US3465674A - Process for generating an explosion - Google Patents

Description

United States Patent O ABSTRACT OF THE DISCLOSURE N-halo amides react explosively with alkyl sulfoxides and active hydrogen compounds such as certain hydroxy compounds and amines. Delayed explosive decompositions occurring after a predetermined time can be produced by selection of components and variation of their proportions.

BACKGROUND OF THE INVENTION The present invention relates to spontaneously explosive compositions and to a method for generating an explosion under predetermined conditions.

Combinations of certain materials are known to be hypergolic, that is, ignition or explosion occurs on contact of the components. Such combinations are useful in rocketry and they are also sometimes employed to trigger a mechanical action or a larger explosion. The action is substantially instantaneous. Delayed action initiators such as the familiar black powder fuse of fireworks or other explosives are also known. Mechanically timed initiating devices have also been used to produce delayed explosions. The present invention provides a means whereby predetermined timed explosions can be produced by a novel chemical process.

SUMMARY OF THE INVENTION It has now been found that when a di lower alkyl sulfoxide or an active hydrogen compound such as any of certain alcohols and amines is intimately contacted with an N-halo amide or N-halo imide, the halogen being bromine or chlorine, the mixture remains substantially unchanged in appearance and temperature for a measurable time ranging from a second or two to several minutes, and in some cases, as long as several hours or even days, then it suddenly decomposes explosively with flame formation and generation of considerable gas and vapor. By choice of particular components and proportions of these, the interval between contact and explosion can be adjusted to a predetermined desired length.

DETAILED DESCRIPTION The N-halo amides of the invention are defined herein by that term as including any carboxamide, sulfonamide,

or corresponding carboximide or sulfonimide having at least one chlorine or bromine atom attached to the amide nitrogen atom. Representative compounds include N- chloroacetamide, N-bromosuccinimide, mono, di, and trichloroisocyanuric acid, 1,Z-dichloro-5,5-dimethyl-hydantoin, 1-bromo-3-chloro 5,5 dimethylhydantoin, N-N-dichloro-p-toluenesulfonamide, p,p oxybis(N,N-dichlorobenzenesulfonamide), N-chloro-Z-pyrrolidone, N-chloro- S-methyl-Z-oxazolidinone, N-chloro-2-morpholinone, N- chlorocaprolactam, and the like. Mixtures of such compounds may be employed. Particularly preferred are N- chloro-2-oxazolidinone and its lower alkyl substituted derivatives.

Organic hydroxy compounds of the present invention include primary and secondary alkanols of 2-7 carbon atoms, benzyl alcohol, phenol, and lower alkyl substituted phenols. Representative of the class of alkanols are ice ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, isoamyl alcohol, and heptyl alcohol. Alkanols such as methanol, tert-butyl alcohol, and cyclohexanol are not operative. The class of lower alkyl substituted phenols includes thecresols, isopropylphenol, tert-butylphenol, xylenol, and their isomers.

Amines useful in the present invention are alkyl primary amines of 3 to about 8 carbon atoms wherein the alkyl group is of primary or secondary configuration. Such amines include propylamine, isopropylamine, n-butylamine, 2-aminooctane, and the like.

Lower alkyl sulfoxides which are operable include dimethyl sulfoxide, diethyl sulfoxide, methyl ethyl sulfoxide, dibutyl sulfoxide, and the like, wherein the alkyl groups are of primary or secondary configuration. The term lower alkyl is used herein in its usual sense to mean alkyl groups of 14 carbon atoms.

Mixtures of alcohols, of amines, of sulfoxides, or combinations of these classes can be used effectively in the invention.

Proportions of reactants which are operative in this invention are 0.02-50 parts by weight of di lower alkyl sulfoxide or an active hydrogen compound per part of N- chloro compound. When proportions of reactants outside this range are employed, the large excess of the one reactant tends to muffie the reaction so that no explosion takes place even though a reaction may occur.

The N-chloro-2-oxazolidinones and N-chloro-Z-morpholinone and their N-bromo analogs are new compounds which are the invention of one of us and these are described and claimed in copending application Ser. No. 679,254, filed concurrently herewith and now abandoned. They may be prepared by halogenating the parent com pounds with a haloisocyanuric acid as set forth in that application or by reacting the heterocycle with chlorine in the presence of an alkali as described by Tafel et al. Berichte 33, 2224 (1900).

The utility of the present invention to generate sudden pressure, initiate a mechanical action, or detonate a conventional explosive is evident, particularly where it is desired to have a short delay between action and reaction. The occasion often arises where it is desirable to provide a known time between the triggering action, as by crushing a capsule of one component in the other component, and the explosion without having to depend on a burning fuse or action of a mechanical timer.

Examples 1-9 A series of tests were conducted wherein one gram of an N-haloamide was contacted with a small amount of isopropyl alcohol and the interval between this contact and explosion of the mixture was measured. During these tests, the mixtures characteristically showed little or no change in appearance or temperature for a definite time, then they suddenly and violently decomposed with an explosive evolution of gas and sometimes with a visible flame.

3 Examples 11-24 A series of tests were run substantially as described above wherein 0.3 ml. (or other quantity as noted) of a hydroxy compound was added to 1 ml. of N-chloro-S- methyl-2-oxazolidinone and the time before explosion was noted.

Hydroxy compound: Time, seconds Ethyl alcohol 78 Propyl alcohol 39 Isopropyl alcohol 4 Butyl alcohol 67 Isobutyl alcohol 39 Sec-butyl alcohol 3 n-Amyl alcohol 34 Isoamyl alcohol 79 n-Hexyl alcohol (0.1 ml.) 32 n-Heptyl alcohol 127 Isoheptyl alcohol 343 3-methyl-1-hexanol 231 Benzyl alcohol 24 o-Cresol (0.1 ml.) 3

Examples 25-27 Tests were run as in the foregoing examples wherein one gram quantities of an N-halo amide was contacted with 0.2 ml. of isopropylamine. In each case, the maximum temperature measured in the exploding mixture was determined.

Time, Maximum N-halo amide seconds temp., C.

Trichloroisocyanuric acid a. 114 N-chloro-5-methyl-2-oxazo1idinone about 1 213 N -bromo-5-methyl-2-oxazolidinone 210 Results comparable to those of Examples 25-27 are obtained when the isopropylamine is replaced by other primary amines as previously defined as n-butylamine, propylamine, n-hexylamine, or Z-aminooctane. In the same way, the N-halo amide can be any of other such compounds as shown in Examples 1-10 and as herein defined with similar results.

Example 28 By the procedure of the foregoing examples, 1.0 gram of N-chloro-5-methyl-2-oxazolidinone was intimately contacted with 0.1 ml. of dimethyl sulfoxide. The mixture exploded after a lapse of 1.5 seconds, the exploding mixture attaining a maximum temperature of 165 C.

Similar results are obtained when another di lower primary or secondary alkyl sulfoxide is employed in place of dimethyl sulfoxide or when the N-halo amide is another as previously defined.

We claim:

1. A process for generating an explosion which comprises intimately contacting at least one N-halo amide, where the halogen is chlorine or bromine, and 0.02 parts based on the weight of N-halo amide of a reactive component which is at least one of a di lower primary or secondary alkyl sulfoxide, a primary or secondary alkyl primary amine of 3-8 carbon atoms, or an organic hydroxy compound which is a primary or secondary alkanol of 2-7 carbon atoms, phenol, a lower alkyl phenol, or benzyl alcohol.

2. The process of claim 1 wherein the N-halo amide is an N-chloro-Z-oxabolidinone and the reactive component is a primary or secondary alkanol of 2-7 carbon atoms.

References Cited UNITED STATES PATENTS 2,149,694 3/1939 Vollrath 149-109 2,769,304 11/1956 Burton 149-109 X 2,771,737 11/1956 Scott et al 149-109 X 2,771,738 11/1956 Scott et al. 149-109 X 2,823,515 2/1958 Webb 149-109 X 2,826,037 3/1958 Scott et al 149-109 X 2,835,106 5/1958 Carter 149-109 X 2,859,587 11/1958 Scott et al. 149-109 X 2,869,320 1/1959 Burton 149-109 X 2,874,535 2/1959 Ayers et a1 149-109 X 2,932,941 4/1960 Ayers et al. 149-109 X CARL D. QUARFORTH, Primary Examiner S. J. LECHERT, Assistant Examiner U.S. Cl. X.R. -211; 149-109