USH991H - Synthesis of nitratomethylmethyloxetane (NMMO) - Google Patents
Synthesis of nitratomethylmethyloxetane (NMMO) Download PDFInfo
- Publication number
- USH991H USH991H US07/296,556 US29655689A USH991H US H991 H USH991 H US H991H US 29655689 A US29655689 A US 29655689A US H991 H USH991 H US H991H
- Authority
- US
- United States
- Prior art keywords
- reaction mixture
- reaction
- nitratomethyl
- methyloxetane
- solution
- 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.)
- Abandoned
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- IXYHLWZRPFVFON-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl nitrate Chemical compound [O-][N+](=O)OCC1(C)COC1 IXYHLWZRPFVFON-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 22
- SHSBMPDSSWZEPU-UHFFFAOYSA-N (2-methyloxetan-2-yl)methanol Chemical compound OCC1(C)CCO1 SHSBMPDSSWZEPU-UHFFFAOYSA-N 0.000 claims description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
- 235000011152 sodium sulphate Nutrition 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims 15
- 239000002904 solvent Substances 0.000 claims 7
- 238000005406 washing Methods 0.000 claims 6
- 238000001035 drying Methods 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 1
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 4
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010961 commercial manufacture process Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UUKYNUQOJMFDSC-UHFFFAOYSA-N (2-methyloxetan-2-yl)methanol;nitric acid Chemical compound O[N+]([O-])=O.OCC1(C)CCO1 UUKYNUQOJMFDSC-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
Definitions
- This invention relates to high energy propellant binders and explosive formulations. More particularly, this invention relates to a method of preparing 3-nitratomethyl-3-methyloxetane (NMMO) that is superior to previously known methods of making 3-nitratomethyl-3-methyloxetane. 3-nitratomethyl-3-methyloxetane is useful as an ingredient in high energy propellant binders and certain explosive formulations.
- NMMO 3-nitratomethyl-3-methyloxetane
- High energy propellant binders have been extensively investigated as a means of increasing the energy and performance of missile propellants over those currently in use.
- a very promising candidate for a new highly energetic binder system contains 3-nitratomethyl-3-methyloxetane.
- 3-nitratomethyl-3-methyloxetane is currently available only in limited quantities.
- acetylnitrate is used to nitrate hydroxymethylmethyloxetane (HMMO) to produce 3-nitratomethyl-3-methyloxetane.
- HMMO hydroxymethylmethyloxetane
- Prior art requires the preparation of acetylnitrate by reacting acetic anhydride with concentrated nitric acid.
- Acetylnitrate is a very hazardous, unstable explosive that can detonate spontaneously in storage which makes large scale commercial manufacture of 3-nitratomethyl-3-methyloxetane difficult and hazardous.
- 3-nitratomethyl-3-methyloxetane produced by this method must be purified by the tedious technique of chromatography.
- This invention eliminates the use of both nitric acid and acetylnitrate in the production of 3-nitratomethyl-3-methyloxetane. Moreover, the 3-nitratomethyl-3-methyloxetane produced by this method is of high purity, eliminating the need for chromatography. This invention is also amenable to large scale commercial manufacture of 3-nitratomethyl-3-methyloxetane.
- An object of this invention is to provide a simple and efficient method of preparing 3-nitratomethyl-3-methyloxetane by the direct liquid phase nitration of hydroxymethylmethyloxetane using dinitrogen pentoxide (N 2 O 5 ) as the nitrating agent.
- a further object of this invention is to provide a method for economical commercial production of 3-nitratomethyl-3-methyloxetane that has a high yield and high purity.
- the starting material is hydroxymethylmethyloxetane. Hydroxymethylmethyloxetane is dissolved in dry chloroform and set aside. Dinitrogen pentoxide (N 2 O 5 ) is then prepared by a known reaction wherein commercially available dinitrogen tetroxide (N 2 O 4 ) gas is contacted with dry ozone until all of the red N 2 O 4 is consumed. See Guye, P. A., U.S. Pat. No. 1,348,873 (1920) for the N 2 O 5 procedure. The resulting N 2 O 5 is captured in solid form in dry ice.
- the N 2 O 5 is then dissolved in dry chloroform to make a solution.
- the N 2 O 5 in solution is then slowly added, using a dropping funnel, to the prepared hydroxymethylmethyloxetane solution while the solution is continually stirred. Stirring continues for about 2 hours after the last of the N 2 O 5 solution has been added to the hydroxymethylmethyloxetane solution. At this point the reaction is complete and the solution contains 3-nitratomethyl-3-methyloxetane.
- the N 2 O 5 also may be dissolved in carbon tetrachloride, methylene chloride or acetonitrile as substitutes for the dry chloroform.
- the solution is then, in succession, washed with distilled water, then with saturated sodium bicarbonate solution, and then with saturated sodium chloride solution.
- Water is then removed from the chloroform and 3-nitratomethyl-3-methyloxetane solution by adding anhydrous sodium sulfate. After 10 minutes the sodium sulfate is removed by filtration.
- the chloroform is then removed under reduced pressure leaving almost pure 3-nitratomethyl-3-methyloxetane.
- the resulting 3-nitratomethyl-3-methyloxetane can be further purified by vacuum distillation.
- the starting material 15 g (150 mmol) hydroxymethylmethyloxetane, was dissolved in 300 milliliters of dry chloroform at 0° C., at atmospheric pressure and set aside.
- Dinitrogen pentoxide (N 2 O 5 ) was then prepared by contacting commercially available dinitrogen tetroxide (N 2 O 4 ) with dry ozone at ambient temperature and pressure until all of the red dinitrogen tetroxide was consumed.
- the solution was then washed, in succession, with 250 ml of distilled water, then 250 ml of aqueous saturated sodium bicarbonate solution, and then 250 ml of aqueous saturated sodium chloride solution.
- Water is then removed from the chloroform and 3-nitratomethyl-3-methyloxetane solution by adding 2 g of anhydrous sodium sulfate. After ten minutes the sodium sulfate was removed by filtration.
- the chloroform was then removed using a rotary evaporator under reduced pressure, 14 torr, leaving almost pure 3-nitratomethyl-3-methyloxetane.
- the 3-nitratomethyl-3-methyloxetane was then purified by vacuum distillation at 0.35 torr at a temperature range between 52 and 62 degrees C. 20 grams of 99% pure 3-nitratomethyl-3-methyloxetane were obtained. NMR showed very clean product. Yield was 91%.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method of preparing 3-nitratomethyl-3-methyloxetane.
Description
1. Field of the Invention
This invention relates to high energy propellant binders and explosive formulations. More particularly, this invention relates to a method of preparing 3-nitratomethyl-3-methyloxetane (NMMO) that is superior to previously known methods of making 3-nitratomethyl-3-methyloxetane. 3-nitratomethyl-3-methyloxetane is useful as an ingredient in high energy propellant binders and certain explosive formulations.
2. Description of the Prior Art
High energy propellant binders have been extensively investigated as a means of increasing the energy and performance of missile propellants over those currently in use. A very promising candidate for a new highly energetic binder system contains 3-nitratomethyl-3-methyloxetane. However, 3-nitratomethyl-3-methyloxetane is currently available only in limited quantities.
The prior art method for making 3-nitratomethyl-3-methyloxetane requires the use of very corrosive and difficult to handle materials. In the prior art, acetylnitrate is used to nitrate hydroxymethylmethyloxetane (HMMO) to produce 3-nitratomethyl-3-methyloxetane. Prior art requires the preparation of acetylnitrate by reacting acetic anhydride with concentrated nitric acid. Acetylnitrate is a very hazardous, unstable explosive that can detonate spontaneously in storage which makes large scale commercial manufacture of 3-nitratomethyl-3-methyloxetane difficult and hazardous. Furthermore, 3-nitratomethyl-3-methyloxetane produced by this method must be purified by the tedious technique of chromatography.
This invention eliminates the use of both nitric acid and acetylnitrate in the production of 3-nitratomethyl-3-methyloxetane. Moreover, the 3-nitratomethyl-3-methyloxetane produced by this method is of high purity, eliminating the need for chromatography. This invention is also amenable to large scale commercial manufacture of 3-nitratomethyl-3-methyloxetane.
An object of this invention is to provide a simple and efficient method of preparing 3-nitratomethyl-3-methyloxetane by the direct liquid phase nitration of hydroxymethylmethyloxetane using dinitrogen pentoxide (N2 O5) as the nitrating agent.
A further object of this invention is to provide a method for economical commercial production of 3-nitratomethyl-3-methyloxetane that has a high yield and high purity.
The starting material is hydroxymethylmethyloxetane. Hydroxymethylmethyloxetane is dissolved in dry chloroform and set aside. Dinitrogen pentoxide (N2 O5) is then prepared by a known reaction wherein commercially available dinitrogen tetroxide (N2 O4) gas is contacted with dry ozone until all of the red N2 O4 is consumed. See Guye, P. A., U.S. Pat. No. 1,348,873 (1920) for the N2 O5 procedure. The resulting N2 O5 is captured in solid form in dry ice.
The N2 O5 is then dissolved in dry chloroform to make a solution. The N2 O5 in solution is then slowly added, using a dropping funnel, to the prepared hydroxymethylmethyloxetane solution while the solution is continually stirred. Stirring continues for about 2 hours after the last of the N2 O5 solution has been added to the hydroxymethylmethyloxetane solution. At this point the reaction is complete and the solution contains 3-nitratomethyl-3-methyloxetane. The N2 O5 also may be dissolved in carbon tetrachloride, methylene chloride or acetonitrile as substitutes for the dry chloroform.
The solution is then, in succession, washed with distilled water, then with saturated sodium bicarbonate solution, and then with saturated sodium chloride solution. Water is then removed from the chloroform and 3-nitratomethyl-3-methyloxetane solution by adding anhydrous sodium sulfate. After 10 minutes the sodium sulfate is removed by filtration. The chloroform is then removed under reduced pressure leaving almost pure 3-nitratomethyl-3-methyloxetane. The resulting 3-nitratomethyl-3-methyloxetane can be further purified by vacuum distillation.
The preferred embodiment of this invention may be further understood by referring to the following examples. These examples are given to illustrate but not limit this invention.
The starting material, 15 g (150 mmol) hydroxymethylmethyloxetane, was dissolved in 300 milliliters of dry chloroform at 0° C., at atmospheric pressure and set aside.
Dinitrogen pentoxide (N2 O5) was then prepared by contacting commercially available dinitrogen tetroxide (N2 O4) with dry ozone at ambient temperature and pressure until all of the red dinitrogen tetroxide was consumed. The resulting dinitrogen pentoxide (N2 O5), 32.4 g, was captured in solid form in a dry ice trap at -78° C.
The 32.4 g of dinitrogen pentoxide (N2 O5) was then dissolved in dry chloroform at 0° C., at atmospheric pressure, to make a 1 Molar solution, approximately 300 milliliters.
The 300 ml of 1 Molar solution of dinitrogen pentoxide (N2 O5) was then slowly added to the prepared hydroxymethylmethyloxetane solution over a 20 minute period using a dropping funnel while stirring continuously. After the addition was completed, the resulting solution was stirred continuously for 2 hours while maintaining the temperature at 0 degrees C. with an ice bath. The solution contained 3-nitratomethyl-3-methyloxetane.
The solution was then washed, in succession, with 250 ml of distilled water, then 250 ml of aqueous saturated sodium bicarbonate solution, and then 250 ml of aqueous saturated sodium chloride solution. Water is then removed from the chloroform and 3-nitratomethyl-3-methyloxetane solution by adding 2 g of anhydrous sodium sulfate. After ten minutes the sodium sulfate was removed by filtration. The chloroform was then removed using a rotary evaporator under reduced pressure, 14 torr, leaving almost pure 3-nitratomethyl-3-methyloxetane.
The 3-nitratomethyl-3-methyloxetane was then purified by vacuum distillation at 0.35 torr at a temperature range between 52 and 62 degrees C. 20 grams of 99% pure 3-nitratomethyl-3-methyloxetane were obtained. NMR showed very clean product. Yield was 91%.
20 ml of 1 molar dinitrogen pentoxide (N2 O5) in dry chloroform was added drop-wise with a dropping funnel over five minutes to a continuously stirred solution of 1 gram of hydroxymethylmethyloxetane in 20 ml of dry chloroform held at 0° C. with an ice-water bath. The solution was then continuously stirred at 0° C. for an additional one and one-half hours. The solution was next washed in succession with 100 ml of water, then 100 ml of aqueous saturated sodium bicarbonate solution, and then 100 ml of aqueous saturated sodium chloride solution. The solution was then dried by adding 1 g of anhydrous sodium sulfate. After 10 minutes the sodium sulfate was removed by filtration. Chloroform was then removed by using a rotary evaporator at 14 torr, yielding 1.5 grams of 3-nitratomethyl-3-methyloxetane.
Claims (16)
1. A method of preparing 3-nitratomethyl-3-methyloxetane comprising the following steps:
dissolving hydroxymethylmethyloxetane in a solvent;
dissolving dinitrogen pentoxide in a solvent;
adding said dinitrogen pentoxide solutions to said hydroxymethylmethyloxetane solution;
holding said reaction mixture at a first reaction temperature;
stirring said reaction mixture for a time sufficient to complete the reaction while holding said reaction mixture at said first reaction temperature;
washing said reaction mixture with water;
washing said reaction mixture with saturated sodium bicarbonate solution;
washing said reaction mixture with saturated sodium chloride solution;
drying said reaction mixture with anhydrous sodium sulfate;
filtering said sodium sulfate from said reaction mixture;
removing said solvent at reduced pressure;
purifying said 3-nitratomethyl-3-methyloxetane by vacuum distillation; and
holding said product at a second reaction temperature while purifying.
2. The method of claim 1 wherein said solvent used to dissolve said dinitrogen pentoxide is dry chloroform.
3. The method of claim 1 wherein said solvent to dissolve said dinitrogen pentoxide is selected from the group consisting of methylene chloride, carbon tetrachloride, or acetonitrile.
4. The method of claim 1 wherein said first reaction temperature is from about -15° to +5° C.
5. The method of claim 1 wherein said first reaction temperature is 0° C.
6. The method of claim 1 wherein said stirring is a continuous stirring action.
7. The method of claim 1 wherein said time for completion of the reaction is from about one and one-half to two hours.
8. The method of claim 1 wherein said water for washing said reaction mixture is about 50% to 250% of the volume of said reaction mixture.
9. The method of claim 1 wherein said saturated sodium bicarbonate solution for washing said reaction mixture is about 50% to 250% of the volume of said reaction mixture.
10. The method of claim 1 wherein said sodium chloride solution for washing said reaction mixture is about 50% to 250% of the volume of said reaction mixture.
11. The method of claim 1 wherein said sodium sulfate for drying said reaction mixture is about 1 to 2 grams.
12. The method of claim 1 wherein said filtrating of said sodium sulfate is about ten minutes after adding said sodium sulfate.
13. The method of claim 1 wherein said reduced pressure for removing said solvent is about 14 torr.
14. The method of claim 1 wherein said vacuum distillation for purifying is at 0.35 torr.
15. The method of claim 1 wherein said second reaction temperature is from about 52° to 62° C.
16. The method of claim 1 wherein said solvent used to dissolve said hydroxymethylmethyloxetane is dry chloroform.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/296,556 USH991H (en) | 1989-01-03 | 1989-01-03 | Synthesis of nitratomethylmethyloxetane (NMMO) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/296,556 USH991H (en) | 1989-01-03 | 1989-01-03 | Synthesis of nitratomethylmethyloxetane (NMMO) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH991H true USH991H (en) | 1991-11-05 |
Family
ID=23142517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/296,556 Abandoned USH991H (en) | 1989-01-03 | 1989-01-03 | Synthesis of nitratomethylmethyloxetane (NMMO) |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH991H (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362848A (en) * | 1992-12-11 | 1994-11-08 | Aerojet-General Corporation | Preparation and polymerization of initiators containing multiple oxetane rings: new routes to star polymers |
| US6177033B1 (en) | 1999-06-01 | 2001-01-23 | The United States Of America As Represented By The Secretary Of The Navy | Nitration of organics in carbon dioxide |
-
1989
- 1989-01-03 US US07/296,556 patent/USH991H/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| Morton-Thiokol, Inc., "High Energy Binders Final Report", Jun. 1985, pp. 8nd 82, Publication 85837. |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362848A (en) * | 1992-12-11 | 1994-11-08 | Aerojet-General Corporation | Preparation and polymerization of initiators containing multiple oxetane rings: new routes to star polymers |
| US5663289A (en) * | 1992-12-11 | 1997-09-02 | Aerojet-General Corporation | Preparation and polymerization of initiators containing multiple oxetane rings: new routes to star polymers |
| US6177033B1 (en) | 1999-06-01 | 2001-01-23 | The United States Of America As Represented By The Secretary Of The Navy | Nitration of organics in carbon dioxide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2227625C (en) | Method of preparing dinitramidic acid and salts thereof | |
| USH991H (en) | Synthesis of nitratomethylmethyloxetane (NMMO) | |
| US4476322A (en) | Synthesis of dimethylmethylene dinitramine | |
| US4028410A (en) | Process of preparing 1,3-bis(2-chloroethyl)-1-nitrosourea | |
| US4614800A (en) | Synthesis of cyclic dinitramines useful as explosive and propellant ingredients, gas generants and in other ordnance applications | |
| Heyboer et al. | Note on the conversion of the amino group of amino acids into the nitroguanidino group | |
| US5659080A (en) | Synthetic method for forming ammonium dinitrammide (ADN) | |
| Cooney et al. | Nitrogen‐15 studies of the mechanisms of acetolyses of hexamethylenetetramine and 3, 7‐diacetyl‐1, 3, 5, 7‐tetraazabicyclo [3.3. 1] nonane (DAPT) | |
| USH447H (en) | Synthesis of 1,3,5-trinitro-1,3,5-triazacyclohexane | |
| US3931347A (en) | Purification of dinitrotoluene | |
| US5659032A (en) | Process for the synthesis of 2,4,6,8-tetranitro-2,4,6,8-tetraazabicyclo (3.3.0) octane | |
| US4154758A (en) | Process for the manufacture of p-hydroxybenzyl cyanide | |
| CA1039309A (en) | PROCESS FOR THE PREPARATION OF .alpha.-ETHYNYL BENZOPHENONES | |
| US3978042A (en) | Process for preparing cyclocytidine derivatives | |
| US4111968A (en) | Process | |
| US3069464A (en) | Method for manufacture of gamma l-glutamyl hydrazide | |
| US2680673A (en) | Process of preparing anhydrous hydrazine | |
| US4469888A (en) | Process for the preparation of 2,4-dinitro-2,4-diazapentane | |
| CA1053703A (en) | Process for working up nitration mixtures | |
| SU1604732A1 (en) | Method of producing nitron salts | |
| CN117865906A (en) | Novel fluorine gem dinitrofurazan energetic compound and preparation method and application thereof | |
| US4046800A (en) | Cis-β-[Trimethylammonium]-acrylonitrile tosylate | |
| US3378576A (en) | Nitrate esters of tetrahydroxy-3, 6-dinitrocyclohexane | |
| US3981975A (en) | Preparation of anhydrous nitric acid | |
| US4233249A (en) | Method for the preparation of alkali metal salts of dinitromethane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: UNITED STATES OF AMERICA, THE, AS REPRESENTED BY T Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:FISCHER, JOHN W.;HOLLINS, RICHARD A.;REEL/FRAME:005007/0174 Effective date: 19881228 |
|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |