Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole

Ott, Donald G; Benziger, Theodore M

Title: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole

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Abstract

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.

Inventors:

Ott, Donald G ^[1]; Benziger, Theodore M ^[2]

Los Alamos, NM
Santa Fe, NM

Issue Date:: 1991-01-01

Research Org.:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

OSTI Identifier:: 867735

Patent Number(s):: 4997987

Assignee:: United States of America as represented by United States (Washington, DC)

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
C07C201/08 - by substitution of hydrogen atoms by nitro groups
C07C201/12 - by reactions not involving the formation of nitro groups
C07C205/12 - the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
C07C205/37 - the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
C07C209/10 - with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
C07C211/52 - the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups

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DOE Contract Number:: W-7405-ENG-36

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: preparation; 5-triamino-2; 6-trinitrobenzene; 5-dichloroanisole; tatb; nitration; relatively; mild; conditions; 5-dichloro-2; 6-trinitroanisole; yield; purity; ammonolysis; latter; compound; desired; route; treatment; thionyl; chloride; dimethylformamide; 5-trichloro-2; product; produced; relatively mild; mild conditions; product produced; thionyl chloride; /999/

Citation Formats


                    Ott, Donald G, and Benziger, Theodore M. Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole.  United States: N. p., 1991. 
        Web.

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                    Ott, Donald G, & Benziger, Theodore M. Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole.  United States.

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                    Ott, Donald G, and Benziger, Theodore M. Tue .  
        "Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole".  United States.  https://www.osti.gov/servlets/purl/867735.

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@article{osti_867735,

  title        = {Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole},

  author       = {Ott, Donald G and Benziger, Theodore M},

  abstractNote = {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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {1991},

  month        = {1}

}

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Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene from 3,5-dichloroanisole

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Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole is described. 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. 8 figures.
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