USH184H - 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method preparation - Google Patents
2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method preparation Download PDFInfo
- Publication number
- USH184H USH184H US06/878,150 US87815086A USH184H US H184 H USH184 H US H184H US 87815086 A US87815086 A US 87815086A US H184 H USH184 H US H184H
- Authority
- US
- United States
- Prior art keywords
- fluoro
- dinitroethoxy
- methane
- bis
- trifluoroethoxy
- 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
- XZAFCRBWIZMWRO-UHFFFAOYSA-N 1-fluoro-2-[(2-fluoro-2,2-dinitroethoxy)-(2,2,2-trifluoroethoxy)methoxy]-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC(OCC(F)(F)F)OCC(F)([N+]([O-])=O)[N+]([O-])=O XZAFCRBWIZMWRO-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- WULGSZRRUOGCCD-UHFFFAOYSA-N 2-[bis(2-fluoro-2,2-dinitroethoxy)methoxy]-1-fluoro-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC(OCC(F)([N+]([O-])=O)[N+]([O-])=O)OCC(F)([N+]([O-])=O)[N+]([O-])=O WULGSZRRUOGCCD-UHFFFAOYSA-N 0.000 claims description 7
- WQOBINOOPNWZJS-UHFFFAOYSA-N 2-[chloro-(2-fluoro-2,2-dinitroethoxy)methoxy]-1-fluoro-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC(Cl)OCC(F)([N+]([O-])=O)[N+]([O-])=O WQOBINOOPNWZJS-UHFFFAOYSA-N 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 abstract description 11
- 239000002360 explosive Substances 0.000 abstract description 7
- 229920002313 fluoropolymer Polymers 0.000 abstract description 4
- 239000004811 fluoropolymer Substances 0.000 abstract description 4
- WSZPRLKJOJINEP-UHFFFAOYSA-N 1-fluoro-2-[(2-fluoro-2,2-dinitroethoxy)methoxy]-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COCOCC(F)([N+]([O-])=O)[N+]([O-])=O WSZPRLKJOJINEP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DKSPPEUUPARRFY-UHFFFAOYSA-N 2-fluoro-2,2-dinitroethanol Chemical compound OCC(F)([N+]([O-])=O)[N+]([O-])=O DKSPPEUUPARRFY-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QUAMCNNWODGSJA-UHFFFAOYSA-N 1,1-dinitrooxybutyl nitrate Chemical compound CCCC(O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QUAMCNNWODGSJA-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 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 description 3
- VBXZSLHHMLUTQR-UHFFFAOYSA-N 2-[bis(2,2,2-trifluoroethoxy)methoxy]-1-fluoro-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC(OCC(F)(F)F)OCC(F)(F)F VBXZSLHHMLUTQR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- PDAUNNPSUVIMFK-UHFFFAOYSA-N (2-fluoro-2,2-dinitroethyl) acetate Chemical compound CC(=O)OCC(F)([N+]([O-])=O)[N+]([O-])=O PDAUNNPSUVIMFK-UHFFFAOYSA-N 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- SWUWMVIPFQAITJ-UHFFFAOYSA-N chlorine difluoride-35cl Chemical compound FClF SWUWMVIPFQAITJ-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/28—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/29—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
Definitions
- This invention relates to plastic-bonded explosives and more particularly to energetic plasticizers for plastic-bonded explosives.
- energetic plasticizers which are currently used in plastic-bonded explosives (PBXs) are bis(2-fluoro-2,2-dinitroethyl)formal (FEFO), butanetriol trinitrate (BTTN), and trimethylolethane trinitrate (TMETN). These compounds have various disadvantages which include limited thermal stability (BTTN, TMETN), high volatility (FEFO), toxicity (FEFO), and high melting point (FEFO). In addition, these energetic plasticizers are not miscible with fluoropolymers and can therefore not be used with these desirable new binder materials for PBXs.
- an object of this invention is to provide a novel organic compound.
- Another object of this invention is to provide a new energetic plasticizer for plastic-bonded explosives.
- a further object of this invention is to provide an energetic plasticizer having good thermal stability.
- Still another object of this invention is to provide an energetic plasticizer having a low volatility.
- Yet a further object of this invention is to provide an energetic plasticizer that is miscible with fluoropolymers.
- TFF 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane
- PBX plastic-bonded explosive
- TFF bis(2-fluoro-2,2-dinitroethyl)formal
- TFF TFF containing PBXs.
- One of the most serious drawbacks of FEFO is its propensity to induce allergic skin reactions in many people coming in contact with it. To date, TFF has not shown this undesirable handling side-effect.
- the most significant difference between TFF and FEFO is, however, the miscibility of TFF with certain fluorinated prepolymers (e.g., Fluorel, Viton A). This permits the formulation of energetic binders based on the use of chemically and thermally stable fluoropolymers.
- 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane CF 3 CH 2 OCH[OCH 2 CF(NO 2 ) 2 ] 2
- 2-fluoro-2,2-dinitroethanol CF(NO 2 ) 2 CH 2 OH
- Tris(2-fluoro-2,2-dinitroethoxy)methane CH[OCH 2 CF(NO 2 ) 2 ] 3
- the conditions of this reaction are illustrated by example 1 which is incorporated from U.S. Pat. No. 3,388,147, entitled “2-Fluoro-2,2-Dinitroethyl Carbonates and Production thereof," which was issued on June 11, 1968, to Mortimer J. Kamlet et al. (see col. 3, example III).
- the residual liquid (14.14 g, 80% yield) was chloro bis(2-fluoro-2,2-dinitroethoxy)methane, free of contaminants by 1 H NMR analysis.
- Anal. Calcd for C 5 H 5 ClF 2 N 4 O 10 C, 16.94; H, 1.42; Cl, 10.00; F, 10.72; N, 15.80. Found: C, 17.10; H, 1.78; Cl, 10.08; F, 10.71; N, 15.42.
- Chloro bis(2-fluoro-2,2-dinitroethoxy)methane (14.11 g, 0.0348 mol), prepared in example 2, was refluxed with 5.00 g (0.0500 mol) of 2,2,2-trifluoroethanol in 30 ml of dichloroethane for 2.5 hours.
- the solution was filtered through 5 g of Silica Gel 60 (EM Reagents) in a short column, followed by a rinse with 50 ml of dichloromethane. Concentration of the solution on a rotary evaporator gave 17 g of liquid residue which was distilled to give a forerun of 2.60 g (bp 37°-48° C./0.04 mm).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane, CF3 CHb.2 OCH[OCH2 CF(NO2)2 ]2, is an energetic plasticizer useful in plastic-bonded explosives. Of particular importance is its miscibility with fluoropolymers.
Description
This invention relates to plastic-bonded explosives and more particularly to energetic plasticizers for plastic-bonded explosives.
Examples of energetic plasticizers which are currently used in plastic-bonded explosives (PBXs) are bis(2-fluoro-2,2-dinitroethyl)formal (FEFO), butanetriol trinitrate (BTTN), and trimethylolethane trinitrate (TMETN). These compounds have various disadvantages which include limited thermal stability (BTTN, TMETN), high volatility (FEFO), toxicity (FEFO), and high melting point (FEFO). In addition, these energetic plasticizers are not miscible with fluoropolymers and can therefore not be used with these desirable new binder materials for PBXs.
Accordingly, an object of this invention is to provide a novel organic compound.
Another object of this invention is to provide a new energetic plasticizer for plastic-bonded explosives.
A further object of this invention is to provide an energetic plasticizer having good thermal stability.
Still another object of this invention is to provide an energetic plasticizer having a low volatility.
Yet a further object of this invention is to provide an energetic plasticizer that is miscible with fluoropolymers.
These and other objects of this invention are achieved by providing a new compound 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method of preparing it.
This invention provides 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane (TFF) which has been found to act as a plasticizer for various energetic and non-energetic prepolymers commonly used in plastic-bonded explosive (PBX) formulations. TFF is a liquid with a melting point of -3° to -1° C. and a density of 1.63g/cm3 (at 25° C.). Its heat of formation is estimated to be -400.0 kcal/mol and the calculated detonation pressure is 232 kbar.
The advantages of TFF as an energetic plasticizer are illustrated by comparing its properties with those of bis(2-fluoro-2,2-dinitroethyl)formal (FEFO), the plasticizer it is intended to replace. The melting point of FEFO is 14° C., that of TFF is -3° to -1° C. Thus, TFF is significantly lower melting, a highly desirable feature which will convey better low-temperature properties to plastic-bonded explosives (PBXs) using TFF instead of FEFO. The volatility of TFF and FEFO were compared by thermogravimetric analysis (TGA) at 117° C. The observed weight-losses were 0.028 mg/min and 0.039 mg/min, respectively. Thus, TFF is less volatile than FEFO. This will facilitate processing and increase the storage life of TFF containing PBXs. One of the most serious drawbacks of FEFO is its propensity to induce allergic skin reactions in many people coming in contact with it. To date, TFF has not shown this undesirable handling side-effect. The most significant difference between TFF and FEFO is, however, the miscibility of TFF with certain fluorinated prepolymers (e.g., Fluorel, Viton A). This permits the formulation of energetic binders based on the use of chemically and thermally stable fluoropolymers.
2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane, CF3 CH2 OCH[OCH2 CF(NO2)2 ]2, can be prepared from 2-fluoro-2,2-dinitroethanol, CF(NO2)2 CH2 OH, by the following reaction sequence as illustrated in Examples 1, 2, and 3: ##STR1##
Tris(2-fluoro-2,2-dinitroethoxy)methane, CH[OCH2 CF(NO2)2 ]3, is a prior art compound which is synthesized by reacting three moles of 2-fluoro-2,2-dinitroethanol with one mole of chloroform by refluxing the reactants in the presence of ferric chloride as a catalyst. The conditions of this reaction are illustrated by example 1 which is incorporated from U.S. Pat. No. 3,388,147, entitled "2-Fluoro-2,2-Dinitroethyl Carbonates and Production thereof," which was issued on June 11, 1968, to Mortimer J. Kamlet et al. (see col. 3, example III).
Next, the tris(2-fluoro-2,2-dinitroethoxy)methane is refluxed with aluminum chloride and acetyl chloride to produce chloro bis(2-fluoro-2,2-dinitroethoxy)methane as illustrated by example 2.
Finally, one mole of 2,2,2-trifluorethanol is reacted with each mole of chloro bis(2-fluoro-2,2-dinitroethoxy)methane to produce the desired product 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane under conditions illustrated by example 3. The choice of a solvent for this step is not critical. Any inert solvent in which the reactants are soluble and which has a suitable boiling point may be used. Suitable solvents include dichloromethane, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, or mixtures thereof.
The general nature of the invention having been set forth, the following examples are presented as specific examples thereof. It will be understood that the invention is not limited to these specific examples but is susceptible to various modifications that will be recognized by one of ordinary skill in the art.
[i.e., tris(2-fluoro-2,2-dinitroethyl)orthoformate]
"A mixture of 0.5 g. anhydrous ferric chloride and 10 ml. chloroform was placed in a 30 ml. round-bottom flask fitted with a magnetic stirrer and a reflux condenser connected through a bubbler to a methanol gas trap. 2-fluoro-2,2-dinitroethanol, 2.0 g. (0.013 mole) was added and the mixture stirred and refluxed for 24 hours, after which time the mixture was collected [sic] to room temperature and the solvent removed in vacuo.
The residue was drowned in iced water, stirred until the ferric chloride dissolved and the crystalline product collected. Recrystallization of this material from chloroform-hexane gave 1.39 g. (68%) pure tris(2-fluoro-2,2-dinitroethyl)orthoformate (FDNEOF) as fine colorless needles, M.P. 110°-11.2°."
A solution of tris(2-fluoro-2,2-dinitroethoxy)methane (23.6 g, 0.050 mol), aluminum chloride (12.0 g, 0.090 mol) and acetyl chloride (200 g) was refluxed for 1.5 hours and then concentrated on a rotary evaporator to a viscous liquid. This was extracted with chloroform (2×50 ml). After treatment with activated charcoal (2 g), this solution was filtered and concentrated (rot. evap., 40° C. bath) to 23 g of residue from which 8.53 g (87%) of 2-fluoro-2,2-dinitroethyl acetate (bp 40°-3° C./0.1 mm) was removed by distillation. The residual liquid (14.14 g, 80% yield) was chloro bis(2-fluoro-2,2-dinitroethoxy)methane, free of contaminants by 1 H NMR analysis. Anal. Calcd for C5 H5 ClF2 N4 O10 : C, 16.94; H, 1.42; Cl, 10.00; F, 10.72; N, 15.80. Found: C, 17.10; H, 1.78; Cl, 10.08; F, 10.71; N, 15.42.
2,2,2-Trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane
Chloro bis(2-fluoro-2,2-dinitroethoxy)methane (14.11 g, 0.0348 mol), prepared in example 2, was refluxed with 5.00 g (0.0500 mol) of 2,2,2-trifluoroethanol in 30 ml of dichloroethane for 2.5 hours. The solution was filtered through 5 g of Silica Gel 60 (EM Reagents) in a short column, followed by a rinse with 50 ml of dichloromethane. Concentration of the solution on a rotary evaporator gave 17 g of liquid residue which was distilled to give a forerun of 2.60 g (bp 37°-48° C./0.04 mm). This was a mixture of 2-fluoro-2,2-dinitroethanol and 2-fluoro-2,2-dinitroethoxy bis(2,2,2-trifluoroethoxy)methane. It was followed by a 1.60 g fraction of pure 2-fluoro-2,2-dinitroethoxy bis(2,2,2-trifluoroethoxy)methane (bp 49° C./0.05mm). The pot residue of 10.98 g. (66%) was the desired product 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane with a trace of tris(2-fluoro-2,2-dinitroethoxy)methane by TLC and NMR analysis: bp 99°-103° C./0.025 mm; 1 H NMR (CDCl3): δ5.67 (s, 1), 4.80 (d, 4, J=17 Hz), 4.03 (q, 2, J=8 Hz).
Anal Calcd for C7 H7 F5 N4 O11 : C, 20.10; H, 1.69; F, 22.72; N, 13.40. Found: C, 20.37; H, 1.42; F, 22.46; N, 13.16.
To those skilled in the art, many modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that the present invention can be practiced otherwise than as specifically described herein and still be within the spirit and scope of the appended claims.
Claims (3)
1. 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane, CF3 CH2 OCH[OCH2 CF(NO2)2 ]2.
2. A method of preparing 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane comprising the following steps in order:
(1) refluxing tris(2-fluoro-2,2-dinitroethoxy)methane with aluminum chloride and acetyl chloride to produce chloro bis(2-fluoro-2,2-dinitroethoxy)methane;
(2) reacting one mole of 2,2,2-trifluoroethanol with each mole of the chloro bis(2-fluoro-2,2-dinitroethoxy)methane to produce 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane; and
(3) isolating the product 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane.
3. The process of claim 2 wherein the reaction in step (2) is run under reflux in a solvent selected from the group consisting of dichloromethane, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, and mixtures thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/878,150 USH184H (en) | 1986-06-23 | 1986-06-23 | 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/878,150 USH184H (en) | 1986-06-23 | 1986-06-23 | 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH184H true USH184H (en) | 1987-01-06 |
Family
ID=25371479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/878,150 Abandoned USH184H (en) | 1986-06-23 | 1986-06-23 | 2,2,2-trifluoroethoxy bis(2-fluoro-2,2-dinitroethoxy)methane and a method preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH184H (en) |
-
1986
- 1986-06-23 US US06/878,150 patent/USH184H/en not_active Abandoned
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| Date | Code | Title | Description |
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Owner name: UNITED STATES OF AMERICA, AS REPRESENTED BY THE SE Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:KOPPES, WILLIAM M.;ADOLPH, HORST G.;REEL/FRAME:004570/0326 Effective date: 19860619 |
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