USH138H - Solid poly(azidomethyl)benzene explosive composition - Google Patents
Solid poly(azidomethyl)benzene explosive composition Download PDFInfo
- Publication number
- USH138H USH138H US06/655,609 US65560984A USH138H US H138 H USH138 H US H138H US 65560984 A US65560984 A US 65560984A US H138 H USH138 H US H138H
- Authority
- US
- United States
- Prior art keywords
- benzene
- azidomethyl
- sub
- product
- hexakis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000002360 explosive Substances 0.000 title claims description 14
- 239000007787 solid Substances 0.000 title claims description 8
- UDLLFLQFQMACJB-UHFFFAOYSA-N azidomethylbenzene Chemical compound [N-]=[N+]=NCC1=CC=CC=C1 UDLLFLQFQMACJB-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 title description 2
- IJUQJBVUGWLVDI-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=C(CN=[N+]=[N-])C(CN=[N+]=[N-])=C(CN=[N+]=[N-])C(CN=[N+]=[N-])=C1CN=[N+]=[N-] IJUQJBVUGWLVDI-UHFFFAOYSA-N 0.000 claims description 9
- KFFIVUABVNWVGJ-UHFFFAOYSA-N 1,2,4,5-tetrakis(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=CC(CN=[N+]=[N-])=C(CN=[N+]=[N-])C=C1CN=[N+]=[N-] KFFIVUABVNWVGJ-UHFFFAOYSA-N 0.000 claims description 4
- BRPQRUPKRTVHDZ-UHFFFAOYSA-N 1,3,5-tris(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=CC(CN=[N+]=[N-])=CC(CN=[N+]=[N-])=C1 BRPQRUPKRTVHDZ-UHFFFAOYSA-N 0.000 claims description 4
- -1 Poly(azidomethyl) Polymers 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 150000001555 benzenes Chemical class 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XJOUCILNLRXRTF-UHFFFAOYSA-N 1,2,3,4,5,6-hexakis(bromomethyl)benzene Chemical compound BrCC1=C(CBr)C(CBr)=C(CBr)C(CBr)=C1CBr XJOUCILNLRXRTF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PFPWPMGJLXTNED-UHFFFAOYSA-N 1,2,3,4-tetrakis(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=CC=C(CN=[N+]=[N-])C(CN=[N+]=[N-])=C1CN=[N+]=[N-] PFPWPMGJLXTNED-UHFFFAOYSA-N 0.000 description 1
- JUWNKMYNRUZXHJ-UHFFFAOYSA-N 1,2,3-tris(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=CC=CC(CN=[N+]=[N-])=C1CN=[N+]=[N-] JUWNKMYNRUZXHJ-UHFFFAOYSA-N 0.000 description 1
- UTXIKCCNBUIWPT-UHFFFAOYSA-N 1,2,4,5-tetrakis(bromomethyl)benzene Chemical compound BrCC1=CC(CBr)=C(CBr)C=C1CBr UTXIKCCNBUIWPT-UHFFFAOYSA-N 0.000 description 1
- SUKCSQNSCGTSOU-UHFFFAOYSA-N 1,3,5-tris(azidomethyl)-2,4,6-trimethylbenzene Chemical compound CC1=C(CN=[N+]=[N-])C(C)=C(CN=[N+]=[N-])C(C)=C1CN=[N+]=[N-] SUKCSQNSCGTSOU-UHFFFAOYSA-N 0.000 description 1
- BHIFXIATEXVOQA-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene Chemical compound CC1=C(CBr)C(C)=C(CBr)C(C)=C1CBr BHIFXIATEXVOQA-UHFFFAOYSA-N 0.000 description 1
- GHITVUOBZBZMND-UHFFFAOYSA-N 1,3,5-tris(bromomethyl)benzene Chemical compound BrCC1=CC(CBr)=CC(CBr)=C1 GHITVUOBZBZMND-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MWYDOXLDDPKKCP-UHFFFAOYSA-N 1,4-bis(azidomethyl)benzene Chemical compound [N-]=[N+]=NCC1=CC=C(CN=[N+]=[N-])C=C1 MWYDOXLDDPKKCP-UHFFFAOYSA-N 0.000 description 1
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FGHAZDVJHATENE-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[NH6+3] Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[NH6+3] FGHAZDVJHATENE-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- WETZJIOEDGMBMA-UHFFFAOYSA-L lead styphnate Chemical compound [Pb+2].[O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C([O-])=C1[N+]([O-])=O WETZJIOEDGMBMA-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/08—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated
- C07C247/10—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being unsaturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
Definitions
- this invention relates to poly(azidomethyl)benzenes for use as an explosive.
- this invention relates to poly(azidomethyl)benzenes having the formula:
- n 3 to 6 inclusive which may be used as an explosive.
- Azidomethyl derivatives of benzene are known; they include 1,4-bis (azidomethyl) benzene (Jour. Amer. Chem. Soc. 79,3491 (1957)) and monoazidomethylbenzene (Encyc. of Explosives and Related Items, Vol. 2, pg. B94). However, due to their physical properties, they have not proved of practical interest as explosives.
- novel explosive compounds of this invention are prepared by heating a poly(halomethyl)benzene with a metallic azide according to the equation:
- X is a halogen, usually chlorine or bromine
- Me is a metal
- n 3 to 6 inclusive.
- the organic solvents which may be used as the reaction medium include ethanol, acetone, ethylene glycol monoethyl ether, dimethyl sulfoxide, dimethyl formamide, and N-methyl pyrrolidinone.
- the product was proven to be hexakis (azidomethyl) benzene by melting point and infra-red spectrum.
- a drop of the product was placed in a test-tube, and heated over a low Bunsen flame at which time it detonated with a loud report.
- hexakis (azidomethyl) benzene has been found to be a white solid melting at 165° C., which can be prepared from inexpensive raw material. It contains nearly 62 percent azide nitrogen. It is more sensitive to impact than lead azide or styphnate, but less sensitive to friction or electric charge. It is stable to heat when tested by the Vacuum Stability Test, and stable to aqueous hydrolysis. It is suitable for use as a hot-wire initiator but is less sensitive than lead styphnate. The compound has been subjected to the mandatory tests required for qualification as an explosive.
- the cited hexakis (azidomethyl) benzene melts in a capillary at 162°-5° C. with gas evolution and darkening. On rapid heating on a spatula, the compound melts and shortly thereafter detonates. It is insoluble in water, and does not undergo any change upon heating in water for one week at 60° C. It is poorly soluble in organic solvents but maybe recrystallized from tetrahydrofuran or toluene. It has been found to undergo surface darkening upon prolonged exposure to light.
- the cited hexakis (azidomethyl) benzene is comparatively stable thermally. Its Auto-ignition Temperature is 173° C. which is in the area of Composition B (174° C.).
- the Five Second Explosive Temperature of 255° C. was determined bny the closed-cup procedure. It has practically the same response as nitroguanidine.
- the Explosion Temperature Test was ran with 20 mg. of explosive. At this lower dosage, the cited compound showed more disruption of the blasting cap, and more splashing of the Woods metal than 40 mg. of RDX.
- the cited hexakis compound has a substantially lower electrostatic and friction sensitivity than other primary explosives.
- the substantially high voltage required is regarded as a safety factor.
- the cited hexakis compound is insoluble in water, stable to hydrolysis, and poorly soluble in organic solvents. It has a density of 1.392 g/cc, explodes in concentrated sulfuric acid, and gradually darkens in light. It passed the Vacuum Stability Test for 40 hours at 100° C., the Five Second Explosion Temperature is 255° C. The activation energy is 30.8 K cal/mole and the Auto-ignition Temperature is 173°.
- the isomers 1,2,3 and 1,2,4 of tris (azidomethyl) benzene, and the isomers 1,2,3,4 and 1,2,3,5 of tetrakis (azidomethyl) benzene may be similarly prepared from the known bromomethyl or chloromethyl analogues.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Poly(azidomethyl)benzenes having the formula
C.sub.6 H.sub.6-N (CH.sub.2 N.sub.3).sub.N
wherein n represents 3 to 6 inclusive. These compounds are for use as novelxplosives.
Description
The invention described herein may be manufactured, used and licensed by or for the Government for Governmental purposes without payment to me of any royalties thereon.
In general, this invention relates to poly(azidomethyl)benzenes for use as an explosive.
More particularly, this invention relates to poly(azidomethyl)benzenes having the formula:
C.sub.6 H.sub.6-N (CH.sub.2 N.sub.3).sub.n
wherein n represents 3 to 6 inclusive which may be used as an explosive.
Azidomethyl derivatives of benzene are known; they include 1,4-bis (azidomethyl) benzene (Jour. Amer. Chem. Soc. 79,3491 (1957)) and monoazidomethylbenzene (Encyc. of Explosives and Related Items, Vol. 2, pg. B94). However, due to their physical properties, they have not proved of practical interest as explosives.
The novel explosive compounds of this invention are prepared by heating a poly(halomethyl)benzene with a metallic azide according to the equation:
C.sub.6 H.sub.6-N (CH.sub.2 X).sub.N +MeN.sub.3 →C.sub.6 H.sub.6-N (CH.sub.2 N.sub.3).sub.N
wherein X is a halogen, usually chlorine or bromine, Me is a metal, and n represents 3 to 6 inclusive. The organic solvents which may be used as the reaction medium include ethanol, acetone, ethylene glycol monoethyl ether, dimethyl sulfoxide, dimethyl formamide, and N-methyl pyrrolidinone.
1. Preparation of hexakis (azidomethyl) benzene.
18.0 g. (0.028 mole) of hexakis (bromomethyl) benzene (prepared in accordance with the Jour. Am. Chem. Soc. 100,2173 (1978) and 15.0 9. (0.23 mole) of sodium azide were reacted in 75 ml of dimethylformamide by mixing at 75°-80° C. for 1 hour. The reaction mixture was cooled and poured into cold water to precipitate the white solid product which was filtered, washed and dried. The yield was 11.5 g. which is 100 percent of theory. The product melted with decomposition at 163° C., and again at the same temperature after recrystallization from dioxane and water.
The identity of the product as hexakis (azidomethyl) benzene was proven by infra-red spectrum, NMR spectral analysis, and elemental analysis for C, H, and N.
Upon heating, a pinch of the material melted on a spatula, and shortly thereafter detonated sharply.
2. Preparation of hexakis (azidomethyl) benzene.
0.5 g. of hexakis (bromomethyl) benzene, 0.4 g. of sodium azide, and 15 ml. of dimethylformamide were mixed by stirring at room temperature for 2 hours. The reaction mixture was poured into water, the solid was filtered, and washed with water and methanol. The yield of product was 0.3 g. which was 100 percent of theory.
The product was proven to be hexakis (azidomethyl) benzene by melting point and infra-red spectrum.
3. Preparation of 1,3,5-tris (azidomethyl) benzene.
1.3 g. (0.0034 mole) of 1,3,5-tris (bromomethyl) benzene (prepared according to Chem. Ber. 106,717 (1973), and 0.8 g. (0.12 mole) of sodium azide were mixed in 15 ml. of dimethylformamide for 5 hours at 75° C. The reaction mixture was poured into water, and an oil separated which was extracted with methylene chloride. The solvent was removed and 0.7 g. of the product, a colorless oil was obtained, which was 86 percent of theory.
The above product was identified as 1,3,5-tris (azidomethyl) benzene by infra-red spectrum.
A drop of the product was placed in a test-tube, and heated over a low Bunsen flame at which time it detonated with a loud report.
4. Preparation of 1,2,4,5-tetrakis (azidomethyl) benzene.
0.9 g. (0.002 mole) of 1,2,4,5-tetrakis (bromomethyl) benzene (prepared in accordance with J. Het. Chem. 983, (1973), and 1.0 g. (0.015 mole) of sodium azide were mixed with stirring in 25 ml. of dimethylformamide for 1 hour at 80° C. The reaction mixture was poured into water, and the solids were filtered and dried. The product yield was 0.6 g. which was 100 percent of theory. The melting point of the solid product was 50° C. It was identified as 1,2,4,5-tetrakis (azidomethyl) benzene by infra-red spectrum. The latter compound detonated upon heating above its melting point.
5. Preparation of 1,3,5-tris(azidomethyl) -2,4,6-trimethylbenzene.
1.0 g. of 1,3,5-tris (bromomethyl) -2,4,6-trimethylbenzene and 0.70. of sodium azide were mixed in 25 ml. of dimethylformamide for 1 hour at 75° C. The reaction mixture was poured into water, and the solid product was filtered. The yield of product was 0.6 g. which was 85 percent of theory. The product melted at 60° C. upon recrystallization from methylcyclohexane. The product was identified by infra-red spectrum. Upon heating above its melting point, the product flashed.
In general, hexakis (azidomethyl) benzene has been found to be a white solid melting at 165° C., which can be prepared from inexpensive raw material. It contains nearly 62 percent azide nitrogen. It is more sensitive to impact than lead azide or styphnate, but less sensitive to friction or electric charge. It is stable to heat when tested by the Vacuum Stability Test, and stable to aqueous hydrolysis. It is suitable for use as a hot-wire initiator but is less sensitive than lead styphnate. The compound has been subjected to the mandatory tests required for qualification as an explosive.
More particularly, the cited hexakis (azidomethyl) benzene melts in a capillary at 162°-5° C. with gas evolution and darkening. On rapid heating on a spatula, the compound melts and shortly thereafter detonates. It is insoluble in water, and does not undergo any change upon heating in water for one week at 60° C. It is poorly soluble in organic solvents but maybe recrystallized from tetrahydrofuran or toluene. It has been found to undergo surface darkening upon prolonged exposure to light.
Specifically, the cited hexakis (azidomethyl) benzene is comparatively stable thermally. Its Auto-ignition Temperature is 173° C. which is in the area of Composition B (174° C.). The Five Second Explosive Temperature of 255° C. was determined bny the closed-cup procedure. It has practically the same response as nitroguanidine. The Explosion Temperature Test was ran with 20 mg. of explosive. At this lower dosage, the cited compound showed more disruption of the blasting cap, and more splashing of the Woods metal than 40 mg. of RDX.
Further, the cited hexakis compound has a substantially lower electrostatic and friction sensitivity than other primary explosives. In the Hot-Wire Initiation Test, the substantially high voltage required is regarded as a safety factor.
In summary, the cited hexakis compound is insoluble in water, stable to hydrolysis, and poorly soluble in organic solvents. It has a density of 1.392 g/cc, explodes in concentrated sulfuric acid, and gradually darkens in light. It passed the Vacuum Stability Test for 40 hours at 100° C., the Five Second Explosion Temperature is 255° C. The activation energy is 30.8 K cal/mole and the Auto-ignition Temperature is 173°.
In conclusion note should be also be taken that the isomers 1,2,3 and 1,2,4 of tris (azidomethyl) benzene, and the isomers 1,2,3,4 and 1,2,3,5 of tetrakis (azidomethyl) benzene may be similarly prepared from the known bromomethyl or chloromethyl analogues.
The foregoing disclosure is merely illustrative of the principles of this invention and is not to be interpreted in a limiting sense. I wish it to be understood that I do not desire to be limited to the exact details of construction shown and described because obvious modifications will occur to a person skilled in the art.
Claims (4)
1. A solid explosive selected from the group consisting of:
a. Hexakis (azidomethyl) benzene,
b. 1,3,5-Tris (azidomethyl) benzene,
c. 1,2,4,5-Tetrakis (azidomethyl) benzene.
2. The solid explosive of claim 1 being Hexakis (azidomethyl) benzene.
3. The solid explosive of claim 1 being 1,3,5-Tris (azidomethyl) benzene.
4. The solid explosive of claim 1 being 1,2,4,5-Tetrakis (azidomethyl) benzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/655,609 USH138H (en) | 1984-09-28 | 1984-09-28 | Solid poly(azidomethyl)benzene explosive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/655,609 USH138H (en) | 1984-09-28 | 1984-09-28 | Solid poly(azidomethyl)benzene explosive composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH138H true USH138H (en) | 1986-10-07 |
Family
ID=24629599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/655,609 Abandoned USH138H (en) | 1984-09-28 | 1984-09-28 | Solid poly(azidomethyl)benzene explosive composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH138H (en) |
-
1984
- 1984-09-28 US US06/655,609 patent/USH138H/en not_active Abandoned
Non-Patent Citations (2)
| Title |
|---|
| McGrath; C.A., 74: 142858n (1971). |
| Sommers, et al.; J.A.C.S., 79, (1957), pp. 3491-3492. |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Cho et al. | Synthesis and characterization of 1‐methyl‐2, 4, 5‐trinitroimidazole (MTNI) | |
| US8273784B2 (en) | Dinitropyrazole derivatives, their preparation, and energetic compositions comprising them | |
| Benz et al. | Krapcho Decarboxylation of ethyl-carbazate: synthetic approach toward 1, 1′-diamino-5, 5′-bistetrazole and its utilization as a high-performing metal-free initiator | |
| Klapötke et al. | N-Functionalisation of 5, 5′-bistetrazole providing 2, 2′-di (azidomethyl) bistetrazole: a melt-castable metal-free green primary explosive | |
| Lei et al. | The Unique Synthesis of a Green Metal‐Free Primary Explosive: 3, 3′‐azo‐5, 5′‐diazido‐1, 2, 4‐triazole | |
| US10752560B2 (en) | 5,5′-bis(2,4,6-Trinitrophenyl)-2,2′-bi(1,3,4-oxadiazole) and bis(2,4,6-trinitrobenzoyl)oxalohydrazide | |
| Singh et al. | Hexanitrostilbene and its properties | |
| USH138H (en) | Solid poly(azidomethyl)benzene explosive composition | |
| US3306939A (en) | Orthoesters of 2,2,2-trinitroethanol | |
| Yang et al. | TACOT-derived new nitrogen rich energetic compounds: synthesis, characterization and properties | |
| Agrawal et al. | Synthesis of 1, 3-bis (1, 2, 4-triazol-3-amino)-2, 4, 6-trinitrobenzene and its thermal and explosive behaviour | |
| US3184286A (en) | Cs2b12h12*csno3 product and process for making same | |
| Zhang et al. | A comparative study of the structures, thermal stabilities and energetic performances of two energetic regioisomers: 3 (4)-(4-aminofurazan-3-yl)-4 (3)-(4-nitrofurazan-3-yl) furoxan | |
| Kumar et al. | Diazido nitro pyrazoles: unlocking high-performance primary explosives with binder capabilities | |
| Sikder et al. | Synthesis, characterization and thermal studies of 2-oxo-1, 3, 5-trinitro-1, 3, 5-triazacyclohexane (Keto-RDX or K-6) | |
| US4529801A (en) | Primary explosive | |
| Li et al. | Synthesis and properties of novel thermally stable and insensitive 3, 6-dinitropyrazolo [4, 3-c] pyrazole-based energetic materials | |
| Mehilal et al. | Synthesis, characterization and explosives properties of 7-(1h-1, 2, 4-triazol-3-amino)-4, 6-dinitrobenzofuroxan (TADNB) and 7-(1h-1, 2, 3, 4-tetrazol-5-amino)-4, 6-dinitrobenzofuroxan (TEADNBF) | |
| Zhang et al. | 1 4, 1 6, 3 4, 3 6, 5 4, 5 6, 7 4, 7 6-Octanitro-2, 4, 6, 8-tetraoxa-1, 3, 5, 7 (1, 3)-tetrabenzenacyclooctaphane and its derivatives: thermally stable explosives with outstanding properties | |
| US3923804A (en) | Nitro-pyrimidines | |
| US3097239A (en) | Condensation products of trinitromethane and dimethylolurea | |
| US4535193A (en) | 1,4,6,9-Tetranitrodiamantane | |
| US3166567A (en) | 2, 3;4, 5-dibenzo-1, 3a, 6, 6a-tetraazapentalenes | |
| Yi et al. | Properties and Application of Nitrogen‐Rich Compound BTATz in Low‐Signature Propellants | |
| US7192497B2 (en) | Thermally stable booster explosive and process for manufacture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| AS | Assignment |
Owner name: UNITED STATES OF AMERICA THE, AS REPRESENTED BY TH Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:GILBERT, EVERETT E.;REEL/FRAME:004661/0929 Effective date: 19840925 |