6423-43-4

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 6423-43-4 differently. You can refer to the following data:
1. Colorless liquid; unpleasant odor. Slightly soluble in water.
2. Propylene glycol dinitrate is an explosive. It is a colorless, high-boiling liquid (solid below -8℃) with a disagreeable odor.

Uses

Different sources of media describe the Uses of 6423-43-4 differently. You can refer to the following data:
1. Torpedo propellant in Otto Fuel II.
2. In the torpedo propellant Otto fuel II

General Description

Colorless 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).

Reactivity Profile

1,2-PROPANEDIOL 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.

Hazard

Toxic by inhalation and skin absorption. Headache and central nervous system impairment.

Health Hazard

Propylene glycol dinitrate (PGDN) is a vasodilator, and at extremely high concentrations it causes methemoglobin formation.

Safety Profile

Poison by ingestion and subcutaneous routes. Moderately toxic by intraperitoneal and intravenous routes. Human systemic effects by inhalation: conjunctiva irritation, headache. An eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also NITRATES.

Potential Exposure

Propylene glycol dinitrate has been used as a torpedo propellant. The explosion potential is similar to ethylene glycol dinitrate.

Carcinogenicity

Negative results were reported in various mutagenic assays including the Ames Salmonella assay (with or without microsomal activation), sister chromatid exchange assay in mouse lymphoma cells, mouse bone marrow cytogenic analysis, and mouse dominant lethal assay.

Shipping

UN0473 Substances, explosive, n.o.s., Hazard Class: 1.1A; Labels:1.1A-Explosive (with a mass explosion hazard); A-Substances which are expected to mass detonate very soon after fire reaches them, Technical Name Required.

Incompatibilities

Explosive. A strong oxidizer. Contact with ammonia compounds, amines, strong acids; reducing agents; combustible materials may result in fire and explo- sion. It is similar to ethylene glycol dinitrate in explosion potential. Propylene glycol dinitrate may explode if strongly shocked or heated. 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 .

InChI:InChI=1/C3H6N2O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3

Upstream product

• 187737-37-7 propene 
• 75-55-8 2-Methylaziridine 
• 601-75-2 ethylmalonic acid 
• 110-94-1 1,5-pentanedioic acid 
• 498-21-5 2-methylbutanedioic acid 
• 7697-37-2 nitric acid 
• 75-56-9 methyloxirane 
• 177944-02-4 2-Methyl-1-trimethylsilanyl-aziridine 
• 137514-23-9 N-nitropropylenimine 
• 57-55-6 propylene glycol 

Downstream Products

• 57-55-6 propylene glycol 

Relevant academic research and scientific papers

Practical catalytic nitration directly with commercial nitric acid for the preparation of aliphatic nitroesters

To pursue a sustainable and efficient approach for aliphatic nitroester preparation from alcohol, europium-triflate-catalyzed nitration, which directly uses commercial nitric acid, has been successfully developed. Gram scalability with operational ease showed its practicability.

Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5)

In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise the impact of this activity on the environment in the future.

Separation of Diastereomeric and Enantiomeric Alkyl Nitrates - Systematic Approach to Chiral Discrimination on Cyclodextrin LIPODEX-D

High-resolution gas chromatographic separation of all diastereomeric monomethyl-substituted cyclohexyl nitrates is shown on a nonpolar methylpolysiloxane stationary phase, and the first application of this procedure to the environmental diastereomeric analysis of alkyl nitrates is presented.Two characteristic signals in the achiral analysis of atmospheric samples could be assigned to the smallest alkyl nitrate containing two asymmetric carbon atoms, 3-methyl-2-pentyl nitrate.Retention indices in the temperature-programmed separation based on the n-alkanes were determined.The homologous series of 1-alkyl nitrates were found to be useful as ECD-visible n-alkanes.Enantiomeric separation of alkyl nitrates was achieved on heptakis(3-O-acetyl,-2,6-di-O-pentyl)-β-cyclodextrin (LIPODEX-D).The influence of the nitrooxy group and the alkyl chain length on the chiral discrimination on LIPODEX-D is discussed for 25 chiral alkyl nitrates.The absolute configurations of some alkyl nitrates were assigned by asymmetric synthesis of enantiomerically pure references.The complexity of the alkyl nitrate mixtures present in air samoles does not allow a direct chiral separation as the alkyl nitrates partly coelute on the LIPODEX-D column.Column coupling of LIPODEX-D with a polar achiral stationary phase like polyalkylenglocol (PAG) was successfully applied to solve this problem, and the chiral alkyl nitrates present in a typical air sample were separated.A systematic nomenclature for alkyl nitrates is introduced to handle the steadily growing number of branched and long-chain nitrates detected in environmental analysis. - Keywords: analytical methods; alkyl nitrates; chiral resolution; cyclodextrins; gas chromatography

Preparation of Di- and polynitrates by ring-opening nitration of epoxides by dinitrogen pentoxide (N2O5)

Eighteen epoxides of various kinds were reacted with N2O5 in chlorinated hydrocarbon solvents (principally CH2Cl2) to give vicinal nitrate ester products by a novel ring-opening nitration reaction. The procedure offers easier temperature control and simpler isolation procedures compared with conventional mixed acid nitrations; it also enables selective nitration reactions to be carried out on polyfunctional substrates. The scope and limitations of the reaction, as well as those of an alternative route utilising N2O4 with in situ oxidation of an intermediate nitrite-nitrate, are discussed.

Process for the production of high energy materials

A process for the production of a high energy nitrate ester involves reacting, in an inert organic solvent, a heterocyclic compound, selected from oxiranes, oxetanes, N-substituted aziridines and N-substituted azetidines, with either N2 O4 or N2 O5, and when the compound is reacted with N2 O4, oxidizing the O- or N-nitrate substituents or substituent in the product to O- or N-nitrate substituent or substituents. The remaining ring carbon atoms on the heterocyclic compound may be substituted or unsubstituted. Preferred substituent groups for the C and/or N ring atoms on the compound include alkyl, cyanoalkyl, haloalkyl, nitroalkyl, and substituted aryl. Several novel nitrate ester are also provided, including nitrated derivatives of polybutadiene, in which between 1% and 25% of the carbon atoms in the polymer are substituted by vicinal nitrate ester (--ONO2) groups.

Nitration by oxides of nitrogen, part 4: Unexpected behaviour of certain aziridines and azetidines upon reaction with dinitrogen pentoxide

Seven aziridines and azetidines, either unsubstituted on ring nitrogen or bearing N-acyl (N,N-dimethylcarbamyl or propionyl) groups, were reacted with N2O5 in halogenated solvents with the following results:- the behaviour of the aziridines was highly dependent on the N-substituent, giving respectively dinitrate esters, nitramine-nitrate or predominantly uncharacterisable products, whereas the azetidines gave in all cases N-nitroazetidine. The different behaviour is believed to result from ring strain effects.

Mechanism of the Gas-Phase Reactions of C3H6 and NO3 Radicals

Gas-phase reactions of propylene with NO3 were investigated in the C3H6-N2O50-O2/N2 system by Fourier transform infrared spectrometry.New type of nitrogen-containing compounds, nitroxyperoxypropyl nitrate (NPPN, CH3CH(ONO2)CH2(OONO2) and/or CH3CH(OONO2)CH2(ONO2)) and nitroxypropyl nitrite (NPN, CH3CH(ONO2)CH2(ONO) and/or CH3CH(ONO)CH2(ONO2)) were identified for the reaction systems with and without O2, respectively.Both nitroxy conpounds were unstable, and their kinetic behaviors suggest that they are intermediate species in the formation of the final product, propylene glycol 1,2-dinitrate (PGDN).The reaction was concluded to be initiated by the addition reaction of the NO3 radical to propylene, and an overall reaction mechanism for the C3H6-N2O5 system was proposed.