USH181H - Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparation - Google Patents
Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparation Download PDFInfo
- Publication number
- USH181H USH181H US06/878,149 US87814986A USH181H US H181 H USH181 H US H181H US 87814986 A US87814986 A US 87814986A US H181 H USH181 H US H181H
- Authority
- US
- United States
- Prior art keywords
- fluoro
- bis
- dinitroethoxy
- acetonitrile
- dinitroethyl
- 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
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- PPNPEVXXZVLBKJ-UHFFFAOYSA-N 2,2-bis(2-fluoro-2,2-dinitroethoxy)acetonitrile Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC(C#N)OCC(F)([N+]([O-])=O)[N+]([O-])=O PPNPEVXXZVLBKJ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims 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 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000004014 plasticizer Substances 0.000 claims abstract description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 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
- 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 6
- 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
- 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
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002360 explosive Substances 0.000 abstract description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 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
- DKSPPEUUPARRFY-UHFFFAOYSA-N 2-fluoro-2,2-dinitroethanol Chemical compound OCC(F)([N+]([O-])=O)[N+]([O-])=O DKSPPEUUPARRFY-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
- 239000007788 liquid Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 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
- UOXCYHLFALVKNS-UHFFFAOYSA-N 2-fluoro-n-(2-fluoro-2,2-dinitroethyl)-2,2-dinitroethanamine Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)CNCC(F)([N+]([O-])=O)[N+]([O-])=O UOXCYHLFALVKNS-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
- 238000005474 detonation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- YHXFOBDRPHWDHW-UHFFFAOYSA-N (2-fluoro-2,2-dinitroethyl) formate Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COC=O YHXFOBDRPHWDHW-UHFFFAOYSA-N 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
- 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
- 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
- 230000005496 eutectics Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
- C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
- C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
- C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
- C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
Definitions
- This invention relates to plastic-bonded explosives and more particularly to energetic plasticizers for plastic-bonded explosives.
- PBXs plastic-bonded explosives
- FEFO bis(2-fluoro-2,2-dinitroethyl)formal
- BTTN butanetriol trinitrate
- TMETN trimethylolethane trinitrate
- an object of this invention is to provide a novel organic compound.
- Another object of this invention is to provide a new energetic coplasticizer for plastic-bonded explosives.
- a further object of this invention is to provide an energetic coplasticizer having good thermal stability.
- Still another object of this invention is to provide new energetic plasticizer mixtures.
- a still further object of this invention is to provide an energetic plasticizer mixture having the same high energy content as FEFO but a lower volatility than FEFO.
- This invention provides bis(2-fluoro-2,2-dinitroethoxy)acetonitrile (CYANO-FEFO), N.tbd.C-CH[OCH 2 CF(NO 2 ) 2 ] 2 , a new composition of matter, which has been found to act as a coplasticizer for bis(2-fluoro-2,2-dinitroethyl)formal (FEFO) in combination with various energetic and non-energetic prepolymers commonly used in plastic-bonded explosive (PBX) formulations.
- Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile is a low melting solid (MP 41°-2° C.) with a liquid density at 23° C. of 1.62 g/cm 3 . Its heat of formation is estimated to be -175 Kcal/mol, and the calculated detonation pressure is 244 Kbar.
- CYANO-FEFO bis(2-fluoro-2,2-dinitroethoxy)acetonitrile
- FEFO bis(2-fluoro-2,2-dinitroethyl)formal
- CYANO-FEFO results in a significant decrease of the plasticizer melting point; this will convey improved lowtemperature properties to plastic-bonded explosives (PBXs) using the plasticizer mixture in place of neat FEFO.
- the volatility of CYANO-FEFO was determined by thermogravimetric analysis (TGA) at 117° C. The weight loss was 0.003 mg/min, compared to 0.039 mg/min for FEFO. Thus, the volatility of CYANO-FEFO is lower than that of FEFO by a factor of ten. The volatility of the plasticizer mixture will therefore be substantially lower than that of neat FEFO, and the volatility of FEFO will be reduced because of its reduced concentration.
- the weight ratio of bis(2-fluoro-2,2-dinitroethyl)formal (FEFO) to bis(2-fluoro-2,2-dinitroethoxy)acetonitrile (CYANO-FEFO) in the energetic plasticizer mixture is preferably from 1:1 to 4:1, more preferably from 3:2 to 4:1 and most preferably about 13:7.
- FEFO bis(2-fluoro-2,2-dinitroethyl)formal
- CYANO-FEFO bis(2-fluoro-2,2-dinitroethoxy)acetonitrile
- Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile can be prepared from 2-fluoro-2,2-dinitroethanol by the following reaction sequence as described in examples 1, 2, and 3: ##STR1##
- 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).
- cyanotrimethylsilane is reacted with each mole of chloro bis(2-fluoro-2,2-dinitroethoxy)methane to produce the desired product, bis(2-fluoro-2,2-dinitroethoxy)acetonitrile, under conditions illustrated by example 3.
- 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.
- Tris(2-fluoro-2,2-dinitroethoxy)methane i.e., tris(2-fluoro-2,2-dinitroethyl)orthoformate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile, N.tbd.C--CH[OCH2 CF(NO..2)2 ]2, is useful as a coplasticizer with bis(2-fluoro-2,2-dinitroethyl)formal in energetic plasticizer mixtures for plastic bonded explosives.
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).
Accordingly, an object of this invention is to provide a novel organic compound.
Another object of this invention is to provide a new energetic coplasticizer for plastic-bonded explosives.
A further object of this invention is to provide an energetic coplasticizer having good thermal stability.
Still another object of this invention is to provide new energetic plasticizer mixtures.
A still further object of this invention is to provide an energetic plasticizer mixture having the same high energy content as FEFO but a lower volatility than FEFO.
These and other objects of this invention are achieved by providing a new compound bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparing it.
This invention provides bis(2-fluoro-2,2-dinitroethoxy)acetonitrile (CYANO-FEFO), N.tbd.C-CH[OCH2 CF(NO2)2 ]2, a new composition of matter, which has been found to act as a coplasticizer for bis(2-fluoro-2,2-dinitroethyl)formal (FEFO) in combination with various energetic and non-energetic prepolymers commonly used in plastic-bonded explosive (PBX) formulations. Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile is a low melting solid (MP 41°-2° C.) with a liquid density at 23° C. of 1.62 g/cm3. Its heat of formation is estimated to be -175 Kcal/mol, and the calculated detonation pressure is 244 Kbar.
The use of bis(2-fluoro-2,2-dinitroethoxy)acetonitrile (CYANO-FEFO) as a coplasticizer for bis(2-fluoro-2,2-dinitroethyl)formal (FEFO) provides several advantages over the use of FEFO as a unitary plasticizer. CYANO-FEFO is equal to FEFO in energy content (detonation pressure). Therefore, its addition to FEFO does not change the energy content of the system. CYANO-FEFO is miscible with FEFO in all proportions, and forms a binary eutectic of the approximate composition, FEFO:CYANO-FEFO=65:35, MP 5° C. Thus, the addition of this amount of CYANO-FEFO results in a significant decrease of the plasticizer melting point; this will convey improved lowtemperature properties to plastic-bonded explosives (PBXs) using the plasticizer mixture in place of neat FEFO. The volatility of CYANO-FEFO was determined by thermogravimetric analysis (TGA) at 117° C. The weight loss was 0.003 mg/min, compared to 0.039 mg/min for FEFO. Thus, the volatility of CYANO-FEFO is lower than that of FEFO by a factor of ten. The volatility of the plasticizer mixture will therefore be substantially lower than that of neat FEFO, and the volatility of FEFO will be reduced because of its reduced concentration.
The weight ratio of bis(2-fluoro-2,2-dinitroethyl)formal (FEFO) to bis(2-fluoro-2,2-dinitroethoxy)acetonitrile (CYANO-FEFO) in the energetic plasticizer mixture is preferably from 1:1 to 4:1, more preferably from 3:2 to 4:1 and most preferably about 13:7. Note that other energetic plasticizers may also be used in the plasticizer mixture. For example bis(2-fluoro-2,2-dinitroethyl)amine (BFDNA) works well with CYANO-FEFO as a coplasticizer.
Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile can be prepared from 2-fluoro-2,2-dinitroethanol by the following reaction sequence as described 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 cyanotrimethylsilane is reacted with each mole of chloro bis(2-fluoro-2,2-dinitroethoxy)methane to produce the desired product, bis(2-fluoro-2,2-dinitroethoxy)acetonitrile, 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.
Tris(2-fluoro-2,2-dinitroethoxy)methane [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°-111.2°."
Chloro bis(2-fluoro-2,2-dinitroethoxy)methane
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.
Cyano bis(2-fluoro-2,2-dinitroethoxy)methane (or bis(2-fluoro-2,2-dinitroethoxy)acetonitrile)
A solution of chloro bis(2-fluoro-2,2-dinitroethoxy)methane (2.45, 6.9 mmol) prepared in example 2 and cyanotrimethylsilane (0.77 g, 7.8 mmol) in 15 ml of dichloroethane was refluxed for 40 hours. NMR analysis showed consumption of the chloroformal and the presence of the cyanoformal together with a small amount of 2-fluoro-2,2-dinitroethyl formate. A 2.45 g residue from concentration of the reaction solution on a rotary evaporator was chromatographed on Silica Gel 60 (70-230 mesh, 25 g) with a 3:2 solvent mixture of hexanes/dichloromethane to give 1.51 g (63%) of bis(2-fluoro-2,2-dinitroethoxy)acetonitrile: mp 41°-2°; IR (film) 2260 (CN, weak) cm-1 ; 1 H NMR (CDCl3): δ5.67 (s,l), 4.87 (d, 4, J=16 Hz); mass spectrum (CI, CH4), m/z (rel intensity): 386 (M+41, 3), 375 (M+30, 2), 319 (100 ), 92 (50).
Anal. Calcd for C6 H5 F2 N5 O10 : C, 20.88; H, 1.46; F, 11.01; N, 20.29. Found: C, 21.05; H, 1.62; F, 10.87; N, 20.38.
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 (7)
1. Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile, N.tbd.C-CH[OCH2 CF(NO2)2 ]2.
2. An energetic plasticizer comprising a mixture of bis(2-fluoro-2,2-dinitroethyl)formal and bis(2-fluoro-2,2-dinitroethoxy)acetonitrile.
3. An energetic plasticizer according to claim 2 wherein the weight ratio of bis(2-fluoro-2,2-dinitroethyl)formal to bis(2-fluoro-2,2-dinitroethoxy)acetonitrile is from 1:1 to 4:1.
4. An energetic plasticizer according to claim 3 wherein the weight ratio of bis(2-fluro-2,2-dinitroethyl)formal to bis(2-fluoro-2,2-dinitroethoxy)acetonitrile is from 3:2 to 4:1.
5. An energetic plasticizer according to claim 4 wherein the weight ratio of bis(2-fluoro-2,2-dinitroethyl)formal to bis(2-fluoro-2,2-dinitroethoxy)acetonitrile is about 13:7.
6. A method of preparing bis(2-fluoro-2,2-dinitroethoxy)acetonitrile 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 cyanotrimethylsilane with one mole of chloro bis(2-fluoro-2,2-dinitroethoxy)methane to produce bis(2-fluoro-2,2-dinitroethoxy)acetonitrile; and
(3) isolating the product bis(2-fluoro-2,2-dinitroethoxy)acetonitrile.
7. The process of claim 6 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 |
|---|---|---|---|
| US06/878,149 USH181H (en) | 1986-06-23 | 1986-06-23 | Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/878,149 USH181H (en) | 1986-06-23 | 1986-06-23 | Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USH181H true USH181H (en) | 1986-12-02 |
Family
ID=25371478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/878,149 Abandoned USH181H (en) | 1986-06-23 | 1986-06-23 | Bis(2-fluoro-2,2-dinitroethoxy)acetonitrile and a method of preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USH181H (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4756777A (en) | 1987-04-03 | 1988-07-12 | The United States Of America As Represent By The Secretary Of The Navy | Bis(2,2,2-fluorodinitroethoxy)-(1,1,1-fluorodinitro-2-propoxy)methane |
-
1986
- 1986-06-23 US US06/878,149 patent/USH181H/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4756777A (en) | 1987-04-03 | 1988-07-12 | The United States Of America As Represent By The Secretary Of The Navy | Bis(2,2,2-fluorodinitroethoxy)-(1,1,1-fluorodinitro-2-propoxy)methane |
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