Propylene glycol dinitrate

Propylene glycol dinitrate
IUPAC name

propylene dinitrate
Other names

propane-1,2-diyl dinitrate;
1,2-bis(nitrooxy)propane
Identifiers
CAS number 6423-43-4
PubChem 22933
ChemSpider 21472 Y
ChEMBL CHEMBL206527 Y
Jmol-3D images Image 1
Properties
Molecular formula C3H6N2O6
Molar mass 166.11 g/mol
Density 1,232 g/cm³ (at 20 °C)[1]
Melting point

−27,7 °C [1]
Boiling point

Decomposes at 121 °C, below boiling point
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Propylene glycol dinitrate (PGDN, 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 -O-NO2 group. It is a characteristically and unpleasantly smelling[2] colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive.

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] [4]

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. One of the byproducts of its burning is a highly toxic cyanide gas.[3][4]

References

  1. ^ a b Record of Propylenglycoldinitrat in the GESTIS Substance Database from the IFA, accessed on 2. Dec. 2009
  2. ^ "TOXICOLOGICAL PROFILE FOR OTTO FUEL II AND ITS COMPONENTS". http://www.atsdr.cdc.gov/toxprofiles/tp77.pdf. 
  3. ^ a b 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. ^ a b 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.