US3098873A - Nitramines, nitrosamines and their preparation - Google Patents
Nitramines, nitrosamines and their preparation Download PDFInfo
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- US3098873A US3098873A US666274A US66627457A US3098873A US 3098873 A US3098873 A US 3098873A US 666274 A US666274 A US 666274A US 66627457 A US66627457 A US 66627457A US 3098873 A US3098873 A US 3098873A
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- diaza
- nitroso
- nitric acid
- nitramines
- nitrosamines
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- 150000004005 nitrosamines Chemical class 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 13
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
- -1 3,6-diaza-1,1,1,6- tetranitroheptane Chemical compound 0.000 description 23
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 18
- 229910017604 nitric acid Inorganic materials 0.000 description 18
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002360 explosive Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 3
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 3
- PCNVGALCIDYDAB-UHFFFAOYSA-N n-(2,2-dinitropropyl)-n-[2-[2,2-dinitropropyl(nitro)amino]ethyl]nitramide Chemical compound [O-][N+](=O)C([N+]([O-])=O)(C)CN([N+]([O-])=O)CCN([N+]([O-])=O)CC(C)([N+]([O-])=O)[N+]([O-])=O PCNVGALCIDYDAB-UHFFFAOYSA-N 0.000 description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VPFMKGYUNKFOIY-UHFFFAOYSA-N n-methyl-n-[2-[nitro(2,2,2-trinitroethyl)amino]ethyl]nitramide Chemical compound [O-][N+](=O)N(C)CCN([N+]([O-])=O)CC([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O VPFMKGYUNKFOIY-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- JGAGBYRIJUMEDB-UHFFFAOYSA-N 2,2,2-trinitroethanol Chemical compound OCC([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O JGAGBYRIJUMEDB-UHFFFAOYSA-N 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical group O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 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
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
Definitions
- R is a hydrogen, alkyl, or nitroalkyl radical
- A is an alkylene radical
- X is a nitroso or a nitro radical
- R is a hydrogen, nitro, alkyl, or nitroalkyl radical.
- the high energy nitramines and nitrosamines of this invention 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 Batent No. 2,470,162, issued May 17, 1949.
- One Way of using the high explosives of this invention 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 suffi'ciently 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 fusemechanism firing a detonating explosive such as lead azide or mercury fulminate.
- the high energy dinitramines of this invention are prepared by reacting nitramines with nitric acid, preferably in the presence of sulfuric acid, in accordance with the general reaction scheme set forth below:
- R is a hydrogen, alkyl or nitroalkyl radical
- A is an alkylene radical
- R is a hydrogen, nitro, alkyl, or nitroalkyl radical.
- nitrosamines of this invention are prepared by reacting an amine with nitric acid in the presence of acetic anhydride in accordance with the general reaction scheme set forth below:
- mice 7 2 wherein A, R and R 'are as defined above.
- An alternate method of preparing the nitrosamines of this invention is to react an amine such as that shown in the above re action scheme with nitrous acid (HNOg).
- HNOg nitrous acid
- the nitrosamines thus obtained are useful as high explosives as noted labove and also serve as starting materials in an alternative method of preparing the nitramines of this invention.
- the nitrosamines of this invention react with nitric acid in the presence of sulfuric acid to yield the nitramines of this invention in accordance with the following general reaetion scheme:
- Example I Preparation of 3,6-Diaza-3-Nitr0s0- 1,1,1,6-Tezranitr0heptane
- 29.0 g. (0.1 mole) of 3,6-diaza-1,1,1,6- tetranitroheptane in ml. of acetic anhydride was added dropwise to 100 ml. of 100% nitric acid while keeping the temperature of said acid at 0-5 C.
- the resulting mixture was poured on ice to yield an oil which crystallized to a cream colored solid.
- the solid was collected, washed with water, and dried in vacuo over potassium hydroxide, thus producing 12.8 g.
- Example II Preparation of 3,6 -Diaza-1,1,1,3,6- Pentanitroheptane
- a mixture of 35 ml. of 100% nitric acid, 25 ml. of concentrated sulfuric acid, and 3.6 g. (0.011 mole) of 3,6- diaza-3-nitroso-1,1,1,6-tetranitroheptane was prepared. The solution was held at 50-55 C. for 30 minutes, cooled, and poured on ice. A white solid was collected, washed with water, and dried in vacuo over potassium hydroxide to yield 3.5 g. (92.5%) of 3,6-diaza-1,1,1,3,6- pentanitrcheptane product having a M.P. of 132-135 C. Recrystallization from ethylene chloride raised the M.P. to 134 135 C.
- Example III.Preparati0n of 3,6-Diaza-1,1,1,3,6- Pentanitroheptane Reaction temperatures are not critical in the practice of this invention and can be varied over Wide ranges, the only effect of temperature variations being a corresponding increase or decrease in reaction rate.
- Sulfuric acid and acetic anhydride are dehydrating agents and their usefulness in the reactions of our invention derives from the fact that they take up water of reaction thus, in effect, shifting the reaction equilibrium to the right and thereby increasing product yields.
- the sulfuric acid functions as a dehydrating agent, it should, for best results, be used in concentrated rather than dilute formexcess Water in the reaction system obviously lowers the efficiency of the sulfuric acid as a dehydrating agent.
- acetic anhydride as a dehydrating agent in the practice of our invention promotes the conversion of the nitramine starting materials to their corresponding nitrosamine nitramine compounds whereas the use of sulfuric acid as a dehydrating agent promotes the conversion of the nitramines to their corresponding dinitrarnine compounds.
- Our invention is not limited to the use of acetic anhydride and/ or sulfuric acid as dehydrating agents, other substances known to those skilled in the art as dehydrating agents may also be used within the scope of the invention.
- relatively weak dehydrating agents such as phosphoric acid or lower organic acid such as butyric acid, propionic acid, etc.
- anhydrides can be used to convert the nitramine starting materials to their corresponding nitrosamines
- strong dehydrating agents such as trifluoroacetic anhydride, phosphoric anhydride, etc. can be used to convert the nitramines to their corresponding dinitramines.
- nitramines used as starting materials for the preparation of the high energy nitramines of the present invention are prepared by condensing nitraza amines, as, for example, 3-nitraza-l-butylamine, with B-geminal polynitro alcohols, such as 2,2,2-trinitro ethanol, as more fully disclosed in our copending US. patent application Serial No. 666,276, filed concurrently with the present application.
- R is a lower alkyl radical and A is a lower alkylene radical.
- R is a radical selected from the group consisting of hydrogen, lower alkyl, and 'lower nitroalkyl radicals
- A is a lower alkylene radical
- X is a radical selected from the group consisting of nitroso and nitro radicals
- R is a radical selected from the group consisting of hydrogen, nitro, lower alkyl and lower nitroalkyl radicals.
- the method of preparing 3,6-diaza-1,1,1,3,61pentanitroheptane comprising the steps of reacting 3,6-diaza-1, 1,1,6-tetranitr0heptane with nitric acid in the presence of 5 acetic anhydride to obtain 3,6-diaza-3-nitroso-1,1,1,6-tetranitroheptane and reacting said 3,6-diaza-3-nitroso-1,1,1, G-tetranitroheptane with nitric acid in the presence of sulfuric acid.
- trinitrononane comprising reacting 3,7-diaza-1,1,7-trinitrononane with nitric acid in the presence of acetic anhydride.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
United States Patent 3,098,873 NITRAMKNES, NITROSAMINES AND THEIR PREPARATION Milton B. Frankel, Pasadena, and Karl Klager, Monrovia, Caiif., assignors to Aerojet-General Corporation, Azusa, Calif., a corporation of Ghio No Drawing. Filed June 13, 1957, Ser. No. 666,274 19 Claims. (Cl. 260-583) This invention relates to new compositions of matter and to the preparation thereof. More specifically, the invention relates to high energy nitramines and nitrosamines having the following general formula:
and particularly to such high energy dinitramines of the following general formula:
wherein R is a hydrogen, alkyl, or nitroalkyl radical; A is an alkylene radical; X is a nitroso or a nitro radical; and R is a hydrogen, nitro, alkyl, or nitroalkyl radical.
The high energy nitramines and nitrosamines of this invention 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 Batent No. 2,470,162, issued May 17, 1949. One Way of using the high explosives of this invention 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 suffi'ciently 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 fusemechanism firing a detonating explosive such as lead azide or mercury fulminate.
The high energy dinitramines of this invention are prepared by reacting nitramines with nitric acid, preferably in the presence of sulfuric acid, in accordance with the general reaction scheme set forth below:
wherein R is a hydrogen, alkyl or nitroalkyl radical; A is an alkylene radical; and R is a hydrogen, nitro, alkyl, or nitroalkyl radical.
The nitrosamines of this invention are prepared by reacting an amine with nitric acid in the presence of acetic anhydride in accordance with the general reaction scheme set forth below:
3,998,873 Patented July 23, 1963 mice 7 2 wherein A, R and R 'are as defined above. An alternate method of preparing the nitrosamines of this invention is to react an amine such as that shown in the above re action scheme with nitrous acid (HNOg). The nitrosamines thus obtained are useful as high explosives as noted labove and also serve as starting materials in an alternative method of preparing the nitramines of this invention. The nitrosamines of this invention react with nitric acid in the presence of sulfuric acid to yield the nitramines of this invention in accordance with the following general reaetion scheme:
NO; NO N02 R-CH D'I-A-OH H2504 To more clearly illustrate our invention, the following examples are presented. It should be understood that these examples are presented merely as a means of illustration and are not intended to limit the scope of the invention in any Way.
Example I.-Preparation of 3,6-Diaza-3-Nitr0s0- 1,1,1,6-Tezranitr0heptane A solution of 29.0 g. (0.1 mole) of 3,6-diaza-1,1,1,6- tetranitroheptane in ml. of acetic anhydride was added dropwise to 100 ml. of 100% nitric acid while keeping the temperature of said acid at 0-5 C. The resulting mixture was poured on ice to yield an oil which crystallized to a cream colored solid. The solid was collected, washed with water, and dried in vacuo over potassium hydroxide, thus producing 12.8 g. (41.2%) of 3,6-diaza-3-nitroso-1,1,1,6-tetranitroheptane product. Recrystallization from ethylene dichloride gave white needles, M.P. 131-132 C. The compound gave a positive Leiberman test for the nitroso group.
Analysis-Calculated for C H N O percent C, 19.30; percent H, 2.92; percent N, 31.51. Found: percent C, 20.20; percent H, 2.95; percent N, 31.27.
Example II.-Preparation of 3,6 -Diaza-1,1,1,3,6- Pentanitroheptane A mixture of 35 ml. of 100% nitric acid, 25 ml. of concentrated sulfuric acid, and 3.6 g. (0.011 mole) of 3,6- diaza-3-nitroso-1,1,1,6-tetranitroheptane Was prepared. The solution was held at 50-55 C. for 30 minutes, cooled, and poured on ice. A white solid was collected, washed with water, and dried in vacuo over potassium hydroxide to yield 3.5 g. (92.5%) of 3,6-diaza-1,1,1,3,6- pentanitrcheptane product having a M.P. of 132-135 C. Recrystallization from ethylene chloride raised the M.P. to 134 135 C.
Analysis.Calculated for C5H9N7010: percent C, 18.35; percent H, 2.77; percent N, 29.27. Found: percent C, 18.86; percent H, 2.68; percent N, 30.02.
Example III.Preparati0n of 3,6-Diaza-1,1,1,3,6- Pentanitroheptane Reaction temperatures are not critical in the practice of this invention and can be varied over Wide ranges, the only effect of temperature variations being a corresponding increase or decrease in reaction rate.
It is preferred, however, in the case of nitration reactions conducted in the presence of acetic .anhydride according to this invention to maintain the reaction temperature between about and about C. due to the occurrence of undesirable side reactions which tend to reduce the yield of the desired product.
Sulfuric acid and acetic anhydride are dehydrating agents and their usefulness in the reactions of our invention derives from the fact that they take up water of reaction thus, in effect, shifting the reaction equilibrium to the right and thereby increasing product yields.
Since the sulfuric acid functions as a dehydrating agent, it should, for best results, be used in concentrated rather than dilute formexcess Water in the reaction system obviously lowers the efficiency of the sulfuric acid as a dehydrating agent.
It is interesting to note that the use of acetic anhydride as a dehydrating agent in the practice of our invention promotes the conversion of the nitramine starting materials to their corresponding nitrosamine nitramine compounds whereas the use of sulfuric acid as a dehydrating agent promotes the conversion of the nitramines to their corresponding dinitrarnine compounds. Our invention is not limited to the use of acetic anhydride and/ or sulfuric acid as dehydrating agents, other substances known to those skilled in the art as dehydrating agents may also be used within the scope of the invention. For example, relatively weak dehydrating agents such as phosphoric acid or lower organic acid such as butyric acid, propionic acid, etc., anhydrides can be used to convert the nitramine starting materials to their corresponding nitrosamines or strong dehydrating agents such as trifluoroacetic anhydride, phosphoric anhydride, etc. can be used to convert the nitramines to their corresponding dinitramines.
The nitramines used as starting materials for the preparation of the high energy nitramines of the present invention are prepared by condensing nitraza amines, as, for example, 3-nitraza-l-butylamine, with B-geminal polynitro alcohols, such as 2,2,2-trinitro ethanol, as more fully disclosed in our copending US. patent application Serial No. 666,276, filed concurrently with the present application.
It will be appreciated that a wide variety of compounds can be prepared in accordance with the teachings of our invention. For example, 3,7-diaza-1,1,7-trinitrononane; 4,7-diaza-2,2,7,9,9-pentanitrodecane; and 5,8- diaza-l,1,3,3,8-pentauitronona11e react with nitric acid in the presence of concentrated sulfuric acid to produce 3,7 diaza 1,1,3,7 -tetranitrononane; 4,7-diaza-2,2,4,7, 9,9-hexanitrodecane; and 5,8-diaza-l,1,3,3,5,8-hexanitrononane, respectively. On the other hand, 3,7-diaza-1,l,7- trinitrononane; 4,7-diam-2,2,7,9,9-pentanitrodecane; and 5 ,S-di-aza-1,1,3,3,8-pentanitrononane react with nitric acid in the presence of acetic anhydride to yield 3,7-diaza-3- nitroso-1,1,7-trinitrononane; 4,7-diaza-4-nitroso-2,2,7,9,9- pentanitrodecane; and 5,8-diaza-5-nitroso-1,1,3,3,8-pentanitrononane, respectively. Other members of this new series of compounds are prepared simply by reacting appropriate starting materials under appropriate conditions depending upon whether or not the nitro or nitroso derivative is desired.
We claim:
1. As a composition of matter, a dinitramine having the general formula:
wherein R is a lower alkyl radical and A is a lower alkylene radical.
2. As a composition of matter, 3,6-diaza-1,l,1,3,6- pentanitroheptane having the structural formula:
3. As a composition of matter, 3,7-diaza-1,l,3,7-tetranitrononane having the structural formula:
4. As a composition of matter, 4,7-diaza-2,2,4,7,9,9- hexanitrodecane having the structural formula:
5. As a composition of matter, 5,8-diaza-1,1,3,3,5,8- hexanitrononane having the structural formula:
6. As a composition of matter, 3,6-diaza-3-ni-troso-1,1, 1,6-tetranitroheptane having the structural formula:
7. As a composition of matter, 3,7-diaza-3-nitroso-1, 1,7-trinitrononane having the structural formula:
8. As a composition of matter, 4,7-diaza-4-nitroso-2,2, 7,9,9-pentanitrodecane having the structural formula:
9. As a composition of matter, 5,8-di aza-5-nitroso- 1,1,3,3,8-pentanitrononane having the structural formula:
10. The method of preparing a high energy nitramine having the general formula:
with nitric acid; wherein R is a radical selected from the group consisting of hydrogen, lower alkyl, and 'lower nitroalkyl radicals; A is a lower alkylene radical; X is a radical selected from the group consisting of nitroso and nitro radicals; and R is a radical selected from the group consisting of hydrogen, nitro, lower alkyl and lower nitroalkyl radicals.
11. The method of preparing 3,6-diaza-3-nitroso-1,1,1, 6-tetranitroheptane comprising reatcing 3,6-diaza-l,1,1,6- tetranitroheptane with nitric acid in the presence of acetic anhydride.
12. The method of preparing 3,6-diaza-1,1,1,3,61pentanitroheptane comprising the steps of reacting 3,6-diaza-1, 1,1,6-tetranitr0heptane with nitric acid in the presence of 5 acetic anhydride to obtain 3,6-diaza-3-nitroso-1,1,1,6-tetranitroheptane and reacting said 3,6-diaza-3-nitroso-1,1,1, G-tetranitroheptane with nitric acid in the presence of sulfuric acid.
13. The method of preparing 3,6-diaz-a-1,1,1,3,6-pentanitroheptane comprising reacting 3,6-diaza-1,1,1,6-tetranitroheptane with nitric acid in the presence of sulfuric acid.
14. The method of preparing 3,7-diaza-1,1,3,7-tetrar1itrononane comprising reacting 3,7-di aza-1,1,7-trinitrononane with nitric acid in the presence of sulfuric acid.
15. The method of preparing 4,7-diaza-2,2,4,7,9,9-hexanitrodecane comprising reacting 4,7-diaza-2,2,7,9,9-pentanitrodecane with nitric acid in the presence of sulfuric acid.
16. The method of preparing 5,8-diaza-1,1,3,3,5,8-heX- anitrononane comprising reacting 5,8-diaza-1,1,3,3,8-pentanitrononane with nitric acid in the presence of sulfuric acid.
17. The method of preparing 3,7-diaza-3-nitroso-1,1,7-
trinitrononane comprising reacting 3,7-diaza-1,1,7-trinitrononane with nitric acid in the presence of acetic anhydride.
18. The method of preparing 4,7-diaza-4-nitroso-2,2, 7,9,9-pentanitrodecane comprising reacting 4,7-diaza-2,2, 7,9,9-pentanitrodecane with nitric acid in the presence of acetic anhydride.
19. The method of preparing 5,8-diaza-5-nitroso-1,1, 3,3,8-pentanitrononane comprising reacting 5,8-diaza-1,1, 3,3,8-pcntanitron0nane with nitric acid in the presence of acetic anhydride.
Claims (1)
1. AS A COMPOSITION OF MATTER, A DINITRAMINE HAVING THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US666274A US3098873A (en) | 1957-06-13 | 1957-06-13 | Nitramines, nitrosamines and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US666274A US3098873A (en) | 1957-06-13 | 1957-06-13 | Nitramines, nitrosamines and their preparation |
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| Publication Number | Publication Date |
|---|---|
| US3098873A true US3098873A (en) | 1963-07-23 |
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| US666274A Expired - Lifetime US3098873A (en) | 1957-06-13 | 1957-06-13 | Nitramines, nitrosamines and their preparation |
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| Country | Link |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731460A (en) * | 1951-07-10 | 1956-01-17 | Nitroglycerin Ab | Process for producing ammonia derivatives of polynitroalcohols |
-
1957
- 1957-06-13 US US666274A patent/US3098873A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731460A (en) * | 1951-07-10 | 1956-01-17 | Nitroglycerin Ab | Process for producing ammonia derivatives of polynitroalcohols |
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