Propylene glycol dinitrate

Structural formula
General
Surname	Propylene glycol dinitrate
other names	Propane-1,2-diyl dinitrate 1,2-bis (nitrooxy) propane PGDN
Molecular formula	C 3 H 6 N 2 O 6
Brief description	colorless, explosive liquid
External identifiers / databases
CAS number 6423-43-4 EC number 229-180-0 ECHA InfoCard 100.026.527 PubChem 22933 Wikidata Q2113171
properties
Molar mass	166.09 g mol −1
Physical state	liquid
density	1.368 g cm −3
Melting point	−7.7 ° C
boiling point	92 ° C (at 10  mmHg )
Vapor pressure	1.1288 Torr (25 ° C)
solubility	little in water (1.3 g l −1 )
safety instructions
GHS hazard labeling no classification available
MAK	Switzerland: 0.05 ml m −3 or 0.35 mg m −3
Toxicological data	463 mg kg −1 ( LD 50 ,  rat ,  sc ) 250 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propylene glycol dinitrate is an organic chemical compound , an ester of nitric acid and propylene glycol . It has a structural similarity to nitroglycerin , is sensitive to impact, explosive and inflammable.

Extraction and presentation

It is produced by nitrating 1,2-propylene glycol with nitrating acid , a mixture of nitric acid and sulfuric acid.

properties

Propylene glycol dinitrate is a colorless, slightly water-soluble, explosive liquid that has a boiling point of 92 ° C under reduced pressure (10  mmHg ). The standard enthalpy of formation is −297 kJ mol ⁻¹ , the heat of explosion 5393 kJ mol ⁻¹ . For the lead block expansion a value of 550 cm was ³ / 10g was measured.

use

Propylene glycol dinitrate is the main component of Otto-2 fuel , which is used in several modern types of torpedoes, including the Mark-46 lightweight torpedo , the Mark-48 torpedo, and the Spearfish .

safety instructions

The LD ₅₀ in rats for subcutaneous administration is 463 milligrams per kilogram of body weight, for oral intake 250 milligrams per kilogram. In humans, ataxias can occur at concentrations of 1.5  ppm or more , nausea, dizziness and headaches, even above 0.5 ppm. Methylene blue can be used as an antidote for poisoning .

Individual evidence

1. ↑ ^{a b c d} Jerrold B. Leikin, Frank P. Paloucek: Poisoning and toxicology handbook. 4th edition, Informa Health Care, 2008, ISBN 978-1-4200-4479-9 , p. 843.
2. ↑ ^{a b} Entry on propane-1,2-diol dinitrate in the GESTIS substance database of the IFA , accessed on February 28, 2017(JavaScript required) .
3. ↑ ^{a b c d} J. Koehler; R. Meyer, A. Homburg: Explosivstoffe , Tenth, completely revised edition, Wiley-VCH, Weinheim 2008, p. 241, ISBN 978-3-527-32009-7
4. ^ RG Fischer; K. Ballschmiter: Determination of vapor pressure, water solubility, gas-water partition coefficient P _GW , Henry's law constant, and octanol-water partition coefficient P _OW of 26 alkyl dinitrates in Chemosphere 36 (1998) 2891-2902. doi : 10.1016 / S0045-6535 (97) 10246-6 .
5. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
6. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 6423-43-4 or propylene glycol dinitrate ), accessed on November 2, 2015.
7. ↑ ^{a b c} Entry on 1,2-propanediol dinitrate in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on February 27, 2018.
8. ^ WC Crater: The Vapor Pressures of Glycerol Trinitrate and Certain Glycol Dinitrates in Ind. Eng. Chem. 21 (1929) 674-675. doi : 10.1021 / ie50235a016
9. ↑ EE Baroody: Heats of formation of propellant compounds , Rpt. NSWC-TR-83-250 by Naval Surface Weapons Center, Silver Spring, MD, 1983, 1-11.