6423-43-4CC(CO[N+](=O)[O-])O[N+](=O)[O-]PSXCGTLGGVDWFU-UHFFFAOYSA-NPropylene glycol dinitrate is a colorless liquid with a disagreeable odor. Mp: -30 °C. Density 1.37 g/cm3 at 20 °C. Slightly soluble in water (7.97 g/L H2O at 24.85 °C).
6423-43-4DTXSID7027627CHEMBL206527log Kow = 1.59 /Estimated/
1.83
1.23 at 77 °F (NIOSH, 2024) - Denser than water; will sink
Relative density (water = 1): 1.2 (25 °C)
1.23 at 77 °F
(77 °F): 1.23
0.1 % (NIOSH, 2024)
In water, 3,262 mg/L @ 25 °C /Estimated/
Solubility in water, g/100ml: 0.1
0.1%
When heated to decomposition it emits toxic fumes of /nitrogen oxide/
121 °C
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P301+P316, P308+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P301+P317, P308+P316, P319, P321, P330, P405, and P501 (click each P-code to see the statement)
Chemical: 1,2-Propanediol, dinitrate
Propylene 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.
Listed in the ACGIH table: Examples of Industrial Chemicals for Which Methemoglobin Formation is NOT the Principal Cause of Toxicity; Headache is a common symptom in new employees, but tolerance develops after repeated exposures. Volunteers exposed at 0.5 ppm for 6 to 8 hours showed impaired performance (ataxia) similar to the effects in these same subjects at high blood alcohol concentrations. Male volunteers exposed to levels from 0.03-1.5 ppm over a range of time showed no significant hematological effects. No evidence of chronic neurological effects was found in a group of 87 workers at a torpedo manufacturing plant where PGDN peak air concentrations measured from not detectable to 0.22 ppm (90% below 0.1 ppm). [ACGIH] An eye irritant; Can induce methemoglobinemia; [ICSC]
The mechanism of propylene glycol dinitrate toxicity is related to its vasodilating capacity. Propylene glycol dinitrate is an organic nitrate and shares many of the cardiovascular properties of therapeutic nitrates Organic nitrates induce peripheral vasodilation, decreased ventricular ejection time, relaxation, and a longer period of coronary blood flow. One of the earliest consequences of overexposure to propylene glycol dinitrate is a vasodilation of the cerebral vessels Should the overexposure be more severe, the relaxation of the vascular smooth muscle can result in a fall in blood pressure followed by a compensatory vasoconstriction.
The metabolism of /propylene glycol, 1,2-dinitrate/, as determined in vitro in blood and in vivo in rats, showed that 50% was broken down in 1 hr, and 50% of the remainder in the following hour.
For /intravenous/ doses of 0.3, 3, and 30 mg/kg /in rats/, the elimination half-time of propylene glycol dinitrate was 8.8, 13.1, and 17.4 hours, respectively. Elimination of the parent compound from blood was monoexponential.
The metabolism of /propylene glycol, 1,2-dinitrate/ (PGDN), as determined in vitro in blood and in vivo in rats, showed that 50% was broken down in 1 hr, and 50% of the remainder in the following hour. Small concentrations of inorganic nitrite were produced during incubation in blood, whereas inorganic nitrate accumulated. At the end of 3 hr, the first time it was measured, there were large amounts of propylene glycol 2-mononitrate (PGMN-2), together with small amounts of PGMN-1). The summed quantities of mononitrates, inorganic nitrate, and nitrite represented 95% of the initial amount added to blood. this metabolism occurred in the erythrocytes. In the intact rat, in contrast to in vitro in the blood, mononitrates undergo further degradation to nitrogen compounds other than the mononitrates and inorganic nitrate. Only 56% of the administered PGDN appeared in the urine as inorganic nitrate. THus, there is qualitatively little to distinguish the in vitro and in vivo metabolism of PGDN from that of /ethylene glycol dinitrate/ (EGDN). The only difference is that PGDN gives rise to two mononitrates and the 2-isomer is predominant, whereas EGDN gives rise only to /ethylene glycol mononitrate/. Quantitatively, there is less dinitrate and inorganic nitrite in the bloodstream after subcutaneous injection from PGDN than from a comparable injection of EGDN. Excretion was complete in 24 hr following a 65 mg/kg PGDN subcutaneous injection in rats.
No reaction records under the current filter.
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18 °F (NIOSH, 2024)
18 °F
-7.7777777778 °C
18 °F
0.07 mmHg at 72 °F (NIOSH, 2024)
0.38 [mmHg]
0.38 mm Hg @ 25 °C /Estimated/
Vapor pressure, Pa at 22.5 °C: 9.3
0.07 mmHg at 72 °F
0.07 [mm Hg] @22 °C
Henry's Law constant = 9.4X10-7 atm-cu m/mol @ 25 °C /Estimated/
Henry's Law constant is approx 1X10-2 atm-cu m/mole /Azeotrope/
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. Propylene glycol dinitrate is included on this list.
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.
PROPYLENE GLYCOL DINITRATE is explosive. Acts as a strong oxidizing agent. Heating 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.
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. 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. Refer for medical attention .
Excerpt from NIOSH Pocket Guide for Propylene glycol dinitrate:
(General first aid procedures)
Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]
0.01 [ppm] ("MAK value applies for the sum of the concentrations of Ethylene glycol dinitrate, Nitroglycerin and Propylene glycol dinitrate in the air."}[German Research Foundation (DFG)]
/To Fight fire use/ powder, water spray, foam, carbon dioxide.
In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.
Evacuate danger area! Consult an expert! Remove all ignition sources. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place. (Extra personal protection: complete protective clothing including self-contained breathing apparatus.)
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
Biodegradation studies have provided conflicting evidence of the biodegradability of propylene glycol dinitrate ... by conventional sewage treatment methods. Suggested alternative treatment methods have included carbon absorption techniques combined with base hydrolysis of propylene glycol dinitrate to the biodegradable propylene glycol, and decomposition of propylene glycol dinitrate using sodium sulfide. Bench-scale wet air oxidation screening tests conducted at 280 C for 60 minutes indicate excellent removal of propylene glycol dinitrate from waste streams that are too dilute to incinerate and too toxic to biotreat.
Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Remove all ignition sources. 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.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 1,2-propanediol dinitrate is expected to have high mobility in soil(SRC). Volatilization of 1,2-propanediol dinitrate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.4X10-7 atm-cu m/mole(SRC), calculated using a fragment constant estimation method(3). 1,2-Propanediol dinitrate forms an azeotrope with water resulting in enhanced volatilization from water(4), but it is unclear whether this will be important in moist soils(SRC). 1,2-Propanediol dinitrate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.38 mm Hg(SRC), determined from a fragment constant method(5). 1,2-Propanediol dinitrate was poorly biodegraded using an activated sewage sludge, a pure culture of Pseudomonas aeruginosa, and a commercially available inoculum employed for the degradation of nitrogen containing wastes(4), suggesting biodegradation in soil will be slow(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that 1,2-propanediol dinitrate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.4X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4); however, laboratory studies have shown that 1,2-propanediol dinitrate forms an azeotrope with water resulting in enhanced volatilization(5). The Henry's Law constant for the azeotrope was estimated to be about 1X10-2 atm-cu m/mole(5). Based on the Henry's Law constant for the azeotrope, the volatilization half-life from a model river and a model lake are estimated as 2 hours and 5 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 1.59(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,2-Propanediol dinitrate was poorly biodegraded using an activated sewage sludge, a pure culture of Pseudomonas aeruginosa, and a commercially available inoculum employed for the degradation of nitrogen containing wastes(5), suggesting biodegradation in water will be slow(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-propanediol dinitrate, which has an estimated vapor pressure of 0.38 mm Hg at 25 °C (SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-Propanediol 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 50 days(SRC), calculated from its rate constant of 3.2X10-13 cu cm/molecule-sec at 25 °C(3).
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
inhalation, skin absorption, ingestion, skin and/or eye contact
Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.
MAY BE ABSORBED! See Inhalation.
Redness. Pain.
See Inhalation.
irritation eyes; conjunctivitis; methemoglobinemia; headache, impaired balance, visual disturbance; In Animals: liver, kidney damage
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,2-propanediol dinitrate can be estimated to be 68(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,2-Propanediol dinitrate is expected to have high mobility in soil(SRC).
Grab samples of air in four U.S. Navy torpedo facilities (Naval Weapons Station, Charleston, South Carolina; Naval Weapons Station, Yorktown, Virginia; Naval Submarine Support Facility, New London, Connecticut; and Naval Torpedo Station, Keyport, Washington) had levels of 1,2-propanediol dinitrate ranging from 0 to 0.22 ppm(1).
/HUMAN EXPOSURE STUDIES/ Human volunteers who repeatedly inhaled propylene glycol dinitrate (PGDN) at 0.2 ppm or higher experienced disruption in the organization of the visual evoked response and headache in the majority of the subjects. Those exposed repeatedly at 0.2 ppm for 8 hours daily developed a tolerance to headache; however, alteration in the visual evoked response appeared cumulative. At 0.5 ppm, marked impairment in balance was manifest after 6.5 hours, and 40 minutes of exposure at 1.5 ppm induced ocular irritation. These symptoms resembled the ataxia seen in these same subjects at 100 to 150 mg/ 10 ml. There was, however, a consistent elevation of the diastolic blood pressure in those normotensive subjects exposed to PGDN at 0.5 pp for 8 hours; ... There was no evidence of a significant biochemical or hematologic effect in these male volunteers.
/HUMAN EXPOSURE STUDIES/ ...A group of 87 Navy personnel who were designated as "chronically exposed" to /propylene glycol, 1,2-dinitrate/ (PGDN) /were studied/. Of these, 29 were tested before and immediately after PGDN exposure during routine torpedo maintenance procedures called "turnarounds". Twenty-one nonexposed controls were similar in sex distribution, race, smoking habits, and caffeine intake; however, the exposed group consumed more than twice as much alcohol as controls. Alcohol is regarded as a substance that aggravates the toxicity of aliphatic nitrates. The duration of exposure of the entire group averaged 47.4 months, and the range was 1-132 months. Air samples were taken during each turnaround procedure. Concentrations ranged from 0.00 to 0.22 ppm and the mean concentration was 0.03 ppm. Only one sample exceeded the then current TLV of 0.2 ppm, and 87.5% of all peak concentrations were equal to or less than one-half the TLV. Neurological tests performed on the chronically exposed Otto fuel workers showed no statistically significant differences from controls. These findings also held for a subgroup of workers who had a longer mean exposure duration of almost 8 years (range of 5 to 11 years). However, quantitative eye tracking tests conducted for 29 turnarounds, showed a significant decrease (p=0.03) in the velocity of eye movement and in latency (p=0.04) when tested before and directly after exposure. Apparent alterations in standing behavior (on one leg for 30 sec) were of questionable significance.
/HUMAN EXPOSURE STUDIES/ .../Propylene glycol, 1,2-dinitrate/ (PGDN) increases the risk of cardiovascular disease through attacks due to nitrate withdrawal 1 to 3 days after last exposure and through a long-term risk which persists long after exposure ceases. The short-term risk was noted first and termed "Monday morning angina." This includes findings of angina, myocardial infarction, arrythmia, and sudden death. Generally, symptoms are not induced by exercise or psychic arousal, and no vascular lesions were found at autopsy.
/HUMAN EXPOSURE STUDIES/ Experimental exposure of volunteers to atmospheres of propylene glycol dinitrate resulted in headaches of presumed vascular origin. The headaches began as mild frontal headaches and became progressively worse and throbbing in nature. Headaches were reported by some subjects exposed to concentrations of propylene glycol dinitrate as low as 0.2 ppm for up to 8 hours. With repeated exposures, the severity and frequency of headaches was observed to decrease. By analogy with the effects of other aliphatic nitrates, the headaches are most likely the result of vasodilation of the meningeal blood vessels.
Using Otto fuel II (76% 1,2-propanediol dinitrate, 22.5% dibutyl sebacate, and 1.5% 2-nitrodiphenylamine) as substrate, 1,2-propanediol dinitrate was shown to be poorly biodegraded using an activated sewage sludge, a pure culture of Pseudomonas aeruginosa, and a commercially available inoculum employed for the degradation of nitrogen containing wastes(1).
An estimated BCF of 3 was calculated for 1,2-propanediol dinitrate(SRC), using an estimated log Kow of 1.6(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 Henry's Law constant for 1,2-propanediol dinitrate is estimated as 9.4X10-7 atm-cu m/mole(SRC) calculated using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,2-propanediol dinitrate is not expected to volatilize from moist soil or water surfaces(2). Laboratory experiments using 10 ml of Otto fuel II (76% 1,2-propanediol dinitrate, 22.5% dibutyl sebacate, and 1.5% 2-nitrodiphenylamine) added to an unspecified amount of water showed that 1,2-propanediol dinitrate in solution does not obey ideal solution behavior and there is a positive deviation in Raoult's Law due to the formation of an azeotrope with water(3). This resulted in the unexpected volatilization of 1,2-propanediol dinitrate from water under aerated laboratory conditions(3). The Henry's law constant for the azeotrope was estimated to be about 1X10-2 atm-cu m/mole(3). Based on the Henry's Law constant for the azeotrope, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). 1,2-Propanediol dinitrate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.38 mm Hg(SRC), determined from a fragment constant method(4).
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. Propylene glycol dinitrate is included on this list.
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.
Metabolic studies show that inorganic nitrate /is/ the major metabolite of propylene glycol dinitrate (PGDN) in rats administered 65 mg/kg subcutaneously; PGDN and nitrite were almost undetectable. Excretion was complete in 24 hours.
... An effort was made to understand the oxidative process /which produces methemoglobin in vivo/ better and explain the role of hemoglobin in detoxifying nitrate esters. The reaction was nonenzymatic and first-order for dinitrate and O2Hb. The rate of oxidation proceeds linearly with dinitrate concentration and does not approach a limit as would be the case if it were enzymatically driven. The rate of oxidation is related complexly to the oxygen concentration. No oxidation occurs at zero oxygen concentration and none at very high concentrations. The stoichiometry was thought to be 1.5 hemes oxidized per ester bond broken in hemolysates and 1.9 to 2.3 per mole reacted ester in whole cells. From these studies, it was reasoned that hemoglobin would fulfill an important role in detoxifying the effects caused by the dinitrates. Hemoglobin in vivo, with the methemoglobin reductase system, acts catalytically to metabolize dinitrates to nitrite and nitrate, and the mononitrates are further degraded by the denitrifying tissue enzymes.
Subcutaneous injection of 65 mg/kg propylene glycol dinitrate in rats caused a rapid increase in blood levels of propylene glycol dinitrate. Appearance of metabolites of propylene glycol dinitrate in the blood was maximal 2-4 hours postinjection and had declined to essentially zero by 8-12 hours postinjection. The predominant metabolite observed in the blood was nitrate, with propylene glycol 2-mononitrate observed at approximately one-half the concentration of inorganic nitrate. The levels of propylene glycol 1-mononitrate and inorganic nitrite were less than half that of propylene glycol 2-mononitrate.
For more Metabolism/Metabolites (Complete) data for 1,2-PROPANEDIOL DINITRATE (6 total), please visit the HSDB record page.
The substance can be absorbed into the body by inhalation, through the skin or by ingestion.
Information supporting the dermal absorption of propylene glycol dinitrate was obtained from studies demonstrating systemic toxicity after dermal exposure in rabbits For example, a transient decrease in hemoglobin was observed following dermal application of doses of propylene glycol dinitrate as low as 1,000 mg/kg/day, 2 hours/day, for 20 days to rabbits. Also, observation of elevated levels of the metabolite nitrate in the urine of rabbits receiving a dermal dose of 4,000 mg/kg/day supported the absorption of propylene glycol dinitrate after dermal exposure.
Exposure of monkeys to concentrations of 1.6 ppm and 4.2 ppm of propylene glycol dinitrate for 20 and 14 days, respectively, resulted in the detection of small amounts of propylene glycol dinitrate in plasma. During exposures to 1 .6 ppm, 35 ug/mL propylene glycol dinitrate was detected in plasma, and during exposures at 4.2 ppm, 170 ug/mL was detected in plasma.
In vitro studies using dog blood have shown that propylene glycol dinitrate preferentially associates with red blood cells in the blood.
For more Absorption, Distribution and Excretion (Complete) data for 1,2-PROPANEDIOL DINITRATE (6 total), please visit the HSDB record page.
Used in Otto Fuel II, a torpedo propellant. [ACGIH]
The principal current use of propylene glycol dinitrate is as a propellant in Otto Fuel II /75% composition/. Nitrates of polyhydric alcohols, of which propylene glycol dinitrate is an example, have been used in medicine for the treatment of angina pectoris, and as explosives since the mid-nineteenth century.
A torpedo propellant called Otto fuel II, used by the Navy, ... /major componet is/ 1,2-propylene glycol dinitrate (PGDN).
UsesIn the torpedo propellant Otto fuel II
UsesTorpedo propellant in Otto Fuel II.
General DescriptionColorless liquid with a disagreeable odor. Mp: -30°C. Density 1.37 g cm-3 at 20°C. Slightly soluble in water (7.97 g L-1 H2O at 24.85°C).
For more Human Toxicity Excerpts (Complete) data for 1,2-PROPANEDIOL DINITRATE (7 total), please visit the HSDB record page.