US2967199A - Nitramides - Google Patents
Nitramides Download PDFInfo
- Publication number
- US2967199A US2967199A US464612A US46461254A US2967199A US 2967199 A US2967199 A US 2967199A US 464612 A US464612 A US 464612A US 46461254 A US46461254 A US 46461254A US 2967199 A US2967199 A US 2967199A
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- US
- United States
- Prior art keywords
- dinitro
- diamine
- nitramides
- nitric acid
- dipropanoyl
- 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.)
- Expired - Lifetime
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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
- This invention relates to new compositions of matter and a method for their preparation.
- this invention relates to nitramides having the general formula:
- R is an alkyl radical and A is an alkylene radical.
- the compounds of this invention are prepared by reacting N,N-diacyl dinitro diamides with nitric acid, in accordance with the general reaction scheme set forth below:
- the dinitro diamides used as starting materials in this invention are prepared by condensing dinitro diamines with acyl anhydrides, as disclosed in assignees copending application Serial No. 210,626, filed February 12, 1951 now abandoned.
- polynitro diamides such as N,N'-dipropanoyl-4,4-dinitro-1,7-heptane diamine, N,N'- dipropanoyl-5,5-dinitro-1,9-nonane diamine, and N,N'- dihexanoyl-6,6-dinitro-1,1l-undecane diamine are readily nitrated with nitric acid to form the corresponding nitramides, namely, N,N'-dinitro-N,N'-dipropanoyl-4,4-dinitro-1,7-heptane diamine, N,N'-dinitro-N,N'-dipropanoyl- 5,5-dinitro-l,9-nonane diamine, and N,N'-dinitro-N,N' dihexanoyl-6,6-dinitro-1,1l-undecane diamine.
- any member of this series of nitramides can be prepared by merely selecting the appropriate polynitro diamide and reacting it with nitric acid, in accordance with the teachings of this invention.
- the nitro compounds 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 Patent 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 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 devejoped 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 fulrninate.
- R is a lower alkyl radical and A is a lower alkylene radical.
- N,N'-dinitro-N,N'- diacetyl-3,3-dinitro-l,5-pentane diamine having the structural formula:
- R is a lower alkyl radical and A is a lower alkylene radical, with nitric acid.
- nitric acid ran-temperature:ofabout 5 0; wherein R is a lower alkyl radical and A is a lower alkylene radical.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Paten NITRAMIDES Milton B. Frankel, Pasadena, and Karl Klager, Monrovia, Califl, assignors to Aerojet-General Corporation, Azusa, Calif., a corporation of Ohio No Drawing. Filed Oct. 25, 1954, Ser. No. 464,612
8 Claims. (Cl. 260-561) This invention relates to new compositions of matter and a method for their preparation. In particular, this invention relates to nitramides having the general formula:
wherein R is an alkyl radical and A is an alkylene radical.
Due to their high oxygen content, these compounds are excellent high explosives. They also find valuable use as oxygen donating additives for propellant fuels.
The compounds of this invention are prepared by reacting N,N-diacyl dinitro diamides with nitric acid, in accordance with the general reaction scheme set forth below:
wherein R and A are as defined above.
The dinitro diamides used as starting materials in this invention are prepared by condensing dinitro diamines with acyl anhydrides, as disclosed in assignees copending application Serial No. 210,626, filed February 12, 1951 now abandoned.
To more clearly illustrate this invention, the following example is presented. It is to be understood, however, that this example is presented merely as a means of illustration, and is not intended to limit the scope of the invention in any way.
EXAMPLE I Preparation of N,N'-dinitro-N,N'-diacetyl-3,3- dinitro-1,5-pentane diamine A nitrating mixture of 250 ml. of 100% nitric acid and 250 ml. ofacetic anhydride was cooled to C. and 98.5 gm. (0.36 mole) of N,N-diacetyl-3,3-dinitro-1,5- pentane diamine was added. The solution was stirred for 40 minutes and then poured onto ice. The creamcolored solid was collected, washed with water and dried, and recrystallized from chloroform to give 65.2 gm. (50%) of N,N'-dinitro-N,N'-diacetyl-3,3-dinitro-1,5-pentane diamine, M.P. 100-101 C., exhibiting an impact stability greater than 100 cm./2 kg. The elemental analysis of the product is as follows:
Calculated for C H N O percent C, 29.51; percent H, 3.85; percent N, 22.95. Found: percent C, 29.84; percent H, 3.83; percent N, 23.67.
We have also found that polynitro diamides such as N,N'-dipropanoyl-4,4-dinitro-1,7-heptane diamine, N,N'- dipropanoyl-5,5-dinitro-1,9-nonane diamine, and N,N'- dihexanoyl-6,6-dinitro-1,1l-undecane diamine are readily nitrated with nitric acid to form the corresponding nitramides, namely, N,N'-dinitro-N,N'-dipropanoyl-4,4-dinitro-1,7-heptane diamine, N,N'-dinitro-N,N'-dipropanoyl- 5,5-dinitro-l,9-nonane diamine, and N,N'-dinitro-N,N' dihexanoyl-6,6-dinitro-1,1l-undecane diamine.
It is apparent that any member of this series of nitramides can be prepared by merely selecting the appropriate polynitro diamide and reacting it with nitric acid, in accordance with the teachings of this invention.
The nitro compounds 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 Patent 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 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 devejoped 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 fulrninate.
We claim:
1. As new compositions of matter, nitramides having the general formula:
wherein R is a lower alkyl radical and A is a lower alkylene radical.
2. As a new composition of matter, N,N'-dinitro-N,N'- diacetyl-3,3-dinitro-l,5-pentane diamine having the structural formula:
3. The method of preparing nitramides having the general formula:
which comprises reacting N,N'-diacyl-dinitro diamines having the general formula:
wherein R is a lower alkyl radical and A is a lower alkylene radical, with nitric acid.
4. The method of preparing N,N'-dinitro-N,N'-diacetyl-3,3-dinitro-1,5-pentane diamine which comprises reacting N,N-diacetyl-3,3-dinitro-1,5-pentane diamine with nitric acid.
7 3 I V fSrAsanew-"comfioition of matter, N,N'-dinitro-N,N'- dipropanoyl-4;4-dinitro-1;7-heptane diamine having the structural formula:
g r m, IIIOa .I Ioi 0 tomorrr c-N-cmomonro-cmom N- c-dmomom N0a 6. As a newcomposition of matter, N,N-dinitro-N,N'- '"dipropanoyl-5,5-dinitro-1,9-nonane diamine having the 'structural formula:
'7. As a new composition ofmatter,,N,N-dinitro N,N'- "dihe'xanoyl-6,6-dinitro-1,1l-undecane diamine having the structural formula:
N02 NO:
8. l'he method of Preparin nitramlideysihmiing lthe'gtcn eral formula:
which comprises reacting "N,N'-diacyl-dinitro diamines having the general formula:
with nitric acid ran-temperature:ofabout 5 0; wherein R is a lower alkyl radical and A is a lower alkylene radical.
' No references cited.
Claims (1)
1. AS NEW COMPOSITIONS OF MATTER, NITRAMIDES HAVING THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US464612A US2967199A (en) | 1954-10-25 | 1954-10-25 | Nitramides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US464612A US2967199A (en) | 1954-10-25 | 1954-10-25 | Nitramides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2967199A true US2967199A (en) | 1961-01-03 |
Family
ID=23844603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US464612A Expired - Lifetime US2967199A (en) | 1954-10-25 | 1954-10-25 | Nitramides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2967199A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290374A (en) * | 1963-04-24 | 1966-12-06 | Sun Chemical Corp | Quaternary ammonium compounds |
| CN115504910A (en) * | 2022-09-14 | 2022-12-23 | 国科温州研究院(温州生物材料与工程研究所) | Acid-responsive released micromolecule aldehyde antibacterial nanoparticles as well as preparation method and application thereof |
-
1954
- 1954-10-25 US US464612A patent/US2967199A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290374A (en) * | 1963-04-24 | 1966-12-06 | Sun Chemical Corp | Quaternary ammonium compounds |
| CN115504910A (en) * | 2022-09-14 | 2022-12-23 | 国科温州研究院(温州生物材料与工程研究所) | Acid-responsive released micromolecule aldehyde antibacterial nanoparticles as well as preparation method and application thereof |
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