Propylene glycol dinitrate

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Propylene glycol dinitrate
PGDN.png
Names
IUPAC name
Propylene dinitrate
Other names
Propane-1,2-diyl dinitrate;
1,2-Bis(nitrooxy)propane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.527 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C3H6N2O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3 Yes check.svgY
    Key: PSXCGTLGGVDWFU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6N2O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3
    Key: PSXCGTLGGVDWFU-UHFFFAOYAG
  • O=[N+]([O-])OC(C)CO[N+](=O)[O-]
Properties
C3H6N2O6
Molar mass 166.089 g·mol−1
Appearancecolorless liquid [1]
Odor disagreeable [1]
Density 1.232 g/cm3 (at 20 °C) [2]
Melting point −27.7 °C (−17.9 °F; 245.5 K) [2]
Boiling point 121 °C (250 °F; 394 K)(decomposes below boiling point)
0.1% (20°C) [1]
Vapor pressure 0.07 mmHg (22°C) [1]
Hazards
Lethal dose or concentration (LD, LC):
930 mg kg−1 (IP, rat) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
none [1]
REL (Recommended)
TWA 0.05 ppm (0.3 mg/m3) [skin] [1]
IDLH (Immediate danger)
N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Propylene glycol dinitrate (PGDN, ttup 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrate group. It is a characteristically and unpleasantly smelling [4] colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive and burns with a clean flame producing water vapor, carbon monoxide, and nitrogen gas.

C3H6(ONO2)2 → 3 CO + 3 H2O + N2

The principal current use of propylene glycol dinitrate is as a propellant in Otto Fuel II, together with 2-nitrodiphenylamine and dibutyl sebacate. Otto Fuel II is used in some torpedoes as a propellant. [3] [5]

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.

PGDN affects blood pressure, causes respiratory toxicity, damages liver and kidneys, distorts vision, causes methoglobinuria, and can cause headache and lack of coordination. It may be absorbed through skin. Its primary toxicity mechanism is methemoglobinemia. It may cause permanent nerve damage.

For occupational exposures, the National Institute for Occupational Safety and Health has set a recommended exposure limit at 0.05 ppm (0.3 mg/m3) over an eight-hour workday, for dermal exposures. [6]

Related Research Articles

Nitroglycerin Chemical compound

Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Invented in 1847 by Ascanio Sobrero, nitroglycerin has been used ever since as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. Since the 1880s, it has been used by the military as an active ingredient and gelatinizer for nitrocellulose in some solid propellants such as cordite and ballistite. It is a major component in double-based smokeless propellants used by reloaders. Combined with nitrocellulose, hundreds of powder combinations are used by rifle, pistol, and shotgun reloaders.

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and many other names (and abbreviations such as "perc" or "PERC", and "PCE"), is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985.

Monomethylhydrazine (mono-methyl hydrazine, MMH) is a highly toxic, volatile hydrazine chemical with the chemical formula CH3(NH)NH2. It is used as a rocket propellant in bipropellant rocket engines because it is “hypergolic” with various oxidizers such as nitrogen tetroxide (N
2O
4) and nitric acid (HNO
3). As a propellant, it is described in specification MIL-PRF-27404.

Propylene oxide Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colorless volatile liquid with an odor similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

Otto fuel II Torpedo fuel

Otto fuel II is a monopropellant used to drive torpedoes and other weapon systems. It is not related to the Otto cycle. Otto fuel II was developed by US Navy in the 1960s for use as fuel in torpedoes. Otto fuel II was invented by Dr. Otto Reitlinger in 1963 ; it is named after Dr. Reitlinger and for being the second iteration of the fuel. The first torpedo to use it was the Mark 48 torpedo in the 1960s.

Barium nitrate Chemical compound

Barium nitrate is the inorganic compound with the chemical formula Ba(NO3)2. It, like most barium salts, is colorless, toxic, and water-soluble. It burns with a green flame and is an oxidizer; the compound is commonly used in pyrotechnics.

Pentaborane(9) Chemical compound

Pentaborane(9) is an inorganic compound with the formula B5H9. It is one of the most common boron hydride clusters, although it is a highly reactive compound. Because of its high reactivity toward oxygen, it was once evaluated as rocket or jet fuel. Like many of the smaller boron hydrides, pentaborane is colourless, diamagnetic, and volatile. It is related to pentaborane(11) (B5H11).

Bromoform Chemical compound

Bromoform (CHBr3) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. Bromoform can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminium bromide. Currently its main use is as a laboratory reagent.

Ethylbenzene Chemical compound

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). It is one of the four isomers of butanol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

2,4-Dinitrotoluene Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

Ethylene glycol dinitrate Chemical compound

Ethylene glycol dinitrate, abbreviated EGDN and NGc, also known as nitroglycol, is a chemical compound a colorless, oily explosive liquid obtained by nitrating ethylene glycol. It is similar to nitroglycerin in both manufacture and properties, though it is more volatile and less viscous. Unlike nitroglycerine, the chemical has a perfect (0) oxygen balance, meaning that its ideal exothermic decomposition would completely convert it to low energy CO2, H2O, and N2, with no excess unreacted O2, H2, C, or other high-energy substances, without needing to react with anything else.

2-Methoxyethanol Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

Dichlorvos

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961 and has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. The insecticide has been banned in EU since 1998.

Nitroethane Chemical compound

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

Glycidol Chemical compound

Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

Tetranitromethane or TNM is an organic oxidizer with chemical formula C(NO2)4. Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric acid.

Dinitro-<i>ortho</i>-cresol Chemical compound

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. DNOC and some related derivatives have been used as herbicides.

Diglycidyl ethers are chemical compounds used as a reactive diluents for epoxy resin. Other uses include treating textiles and stabilizing chlorinated organic compounds. Diglycidyl ether itself is extremely toxic, and can prove fatal or cause permanent damage if inhaled or consumed orally. As a class of compounds, there are a number of them available commercially with much lower toxicity profiles. One such example is epoxy resin itself Bisphenol A diglycidyl ether

References

  1. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0535". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 Record of Propylenglycoldinitrat in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2. Dec. 2009.
  3. 1 2 Forman, S (1988). "A review of propylene glycol dinitrate toxicology and epidemiology". Toxicology Letters . 43 (1–3): 51–65. doi:10.1016/0378-4274(88)90020-3. PMID   3051528.
  4. ↑ "TOXICOLOGICAL PROFILE FOR OTTO FUEL II AND ITS COMPONENTS" (PDF).
  5. ↑ Horvath, Edward P.; Ilka, Richard A.; Boyd, James; Markham, Thomas (1981). "Evaluation of the neurophysiologic effects of 1,2-propylene glycol dinitrate by quantitative ataxia and oculomotor function tests". American Journal of Industrial Medicine. 2 (4): 365–78. doi:10.1002/ajim.4700020407. PMID   6980592.
  6. ↑ "Propylene glycol dinitrate". NIOSH Pocket Guide to Chemical Hazards. Centers for Disease Control and Prevnetion.


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