Glyceryl nitrate

It is slightly less impact-sensitive than glyceryl nitrate. 

It is extremely shock-sensitive, a 4.0 kg cm shock causing detonation in 50% of test runs (cf. 3.5 kg cm for propargyl bromide 2.0 kg cm for glyceryl nitrate). The intermediate bis-chlorosulfite involved in the preparation needs low temperatures to avoid vigorous decomposition. The corresponding diiodo derivative was expected to be similarly hazardous [1], and this has been confirmed [2]. Improvements in preparative techniques (use of dichloromethane solvent at —30°C) to avoid violent reaction have also been described [3], An attempt to distill the compound (b.p. 55-58°C/0.6 mbar, equivalent to about 230°C/l bar) at atmospheric pressure from a heating mantle led to a violent explosion [4], The compound involved was erroneously given as l,6-dichloro-2,4-hexadiene [5],... 

The neat material is about three times as shock-sensitive as glyceryl nitrate, and should not be handled undiluted [1]. It exploded during vacuum distillation at 3.3 mbar from a bath at 140°C. Impact- and spark-sensitivities were determined, and autoignition occurred after 30 s at 107°C [2], An explosion occurred during distillation at a pot temperature of 80°C. Full handling precautions are detailed. Dilution of neat material with solvent eliminates shock-sensitivity [3],... 

Mixtures with calcium hydride or strontium hydride may explode readily, and interaction of the molten chlorate is, of course, violent. A mixture of syrupy sodium phosphinate ( hypophosphite ) and the powdered chlorate on heating eventually explodes as powerfully as glyceryl nitrate. Calcium phosphinate mixed with the chlorate and quartz detonates (the latter producing friction to initiate the mixture). Dried mixtures of barium phosphinate and the chlorate are very sensitive and highly explosive under the lightest confinement (screwed up in paper). 

During the preparation of this explosive liquid by interaction of sulfuryl chloride fluoride and sodium azide, traces of chlorine must be eliminated from the former to avoid detonation. The product is nearly as shock-sensitive as glyceryl nitrate and may explode on rapid heating. Solutions (25 wt%) in solvents may be handled safely. The corresponding fluoride is believed to behave similarly. 

Charging mixed nitrating acid into an insufficiently cleaned glycerol drum led to a violent explosion. Formation and detonation of glyceryl nitrate may have added to the oxidation energy release. 

A plant explosion involved a mixture of nitrobenzene, nitric acid and a substantial quantity of water. Detonation occurred with a speed and power comparable to TNT. This was unexpected in view of the presence of water in the mixture [1]. The later reference deals with a detailed practical and theoretical study of this system and determination of the detonability limits and shock-sensitivity. The limits of detonability coincided with the limits of miscibility over a wide portion of the ternary composition diagram. In absence of water, very high sensitivity (similar to that of glyceryl nitrate) occurred between 50 and 80% nitric acid, the stoicheiometric proportion being 73% [2],... 

It is a low-melting solid, as shock-sensitive as glyceryl nitrate. 

The explosion limits have been determined for liquid systems containing hydrogen peroxide, water and acetaldehyde, acetic acid, acetone, ethanol, formaldehyde, formic acid, methanol, 2-propanol or propionaldehyde, under various types of initiation [1], In general, explosive behaviour is noted where the ratio of hydrogen peroxide to water is >1, and if the overall fuel-peroxide composition is stoicheiometric, the explosive power and sensitivity may be equivalent to those of glyceryl nitrate [2],... 

Ramsay, J. B. et al., Proc. 6th Int. Symp. Detonation, 1976, 723-728 Liquid nitrogen oxide and other cryogenic oxidisers (ozone, fluorine in presence of water) are very sensitive to detonation in absence of fuel, and can be initiated as readily as glyceryl nitrate [1,2]. Detonation of the endothermic liquid oxide close to its b.p. (-152°C) generated a 100 kbar pulse and fragmented the test equipment. It is the simplest molecule that is capable of detonation in all 3 phases [3], The liquid oxide is sensitive and may explode dining distillation [4],... 

Mixtures of sodium (or its alloy with potassium) and nitromethane, trichloroni-tromethane, nitrobenzene, dinitrobenzene, dinitronaphthalene, ethyl nitrite, ethyl nitrate or glyceryl nitrate are shock-sensitive, the sensitivity increasing with the number of nitro groups. 

H. Laufen, M. Leitold, The Pattern of Glyceryl Nitrates after Oral Administration of Glyceryl Trinitrate , Arzneim.-b orsch. 1988,38, 103-105. 

DOT CLASSIFICATION 6.1 Label KEEP AWAY FROM FOOD SAFETY PROFILE Poison by ingestion and intraperitoneal routes. Moderately toxic by inhalation. Experimental reproductive effects. A severe eye irritant. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. A chemosterilant for rodents. Combustible when exposed to heat or flame. Reaction with perchloric acid forms a sensitive explosive product more powerful than glyceryl nitrate. When heated to decomposition it emits toxic fumes of Cl". 

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