USH973H - 5-carboxyl-1,3-diamino-2,4,6-trinitrobenzene and method of preparation - Google Patents

5-carboxyl-1,3-diamino-2,4,6-trinitrobenzene and method of preparation Download PDF

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USH973H
USH973H US06/596,123 US59612384A USH973H US H973 H USH973 H US H973H US 59612384 A US59612384 A US 59612384A US H973 H USH973 H US H973H
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trinitrobenzene
diamino
datba
carboxy
preparation
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US06/596,123
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Michael Chaykovsky
Horst G. Adolph
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US Department of Navy
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Assigned to UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE NAVY reassignment UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE NAVY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ADOLPH, HORST G., CHAYKOVSKY, MICHAEL
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions

Definitions

  • This invention generally relates to aromatic nitro compounds and more particularly to 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene and a method of preparation thereof.
  • DATB 1,3-diamino-2,4,6-trinitrobenzene
  • TATB 1,3,5-triamino-2,4,6-trinitrobenzene
  • DATB and TATB are mixed with TNT, RDX, HMX, or mixtures thereof to provide explosives which are less sensitive but which provide comparable detonation pressures.
  • Another object of this invention is to provide a new explosive having a high energy density.
  • a further object of this invention is to provide a safer explosive which is less likely to detonate accidently.
  • 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene and a method of preparation thereof.
  • the compound is prepared by reacting 5-fluoro-1,3-diamino-trinitrobenzene with cyanotrimethylsilane to produce 5-cyano-1,3-diamino-2,4,6-trinitrobenzene which is then hydrolyzed to form the desired 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene.
  • DATBA 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene
  • DATBA 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene
  • TATB 1,3,5-triamino-2,4,6-trinitrobenzene
  • DATBA should be less sensitive than DATB due to the presence of an additional carboxyl group.
  • DATBA is potentially less expensive than TATB if it is made from commercially available 3,5-diaminobenzoic acid.
  • DATBA should be a more effective desensitizing agent than TATB or DATB and should permit the formulation of explosive compositions with improved sensitivity vs. performance characteristics.
  • DATBA is combined with another explosive filler such as HMX or RDX in the desired ratio and processed into a PBX or Octol type composite under the same conditions used for RDX or HMX alone.
  • Examples 1 to 2 illustrate a method of preparing the starting material 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene from 1,3,5-trifluorobenzene.
  • the intermediate compound 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (DATBN) is obtained by the reaction of 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene (F-DATB) with cyanotrimethylsilane, ##STR4##
  • Example 3 illustrates the reaction conditions and a method purification
  • DATBN is hydrolyzed with a strong acid to produce the final product 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR5##
  • DATBA 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene
  • Example 4 illustrates the conditions for this reaction and a method for purifying the final product DATBA.
  • Example 1 is incorporated from U.S. Pat. No. 4,173,591, entitled "Process for the Preparation of 1,3,5-trifloro-2,4,6-trinitrobenzene," which issued on Nov. 6, 1979, to William M. Koppes, Horst G. Adolph, and Michael E. Wegmann. This example illustrates a method of preparing the 1,3,5-trifluoro-2,4,6-trinitrobenzene starting material.
  • the reaction flask was placed in an oil bath and 1,3,5-trifluorobenzene (56.0 g, 0.424 mol) was added through an addition funnel. The addition rate was controlled to maintain the temperature at about 50° C.
  • the funnel was exchanged for a condenser protected with a drying tube (Drierite) and the mixture was heated at 153°-156° C. for 72 hours.
  • Example 2 illustrates a method of preparing the 5-fluoro-1,3-diamino-2,4,6-tetranitrobenzene (F-DATB) starting material from 1,3,5-trifluoro-2,4,6-trinitrobenzene.
  • F-DATB 5-fluoro-1,3-diamino-2,4,6-tetranitrobenzene
  • Example 3 illustrates the preparation of the new intermediate compound 5-cyano-1,3-diamino-2,4,6-trinitrobenzene.
  • Example 4 illustrates the hydrolysis of 5-cyano-1,3-diamino-2,4,6-trinitrobenzene to form the final produce 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR1## which is prepared by reacting 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene with cyanotrimethylsilane to form 5-cyano-1,3-diamino-2,4,6-trinitrobenzene which is then hydrolyzed with a strong acid to form the DATBA.

Description

BACKGROUND OF THE INVENTION
This invention generally relates to aromatic nitro compounds and more particularly to 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene and a method of preparation thereof.
Currently used explosive charges contain TNT, RDX, and HMX as the principal ingredients. These compounds are relatively sensitive to impact and other stimuli. Explosive compounds such as 1,3-diamino-2,4,6-trinitrobenzene (DATB) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) are less sensitive to impact at comparable performance levels. DATB and TATB are mixed with TNT, RDX, HMX, or mixtures thereof to provide explosives which are less sensitive but which provide comparable detonation pressures.
It would be desirable to provide explosive compositions which are even less sensitive to impact and temperature while still providing high detonation pressures.
SUMMARY OF THE INVENTION
Accordingly, it is an object of this invention to provide a new explosive compound and a method of preparing it.
Another object of this invention is to provide a new explosive having a high energy density.
A further object of this invention is to provide a safer explosive which is less likely to detonate accidently.
These and other objects of this invention are accomplished by providing 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene and a method of preparation thereof. The compound is prepared by reacting 5-fluoro-1,3-diamino-trinitrobenzene with cyanotrimethylsilane to produce 5-cyano-1,3-diamino-2,4,6-trinitrobenzene which is then hydrolyzed to form the desired 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene.
BRIEF DESCRIPTION OF THE DRAWING
A more complete understanding of the invention and the many attendant advantages thereto will be readily appreciated as the same becomes better understood by reference to the following detailed description when considered in connection with the accompanying drawing wherein the impact sensitivity-detonation pressure relationships for 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA) and three known explosives (TNT, TATB, and RDX) are plotted.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
Referring to the FIGURE, 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR2## combines a detonation pressure greater than TNT with a high degree of impact insensitivity. Moreover, DATBA offers advantages over other impact insensitive explosives such as 1,3-diamino-2,4,6-trinitrobenzene (DATB) and 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). DATBA should be less sensitive than DATB due to the presence of an additional carboxyl group. Moreover, DATBA is potentially less expensive than TATB if it is made from commercially available 3,5-diaminobenzoic acid. Finally, the decarboxylation step occurring near 240° C., ##STR3## provides an energy sink when DATBA is exposed to elevated temperature and thus should increase its resistance to cookoff and thermal explosion. Therefore, DATBA should be a more effective desensitizing agent than TATB or DATB and should permit the formulation of explosive compositions with improved sensitivity vs. performance characteristics.
In a typical application, DATBA is combined with another explosive filler such as HMX or RDX in the desired ratio and processed into a PBX or Octol type composite under the same conditions used for RDX or HMX alone.
Examples 1 to 2 illustrate a method of preparing the starting material 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene from 1,3,5-trifluorobenzene.
The intermediate compound 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (DATBN) is obtained by the reaction of 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene (F-DATB) with cyanotrimethylsilane, ##STR4##
Example 3 illustrates the reaction conditions and a method purification
In the final step, the DATBN is hydrolyzed with a strong acid to produce the final product 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (DATBA), ##STR5## Example 4 illustrates the conditions for this reaction and a method for purifying the final product DATBA.
The general nature of the invention having been set forth, the following examples are presented as specific illustrations 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.
Example 1 is incorporated from U.S. Pat. No. 4,173,591, entitled "Process for the Preparation of 1,3,5-trifloro-2,4,6-trinitrobenzene," which issued on Nov. 6, 1979, to William M. Koppes, Horst G. Adolph, and Michael E. Sitzmann. This example illustrates a method of preparing the 1,3,5-trifluoro-2,4,6-trinitrobenzene starting material.
EXAMPLE 1 1,3,5-trifluoro-2,4,6-trinitrobenzene Prior Art ##STR6##
A 3 liter 3-necked Morton flask equipped with Teflon™ paddle stirrer and thermometer and containing 1200 ml of 30% fuming sulfuric acid (8.78 mol SO3) was cooled with an icebath while 280 g (2.76 mol) of KNO3 were added in portions to maintain a temperature not exceeding 50° C. The reaction flask was placed in an oil bath and 1,3,5-trifluorobenzene (56.0 g, 0.424 mol) was added through an addition funnel. The addition rate was controlled to maintain the temperature at about 50° C. The funnel was exchanged for a condenser protected with a drying tube (Drierite) and the mixture was heated at 153°-156° C. for 72 hours. The mixture was allowed to cool to 30° C. and extracted in the reaction flask with CH2 Cl2 (3×1200 ml). The combined extracts were concentrated by distillation to 250 ml and this solution treated with Na2 SO4 and filtered. Dry hexane (150 ml) was added to the hot filtrate. After treatment with charcoal the hot solution was filtered. A total of 60.8 g of 1,3,5-trifluoro-2,4,6-trinitrobenzene mp 80°-82° C. (54%) was obtained by concentration of the solution and further addition of hexane. Evaporation of the mother liquor left a 1.4 g residue composed of a 26/74 mixture of 1,3,5-trifluoro-2,4,6-trinitrobenzene and 1,3,5-trifluoro-2,4-dinitrobenzene as determined by gas-liquid phase chromatography.
Example 2 illustrates a method of preparing the 5-fluoro-1,3-diamino-2,4,6-tetranitrobenzene (F-DATB) starting material from 1,3,5-trifluoro-2,4,6-trinitrobenzene.
EXAMPLE 2 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene Prior Art ##STR7##
2-amino-2-methylpropane (5.5 g, 75 mmol), in dry dichloromethane (1 500 ml) was added dropwise at 5 ml min1 to a well stirred mixture of 1,3,5-trifluoro-2,4,6- trinitrobenzene (10.0 g, 37.4 mmol), potassium hydrogencarbonate (15.0 g, 150 mmol), and dry dichloromethane (400 ml) at -30° C. under nitrogen. Stirring for 15 hours at room temperature, filtration, and evaporation of the solvent gave a product (14.2 g) which had three components by t.l.c. (benzene solvent). This mixture was stirred for 20 hours in trifluoroacetic acid (50 ml) and dichloromethane (10 ml), and the yellow solid filtered off and extracted with boiling 1,2-dichloromethane (1 600 ml). Filtration gave insoluble 1,3,5-triamino-4,5,6-trinitrobenzene (1.15 g). Concentration of the filtrate to 150 ml gave the desired 5-fluoro-1,3-diamino2,4,6-trinitrobenzene (6.93 g, 70%), m.p. 219°-221° C.
Example 3 illustrates the preparation of the new intermediate compound 5-cyano-1,3-diamino-2,4,6-trinitrobenzene.
EXAMPLE 3 5-Cyano-1,3-diamino-2,4,6-trinitrobenzene ##STR8##
A solution of 5-fluoro-1,3-diamino-2,4,6-trinitrobenzene (F-DATB) (5.22 g, 20 mmol) and cyanotrimethylsilane (4.96 g, 50 mmol) in CH3 NO2 (100 ml) was refluxed for two hours and then evaporated under vacuum to leave a solid residue. Recrystallization from acetonitrile (100 ml) gave 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (4.4 g, 82%) as orange-brown crystals: mp 212°-217° C. dec. An additional recrystallization gave the analytical sample: mp 220°-221° C.; mass spectrum (CI, CH4) m/z 269 (M+1, 100).
Anal. calcd for C7 H4 N6 O6 : C, 31.35; H, 1.50; N, 31.34.
Found: C, 31.39; H, 1.74; N, 31.19.
Example 4 illustrates the hydrolysis of 5-cyano-1,3-diamino-2,4,6-trinitrobenzene to form the final produce 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene.
EXAMPLE 4 5-Carboxy-1,3-diamino-2,4,6-trinitrobenzene ##STR9##
A solution of 5-cyano-1,3-diamino-2,4,6-trinitrobenzene (1.34 g, 5 mmol) in sulfuric acid (30 ml) and H2 O (15 ml) was heated at 100° C. for 90 minutes, cooled, and then poured onto a mixture of ice and H2 O (250 ml). The solid was filtered, washed with H2 O, and dried to give 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene (1.33 g, 92.7%). Recrystallization from acetonitrile gave yellow needles: mp 240°-245° C. (loss of CO2) and 280°-282° C. dec: mass spectrum (EI, CH4) m/z 244 (M+1-CO2, 100), 272 (m+C2 H5 -CO2, 9.2), 284 (M+C3 H5 -CO2, 4.5).
Anal. Calcd for C7 H5 N5 O8 : C, 29.28; H, 1.76; N, 24.39.
Found: C, 29.33: H, 1.84; N, 24.16.
Obviously, numerous modifications and variations of the present invention are possible in 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 herein.

Claims (2)

What is claimed as new and desired to be secured by Letters Patent of the United States is:
1. 5-carboxy-1,3-diamino-2,4,6-trinitrobenzene, ##STR10##
2. 5-cyano-1,3-diamino-2,4,6-trinitrobenzene, ##STR11##
US06/596,123 1984-04-02 1984-04-02 5-carboxyl-1,3-diamino-2,4,6-trinitrobenzene and method of preparation Abandoned USH973H (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040200378A1 (en) * 2003-03-10 2004-10-14 Schaefer Ruth A. Additive for composition B and composition B replacements that mitigates slow cook-off violence

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US1079246A (en) 1912-07-18 1913-11-18 Riedel J D Ag Process for the manufacture of nitroso derivatives of phenyl-glycin-ortho-carboxylic acid.
US2603659A (en) 1950-06-16 1952-07-15 Du Pont Photographic developers
CA727657A (en) 1966-02-08 Hooker Chemical Corporation Preparation of 3-nitro and 3,5-dinitrobenzoic acid and their acid chlorides
US3314989A (en) 1963-07-01 1967-04-18 Mallinckrodt Chemical Works Process of preparing n-methyl-5-nitroisophthalamic acid
US3485865A (en) 1967-04-05 1969-12-23 Velsicol Chemical Corp N-methoxy and n-ethoxy benzamides
US3576836A (en) 1967-06-29 1971-04-27 Du Pont Preparation of aromatic isocyanates
US3867452A (en) 1970-12-30 1975-02-18 Merrill Wilcox 2-Nitrophenylhydrazines
US4101721A (en) 1976-12-09 1978-07-18 Wisconsin Alumni Research Foundation Solid phase synthesis of protected peptides
US4173591A (en) 1978-08-28 1979-11-06 The United States Of America As Represented By The Secretary Of The Navy Process for the preparation of 1,3,5-trifluoro-2,4,6-trinitrobenzene
US4399303A (en) 1981-08-17 1983-08-16 E. I. Du Pont De Nemours And Company Preparation and use of nitroterephthalamic acids

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA727657A (en) 1966-02-08 Hooker Chemical Corporation Preparation of 3-nitro and 3,5-dinitrobenzoic acid and their acid chlorides
US1079246A (en) 1912-07-18 1913-11-18 Riedel J D Ag Process for the manufacture of nitroso derivatives of phenyl-glycin-ortho-carboxylic acid.
US2603659A (en) 1950-06-16 1952-07-15 Du Pont Photographic developers
US3314989A (en) 1963-07-01 1967-04-18 Mallinckrodt Chemical Works Process of preparing n-methyl-5-nitroisophthalamic acid
US3485865A (en) 1967-04-05 1969-12-23 Velsicol Chemical Corp N-methoxy and n-ethoxy benzamides
US3576836A (en) 1967-06-29 1971-04-27 Du Pont Preparation of aromatic isocyanates
US3867452A (en) 1970-12-30 1975-02-18 Merrill Wilcox 2-Nitrophenylhydrazines
US4101721A (en) 1976-12-09 1978-07-18 Wisconsin Alumni Research Foundation Solid phase synthesis of protected peptides
US4173591A (en) 1978-08-28 1979-11-06 The United States Of America As Represented By The Secretary Of The Navy Process for the preparation of 1,3,5-trifluoro-2,4,6-trinitrobenzene
US4399303A (en) 1981-08-17 1983-08-16 E. I. Du Pont De Nemours And Company Preparation and use of nitroterephthalamic acids

Non-Patent Citations (2)

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Title
Ammon et al., "Crystallographic Studies 3,5-diamino 2-4,6-trinitrobenzamide" Acta Cryst. (1982) B38 2083.
Goldstein, et al., "Sur l'acide dinitro-3,5-fluoro-2-benzoique", Helv. Ch Acta., v. 37, 1954, No. 134, p. 1121.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040200378A1 (en) * 2003-03-10 2004-10-14 Schaefer Ruth A. Additive for composition B and composition B replacements that mitigates slow cook-off violence
US7033449B2 (en) 2003-03-10 2006-04-25 Alliant Techsystems Inc. Additive for composition B and composition B replacements that mitigates slow cook-off violence

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