US3020318A - Polynitro alcohols and their method of preparation - Google Patents
Polynitro alcohols and their method of preparation Download PDFInfo
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- US3020318A US3020318A US675799A US67579957A US3020318A US 3020318 A US3020318 A US 3020318A US 675799 A US675799 A US 675799A US 67579957 A US67579957 A US 67579957A US 3020318 A US3020318 A US 3020318A
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- Prior art keywords
- polynitro
- alcohols
- sodium borohydride
- chloride
- percent
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- 150000001298 alcohols Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 description 13
- 229910000033 sodium borohydride Inorganic materials 0.000 description 13
- -1 lithium aluminum hydride Chemical compound 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 230000001603 reducing effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002360 explosive Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- IVLKBZHWMZOSPZ-UHFFFAOYSA-N 3,3,3-trinitropropan-1-ol Chemical compound OCCC([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O IVLKBZHWMZOSPZ-UHFFFAOYSA-N 0.000 description 3
- SLNJEYHCDJTPAU-UHFFFAOYSA-N 4,4,4-trinitrobutan-1-ol Chemical compound OCCCC([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O SLNJEYHCDJTPAU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MFJJAPUWCYDEHI-UHFFFAOYSA-N 4,4,4-trinitrobutanoyl chloride Chemical compound [O-][N+](=O)C([N+]([O-])=O)([N+]([O-])=O)CCC(Cl)=O MFJJAPUWCYDEHI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MHWLNQBTOIYJJP-UHFFFAOYSA-N mercury difulminate Chemical compound [O-][N+]#C[Hg]C#[N+][O-] MHWLNQBTOIYJJP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
- C07C205/15—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a saturated carbon skeleton
Definitions
- This invention relates to new and useful polynitro alcohols and to a method for their preparation.
- this invention is directed to polynitro alcohols having the general formula:
- A is either an alkylene or nitroalkylene radical.
- the polynitro alcohols of our invention find valuable use as intermediates in the preparation of high explosive compounds.
- 4,4,4-trinitrobutanol can be condensed with methyl isocyanate according to the method disclosed in assignees copending United States patent application Serial No. 482,410, filed January 17, 1955, now U.S..Patent No. 2,978,492, to yield N methyl 4,4,4-trino-- trobutyl carbar'nate.
- the compounds thus prepared are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge.
- An example of such a missile is disclosed in United States Patent Number 2,470,162, issued May 17, 1949.
- One way of using the high exploives in a device such as that disclosed in United States Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile.
- the crystals can be first pelletized and then; packed.
- a charge thus prepared is sufficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from'a rocket launching tube under the pressure developed from ignition of a propellant charge, and can be caused to explode on operation of an impactor time-fuse mechanism firing a detonating explosive such as lead azide or mercury fulminate.
- acyl halides may be reduced to their corresponding alcohols with reducing agents such as lithium aluminum hydride, and hydrogen in the presence of a catalyst.
- reducing agents such as lithium aluminum hydride
- these conventional reducing agents all possess such strong reducing properties that the destruction of functional groups, such as aliphatic nitro groups, usually accompanies the reduction of the carbonyl group.
- A is an alkylene or nitroalkylene radical
- X is a halogen radical
- the reduction is effected by adding a solution of a nitrocontaining acyl halide to a suspension of sodium borohydride.
- 1,4-dioxane is the preferred solvent due to its inert A behavior and volatility.
- be used such as 2,4-dimethylsulfolane; however, dioxane
- Any inert organic solvent can is preferred since it can "be separated from the product with greater ease.
- the compounds thus produced are obtained in a relatively pure form from the reaction mixture by hydrolyzing the sodium borohydride and its oxidation products in the aqueous phase, with a mineral acid, and recovering the product by crystallization,extraction or distillation from the non' aqueous phase.
- The'product an oil
- was fractionally distilled at reduced pressure at a temperature of about 80 to C. to yield a colorless mobile fluid, n l.4720, B.P. 80-l10 C./ 0.5 mm.
- the elemental analysis of the product is as follows:
- the 4,4,4-trinitrobutyl-p-nitrobenzoate' derivative was prepared by treating the product with nitrobenzoyl chloride in the conventional manner.
- the derivative had a melting point of 1131 14 C. and the following analysis:
- compositions of matter having the general formula:
- A is a radical selected from the group consisting of lower alkylene and lower nitroalkylene radicals.
- composition of matter 4,4,4-trinitro-l-butanol having the structural formula 3.
- composition of matter 3,3,3-trinitro1-propanol having the structural formula 4.
- composition of matter 4,4,6,6,6-pehtanitro-1- hexanol having the structural formula:
- A is a radical selected from the group consisting of lower alkylene and lower nitroalkylene radicals and X is a halogen radical.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,020,318 POLYNITRO ALCOHOLS AND THEIR METHOD 0F PREPARATION Marvin H. Gold and Gustave B. Linden, Pasadena, Calif., assignors to Aerojet-General Corporation, Azusa, Califi, a corporation of Ohio No Drawing. Filed July 25, 1957, Ser. No. 675,799
14 Claims. ((11. 260-632) This invention relates to new and useful polynitro alcohols and to a method for their preparation. In particular, this invention is directed to polynitro alcohols having the general formula:
wherein A is either an alkylene or nitroalkylene radical.
The polynitro alcohols of our invention find valuable use as intermediates in the preparation of high explosive compounds. For example, 4,4,4-trinitrobutanol can be condensed with methyl isocyanate according to the method disclosed in assignees copending United States patent application Serial No. 482,410, filed January 17, 1955, now U.S..Patent No. 2,978,492, to yield N methyl 4,4,4-trino-- trobutyl carbar'nate. The compounds thus prepared are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge. An example of such a missile is disclosed in United States Patent Number 2,470,162, issued May 17, 1949. One way of using the high exploives in a device such as that disclosed in United States Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then; packed. A charge thus prepared is sufficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from'a rocket launching tube under the pressure developed from ignition of a propellant charge, and can be caused to explode on operation of an impactor time-fuse mechanism firing a detonating explosive such as lead azide or mercury fulminate.
1 It is well known that acyl halides may be reduced to their corresponding alcohols with reducing agents such as lithium aluminum hydride, and hydrogen in the presence of a catalyst. However, these conventional reducing agents all possess such strong reducing properties that the destruction of functional groups, such as aliphatic nitro groups, usually accompanies the reduction of the carbonyl group. This method of further complicated by the sensitivity of nitro groups to basic media, hence these reducing agents, although capable of effecting the reduction, nevertheless have many undesirable features making it advantageous to find some more convenient method.
We have now found that polynitro alcohols can be prepared from their corresponding acyl halides by reduction with sodium borohydride in accordance with the general reaction scheme set forth below:
wherein A is an alkylene or nitroalkylene radical, and X is a halogen radical.
The reduction is effected by adding a solution of a nitrocontaining acyl halide to a suspension of sodium borohydride.
Optimum results are obtained using a suspension of powdered sodium borohydride, about 200% excess, in an inert solvent such as dioxane.
1,4-dioxane is the preferred solvent due to its inert A behavior and volatility. be used such as 2,4-dimethylsulfolane; however, dioxane Any inert organic solvent can is preferred since it can "be separated from the product with greater ease.
The compounds thus produced are obtained in a relatively pure form from the reaction mixture by hydrolyzing the sodium borohydride and its oxidation products in the aqueous phase, with a mineral acid, and recovering the product by crystallization,extraction or distillation from the non' aqueous phase.
The following example is presented to more clearly illustrate our invention. This example is presented purely as a means of illustration and does not in any way define either the limits or the scope of our invention.
dioxane and 3.2 gm. (0.07 mole). sodium borohydride, which had been well ground in a ball mill. The mixture was distilled and additional dioxane was periodically.
added until the distillate was no longer basic.
Heating ofthe mixture was then. discontinued and a solution of 0.6 ml. (0.01 mole) acetic acid in 10 dioxane was added dropwise to the sodium borohydride suspension. The distillation apparatus was removed and utes during which time the temperature of the reaction replaced with an internalthermometer. A solution of 4.8 gm. (0.02 mole) 4,4,4-trinitrobutyryl chloride in20 ml. dioxane was added dropwise over aperiod of minmixture was maintained between 15 C. and 20 C. The reaction was mildly exothermic during the first hour and the mixture had a very pale yellow color. The reaction mixture was hydrolyzed with 20 ml. 50:50 water-acetic acid and 20 ml. 2 N hydrochloric acid and the resulting clear solution was evaporated almost to dryness under vacuum. Water was added and the product was extracted with'ether. The ethersolution was washed with saturated sodium chloride and diluted with benzene. The solution was dried 2 hours over anhydrous sodium sulfate, then i filtered and evaporated to dryness at room temperature under vacuum to yield 3.0 gm. of yellow oil, n =1.47l6, B.P. ll0 C./0.5 mm.
The'product, an oil, was fractionally distilled at reduced pressure at a temperature of about 80 to C. to yield a colorless mobile fluid, n =l.4720, B.P. 80-l10 C./ 0.5 mm. The elemental analysis of the product is as follows:
Calculated: percent C, 22.97; percentH, 3.37; percent N,
Found: percent C, 23.48; percent H, 3.50; percent N,
The 4,4,4-trinitrobutyl-p-nitrobenzoate' derivative was prepared by treating the product with nitrobenzoyl chloride in the conventional manner. The derivative had a melting point of 1131 14 C. and the following analysis:
Calculated: percent C, 36.88; percent H, 2.81; percent N,
Found: percent C, 37.21; percent H, 2.93; percent N,
containing aldehyde followed by oxidation to the desired acid.
Other members of the class of compounds of our invention are prepared in the manner described above; for example, 3,3,3-trinitropropanol; 4,4,6,6,6-pentanitro-1- hexanol; 4,4,6,6,8,8,S-heptanitro-l-octanol; and 4,4,6,8,8, 8-hexanitro-1-octanol are prepared by reducing 3,3,3-t-rinitropropanoyl chloride; 4,4,6,6,G-pentanitro-hexanoyl chloride; 4,4,6,6,8,8,8-heptanitro-octanoyl chloride and 4,4,6,8,8,8-heXanitro-octanoyl chloride respectively with sodium borohydride in accordance with the teachings of this invention. It will be appreciated by those skilled in the art that other members of this new class of compounds can be prepared in the same manner simply by reacting appropriate starting materials. It is preferred in the practice of our invention to utilize polynitro acid chlorides as starting materials for reasons of cost and convenience, however it should be understood that any of the acid halides can be used. It will also be appreciated that reaction temperatures are not critical in the practice of our invention, and that both higher and lower temperatures and conditions can be used if desired without affecting the course of the reaction.
This application is a continuation in part of our copending U.S. patent application Serial No. 392,471, filed November 16, 1953, now abandoned.
We claim:
1. As compositions of matter the polynitro alcohols having the general formula:
wherein A is a radical selected from the group consisting of lower alkylene and lower nitroalkylene radicals. 7
'2. As a composition of matter, 4,4,4-trinitro-l-butanol having the structural formula 3. As a composition of matter 3,3,3-trinitro1-propanol having the structural formula 4. As a composition of matter 4,4,6,6,6-pehtanitro-1- hexanol having the structural formula:
5. As a composition of matter 4,4,6,6,8,8,8-heptanitrol-octanol having the structural formula:
IIIO: T N02 NOr-C-CHz-C-CH3-CGHzCHaCHgOH NO: NO: NO:
6. As a composition of matter 4,4,6,8,8,8-hexanitro-loctanol having the structural formula:
1 0. No, not Nor-o-onr-on-om-o-wmomomon 7. A method of preparing polynitro alcohols having the general formula:
which comprises reducing a polynitro acid halide having the general formula:
with sodium borohydride wherein A is a radical selected from the group consisting of lower alkylene and lower nitroalkylene radicals and X is a halogen radical.
8. The method of claim 7 wherein the reaction is con- I ducted in the presence of an inert organic solvent.
9. The method of claim 7 wherein the reaction is conducted inthe presence of 1,4-dioxane.
' 10. The method of preparing 4,4,4-trinitro-1-butanol which comprises reducing 4,4,4-trinitrobutyryl chloride with sodium borohydride.
11. The method of preparing 3,3,3-trinitro-l-propanol which comprises reducing 3,3,3trinitro-propanoyl chloride with sodium borohydride.
12. The method of preparing 4,4,6,6,6-pentanitro-1- hexanol which comprises reducing 4,4,6,6,6-pentanitrohexanoyl chloride with sodium borohydride.
13. The method of preparing 4,4,6,6,8,8,8-heptanitr l-octanol which comprises reducing 4,4,6,6,8,8,8-heptanitro-octanoyl-chloride with sodium borohydride.
14. The method of preparing 4,4,6,8,8,8-hexanitro-loctanol which comprises reducing 4,4,6,8,8,8-hexanitrooct'anoyl chloride with sodium borohydride.
References Cited in the file of this patent FOREIGN PATENTS 698,138 Great Britain Oct. 7, 1953 OTHER REFERENCES Hurd: Chemistry of the Hydrides, New York, John Wiley & Sons, Inc. (1952), p. 162.
Schechter et al.: J.A.C.S., vol. 74 (1952), pp. 3664-8.
Claims (1)
1. AS COMPOSITION OF MATTER THE POLYNITRO ALCOHOLS HAVING THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US675799A US3020318A (en) | 1957-07-25 | 1957-07-25 | Polynitro alcohols and their method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US675799A US3020318A (en) | 1957-07-25 | 1957-07-25 | Polynitro alcohols and their method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3020318A true US3020318A (en) | 1962-02-06 |
Family
ID=24712020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US675799A Expired - Lifetime US3020318A (en) | 1957-07-25 | 1957-07-25 | Polynitro alcohols and their method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3020318A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB698138A (en) * | 1950-07-07 | 1953-10-07 | Nitroglycerin Ab | Process for producing trinitroalcohols and esters thereof |
-
1957
- 1957-07-25 US US675799A patent/US3020318A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB698138A (en) * | 1950-07-07 | 1953-10-07 | Nitroglycerin Ab | Process for producing trinitroalcohols and esters thereof |
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