hungryman - 1-10-2013 at 08:47
i readed the post about hexanitrobenzene and the synthesis(working?) in wiki but ther is no other more simple way of producing hexanitrobenzene? or
atleast other explosive nitrobenzenes?.
i thought about it when i readed about the "ipso nitration" in the wiki article about nitration that talking about reacting sodium nitrite with
chlorinated hydrocarbons that replace the chlorine atoms with nitro molecules
ipso nitration
the same thing can be done with chlorobenzene's like hexachlorobenzene?
hungryman - 2-10-2013 at 20:36
somebody can tell me if atleast partial nitration of chlorinated benzene can be done by reaction with sodium nitrite?,tell me your opinion if you are
not sure.
I had the same idea
franklyn - 2-10-2013 at 22:23
www.sciencemadness.org/talk/viewthread.php?tid=1226#pid17906...
This is well outside of the box of conventional proceedures
.
Nicodem - 3-10-2013 at 06:01
The nucleophilic aromatic substitution (NAS) of picryl chloride, 2-chloro-1,3-dinitrobenzene, 1-chloro-2,6-dinitro-4-trifluromethylbenzene and some
other nitrochlorobenzenes with NaNO2 in dichloromethane using 18-crown-6 as the PTC catalyst gives the corresponding polynitrobenzenes. At
least according to: Badea, Florin et al., Revue Roumaine de Chimie, 44, 351-356 (2000). Unfortunately, the journal is digitalized only from
2006 onward. So, those interested should either email the authors and request a copy or use the interlibrary exchange.
The nitro group can be a leaving group for NAS reactions, especially if there are nitro groups ortho or para to each other, so it is
unlikely that the substitution could ever go to pernitrobenzene product. In order to make the substitution irreversible, AgNO2 should be
used.
The perchlorination of nitrobenzene is described in SyntheticPage 483 (DOI: 10.1039/SP483).
Should be applicable to benzene, chlorobenzene or para-dichlorobenzene as well.
hungryman - 3-10-2013 at 09:47
it is nice to know that this wasn't just a dumb idea that crossed my mind.
so basicaly..sodium nitrite can react with 1,3,5 trichlorobenzene to make 1,3,5 trinitrobenzene explosive?,and what with the hexanitrobenzene? you
(franklyn) or someone else tried and succeeded/failed to make it from hexachlorobenzene?.
[Edited on 3-10-2013 by hungryman]
killswitch - 3-10-2013 at 14:13
Does the procedure require crown ether? And what solvent would work with silver nitrite?
And of course, there is the tried-and-true method of NAS with ammonia to 1,3,5-triamino-2,4,6-trichlorobenzene, then oxidation of the amines to nitro
groups with sulfuric acid and hydrogen peroxide, then NAS of the chlorine with ammonia, then oxidation of the new amines to nitro groups with sulfuric
acid and hydrogen peroxide.
DubaiAmateurRocketry - 5-10-2013 at 00:38
what about hexaazidobenzene ?