US3222233A - Methylamine nitroform oxidizer in nitrocellulose, aluminum and metriol trinitrate propellants - Google Patents
Methylamine nitroform oxidizer in nitrocellulose, aluminum and metriol trinitrate propellants Download PDFInfo
- Publication number
- US3222233A US3222233A US348903A US34890364A US3222233A US 3222233 A US3222233 A US 3222233A US 348903 A US348903 A US 348903A US 34890364 A US34890364 A US 34890364A US 3222233 A US3222233 A US 3222233A
- Authority
- US
- United States
- Prior art keywords
- nitroform
- methylamine
- oxidizer
- nitrocellulose
- aluminum
- 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
- MKWFSTZSLLWEJO-UHFFFAOYSA-N methanamine;trinitromethane Chemical compound NC.[O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O MKWFSTZSLLWEJO-UHFFFAOYSA-N 0.000 title claims description 14
- 239000003380 propellant Substances 0.000 title claims description 10
- 239000007800 oxidant agent Substances 0.000 title claims description 6
- IPPYBNCEPZCLNI-UHFFFAOYSA-N trimethylolethane trinitrate Chemical compound [O-][N+](=O)OCC(C)(CO[N+]([O-])=O)CO[N+]([O-])=O IPPYBNCEPZCLNI-UHFFFAOYSA-N 0.000 title claims description 5
- 239000000020 Nitrocellulose Substances 0.000 title claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052782 aluminium Inorganic materials 0.000 title claims description 4
- 229920001220 nitrocellulos Polymers 0.000 title claims description 4
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 title description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 14
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000002360 explosive Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000015 trinitrotoluene Substances 0.000 description 2
- NYTOUQBROMCLBJ-UHFFFAOYSA-N Tetranitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O NYTOUQBROMCLBJ-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- -1 nitrogen-containing nitroform derivative Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- This invention relates to a novel, nitrogen-containing nitroform derivative and the method of its preparation. Specifically, the invention is directed to the preparation of methylamine nitroform, a novel composition of matter.
- Organic nitro and polynitro compounds have been known for many years as substances which release large amounts of energy upon decomposition initiated by thermal energy or shock energy. Examples of such substances are TNT (trinitrotoluene) and tetranitromethane. More recently, certain polynitro compounds have been incorporated into composite rocket propellant formulations in order to increase the specific impulse of the formulations.
- nitroform Although known for some time and although apparently an explosive substance, has not been used as an explosive because of a number of serious, inherent disadvantages. Among these are:
- Nitroform is very unstable, decomposing at temperatures only slightly higher than room temperature (e.g. 30 0.).
- nitroform itself, is not suitable as an explosive, it has now been found that it is possible to prepare a derivative thereof which possesses properties mak ing it useful as an oxidizer and thereby desirable as an .ingredient in high energy propellants.
- methylamine may be reacted with nitroform to form an adduct, methylamine nitroform.
- the reaction involves bubbling a stream of gaseous methylamine into a solution of nitroform in carbon tetrachloride.
- Methylamine nitroform may be mixed into suitable explosive and propellant formulations.
- suitable explosive and propellant formulations include, as other major ingredients, nitrocellulose, aluminum and metriol trinitrate, increasesthe specific impulse of the system.
- Sensitivity and stability data obtained on pure methylamine nitroform show that the compound is reasonably stable and insensitive as compared to other high energy oxidizers.
- Ignition temperature "112 C. Vacuum stability 60 C. (0.5 g.):
- reaction proceeds quite simply and no particular precautions are necessary.
- the reaction conditions are not critical and may be varied according to the particular situation.
- the reaction proceeds at room temperature or at temperatures higher or lower than room temperature.
- the rate of feed of the gaseous methylamine stream is not critical, it merely being necessary that suificient methylamine be fed into the reaction mixture to sustain the reaction.
- methylamine nitroform may be incorporated as an oxidizer in a propellant formulation.
- a typical propellant formulation, containing methylamine nitroform is as follows:
- a process for preparing methylamine nitroform which comprises, reacting methylamine with a solution of nitroform in carbon tetrachloride.
- a propellant composition comprising nitrocellulose, aluminum and metriol trinitrate the improvement comprising methylamine nitroform as an oxidizer in said composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,222,233 METHYLAMINE NITROFORM OXIDIZER IN NI- TROCELLULOSE, ALU I AND METRIOL TRINITRATE PROPELLANT Anthony .F. Matuszko and Marguerite S. Chang, both of Washington, D.C., assignors to the United States of America as represented by the Secretary of the Navy No Drawing. Filed Feb. 27, 1964, Ser. No. 348,903 3 Claims. (Cl. 149--92) (Granted under Title 35, US. Code (1952), see. 266) The invention described herein may be manufactured and used by or for the Government of the United States of America for governmental purposes without the payment of any royalties thereon or therefor.
This invention relates to a novel, nitrogen-containing nitroform derivative and the method of its preparation. Specifically, the invention is directed to the preparation of methylamine nitroform, a novel composition of matter.
Organic nitro and polynitro compounds have been known for many years as substances which release large amounts of energy upon decomposition initiated by thermal energy or shock energy. Examples of such substances are TNT (trinitrotoluene) and tetranitromethane. More recently, certain polynitro compounds have been incorporated into composite rocket propellant formulations in order to increase the specific impulse of the formulations.
In contrast to many polynitro compounds, nitroform, although known for some time and although apparently an explosive substance, has not been used as an explosive because of a number of serious, inherent disadvantages. Among these are:
1) Pure nitroform (M.P. 56 C.) will not detonate and is very diflicult to initiate;
(2) Because it is easily soluble in water, nitroform is hygroscopic-a property not desirable in an explosive;
(3) Nitroform is very unstable, decomposing at temperatures only slightly higher than room temperature (e.g. 30 0.).
Although nitroform, itself, is not suitable as an explosive, it has now been found that it is possible to prepare a derivative thereof which possesses properties mak ing it useful as an oxidizer and thereby desirable as an .ingredient in high energy propellants.
Accordingly, it has been discovered that methylamine may be reacted with nitroform to form an adduct, methylamine nitroform. The reaction involves bubbling a stream of gaseous methylamine into a solution of nitroform in carbon tetrachloride.
Methylamine nitroform may be mixed into suitable explosive and propellant formulations. For example, incorporation of methylamine nitroform in a propellant system including, as other major ingredients, nitrocellulose, aluminum and metriol trinitrate, increasesthe specific impulse of the system. Sensitivity and stability data obtained on pure methylamine nitroform show that the compound is reasonably stable and insensitive as compared to other high energy oxidizers.
A specific embodiment of the invention is described in the following example. It is to be understood, however, that the example is merely for purposes of illustration and that it is not intended that the scope of the invention be limited thereby.
3,222,233 Fatented Dec. 7, 1965 Example A solution of 3 g. (0.02 mole) of nitroform in 15 ml. of carbon tetrachloride was cooled in an ice bath while a stream of gaseous methylamine was bubbled into the solution for 10 to 15 minutes. A yellow precipitate was formed immediately upon contact of the gas with the nitroform solution. After the reaction was completed, the yellow solid was separated by filtration and 3.0 g. (79% of theoretical) of methylamine nitroform was obtained. Upon recrystallization from methanol/carbon tetrachloride, yellow needles were obtained which melted, with decomposition, at 126128 C.
Analysis.Calculated (C I-I N O C, 13.18; H, 3.29; N, 30.76. Found: C, 13.29; H, 3.36; N, 30.41.
Ignition temperature "112 C. Vacuum stability 60 C. (0.5 g.):
2 hr. cc. gas 0.82
24 hr do 0.95
43 hr. do 1.02
48 hr d0 1.02
The reaction proceeds quite simply and no particular precautions are necessary. The reaction conditions are not critical and may be varied according to the particular situation. Thus, the reaction proceeds at room temperature or at temperatures higher or lower than room temperature. Similarly, the rate of feed of the gaseous methylamine stream is not critical, it merely being necessary that suificient methylamine be fed into the reaction mixture to sustain the reaction.
As indicated above, methylamine nitroform may be incorporated as an oxidizer in a propellant formulation. A typical propellant formulation, containing methylamine nitroform is as follows:
Percent Nitrocellulose (12.0% nitrogen) 14.4 Aluminum 21.0 Adiponitrile 1.0 2-nitro diphenylamine 1.0 Metriol trinitrate 28.0 Methylarnine nitroform 34.6
Obviously many modifications and variations of the present invention are possible in the light of the above teachings. It is therefore to be understood that, within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.
Having thus described the invention, what is claimed and desired to be secured by Letters Patent of the United States is:
1. A process for preparing methylamine nitroform which comprises, reacting methylamine with a solution of nitroform in carbon tetrachloride.
2. The process of claim 1 wherein the reaction is conducted at room temperature.
3. In a propellant composition comprising nitrocellulose, aluminum and metriol trinitrate the improvement comprising methylamine nitroform as an oxidizer in said composition.
Claims (2)
1. A PROCESS FOR PREPARING METHYLAMINE NITROFORM WHICH COMPRISES, REACTING METHYLAMINE WITH A SOLUTION OF NITROFORM IN CARBON TETRACHLORIDE.
3. IN A PROPELLANT COMPOSITION COMPRISING NITROCELLULOSE, ALUMINUM AND METRIOL TRINITRATE THE IMPROVEMENT COMPRISING METHYLAMINE NITROFORM AS AN OXIDIZER IN SAID COMPOSITION.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US348903A US3222233A (en) | 1964-02-27 | 1964-02-27 | Methylamine nitroform oxidizer in nitrocellulose, aluminum and metriol trinitrate propellants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US348903A US3222233A (en) | 1964-02-27 | 1964-02-27 | Methylamine nitroform oxidizer in nitrocellulose, aluminum and metriol trinitrate propellants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3222233A true US3222233A (en) | 1965-12-07 |
Family
ID=23370063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US348903A Expired - Lifetime US3222233A (en) | 1964-02-27 | 1964-02-27 | Methylamine nitroform oxidizer in nitrocellulose, aluminum and metriol trinitrate propellants |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3222233A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3344005A (en) * | 1966-02-23 | 1967-09-26 | Trojan Powder Co | Pentaerythritol tetranitrate-trimethylolethane trinitrate explosives |
| US3376174A (en) * | 1965-09-21 | 1968-04-02 | France Etat | Powder containing nitrocellulose, metal or metal hydride and a superficial layer of moderating agent |
| US3634158A (en) * | 1969-05-13 | 1972-01-11 | Us Navy | Liquid nitrate ester monopropellant composition |
| US3861970A (en) * | 1968-06-25 | 1975-01-21 | Us Air Force | Propellant composition containing beryllium hydride, nitrocellulose and nitrate co-plasticizers |
| US4002514A (en) * | 1965-09-30 | 1977-01-11 | The Dow Chemical Company | Nitrocellulose propellant composition |
| US4269637A (en) * | 1979-07-19 | 1981-05-26 | Rockwell International Corporation | High-performance MHD solid gas generator |
| US4371409A (en) * | 1981-06-01 | 1983-02-01 | Hercules Incorporated | Gelatinized high explosive composition and method of preparation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103882A (en) * | 1949-01-15 | 1963-09-17 | William L Gilliland | Explosive cartridges and explosives |
-
1964
- 1964-02-27 US US348903A patent/US3222233A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3103882A (en) * | 1949-01-15 | 1963-09-17 | William L Gilliland | Explosive cartridges and explosives |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376174A (en) * | 1965-09-21 | 1968-04-02 | France Etat | Powder containing nitrocellulose, metal or metal hydride and a superficial layer of moderating agent |
| US4002514A (en) * | 1965-09-30 | 1977-01-11 | The Dow Chemical Company | Nitrocellulose propellant composition |
| US3344005A (en) * | 1966-02-23 | 1967-09-26 | Trojan Powder Co | Pentaerythritol tetranitrate-trimethylolethane trinitrate explosives |
| US3861970A (en) * | 1968-06-25 | 1975-01-21 | Us Air Force | Propellant composition containing beryllium hydride, nitrocellulose and nitrate co-plasticizers |
| US3634158A (en) * | 1969-05-13 | 1972-01-11 | Us Navy | Liquid nitrate ester monopropellant composition |
| US4269637A (en) * | 1979-07-19 | 1981-05-26 | Rockwell International Corporation | High-performance MHD solid gas generator |
| US4371409A (en) * | 1981-06-01 | 1983-02-01 | Hercules Incorporated | Gelatinized high explosive composition and method of preparation |
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