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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 414583242
| Watchedfields = changed
⚫ | ImageFileL1 =Hexanitrodiphenylamine.png
⚫ | verifiedrevid = 426898825
| ImageSizeL1 =120px
| ImageFileR1=Hexanitrodiphenylamine-3D-balls.png | ImageFile1 = Hexanitrodiphenylamine.svg
⚫ | ImageFile2 = Hexanitrodiphenylamine-3D-balls.png
| ImageSizeR1=120px
| IUPACName = 2,4,6-Trinitro-''N''-(2,4,6-trinitrophenyl)aniline | PIN = 2,4,6-Trinitro-''N''-(2,4,6-trinitrophenyl)aniline
| OtherNames = HNDA; HNDPA; Dipicrylamine; Hexamine; hexil; hexyl; hexite; hexamin; GE - Hexa; IT - Esanitro difenilamina | OtherNames = bis(2,4,6-Trinitrophenyl)amine<br />HNDA<br />HNDPA<br />Dipicrylamine<br />Hexamine<br />Hexil<br />Hexyl<br />Hexite<br />Hexamin
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 131-73-7 | CASNo = 131-73-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 14STR4KG8T
| EINECS = 205-037-8
| PubChem = 8576 | PubChem = 8576
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8258
| SMILES = C1=C(C=C(C(=C1(=O))NC2=C(C=C(C=C2(=O))(=O))(=O))(=O))(=O) | SMILES = C1=C(C=C(C(=C1(=O))NC2=C(C=C(C=C2(=O))(=O))(=O))(=O))(=O)
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H5N7O12/c20-14(21)5-1-7(16(24)25)11(8(2-5)17(26)27)13-12-9(18(28)29)3-6(15(22)23)4-10(12)19(30)31/h1-4,13H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CBCIHIVRDWLAME-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=12|H=5|N=7|O=12 | C=12 | H=5 | N=7 | O=12
| Appearance = Crystalline solid. Yellow to orange. As ordinarily manufactured, it is yellow brown. | Appearance = Crystalline solid. Yellow to orange. As ordinarily manufactured, it is yellow brown.
| Density = 1.64 g/cm<sup>3</sup> (pressed) | Density = 1.64 g/cm<sup>3</sup> (pressed)
| MeltingPt = 469° to 473° F (243° to 245° C) with decomposition. | MeltingPtF = 469 to 473
| MeltingPt_notes = with decomposition
| BoilingPt = | BoilingPt =
| Solubility = Soluble in acetone, warm glacial acetic acid, nitric acid, or aqueous alkalies except potassium hydroxide.}} | Solubility = Soluble in acetone, warm glacial acetic acid, nitric acid, or aqueous alkalies except potassium hydroxide.}}

⚫ | ExplosiveV = 7100 m/s
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
|Section4={{Chembox Explosive
⚫ | DetonationV = 7100 m/s
}}
}} }}


'''Hexanitrodiphenylamine''' (abbreviated HND), is an explosive chemical compound with the formula C<sub>12</sub>H<sub>5</sub>N<sub>7</sub>O<sub>12</sub>. HND was used extensively by the Japanese during ] but was discontinued due to its toxicity. '''Hexanitrodiphenylamine''' (abbreviated HND), is an explosive chemical compound with the formula C<sub>12</sub>H<sub>5</sub>N<sub>7</sub>O<sub>12</sub>. Since it is made from readily available raw materials, HND was used extensively by the ] and less extensively by Nazi Germany during ] but was discontinued due to its toxicity.


==Preparation== ==Preparation==
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==Applications== ==Applications==
HND is a booster-class explosive that was used in ] by the Germans as a component of ] (60% TNT - 40% HND) and by the Japanese as a component of Kongo (Type 98 H<sub>2</sub>) (60% Trinitroanisol - 40% HND) for use in bombs, sea mines and depth charges; Seigate (Type 97 H) (60% TNT - 40% HND) for use in torpedo warheads and depth charges; and also in Otsu-B (60% TNT, 24% HND & 16% aluminium powder) for use in torpedo warheads. HND is a booster-class explosive that was used in ] by the ] as a component of ] (60% TNT - 40% HND) and by the Japanese as a component of Kongo (Type 98 H<sub>2</sub>) (60% ] - 40% HND) for use in bombs, sea mines and depth charges; Seigate (Type 97 H) (60% TNT - 40% HND) for use in torpedo warheads and depth charges; and also in Otsu-B (60% TNT, 24% HND & 16% aluminium powder) for use in torpedo warheads.


Its ammonium salt, also known as '''Aurantia''' or '''Imperial Yellow''', was discovered in 1873 by ] and used as a yellow colorant for leather, wool and silk in the 19th and early 20th centuries<ref></ref>. Its ammonium salt, also known as '''Aurantia''' or '''Imperial Yellow''', was discovered in 1873 by ] and used as a yellow colorant for leather, wool and silk in the 19th and early 20th centuries.<ref></ref>


==Safety and toxicity== ==Safety and toxicity==
A most toxic and poisonous explosive, it attacks the skin, causing blisters which resemble burns. Dust from HND is injurious to the mucous membranes of the mouth, nose, and lungs. A most toxic and poisonous explosive, it attacks the skin, causing blisters which resemble burns. Dust from HND is injurious to the mucous membranes of the mouth, nose, and lungs. Several ] explosives, including HND, have been found to be ].<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/11817|title=2,4,6-Trinitroanisole - Non-Human Toxicity Excerpts|last=PubChem|date=|website=pubchem.ncbi.nlm.nih.gov|language=en|archive-url=|archive-date=|access-date=2019-09-14}}</ref>

==Incidents==
On 12 May 2022, construction of the ] in Germany was halted, after traces of the explosive were found in the excavated material. The road passes over a former explosives factory near ]. The factory had been demolished after World War II, and it was not expected that traces of explosives had remained in the ground.<ref>{{Cite news|url=https://www.hessenschau.de/panorama/sprengstoff-stopp-an-a49-baustelle,a49-baustelle-sprengstoff-fund-hexyl-100.html|title="Hexyl" im Erdaushub: Sprengstoff-Stopp an A49-Baustelle|website=hessenschau.de|language=de|date=13 May 2022|access-date=13 May 2022|archive-date=13 May 2022|archive-url=https://web.archive.org/web/20220513000015/https://www.hessenschau.de/panorama/sprengstoff-stopp-an-a49-baustelle%2Ca49-baustelle-sprengstoff-fund-hexyl-100.html|url-status=dead}}</ref>


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


== References == ==References==
* {{cite book |title=TM 9-1985-4 Japanese Explosive Ordnance (Bombs, Bomb fuzes, Land mines, Grenades, Firing Devices and Sabotage Devices) |publisher= Departments of the Army and Air Force |year=1953 |month=March }} *{{cite book |title=TM 9-1985-4 Japanese Explosive Ordnance (Bombs, Bomb fuzes, Land mines, Grenades, Firing Devices and Sabotage Devices) |publisher= Departments of the Army and Air Force |date=March 1953 }}
* {{cite book |title=TM 9-1985-5 Japanese Explosive Ordnance (Army Ammunition, Navy Ammunition) |publisher= Departments of the Army and Air Force |year=1953 |month=March }} *{{cite book |title=TM 9-1985-5 Japanese Explosive Ordnance (Army Ammunition, Navy Ammunition) |publisher= Departments of the Army and Air Force |date=March 1953 }}
* {{cite report|title=Japanese Explosives (USNTMJ-200E-0551-0578 Report 0-25) |publisher= U.S. Naval Technical Mission to Japan |year=1945 |month=December }} *{{cite report|title=Japanese Explosives (USNTMJ-200E-0551-0578 Report 0-25) |publisher= U.S. Naval Technical Mission to Japan |date=December 1945 }}
<references/> <references />


] ]
] ]
] ]

]
]

Latest revision as of 13:08, 6 August 2024

Hexanitrodiphenylamine
Names
Preferred IUPAC name 2,4,6-Trinitro-N-(2,4,6-trinitrophenyl)aniline
Other names bis(2,4,6-Trinitrophenyl)amine
HNDA
HNDPA
Dipicrylamine
Hexamine
Hexil
Hexyl
Hexite
Hexamin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.581 Edit this at Wikidata
EC Number
  • 205-037-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H5N7O12/c20-14(21)5-1-7(16(24)25)11(8(2-5)17(26)27)13-12-9(18(28)29)3-6(15(22)23)4-10(12)19(30)31/h1-4,13HKey: CBCIHIVRDWLAME-UHFFFAOYSA-N
SMILES
  • C1=C(C=C(C(=C1(=O))NC2=C(C=C(C=C2(=O))(=O))(=O))(=O))(=O)
Properties
Chemical formula C12H5N7O12
Molar mass 439.209 g·mol
Appearance Crystalline solid. Yellow to orange. As ordinarily manufactured, it is yellow brown.
Density 1.64 g/cm (pressed)
Melting point 243 to 245 °C; 469 to 473 °F; 516 to 518 K with decomposition
Solubility in water Soluble in acetone, warm glacial acetic acid, nitric acid, or aqueous alkalies except potassium hydroxide.
Explosive data
Detonation velocity 7100 m/s
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

Hexanitrodiphenylamine (abbreviated HND), is an explosive chemical compound with the formula C12H5N7O12. Since it is made from readily available raw materials, HND was used extensively by the Japanese and less extensively by Nazi Germany during World War II but was discontinued due to its toxicity.

Preparation

Dinitrodiphenylamine is treated with 98% nitric acid. The starting material, dinitrodiphenylamine, is obtained from the reaction of aniline, dinitrochlorobenzene, and soda ash.

Applications

HND is a booster-class explosive that was used in World War II by the Germans as a component of Hexanite (60% TNT - 40% HND) and by the Japanese as a component of Kongo (Type 98 H2) (60% Trinitroanisole - 40% HND) for use in bombs, sea mines and depth charges; Seigate (Type 97 H) (60% TNT - 40% HND) for use in torpedo warheads and depth charges; and also in Otsu-B (60% TNT, 24% HND & 16% aluminium powder) for use in torpedo warheads.

Its ammonium salt, also known as Aurantia or Imperial Yellow, was discovered in 1873 by Emil Kopp and used as a yellow colorant for leather, wool and silk in the 19th and early 20th centuries.

Safety and toxicity

A most toxic and poisonous explosive, it attacks the skin, causing blisters which resemble burns. Dust from HND is injurious to the mucous membranes of the mouth, nose, and lungs. Several nitroaromatic explosives, including HND, have been found to be mutagens.

Incidents

On 12 May 2022, construction of the Bundesautobahn 49 in Germany was halted, after traces of the explosive were found in the excavated material. The road passes over a former explosives factory near Stadtallendorf. The factory had been demolished after World War II, and it was not expected that traces of explosives had remained in the ground.

See also

References

  • TM 9-1985-4 Japanese Explosive Ordnance (Bombs, Bomb fuzes, Land mines, Grenades, Firing Devices and Sabotage Devices). Departments of the Army and Air Force. March 1953.
  • TM 9-1985-5 Japanese Explosive Ordnance (Army Ammunition, Navy Ammunition). Departments of the Army and Air Force. March 1953.
  • Japanese Explosives (USNTMJ-200E-0551-0578 Report 0-25) (Report). U.S. Naval Technical Mission to Japan. December 1945.
  1. Science & Society Picture Library: Synthetic colorant, c 1900
  2. PubChem. "2,4,6-Trinitroanisole - Non-Human Toxicity Excerpts". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-09-14.
  3. ""Hexyl" im Erdaushub: Sprengstoff-Stopp an A49-Baustelle". hessenschau.de (in German). 13 May 2022. Archived from the original on 13 May 2022. Retrieved 13 May 2022.
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