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Author: Subject: Hexanitrobenzene
Zinc
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[*] posted on 15-6-2006 at 12:26
K6C6O6


Quote:
Originally posted by Polverone
If you read old texts (say, Muspratt) about the carbothermic production of potassium you will be informed that this compound is a treacherous explosive.



Does it detonate? If yes what is the VOD? Can it be initiated by a fuse?

[Edited on 16-6-2006 by Zinc]
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franklyn
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[*] posted on 21-6-2010 at 15:35


http://www.sciencemadness.org/talk/viewthread.php?tid=1226#p...

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[*] posted on 22-6-2010 at 08:57


Quote: Originally posted by Polverone  
I don't know exactly what the composition of the explosive material is, given that Muspratt doesn't know and I don't have a good inorganic reference at my current location. I do know that texts on the carbothermic production of potassium warn that the black material you get along with potassium metal when you strongly heat carbon and potassium carbonate together is explosive and should be removed from the metal as soon as possible.



Carbonyl are discussed in Mellor's 16 volume opus. 5:950-62.

And by da .... [Mellor] "The corresponding sodium
carbonyl,Na2C2O2 is obtained in a similar manner as a white
owder with a lilac tint. It detonates at 90o in vacuo, or when
rought in contact with air or water.... When it detonates, very
little gas is evolved, and a small quantity of sodium cyanide is
formed, but the principal reaction is represented by the equation
2NaC2O2 = NaCO3 + Na2O + 3C. "


I own an original copy of Muspratt and to fill in the blanks would quote him.

p. 725
The grey powder is possessed of most powerfully explosive
properties, and if the greatest care not be exercised in removing it
from the apparatus—such as carefully excluding it form the
atmosphere until quite cool, and soaking well in naphtha previous
to attempting its removal — the most dangerous accidents may
occur.
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[*] posted on 22-6-2010 at 09:20


Quote: Originally posted by Polverone  
If you read old texts (say, Muspratt) about the carbothermic production of potassium you will be informed that this compound is a treacherous explosive. Just warning anybody who might be about to (ha!) synthesize it.



Production of potassium from potassium carbonate and charcoal
with calcium carbonate is discussed with sufficient detail in —

ENCYCLOPÆDIA OF CHEMISTRY THEORETICAL, PRACTICAL, AND
ANALYTICAL AS APPLIED TO THE ARTS AND MANUFACTURES.
BY WRITERS OF EMINENCE.
ILLUSTRATED WITH NUMEROUS WOOD-CUTS AND STEEL-PLATE ENGRAVINGS.
VOL. II.
GLASS - ZINC.
PHILADELPHIA:
J. B. LIPPINCOTT & CO.
1879.

I own the 1880 version, you can read/DL yours at/from Google.com/books

http://tinyurl.com/287p7zh

p. 672 Search for Curaudau.
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[*] posted on 22-6-2010 at 09:26


Quote: Originally posted by The WiZard is In  

Production of potassium from potassium carbonate and charcoal
with calcium carbonate is discussed with sufficient detail in —

ENCYCLOPÆDIA OF CHEMISTRY THEORETICAL, PRACTICAL, AND
ANALYTICAL AS APPLIED TO THE ARTS AND MANUFACTURES.
BY WRITERS OF EMINENCE.
ILLUSTRATED WITH NUMEROUS WOOD-CUTS AND STEEL-PLATE ENGRAVINGS.
VOL. II.
GLASS - ZINC.
PHILADELPHIA:
J. B. LIPPINCOTT & CO.
1879.


Noted in passing... This 2-volume American edition is a reprint of
the original 8-volume English edition.
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JohnWW
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[*] posted on 22-6-2010 at 17:53


Quote: Originally posted by The WiZard is In  
Quote: Originally posted by Polverone  
If you read old texts (say, Muspratt) about the carbothermic production of potassium you will be informed that this compound is a treacherous explosive. Just warning anybody who might be about to (ha!) synthesize it.


Production of potassium from potassium carbonate and charcoal with calcium carbonate is discussed with sufficient detail in —
ENCYCLOPÆDIA OF CHEMISTRY THEORETICAL, PRACTICAL, AND
ANALYTICAL AS APPLIED TO THE ARTS AND MANUFACTURES.
BY WRITERS OF EMINENCE.
ILLUSTRATED WITH NUMEROUS WOOD-CUTS AND STEEL-PLATE ENGRAVINGS.
VOL. II. GLASS - ZINC.
PHILADELPHIA: J. B. LIPPINCOTT & CO. 1879.

I own the 1880 version, you can read/DL yours at/from Google.com/books
http://tinyurl.com/287p7zh
p. 672 Search for Curaudau.

It cannot be downloaded, or even read online, from that page, or from any link on it. However, I think Muspratt's volumess may be available from archive.org and elsewhere.
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[*] posted on 22-6-2010 at 17:58


Quote: Originally posted by JohnWW  



ENCYCLOPÆDIA OF CHEMISTRY THEORETICAL, PRACTICAL, AND
ANALYTICAL AS APPLIED TO THE ARTS AND MANUFACTURES.
BY WRITERS OF EMINENCE.
ILLUSTRATED WITH NUMEROUS WOOD-CUTS AND STEEL-PLATE ENGRAVINGS.
VOL. II. GLASS - ZINC.
PHILADELPHIA: J. B. LIPPINCOTT & CO. 1879.

I own the 1880 version, you can read/DL yours at/from Google.com/books
http://tinyurl.com/287p7zh
p. 672 Search for Curaudau.[/rquote]


It cannot be downloaded, or even read online, from that page, or from any link on it. However, I think Muspratt's volumess may be available from archive.org and elsewhere.



Did you as I instructed search for — Curaudau?

On the left side of the page - "Search in this book."

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[*] posted on 23-6-2010 at 19:57


To answer the original question on the post, ICCI might react with a polyvinyl-trimethylammonium nitrite to make a low yield of dinitroacetylene.

--CH2CH(N(+)[CH3]3)---


--CH2CH(N[CH3]2)-- can be turned into the above with a methylating agent such as CH3SO3F methyl fluorosulfonate, which acts as a CH3+ carbenium cation, but methylating agents are highly toxic.

Or possibly (NO2)BrHCCBrH(NO2) and anyhydrous liquid tetramethylammonium hydroxide will make dinitroacetylene, since 2HBr's will be pulled off.

As a sidenote: hexa nitroso (NO) benzene shares resonance states with the trifuroxan.

[Edited on 24-6-2010 by Anders Hoveland]

[Edited on 24-6-2010 by Anders Hoveland]

[Edited on 24-6-2010 by Anders Hoveland]
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[*] posted on 24-6-2010 at 03:26


Quote: Originally posted by Anders Hoveland  
To answer the original question on the post, ICCI might react with a polyvinyl-trimethylammonium nitrite to make a low yield of dinitroacetylene.

--CH2CH(N(+)[CH3]3)---


--CH2CH(N[CH3]2)-- can be turned into the above with a methylating agent such as CH3SO3F methyl fluorosulfonate, which acts as a CH3+ carbenium cation, but methylating agents are highly toxic.

Or possibly (NO2)BrHCCBrH(NO2) and anyhydrous liquid tetramethylammonium hydroxide will make dinitroacetylene, since 2HBr's will be pulled off.

As a sidenote: hexa nitroso (NO) benzene shares resonance states with the trifuroxan.

Maybe the base will be so strong it will exchange one of the NO2 for a OH...this could also occure from the H2O that was set free by the base catching the HBr and forming a salt.
Remember that hexanitrobenzene is very prompt to hydrolisis, amonolysis... because two vicinal NO2 groups separated by a double bond (thus on sp2 carbons) tends to favourise nitro-nitrite rearangement.This effect might be event stronger in the case of tripple bonding (sp) explaining the relative unstability of acetylenic compounds vs ethylenic ones.
O2N-C#C-NO2 <==> O2N-C#C-O-N=O
O2N-C#C-O-N=O + H2O <--==> O2N-C#C-OH + HO-NO
O2N-C#C-OH <==> O2N-CH=C=O
Then it can be very complex because you have so many reactants that can interfere that the course of the reaction is uncertain (H2O, H(+), N=O(+))

You mighte even consider internal oxydoredox like from HNO3, mercury and ethanol that end up with a fulminic acid.
O2N-CH=C=O <==> HO-N=C + CO2



[Edited on 24-6-2010 by PHILOU Zrealone]




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[*] posted on 27-6-2010 at 14:52


I wonder if the nitrosyl NO+ would react with acetylene H2C2 and conserve the triple bond? H2C2 + 2NO(+) --> C2(NO)2 + 2 H(+)
I cannot envison how NO+ would react with a triple bond, as nitric oxide is a reducing agent and the positive charge will not take to a carbon.
Trimerized, this would make hexanitrosobenzene.
Reduced with HSO3- , this would make HONHCCNHOH which would become dinitrosoethylene ONCH=CHNO. This in turn could be further reduced by HSO3- to
dihydroxylaminoethane HONHCH2CH2NHOH. These reductions are not direct hydrogenations of double bonds, but come about through more complex intermediates. Bisulfite will not hydrogenate acetylene, for example.
Somebody correct my chemical name mistakes. What exactly are the correct names for ONCH=CHNO and ONCH2CH2NO ?
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[*] posted on 17-9-2010 at 14:29
Dinitroacetylene from the Diiodo-


Let me refer your attention to the prepublication section:
http://www.sciencemadness.org/talk/viewthread.php?tid=4915#p...

[Edited on 17-9-2010 by Anders2]
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[*] posted on 2-1-2014 at 22:41


Quote: Originally posted by madscientist  

Nitration of 1,4-diaminobenzene in mixed acid. I'm fairly confident the nitration will go all the way to 2,3,5,6-tetranitro-1,4-diaminobenzene. 1,4-diaminobenzene might be prepared by oxidizing xylene to its dicarboxylic acid, then reacting with urea, then reacting with calcium hypochlorite. The 2,3,5,6-tetranitro-1,4-diaminobenzene would then be oxidized to 1,2,3,4,5,6-hexanitrobenzene with Caro's acid.


that compound you mentioned 2,3,5,6-tetranitro-1,4-diaminobenzene sound interesting as a high density insensitive explosive. 1,4-diaminobenzene Do exist, http://en.wikipedia.org/wiki/P-Phenylenediamine
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[*] posted on 7-1-2014 at 03:31


I do know of this method of making HNB, however, I have never tried it, nor know how it works. It is from a (almost certainly) reliable source. It is from a book that details the preparation of several different explosives, but I do not have its title.

Chemicals required:
Methanol - 317 ubw
Ethyl acetate - 45 ubw
TNT - 50 ubw
Sodium hypochlorite (5% solution) - 145 ubw
Sodium hydroxide - 2 ubw

Other materials required:
Heat/acid resistant container
2 acid resistant containers
Heat source
Stirring rod

1. Pour the ethyl acetate into the heat/acid resistant container and then add 250 pbv of methanol.
2. Put the TNT into the benzene/methanol mixture and stir the mixture.
3. Put the heat/acid resistant container on the heat source and heat it to 50oC to completely dissolve the
TNT.
4. Pour the sodium hypochlorite solution into the first acid resistant container, and then add the sodium hy-
roxide. Stir it to dissolve the sodium hydroxide.
5. When the benzene/methanol/TNT mixture reaches 50oC, add the sodium hypochlorite/sodium hydroxide
mixture to it drop-wise, one drop every 10 seconds. Stir the benzene/methanol/TNT mixture and maintain the temperature around 50oC the whole time.
6. Once all the sodium hypochlorite/sodium hydroxide mixture has been added, immediately remove the
heat/acid resistant container from the heat source.
7. Filter off the crystals, and while they are still in the filter paper, pour 75 pbv of methanol over them to
wash them.
8. Pour another 75 pbv of methanol over them to wash them.
9. Pour 500 pbv of COLD water over the crystals 3 times.
10. Let the crystals, which are HNB, air dry.


ALTERNATIVE METHOD OF MANUFACTURE

Chemicals required:
Benzene - 20 pbv
Methanol - 260 pbv
TNT - 20 ubw
Sodium hydroxide - 1 ubw
Sodium hypochlorite solution (5% solution) - 70 pbv

Other materials required:
Heat/acid resistant container
2 acid resistant containers
Heat source
Stirring rod

1. Pour the benzene into the heat/acid resistant container and then add 160 pbv of methanol.
2. Put the TNT into the benzene/methanol mixture and stir the mixture.
3. Put the heat/acid resistant container on the heat source and heat it to 40oC to completely dissolve the
TNT.
4. Pour the sodium hypochlorite solution into the first acid resistant container, and then add the sodium hydroxide. Stir it to dissolve the sodium hydroxide.
5. When the benzene/methanol/TNT mixture reaches 40oC, add the sodium hypochlorite/sodium hydroxide
mixture to it drop-wise, one drop every 5 seconds. Stir the benzene/methanol/TNT mixture and maintain
the temperature at 40oC the whole time.
6. Once all the sodium hypochlorite/sodium hydroxide mixture has been added, continue heating the mix-
ture for 1 hour, stirring every 5 minutes.
7. Remove the heat/acid resistant container from the heat source, and allow the mixture to cool to room
temperature.
8. Filter off the crystals, and while they are still in the filter paper, pour 100 pbv of methanol over them to
wash them.
9. Let the crystals, which are HNB, air dry.




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[*] posted on 10-1-2014 at 08:06


@eidolonicaurum
The preparations mentionned are likely not to work...and obviously from a dubbious source.

This because of the extreme sensitivity of HNB towards moisture and thus dilluted water solutions (and especially strong bases like aqueous NaOH) would all end up with TNPhloroglucidol...




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