Mr.O-Nitrate
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nitrating
What makes a substance a cannidate for nitrating?(with HNO3 and H2SO4)
What about wood carbon? could that be nitrated?
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Mr.O-Nitrate
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OH
Can you nitrate somthing without the OH group?
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DDTea
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To answer the second question first, a substance does not require a Hydroxy group to be nitrated. The best example I can think of is Toluene, which as
you know, can be nitrated to Mono-, Di-, an Trinitrotoluene.
Another example is the formation of 1,1,2,2-Tetrachloro-1,2-Dinitroethane by reacting 1,1,2,2-Tetrachloroethene with N2O5 (look these molecules up on
Chemfinder.com, if you have to, to get an idea of their structures). No, it's not straight Nitric Acid, but the effect is the same in that it is
a Nitration. This molecule does not contain a Hydroxy group either.
I imagine that any substance (save for those that are very unreactive, e.g. Noble gases), can have a Nitro- group thrown onto it. Hell, any molecule
you can imagine, in theory, can be made. The big question, particularly as it relates to explosives, is safety (of course, we can't forget other
things like practicality, availability of precursors, etc.).
But, good question-- what DOES make a substance a good candidate to be nitrated?? Were explosives made by first imagining a final, super-energetic
compound, and THEN trying to synthesize it? Or by nitrating whatever was around, and seeing what happened? My guess is, probably a little bit of both,
considering many advancements in the area of explosives were made in the 19th century-- a time when most chemists were wealthy amateurs with time to
spare. And, as we all know, the amateur is a adventurous and creative  .
In this respect, I'm sure the various Cellulose molecules or other Carbon compounds in wood could, in fact, be nitrated. It may not involve the
straight forward H2SO4/HNO3 route, but it most certainly could be done, should an adventurous amateur be willing to do it.
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The_Davster
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A while ago i read that sawdust could be nitrated to nitrocellulose (i think it was in "the blasters training manual" . i think, that when sawdust is nitrated, you would get a finer more powdery product
than in the nitration of cotton balls or TP due to it not being in strand form before the nitration. Has anyone tried this or has the knowledge to
shoot my little theory down
 
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JDP
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Yep.
I have nitrated sawdust befor with moderately good results. The nitrated product burned alot like Nitro-Starch, but Nitro sawdust seems to burn much
hotter. It does produse a nice fine product. Not to mention that saw dust is vertually free.
[Edited on 30-11-2003 by JDP]
~JDP
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Mr.O-Nitrate
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cool
I just might try that.
As for the wood carbon, I dont think I will try that unless it has been tryed and synthized.
But, If nobodys made it before then you just created an all new explosive!
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guaguanco
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If a compound is prone to electrophilic substitution, it's a good candidate. It's the
NO2+ cation that is the active agent. So a compound like phenol (with relatively high electron density at the 2,4,6 positions) is easily nitrated to
form picric acid, whereas something like the pyridinum ion (pyridine in acid solution) requires more forcing conditions. Since nitric acid is also a
good oxidizer, it can also remove labile hydrogen atoms on things like acetic anhydride to ultimately form tetranitromethane.
Since nitrate esters are relatively stable, almost any compound with unhindered -OH groups is a candidate, although you get competing oxidation
reactions that can get very violent if you don't control the temperature.
[Edited on 2-12-2003 by guaguanco]
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KABOOOM(pyrojustforfun)
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generally, wood consists of:
67-80% holocellulose: it's the entire water-insoluble carbohydrate fraction of wood which is composed of alpha-cellulose and hemicelluloseand
other hexosan and pentosan polymers. these all are good candidates for nitration.
17-18% lignin: a phenylpropene polymer of amorphous structure. may form polynitroaromatic compounds. if the c-c bond tears, various explosives can
form including picric acid (atleast I know TNP is one of the nitration products of wood)
low percentages of resines (carboxylic acids, essential oils ... not interesting at all), terpenes (runaway reactions?), aldehydes (are oxidysed to
corresponding carboxylic acids liberating NO<sub>x</sub> which may cause runaway reactions) sugars (form explosive nitric esters),ketones
(form weak explosives. IIRC these are unstable) water (obviously degrades the mixed acid), inorganic materials eg potassium compounds (don't
have serious effects on nitration)
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