US3000889A - Tris n-alkylenepolynitro hexahydro s-triazines - Google Patents
Tris n-alkylenepolynitro hexahydro s-triazines Download PDFInfo
- Publication number
- US3000889A US3000889A US636838A US63683857A US3000889A US 3000889 A US3000889 A US 3000889A US 636838 A US636838 A US 636838A US 63683857 A US63683857 A US 63683857A US 3000889 A US3000889 A US 3000889A
- Authority
- US
- United States
- Prior art keywords
- tris
- triazines
- hexahydro
- formula
- percent
- 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
Links
- 239000007983 Tris buffer Substances 0.000 title description 9
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical class C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 title 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- -1 3,3,3-trinitropropyl Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000002360 explosive Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- BXEQKRXVVGOFOE-UHFFFAOYSA-N 3,3-dinitrobutan-1-amine;hydrochloride Chemical compound Cl.[O-][N+](=O)C([N+]([O-])=O)(C)CCN BXEQKRXVVGOFOE-UHFFFAOYSA-N 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 239000011707 mineral Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003918 triazines Chemical class 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
Definitions
- A is an alkylene radical and R is a nitro or alkyl radical.
- compositions 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 sufliciently 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.
- the compounds of this invention are prepared by condensing a primary amine with formaldehyde, in accordance with the general reaction scheme set forth below:
- A is an alkylene radical and R is a nitro or alkyl radical.
- the amines used as starting materials in this invention are prepared by reacting a strong mineral acid with a polynitro isocyanate, which may be prepared by reacting a polynitro acid halide with sodium azide, as disclosed in assignees copending application No. 405,515, now abandoned, filed January 21, 1954.
- the explosive power of the compound is as follows:
- N-nitroalkyl-1,3,5- triazines having the formula:
- A is a lower alkylene radical and R is a radical selected from the group consisting of lower alkyl and 'nitro radicals.
- N-nitroalkyl-l,3,5- triazines having the formula:
- N-nitroalkyl-1,3,5- triazines having the formula:
- A is a lower alkylene radical and R is a lower alkyl radical.
- A is a lower alkylene radical and R is a radical selected from the group consisting of lower alkyl and nitro radicals.
- A is a lower alkylene radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
3,000,889 TRIS N ALKYLENEPOLYNITRO HEXAHYDRU S-TRIAZINES Milton B. Frankel, Pasadena, Calif., assignor to Aerojetgeneral Corporation, Azusa, Califi, a corporation of re No Drawing. Filed Jan. 28, 1957, Ser. No. 636,838 16 Claims. (Cl. 260-448) This invention relates to new compositions of matter and a method for their preparation. In particular this invention relates to 1,3,5-triazines having the general formula:
wherein A is an alkylene radical and R is a nitro or alkyl radical.
This application is a continuation in part of my copehding United States patent application No. 408,608 filed February 5, 1954, now abandoned.
The compositions 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 sufliciently 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.
The compounds of this invention are prepared by condensing a primary amine with formaldehyde, in accordance with the general reaction scheme set forth below:
wherein A is an alkylene radical and R is a nitro or alkyl radical.
The amines used as starting materials in this invention are prepared by reacting a strong mineral acid with a polynitro isocyanate, which may be prepared by reacting a polynitro acid halide with sodium azide, as disclosed in assignees copending application No. 405,515, now abandoned, filed January 21, 1954.
To more fully illustrate this invention, the following examples are presented. It is to be understood, however, 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 1 Preparation of 1,3,5-tris(3,3,3'-trinitropr0pyl)-hexahydro-1 ,3,5-triazine in a flask, fitted with a mechanical stirrer and dropping funnel, was placed 34.5 gm. (0.15 mole) of 3,3,3-trinitropropyl amine hydrochloride, 75 ml. of water, and 12.1
Patented Sept. 19, 1961 gm. (0.15 mole) of sodium acetate in 50 ml. of Water. A yellow solid was immediately precipitated, which was collected, washed with water, and dried, to give: 30.7 gm. (99.4%) of product. (The product exhibited an impact stability of 9 cm./2 kg. Recrystallization from a large volume of methanol gave yellow plates, M.P. 12.1123 C. dec. The elemental analysis of the product is as follows:
Calculated for C 1H N O Percent C, 23.31; percent H, 2.93; percent N, 27.19. Found: Percent C, 2.3 .78; percentlH, 2.88; percent N, 27.21.
The explosive power of the compound is as follows:
Lead block value 130 T.N.T.= Ballistic mortar value 140. T.N.T.=100
EXAMPLE II Preparation of l,3,5-tri.st(3',3'-dinitr0buryl)-hexahydr0- 1,3,5-triazina Twenty grn. (0.1 mole) of 3,3-dinitrobutylamine hydrochloride, 25 ml. of water, and 8.1 gm. (0.1 mole) of 37% formalin was placed in a 300 m1. 3-necked flask, fitted with a mechanical stirrer and dropping funnel. To this solution was added dropwisea solution of 8.2 gm. (0.1 mole) of sodium acetate in 15 ml. of water. A yellow solid was immediately precipitated. After the addition was complete, stirring was continued for an additional 30 minutes. The product was collected, washed with water, and dried; the yield was 17 gm. (97%). Two recrystallizations from ethyl acetate yielded a product having a M.-P. of 131-132 C. (dec.), and 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, 34.29; per cent H, 5.18; percent N, 23.99. Found: Percent C, 34.76; percent H, 5:36; percent N, 24.62.
I have also found that related amines, namely, 4,4,4- trinitrobutyl amine, 3,3-dinitropentyl amine, and 4,4-dinitropentyl amine will also condense with formaldehyde to produce the corresponding triazines, namely, 1,3,5-tris- (4',4,4-trinitrobutyl) -hexahydro-1,3,5-triazine, 1,3 ,5 -tris- (3',3'-dinitropentyl)-hexahydro-1,3,5-tria2ine, and 1,3,5- tris( 4',4-dinitropentyl -hexahydro-1,3 ,5 -tri azine.
From this it is apparent that any 1,3,5-triazine of this series can be prepared by merely condensing an appropriate intro-containing amine with formaldehyde, in accordance withthe teachings of this invention.
I claim:
1. As compositions of matter, the N-nitroalkyl-1,3,5- triazines having the formula:
wherein A is a lower alkylene radical and R is a radical selected from the group consisting of lower alkyl and 'nitro radicals.
2. As compositions of matter, the N-nitroalkyl-l,3,5- triazines having the formula:
wherein -A is a lower alkylene radical.
i p 3 3. As compositions of matter, the N-nitroalkyl-1,3,5- triazines having the formula:
wherein A is a lower alkylene radical and R is a lower alkyl radical.
4. As a composition of matter, 1,3,5-tris(3',3',3'-trinitropropyl)-hexahydro-1,3,5-t1iazine, having the structural formula:
IITO! Cg: IIQ'OI Noi-conlonr-N n-omcmcavo,
N02 CH9 OH: NO:
N NO 1 GHQ-CH: I NO:
5. As a. composition of matter, 1,3,5-tris(3',3'-dinitrohutyl)-hexahydro-1,3,5-triazine, having the structural formula:
N02 /GH2 NO: CHa-?-CHCHr-N N-CHaCHz-l -CHI NO; CH: Ha NO;
N No:
CHr-CH: I -OH:
nitropentyl)-hexahydro-1,3,5-triazine, having the structural formula:
9. The method of preparing N-nitroalkyl-l,3,5-triazines having the formula:
which comprises condensing formaldehyde with a nitrocontaining amine having the formula:
$02 RCANH:
wherein A is a lower alkylene radical and R is a radical selected from the group consisting of lower alkyl and nitro radicals.
10. The method of preparing N-nitroa1kyl-1,3,5-triazines which comprises condensing formaldehyde with an amine having the formula:
NOz-C-A-NH:
wherein A is a lower alkylene radical.
6. As a composition of matter, l,3,5-tris(4,4',4'-trinitrobutyl)-hexahydro-1,3,5-triazine having the structural formula:
7. As a composition of matter, 1,3,5-tris (3,3-dinitropentyl)-hex3a.hydro-1,3,-5-111iazine, having the structural formula:
8. As a composition of matter, 1,3,5-tris(4',4'-di- 11. The method of preparing N-nitroalkyl-1,3,5-triazines which comprises condensing formaldehyde with an amine having the formula:
v No references cited.
Claims (2)
1. AS COMPOSITIONS OF MATTER, THE N-NITROALKYL-1,3,5TRIAZINES HAVING THE FORMULA:
9. THE METHOD OF PREPARING N-NITROALKYL-1,3,5-TRIAZINES HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US636838A US3000889A (en) | 1957-01-28 | 1957-01-28 | Tris n-alkylenepolynitro hexahydro s-triazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US636838A US3000889A (en) | 1957-01-28 | 1957-01-28 | Tris n-alkylenepolynitro hexahydro s-triazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3000889A true US3000889A (en) | 1961-09-19 |
Family
ID=24553546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US636838A Expired - Lifetime US3000889A (en) | 1957-01-28 | 1957-01-28 | Tris n-alkylenepolynitro hexahydro s-triazines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3000889A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915970A (en) * | 1972-03-24 | 1975-10-28 | Coalite Chem Prod Ltd | Hexahydro-1,3,5-triazines |
| WO2014069668A1 (en) * | 2012-11-02 | 2014-05-08 | 住友化学株式会社 | Method for producing compound |
-
1957
- 1957-01-28 US US636838A patent/US3000889A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915970A (en) * | 1972-03-24 | 1975-10-28 | Coalite Chem Prod Ltd | Hexahydro-1,3,5-triazines |
| WO2014069668A1 (en) * | 2012-11-02 | 2014-05-08 | 住友化学株式会社 | Method for producing compound |
| JPWO2014069668A1 (en) * | 2012-11-02 | 2016-09-08 | 住友化学株式会社 | Method for producing compound |
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