Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Mitchell, Alexander R; Pagoria, Philip F; Schmidt, Robert D

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Title: Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Abstract

The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from the group consisting of --H and --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen; with an effective amount of 1-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxamine to produce DATB or TATB; in the presence of a strong base selected from sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof; in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformide, dimethylacetamide and mixtures thereof, provided that when alcohols are present or when hydroxylamine or its O-alkyl derivatives replace ATA primarily DATB is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are important and useful specialty explosives and intermediates for other materials.

Inventors:

Mitchell, Alexander R ^[1]; Pagoria, Philip F ^[1]; Schmidt, Robert D ^[1]

Livermore, CA

Issue Date:: 1997-01-01

Research Org.:: Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

OSTI Identifier:: 870969

Patent Number(s):: 5633406

Assignee:: Regents of University of California (Oakland, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C209/02 - by substitution of hydrogen atoms by amino groups

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DOE Contract Number:: W-7405-ENG-48

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: vicarious; nucleophilic; substitution; 4-amino-1; 4-triazole; hydroxylamine; o-alkylhydroxylamine; prepare; 3-diamino-2; 6-trinitrobenzene; 5-triamino-2; relates; process; produce; datb; -trinitrobenzene; tatb; reacting; ambient; pressure; temperature; degree; 50; 24; trinitroaromatic; compound; structure; str1; z; independently; selected; consisting; -h; -nh; proviso; hydrogen; effective; amount; 1-amino-1; o-alkylhydroxamine; presence; strong; base; sodium; butoxide; potassium; propoxide; ethoxide; methoxide; combinations; solvent; methanol; ethanol; propanol; butanol; dimethylsulphoxide; n-methylpyrrolidone; hexamethylphosphoramide; dimethylformide; dimethylacetamide; mixtures; provided; alcohols; o-alkyl; derivatives; replace; ata; primarily; formed; isolating; produced; useful; specialty; explosives; intermediates; materials; aromatic compound; independently selected; effective amount; nucleophilic substitution; strong base; ambient pressure; base selected; solvent selected; vicarious nucleophilic; /999/

Citation Formats


                    Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene.  United States: N. p., 1997. 
        Web.

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                    Mitchell, Alexander R, Pagoria, Philip F, & Schmidt, Robert D. Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene.  United States.

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                    Mitchell, Alexander R, Pagoria, Philip F, and Schmidt, Robert D. Wed .  
        "Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene".  United States.  https://www.osti.gov/servlets/purl/870969.

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@article{osti_870969,

  title        = {Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene},

  author       = {Mitchell, Alexander R and Pagoria, Philip F and Schmidt, Robert D},

  abstractNote = {The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from the group consisting of --H and --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen; with an effective amount of 1-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxamine to produce DATB or TATB; in the presence of a strong base selected from sodium butoxide, potassium butoxide, potassium propoxide, sodium propoxide, sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide, and combinations thereof; in a solvent selected from the group consisting of methanol, ethanol, propanol, butanol, dimethylsulphoxide, N-methylpyrrolidone, hexamethylphosphoramide, dimethylformide, dimethylacetamide and mixtures thereof, provided that when alcohols are present or when hydroxylamine or its O-alkyl derivatives replace ATA primarily DATB is formed; and (b) isolating the DATB or TATB produced. DATB and TATB are important and useful specialty explosives and intermediates for other materials.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {1997},

  month        = {1}

}

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Works referenced in this record:

Preparation of Picramide
journal, September 1946

Spencer, E. Y.; Wright, George F.
Canadian Journal of Research, Vol. 24b, Issue 5
https://doi.org/10.1139/cjr46b-026

The Reaction of Chloramine with Tertiary Amines. ¹ 1,1,1-Trisubstituted Hydrazinium Salts ²
journal, March 1956

Omietanski, George M.; Sisler, Harry H.
Journal of the American Chemical Society, Vol. 78, Issue 6
https://doi.org/10.1021/ja01587a033

Direct amination of nitrobenzenes by vicarious nucleophilic substitution
journal, December 1986

Katritzky, Alan R.; Laurenzo, Kathleen S.
The Journal of Organic Chemistry, Vol. 51, Issue 25
https://doi.org/10.1021/jo00375a062

Identification of 1,3,5-triamino-2,4-6-trinitrobenzene impurities by two-dimensional thin-layer chromatography
journal, September 1972

Yasuda, Stanley K.
Journal of Chromatography A, Vol. 72, Issue 3
https://doi.org/10.1016/S0021-9673(01)91902-8

Synthesis of polynitro compounds. Hexasubstituted benzenes
journal, August 1986

Atkins, Ronald L.; Hollins, Richard A.; Wilson, William S.
The Journal of Organic Chemistry, Vol. 51, Issue 17
https://doi.org/10.1021/jo00367a003

Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen
journal, August 1992

Makosza, Mieczyslaw; Bialecki, Maciej
The Journal of Organic Chemistry, Vol. 57, Issue 18
https://doi.org/10.1021/jo00044a002

Vicarious nucleophilic substitution of hydrogen
journal, August 1987

Makosza, Mieczyslaw; Winiarski, Jerzy
Accounts of Chemical Research, Vol. 20, Issue 8
https://doi.org/10.1021/ar00140a003

Shock Sensitivity of Explosives Clarified
journal, August 1987

Worthy, Ward
Chemical & Engineering News Archive, Vol. 65, Issue 32
https://doi.org/10.1021/cen-v065n032.p025

Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles
journal, August 1988

Katritzky, Alan R.; Laurenzo, Kathleen S.
The Journal of Organic Chemistry, Vol. 53, Issue 17
https://doi.org/10.1021/jo00252a018

Über die Alkylierung des Hydrazins
journal, May 1941

Westphal, Otto
Berichte der deutschen chemischen Gesellschaft (A and B Series), Vol. 74, Issue 5
https://doi.org/10.1002/cber.19410740515

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Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Patent Mitchell, A R; Pagoria, P F; Schmidt, R D

The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0 and 50 C for between about 0.1 and 24 hr, a trinitroaromatic compound of the structure shown where X, Y, and Z are each independently selected from the group consisting of -H and -NH{sub 2}, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen; with an effective amount of 1-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxamine to produce DATB or TATB; in the presence of a strong base selectedmore » « less
Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

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The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from --H, or --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen, with an amount effective to produce DATB or TATB of 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide is selected frommore » « less
Full Text Available
Vicarious nucleophilic substitution to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Patent Mitchell, A R; Pagoria, P F; Schmidt, R D

The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,trinitrobenzene (TATB) by: (a) reacting at ambient pressure and a temperature of between about 0 and 50 C for between about 0.1 and 24 hr, a trinitroaromatic compound of the structure shown within where X, Y, and Z are each independently selected from --H, or --NH{sub 2}, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen, with an amount effective to produce DATB or TATB, or 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide ismore » « less
Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene of submicron particle size

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A method is disclosed for the preparation of very small particle size, relatively pure 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). Particles of TATB prepared according to the disclosed method are of submicron size and have a surface area in the range from about 3.8 to 27 square meters per gram.
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Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloranisole

Patent Ott, Donald G [Los Alamos, NM]; Benziger, Theodore M [Santa Fe, NM]

Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.
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Title: Vicarious nucleophilic substitution using 4-amino-1,2,4-triazole, hydroxylamine or O-alkylhydroxylamine to prepare 1,3-diamino-2,4,6-trinitrobenzene or 1,3,5-triamino-2,4,6-trinitrobenzene

Abstract

Citation Formats

Preparation of Picramide journal, September 1946

The Reaction of Chloramine with Tertiary Amines. 1 1,1,1-Trisubstituted Hydrazinium Salts 2 journal, March 1956

Direct amination of nitrobenzenes by vicarious nucleophilic substitution journal, December 1986

Identification of 1,3,5-triamino-2,4-6-trinitrobenzene impurities by two-dimensional thin-layer chromatography journal, September 1972

Synthesis of polynitro compounds. Hexasubstituted benzenes journal, August 1986

Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen journal, August 1992

Vicarious nucleophilic substitution of hydrogen journal, August 1987

Shock Sensitivity of Explosives Clarified journal, August 1987

Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles journal, August 1988

Über die Alkylierung des Hydrazins journal, May 1941

Preparation of Picramide
journal, September 1946

The Reaction of Chloramine with Tertiary Amines. ¹ 1,1,1-Trisubstituted Hydrazinium Salts ²
journal, March 1956

Direct amination of nitrobenzenes by vicarious nucleophilic substitution
journal, December 1986

Identification of 1,3,5-triamino-2,4-6-trinitrobenzene impurities by two-dimensional thin-layer chromatography
journal, September 1972

Synthesis of polynitro compounds. Hexasubstituted benzenes
journal, August 1986

Reactions of organic anions. 194. Amination of nitroarenes with sulfenamides via vicarious nucleophilic substitution of hydrogen
journal, August 1992

Vicarious nucleophilic substitution of hydrogen
journal, August 1987

Shock Sensitivity of Explosives Clarified
journal, August 1987

Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1,2,4-triazoles
journal, August 1988

Über die Alkylierung des Hydrazins
journal, May 1941