Propylene glycol dinitrate

Propylene glycol dinitrate

Names
IUPAC name Propylene dinitrate
Other names Propane-1,2-diyl dinitrate; 1,2-Bis(nitrooxy)propane
Identifiers
CAS Number	6423-43-4
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL206527
ChemSpider	21472
ECHA InfoCard	100.026.527
PubChem	22933
InChI InChI=1S/C3H6N2O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3 Key: PSXCGTLGGVDWFU-UHFFFAOYSA-N InChI=1/C3H6N2O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3 Key: PSXCGTLGGVDWFU-UHFFFAOYAG
SMILES O=[N+]([O-])OC(C)CO[N+](=O)[O-]
Properties
Chemical formula	C3H6N2O6
Molar mass	166.09 g·mol^−1
Appearance	colorless 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)
Solubility in water	0.1% (20°C)[1]
Vapor pressure	0.07 mmHg (22°C)[1]
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	930 mg kg^−1 (IP, rat)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 0.05 ppm (0.3 mg/m^3) [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, 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^[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, carbon monoxide, and nitrogen.

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]

References

1. "NIOSH Pocket Guide to Chemical Hazards #0535". National Institute for Occupational Safety and Health (NIOSH).
2. Record of Propylenglycoldinitrat in the GESTIS Substance Database of the IFA, accessed on 2. Dec. 2009
3. 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.