Explosive compound

Information

  • Patent Grant
  • 4600536
  • Patent Number
    4,600,536
  • Date Filed
    Friday, October 19, 1984
    39 years ago
  • Date Issued
    Tuesday, July 15, 1986
    37 years ago
Abstract
A new polynitro compound pentanitrophenyl azide is disclosed, and a method of preparation is disclosed wherein hexanitrobenzene is reacted with sodium azide. This new polynitro compound is useful as an explosive.
Description

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a composition of matter and a method for producing the same, and is particularly related to a polynitro compound used as an explosive.
2. Description of the Prior Art
Many useful explosives contain nitro groups. However, there are few practical synthetic methods available for introduction of a nitro group attached to a carbon into an organic molecule. Known methods such as nitration, peroxytrifluoroacetic acid oxidation of amines, oximes and hydroxylamines or reactions of halides with nitrite ion, all have limitations.
In particular, there are very few methods broadly applicable to the synthesis of polynitro compounds.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a new polynitro compound and a method of synthesis. The compound pentanitrophenyl azide is prepared by reacting hexanitrobenzene and sodium azide.
DESCRIPTION OF THE PREFERRED EMBODIMENT
The reaction of hexanitrobenzene with an azide ion has been found to yield a powerful new explosive, pentanitrophenyl azide in a high yield.
The reaction is conducted by stirring a benzene solution of hexanitrobenzene with a slight excess of sodium azide (aqueous solution) at 25.degree. C. After separating and drying the benzene solution, the solvent is removed leaving pure pentanitrophenyl azide. Recrystallization from carbon tetrachloride gives either long, flat yellow prisms (.alpha.-form) or chunky, orange-yellow rosettes (.beta.-form) of pentanitrophenyl azide.
The properties of both forms are listed in the following table:
______________________________________TABLE OF PROPERTIESProperty Alpha Beta______________________________________Impact sensitivity, H.sub.50, 43 172.5 Kg wt, cmDensity, g/cm.sup.3 1.76.sup. 1.79.sup. 1.88.sup.a 1.88.sup.aDetonation velocity, mm/.mu.s 8.67.sup.b 8.78.sup.b 9.21.sup.c 9.21.sup.cDetonation pressure, Kbar 329.sup.b 341.sup.b 404.sup.c 404.sup.cMelting Point, .degree.C. 120.sup. 120.sup.Decomposition Temperature 120.sup. 120.sup.______________________________________ .sup.a calculated by Holden's method .sup.b calculated from the heat of formation by Kamlet's method .sup.c calculated by Rothstein's method
The most notable property of pentanitrophenyl azide is its brisance. The steel anvils employed in the impact test are significantly dented by the explosion, in contrast to the behavior of most explosives. A typical result in this test is the formation of no dent whatsoever, as with cyclotetramethylenetetranitramine (HMX).
The two crystalline forms of pentanitrophenyl azide exhibit significantly different impact sensitivities. Their densities are similar and lower than calculated by Holden's method. The explosive is quite energetic and comparable to cyclotrimethylenetrinitramine (RDX).
The alpha form of pentanitrophenyl azide is unusually insensitive for such a powerful explosive. It decomposes at its melting point which is lower than that of RDX and HMX. Owing to the decomposition on melting, it would not be possible to melt cast the material.





Pentanitrophenyl azide can be prepared by carrying out the procedure set forth in the following specific example.
EXAMPLE
Hexanitrobenzene (2.00 g) is dissolved in 75 ml of benzene. Sodium azide (0.411 g) in 45 ml of water is added and the mixture is stirred vigorously for 90 minutes, at 25.degree. C. The benzene layer is then separated, dried with magnesium sulfate, and concentrated to dryness. The yield of crude pentanitrophenyl azide is 1.87 g (95%).
Recrystallization from a hot saturated carbon tetrachloride solution yields 0.82 g of the alpha form, long flat yellow prisms, having a melting point of 119.5-121.degree. C.
Analysis calculated for C.sub.6 N.sub.8 O.sub.10 : C, 20.94%; N, 32.56%. Found: C, 20.88%; N, 32.37%; H, 0.07%.
The beta form can be obtained as chunky orange-yellow rosettes by recrystallization from dilute carbon tetrachloride solution, and has a melting point of 120-121.degree. C.
Both alpha and beta forms may also be obtained by seeding a warm saturated solution of carbon tetrachloride and of the crude pentanitrophenyl azide, with the appropriate crystals.
Claims
  • 1. A method for producing alpha-pentanitrophenyl azide comprising the steps of:
  • dissolving pentanitrophenyl azide in carbon tetrachloride to form a saturated solution; and
  • recrystallizing to yield the alpha product.
  • 2. A method for producing beta-pentanitrophenyl azide comprising the steps of:
  • dissolving pentanitrophenyl azide in carbon tetrachloride to form a dilute solution; and
  • recrystallizing to yield the beta product.
US Referenced Citations (3)
Number Name Date Kind
1824848 Turek Sep 1931
3948957 Beck Apr 1976
4262148 Nielsen et al. Apr 1981
Non-Patent Literature Citations (2)
Entry
Patai, et al., "The Chemistry of Halides Pseudo-Halides and Azides", Part (1983), p. 344, John Wiley & Sons, N.Y.
Boyer, et al., Chemical Reviews, 54, (1954), pp. 2 and 8.