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Author: Subject: Nitration Effeciency at Varying Temps.
Swany
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[*] posted on 21-2-2006 at 18:15
Nitration Effeciency at Varying Temps.


Well, I have found a potential science project. The name basically suggests what it is. I plan on nitrating both a nitric acid ester, and a nitrocompound, and find the yeilds at various tempatures.

Now, what could be bad about this? Free reagents to do some legit reseach. The nitrocompounds and acid esters have to be as insensitive/non-explosive as possible. They should also be relitivively easy to obtain, in order to nitrate, and have definite melting points to determine purity, or other sure ways to find purity.

I will be using HNO3, 70% ideally, though if required I shall use higher, and 98.5% H2SO4. What is the best part about this all? If I can take care of a few problems, its all free. :cool:

And, please do not tell me that someone has already written a book about this? If so, some sources please!

I am happy to bear your comments and critisism.




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The_Davster
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[*] posted on 21-2-2006 at 22:30


I am gathering that this is some sort of school project?
A good nitro compound that is pretty much non-explosive is to make mononitro toluene or mononitrobenzene. There are hundreds of 'optimized' procedures for nitrobenzene in lab manuals from the 60s. These compounds are rather poisonous, but with the schools resources (fumehood) you should be fine.

Off the top of my head I cannot think of a nitric ester that is not explosive, or even just insensitive. The nitric esters of simple alcohols(methyl and ethyl...don't even think of nitrating IPA in the standard way...) are pretty explosive. Perhaps some sugar with only a couple of OH's on it would work decently.

I have a nagging suspicion in my head about a potential difficulty with this project idea, but am unable to articulate it, I may edit this post later.

(And you mean nitrating a compound to a nitro compound and another to a nitric ester right? not "nitrating both a nitric acid ester, and a nitrocompound"...You know as much as you want to try...some stuff just doesent want more nitros on it;):P)




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Chris The Great
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[*] posted on 22-2-2006 at 01:34


I'd go with mononitrotoluene. Urbanski vol 1 has a large amount of info on the yeild against various influences such as temperature, and it is very easy to do. It smells VERY strongly however, it is kinda a nice smell in a way, but very strong and penetrating. I like it, my dad who needed the shop after a synth didn't. The nitrotoluenes are less toxic than those of benzene, which is a big plus if you're doing this at school. Also easier to get toluene than to get benzene, less safety concerns etc.

Methyl is more than "pretty" explosive, it gets 240% of TNT by the plate cutting test. So it's DEFINATELY out, same with the ethyl nitrate. I don't there are any nitric esters that aren't highly explosive and easily accesable.

Personally, it would be better to compare only nitro compounds (no esters) since
1) mono and dinitros are either non-explosive or very insensitive
2) data is more meaningful since it can be compared since the compounds are similar

Also, consider the POINT of it. The POINT of an experiment is a big thing for teachers these days. "It's fun an interesting doesn't cut it" :(
Even if it's a bunch of BS, you'll need it. Make it seem good. It doesn't matter how good your results are, if you don't have a point no judge is going to like it. Also, judges these days are all touchy-feely. Making it cheaper for the army to blow up Jihadiis is probably NOT a good idea.
Think safety and progess when making up your point. Or maybe it will help sciencetists synthesize new drugs because the nitro group is helpful in numerous organic reactions.


I wish my school had science fairs. Then this hobby could net me some extra credit, which would be good since I focus on it and not school.
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Swany
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[*] posted on 22-2-2006 at 06:39


Thanks for the mutual feelings, most of your concerns and thoughts, I thought about... exept MNT.

It does have a point, though the point is mostly known, hopefully the Judges aren't industrial chemists for DuPont. ;) I think it would be neat to see how much the yeilds differ on paper, for such compounds. Plus, I get some pretty graphs in the end, and hopefully some high purity reagents for my own use. Sadly, I will nearly positively have to kill my produced reagents, chemically (and not by sudden decomposition), in the lab, rather than where I would rather get rid of them.

I don't know if I can make myself make MNT with nitric acid.... I suppose I will get over it, and look for some terribly exotic and complex sugar who's explosive properties are virtually unknown. This sounds better than saying 'Yeild Tests Using Nitroglycerine'. :P

Rogue: Yeah, your thoughts in parenthesis are correct.

And, what would you think of using microcrytalline chemically pure cellulose for a potential nitric acid ester? N content is fairly easy to verify...

Also, how would be the best way to determine purity, and purify products? I do not know how effectively recrystallizations will get rid of lower nitrates.

One more thing, what would you think about benzoic acid, for the nitrocompound? It cannot form higher nitrated products with simply HNO3...

[Edited on 22-2-2006 by Swany]




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neutrino
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[*] posted on 22-2-2006 at 18:48


Don't bother with nitrated sucrose, that explosive decomposes very quickly. You wouldn't be able to get a good analysis with that. Other sugars are probably similar, so don’t bother with them.
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[*] posted on 23-2-2006 at 06:31


Picric acid was produced by the nitration of wool and horn, etc. This would be a idea to present the dyestuff industry in a developmental perspective.
Analine from coal tar was nitated to produce a beautiful purple and mauve. Indigo (already a dye of course) has produced the best PA I have ever seen; a classic sunburst yellow. I still have a bunch of Indigo from nitrations of it and wintergreen oil from several months back. Those experiments went very well all in all (were fun too).
---------------> Just a thought....




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