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{{Distinguish|text=], a highly sensitive ]}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 401616025 | verifiedrevid = 470476118
| ImageFile = Triaminotrinitrobenzene.png | ImageFile = Triaminotrinitrobenzene.png
| ImageFile1 = TATB-3D-vdW.png | ImageFile1 = TATB-3D-vdW.png
| ImageSize = 150px | ImageSize = 150px
| IUPACName = 1,3,5-triamino-2,4,6-trinitrobenzene | PIN = 2,4,6-Trinitrobenzene-1,3,5-triamine
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17272 | ChemSpiderID = 17272
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JDFUJAMTCCQARF-UHFFFAOYSA-N | StdInChIKey = JDFUJAMTCCQARF-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 3058-38-6 | CASNo = 3058-38-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CJP3UNX7Z7
| PubChem = 18286 | PubChem = 18286
| SMILES = c1(c(c(c(c(c1(=O))N)(=O))N)(=O))N | SMILES = c1(c(c(c(c(c1(=O))N)(=O))N)(=O))N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 6 | H = 6 | N = 6 | O = 6 | C=6 | H=6 | N=6 | O=6
| MolarMass = 258.15 g/mol | MolarMass = 258.15 g/mol
| Appearance = Yellow or brown powdered crystals (]) | Appearance = Yellow or brown powdered crystals (])
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| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
| Section6 = {{Chembox Explosive |Section6={{Chembox Explosive
| ShockSens = Insensitive | ShockSens = Insensitive
| FrictionSens = Insensitive | FrictionSens = Insensitive
| ExplosiveV = 7350 ] | DetonationV = 7350 ] (at 1.80 g/cm<sup>3</sup>)
| REFactor = }} | REFactor = }}
}} }}


'''TATB''', or '''triaminotrinitrobenzene''', is an ] explosive, based on the basic six-carbon ] ring structure with three ]s (NO<sub>2</sub>) and three ] (NH<sub>2</sub>) groups attached, alternating around the ring. '''TATB''', '''triaminotrinitrobenzene''' or '''2,4,6-triamino-1,3,5-trinitrobenzene''' is an ] explosive, based on the basic six-carbon ] ring structure with three ]s (NO<sub>2</sub>) and three ] (NH<sub>2</sub>) groups attached, alternating around the ring.


TATB is a powerful explosive (somewhat less powerful than ], but more than ]), but it is extremely insensitive to ], ], ], or ]. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme ] is required, such as the explosives used in ]s, where accidental detonation during an airplane crash or rocket misfiring would present extreme dangers. All British <ref>, UK MOD position statement, 23 January 2006</ref> TATB is a very powerful explosive (somewhat less powerful than ], but more than ]), but it is extremely insensitive to ], ], ], or ]. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme ] is required, such as the explosives used in ]s, where accidental detonation during an airplane crash or rocket misfiring could potentially detonate the fissile core. All British ]s use TATB-based explosives in their ].<ref>, UK MOD position statement, 23 January 2006</ref> According to ], ] used TATB to increase their safety.<ref name="Albright">{{cite magazine|url=https://books.google.com/books?id=VAwAAAAAMBAJ&pg=PA37|author=David Albright|magazine=Bulletin of the Atomic Scientists|title=South Africa and the Affordable Bomb|date=July 1994|page=44}}</ref>
and almost all US ]s, except those where weight is factor, {{Fact|date=March 2008}} are believed to use TATB based explosives for main explosive charges. According to ], ] used TATB to increase their safety.<ref name="Albright">{{cite journal|url=http://books.google.com/?id=VAwAAAAAMBAJ&pg=PA37#v=onepage&q=|author=David Albright|journal=Bulletin of Atomic Scientists|title=South Africa and the Affordable Bomb|month=July|year=1994|page=p. 44}}</ref>


TATB is normally used as the explosive ingredient in ] compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% ]). These formulations are described as ''']''' or '''IHE''' in nuclear weapons literature. TATB is normally used as the explosive ingredient in ] compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% ]). These formulations are described as ] (IHEs) in nuclear weapons literature.


Though it could theoretically be mixed with other explosive compounds in ] mixtures or other use forms, the applications for such forms would be unclear since they would largely undo the insensitivity of pure TATB. Though it could theoretically be mixed with other explosive compounds in ] mixtures or other use forms, the applications for such forms would be unclear since they would largely undo the insensitivity of pure TATB.

TATB's chemical structure is somewhat similar to the powerful experimental insensitive high explosive ].


==Properties== ==Properties==
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At a pressed density of 1.80, TATB has a velocity of ] of 7,350 meters per second. At a pressed density of 1.80, TATB has a velocity of ] of 7,350 meters per second.


TATB has a crystal density of 1.93 grams/cm<sup>3</sup>, though most use forms have no higher density than 1.80. TATB melts at 350 °C. The chemical formula for TATB is C<sub>6</sub>(NO<sub>2</sub>)<sub>3</sub>(NH<sub>2</sub>)<sub>3</sub>. TATB has a crystal density of 1.93 grams/cm<sup>3</sup>, though most forms currently in use have no higher density than 1.80 grams/cm<sup>3</sup>. TATB melts at 350&nbsp;°C. The chemical formula for TATB is C<sub>6</sub>(NO<sub>2</sub>)<sub>3</sub>(NH<sub>2</sub>)<sub>3</sub>.


TATB is a bright yellow color. Pure TATB has a bright yellow color.


TATB has been found to remain stable at temperatures at least as high as 250 °C for prolonged periods of time. TATB has been found to remain stable at temperatures at least as high as 250&nbsp;°C for prolonged periods of time.


==Production== ==Production==


TATB is produced by ] of ] to ], then the chlorine atoms are ] with amine groups. TATB is produced by ] of ] to ], then the chlorine atoms are ] with amine groups using ammonolysis.


However, it is likely that the production of TATB will be switched over to a process involving the nitration and ] of ], since this process is milder, cheaper, and reduces the amount of ] salt produced in waste effluents (greener). However, it is likely that the production of TATB will be switched over to a process involving the nitration and ] of ], since this process is milder, cheaper, and reduces the amount of ] salt produced in waste effluents (greener){{citation needed|date=October 2012}}.


Still another process has been found for the production of TATB from materials that are surplus to military use. ] (TMHI) is formed from the rocket fuel ''uns''-dimethylhydrazine (]) and ], and acts as a ] (VNS) ] reagent. When ], which is easily produced from ], is reacted with TMHI it is aminated to TATB. Thus, materials that would have had to have been destroyed when no longer needed are converted into a high value explosive. Still another process has been found for the production of TATB from materials that are surplus to military use. ] (TMHI) is formed from the rocket fuel unsymmetrical dimethylhydrazine (]) and ], and acts as a ] (VNS) ] reagent. When ], which is easily produced from ], is reacted with TMHI it is aminated to TATB.<ref>{{cite tech report|last1=Mitchell |first1=Alexander R.|first2=P. F. |last2=Pagoria|first3=R. D. |last3=Schmidt|title=Conversion of the Rocket Propellant UDMH to a Reagent Useful in Vicarious Nucleophilic Substitution Reactions|url=https://digital.library.unt.edu/ark:/67531/metadc670413/m2/1/high_res_d/226422.pdf|publisher=Lawrence Livermore National Laboratory|number=UCRL-JC-122489|date=10 November 1995|s2cid=54794595}}</ref> Thus, materials that would have to be destroyed when no longer needed are converted into a high value explosive.<ref>{{cite journal|doi=10.1016/S0040-6031(01)00806-1 |title=Advances in the chemical conversion of surplus energetic materials to higher value products |year=2002 |last1=Mitchell |first1=Alexander R. |last2=Coburn |first2=Michael D. |last3=Schmidt |first3=Robert D. |last4=Pagoria |first4=Philip F. |last5=Lee |first5=Gregory S. |journal=Thermochimica Acta |volume=384 |issue=1–2 |pages=205–217 }}</ref>


==See also== ==See also==
*] *]
*] *]
*]


==Notes== ==Notes==
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==References== ==References==
* Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996. ISBN 0-471-18636-8 * Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996. {{ISBN|0-471-18636-8}}
* Michell, Alexander R., et al.; ''Conversion of the Rocket Propellant UDMH to a Reagent Useful in Vicarious Nucleophilic Substitution Reactions''; Lawrence Livermore National Laboratory; UCRL-JC-122489


] ]
] ]
] ]

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Latest revision as of 10:11, 1 November 2024

Not to be confused with TATP, a highly sensitive primary explosive.
TATB
Names
Preferred IUPAC name 2,4,6-Trinitrobenzene-1,3,5-triamine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.362 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6N6O6/c7-1-4(10(13)14)2(8)6(12(17)18)3(9)5(1)11(15)16/h7-9H2Key: JDFUJAMTCCQARF-UHFFFAOYSA-N
  • InChI=1/C6H6N6O6/c7-1-4(10(13)14)2(8)6(12(17)18)3(9)5(1)11(15)16/h7-9H2Key: JDFUJAMTCCQARF-UHFFFAOYAO
SMILES
  • c1(c(c(c(c(c1(=O))N)(=O))N)(=O))N
Properties
Chemical formula C6H6N6O6
Molar mass 258.15 g/mol
Appearance Yellow or brown powdered crystals (rhombohedral)
Density 1.93 g/cm
Melting point 350 °C (662 °F; 623 K)
Explosive data
Shock sensitivity Insensitive
Friction sensitivity Insensitive
Detonation velocity 7350 m/s (at 1.80 g/cm)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an aromatic explosive, based on the basic six-carbon benzene ring structure with three nitro functional groups (NO2) and three amine (NH2) groups attached, alternating around the ring.

TATB is a very powerful explosive (somewhat less powerful than RDX, but more than TNT), but it is extremely insensitive to shock, vibration, fire, or impact. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme safety is required, such as the explosives used in nuclear weapons, where accidental detonation during an airplane crash or rocket misfiring could potentially detonate the fissile core. All British nuclear warheads use TATB-based explosives in their primary stage. According to David Albright, South Africa's nuclear weapons used TATB to increase their safety.

TATB is normally used as the explosive ingredient in plastic bonded explosive compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% HMX). These formulations are described as insensitive high explosives (IHEs) in nuclear weapons literature.

Though it could theoretically be mixed with other explosive compounds in castable mixtures or other use forms, the applications for such forms would be unclear since they would largely undo the insensitivity of pure TATB.

Properties

At a pressed density of 1.80, TATB has a velocity of detonation of 7,350 meters per second.

TATB has a crystal density of 1.93 grams/cm, though most forms currently in use have no higher density than 1.80 grams/cm. TATB melts at 350 °C. The chemical formula for TATB is C6(NO2)3(NH2)3.

Pure TATB has a bright yellow color.

TATB has been found to remain stable at temperatures at least as high as 250 °C for prolonged periods of time.

Production

TATB is produced by nitration of 1,3,5-trichlorobenzene to 1,3,5-trichloro-2,4,6-trinitrobenzene, then the chlorine atoms are substituted with amine groups using ammonolysis.

However, it is likely that the production of TATB will be switched over to a process involving the nitration and transamination of phloroglucinol, since this process is milder, cheaper, and reduces the amount of ammonium chloride salt produced in waste effluents (greener).

Still another process has been found for the production of TATB from materials that are surplus to military use. 1,1,1-trimethylhydrazinium iodide (TMHI) is formed from the rocket fuel unsymmetrical dimethylhydrazine (UDMH) and methyl iodide, and acts as a vicarious nucleophilic substitution (VNS) amination reagent. When picramide, which is easily produced from Explosive D, is reacted with TMHI it is aminated to TATB. Thus, materials that would have to be destroyed when no longer needed are converted into a high value explosive.

See also

Notes

  1. Memorandum from Prospect, UK MOD position statement, 23 January 2006
  2. David Albright (July 1994). "South Africa and the Affordable Bomb". Bulletin of the Atomic Scientists. p. 44.
  3. Mitchell, Alexander R.; Pagoria, P. F.; Schmidt, R. D. (10 November 1995). Conversion of the Rocket Propellant UDMH to a Reagent Useful in Vicarious Nucleophilic Substitution Reactions (PDF) (Technical report). Lawrence Livermore National Laboratory. S2CID 54794595. UCRL-JC-122489.
  4. Mitchell, Alexander R.; Coburn, Michael D.; Schmidt, Robert D.; Pagoria, Philip F.; Lee, Gregory S. (2002). "Advances in the chemical conversion of surplus energetic materials to higher value products". Thermochimica Acta. 384 (1–2): 205–217. doi:10.1016/S0040-6031(01)00806-1.

References

  • Cooper, Paul W., Explosives Engineering, New York: Wiley-VCH, 1996. ISBN 0-471-18636-8
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