can cause headache, dizziness, nausea, vomiting, abdominal pain, and may affect the cardiovascular system, causing a fall in blood pressure. High levels can interfere with the blood's ability to carry oxygen (methemoglobinemia). Exposure may result in death. The effects may be delayed. Skin contact can cause a rash or burning feeling on contact. Exposure to small amounts of ethylene glycol dintrate and/or nitroglycerin by skin exposure, inhalation, or swallowing may cause severe throbbing headaches. With large exposure, nausea, vomiting, cyanosis, palpitations of the heart, coma, cessation of breathing, and death may occur. A temporary tolerance to the headache may develop, but this is lost after a few days without exposure. On some occasions a worker may have anginal pains a few days after discontinuing repeated daily exposure. Long Term Exposure: EGDN can damage the heart causing pain in the chest and/or increased heart rate or cause arrhythmia (irregular heart beat). This can be fatal. High exposure may affect the nervous system. May damage the red blood cells leading to anemia.

For more Human Toxicity Excerpts (Complete) data for Ethylene glycol dinitrate (19 total), please visit the HSDB record page.

Ethylene glycol dinitrate's production and use as a plasticizer for nitrocellulose explosives(1), as an explosive(2), and in low freezing explosives(3) may result in either its direct release to the environment or its release to the environment through various waste streams(SRC).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/29/2006; Reporting date: 11/28/2006.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Ethanediol, dinitrate is included on this list. Effective date 9/29/2006; Sunset date: 11/28/2006.

Ethylene glycol dinitrate incubated with rat whole blood or with erythrocytes broke down into inorg nitrate and ethylene glycol mononitrate (EGMN). Free ethylene glycol dinitrate in the blood of rats which were injected subcutaneously with ethylene glycol dinitrate (65 mg ethylene glycol dinitrate/kg) reached a peak 30 min after injection and fell to zero at 8 hr. Inorg nitrate was major metabolite found in urine from degradation of ethylene glycol dinitrate.

Ethylene glycol dinitrate in vivo is metabolized mainly into ethylene glycol mononitrate, which in turn is converted into inorganic nitrates and ethylene glycol ...

... When animals and humans are exposed to ethylene glycol dinitrate the material appears in the blood immediately, peaking in concn in about 30 min. Apparently it is rapidly metabolized, for it disappears in about 4 hr with very little found excreted in the urine. Blood analysis shows that inorganic nitrite, inorganic nitrate, and ethylene glycol mononitrate are the main metabolites.

Nitroglycol concn in the blood reached max 1 hr after its admin to mice. It decr rapidly, and only a trace amt was left at 6 hr. Sodium nitrate and ethylene glycol were metabolites of nitroglycol. The concn of sodium nitrate incr and peaked approx 3 hr after admin and remained almost constant thereafter. In contrast, the level of ethylene glycol reached a max at 2 hr after admin and declined thereafter.

For more Metabolism/Metabolites (Complete) data for Ethylene glycol dinitrate (6 total), please visit the HSDB record page.

In animals it is absorbed more rapidly through skin, lungs and gastrointestinal tract ... than nitroglycerin ...

... The magnitude of the dose obtained by the cutaneous route relative to that by inhalation is variable and unknown; EGDN is known, however, to be absorbed with considerable ease through the intact skin.

Nitroglycerin and ethylene glycol dinitrate are absorbed through the lungs and the skin. Absorption through the skin is usually the major route of exposure for workers who have direct dermal contact with nitroglycerin or ethylene glycol dinitrate.

... The rate of disappearance of ethylene glycol dinitrate from human blood in vitro /was determined/. Concentrations of ethylene glycol dinitrate were measured by gas chromatography with an electron-capture dectector. One-half the ethylene glycol dinitrate disappeared in 20 hr from a human blood sample that had originally contained 0.18 ppm ethylene glycol dinitrate, in 10 hr from a sample that had contained 0.08 ppm ethylene glycol dinitrate, and in about 2 hr from a sample that had contained 0.04 ppm ethylene glycol dinitrate. Since the rate of disappearance was more rapid when ethylene glycol dinitrate concentrations were lower, the authors suggested that ethylene glycol dinitrate concentrations in human urine and blood be measured as soon as possible after the samples are taken.

Inorganic nitrate levels in the blood peaked in about 3.5 hr, then returned to normal levels in 12 hr. During this period, sufficient inorganic nitrate was excreted in the urine to account for approximately 60 percent of the amount of ethylene glycol dinitrate administered. The fate of the other 40 percent of inorganic nitrate is not known.

Used as an explosive; [ACGIH]

Plasticizer (nitrocellulose explosives)

Liquid explosive

Low-freezing dynamites

2023: 1,153,074 lb

(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

1,2-Ethanediol, 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#1546]

ETHYLENE GLYCOL DINITRATE IS PRODUCED BY NITRATING A MIXTURE OF GLYCERINE AND ETHYLENE GLYCOL IN THE SAME REACTOR, IN THE PRESENCE OF SULFURIC ACID.

Ethylene glycol dinitrate is made by nitration of ethylene glycol with mixed acid with a yield of ca. 93%.

Explosives Manufacturing

1,2-Ethanediol, 1,2-dinitrate: ACTIVE

Ethylene glycol dinitrate is an excellent solvent for low-grade nitrocellulose, is comparable to nitroglycerin in explosive energy, and is less sensitive and more stable. It can detonate at high and low velocities (8000 and 100-3000 m/s) ... it is an excellent substitute for nitroglycerin in dynamite.

The increasing use of ammonium nitrate-fuel oil and slurry explosives to replace dynamites has greatly decreased the demand for ethylene glycol dinitrate.

ANALOGOUS STRUCTURE TO NITROGLYCERIN

Ethylene glycol dinitrate is mixed with nitroglycerin currently in a ratio of about 8:2, to lower the freezing point of the dynamite mixture and increase its stability, making it safer to manufacture and use.