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APO
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Nitration with Anhydrous Copper Nitrate
I want to anhydrous copper nitrate to replace nitric acid for the following reactions:
Isopropyl Nitrate
Pentaerythritol Tetranitrate
Tetrahexamine Tetranitramine
If I use the equivilant amount of anhydrous copper nitrate instead of nitric acid, will it work?
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Motherload
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It probably would if you used it H2SO4 to make a nitrating mix.
Which essentially means you have HNO3 in there to Nitrate.
Why wouldn't you just use NaNO3 or KNO3 ?
Mixed acids won't work to form Nitramines.
"Chance favours the prepared mind"
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APO
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I was told that anhydrous copper nitrate is a strong enough nitrating agent, it can replace nitric acid.
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virgilius1979
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I had a similar idea, but using AgNO3 to replace halogens with NO3- groups in some halo-alkanes, and AgX precipitating. (x=halogen).
Is it possible to react 1,1-2,2 tetrachloroetylene with AgNO3 ? or other similar product ? what solvent is best suited for this ?
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Motherload
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Well reacting AgNO3 with organic halides is not nitration. It's a double displacement.
The only reason it works is cause the ppt...ing AgCl drives the reaction forward.
And it doesn't work in every instance.
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DraconicAcid
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Quote: Originally posted by virgilius1979  | I had a similar idea, but using AgNO3 to replace halogens with NO3- groups in some halo-alkanes, and AgX precipitating. (x=halogen).
Is it possible to react 1,1-2,2 tetrachloroetylene with AgNO3 ? or other similar product ? what solvent is best suited for this ?
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Nitrate's not a very good nucleophile, and haloalkenes are not generally subject to nucleophilic attack. It *might* work with a different haloalkane,
but you've need a fairly polar solvent to dissolve the silver nitrate, and it would have to be a solvent that wasn't nucleophilic (if you used water
or an alcohol, you'd end up with an alcohol or ether forming). Acetone *might* work, but you'd have to make sure it's completely dry.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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virgilius1979
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Ok guys, thanks for explaining !
I could reflux acetone with Ca metal to dehydrate it, i guess. I'm not sure how to extract the water which could be bound to AgNO3: does normal
dessicatants work ?
I 'm thinking that using AgClO4 to make organic perchlorate is even more difficult to achieve. Sorry for the off topic.
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APO
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Anyways, can I run my nitrations with anhydrous copper nitrate to replace nitric acid?
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Motherload
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To the best of my knowledge .... A salt can't replace an acid.
But if you feel so inclined .... Try nitrating Pentaerythritol.
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APO
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Hmm... Is there a concentration of nitric acid that won't burn skin?
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Motherload
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70% will turn skin yellow instantaneously !
Never touched WFNA. And I don't plan on either.
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AndersHoveland
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Generally that is correct, but there are numerous exceptions. Urea and guanidine being the most obvious. The condensation product between acetamide
and formaldehyde can also be nitrated with mixed acids. Even for hexamine, it is not entirely impossible for it to undergo a mixed acid nitration,
although the product is a lesser nitramine compound:
http://www.sciencemadness.org/talk/viewthread.php?tid=19103
| Quote: Originally posted by virgilius1979 | | Is it possible to react 1,1-2,2 tetrachloroetylene with AgNO3 ? or other similar product ? what solvent is best suited for this ?
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Again, the answer to this question is not a clear yes or no. The rate of reaction for the displacement of chlorine from organic compounds is generally
too negligible to be practical. Bromine or iodine atoms displace off much more easily. Indeed, bromomethane has been used as a fumigrant because of
its poisonous alkylating properties.
Putting two nitrate groups on the same carbon is not practical. Methylene dinitrate, for example, is not even stable at room temperature. You would
not get any useful product from your proposed reaction, or variant thereof. If you want to know exactly what would form, I am not entirely sure but I
would guess they would include various byproducts such as oxalic acid, carbon monoxide, carbon dioxide, dichloroacetic acid.
There are quite a few different reasons your proposed reaction has no hope of producing anything useful. It is a complex subject, and I am not going
to thoroughly go into all the details. I think it has been adequately covered in various other threads in this forum.
If you get concentrated nitric acid burns, they should be immediately be rinsed with water, but then afterwards the skin should be repeatedly rubbed
with a piece of cotton soaked in bleach, until most of the yellow discoloration has been washed off. Otherwise the nitrated proteins will act as
allergens and hinder the healing process.
Nitric acid below around 12% concentration generally does not have oxidizing properties. There is actually no clear point where it is no longer an
oxidizer, but a lower concentrations the oxidizing reaction rate decreases exponentially. At much lower concentrations nitric acid will essentially
behave like any other strong acid. 2% nitric acid failed to dissolve a piece of copper foil after 24 hours. You could probably dip your hand in 2%
nitric acid if you quickly rinsed it off with plenty of water afterwards.
Be sure to wear long gloves when pouring 70% nitric acid. Even when one is very careful, there are always little micro droplets that splash upwards.
Likely you will not see any splashing, but you can feel the tiny droplets when they get on your skin.
I think acetone might condense into a resin in the presence of a strong base.
[Edited on 19-2-2013 by AndersHoveland]
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Motherload
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I know about urea and guanidine.
But the question wasn't about them.
It was about a hexamine type derivative.
Tetraminetetramine.
[Edited on 19-2-2013 by Motherload]
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APO
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If I have a respirator, goggles, gloves, a lab coat, and a solution of sodium bicarbonate on hand, will that be enough safety to work with 70% or
white fuming nitric acid? Also are there any gloves that are invunerable to nitric acid?
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APO
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Also I'm gonna ask my teacher if any nitrate salt can be used to run a nitration.
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AndersHoveland
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I doubt he would know. This specific subject is not really a basic area in chemistry.
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bahamuth
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| Quote: Originally posted by AndersHoveland |
If you get concentrated nitric acid burns, they should be immediately be rinsed with water, but then afterwards the skin should be repeatedly rubbed
with a piece of cotton soaked in bleach, until most of the yellow discoloration has been washed off. Otherwise the nitrated proteins will act as
allergens and hinder the healing process. |
Hmm, I find that nitrated skin works like a very good "band aid" until new bright pink skin forms underneath the burn until the yellow patch of
nitrated skin easily sheds by itself. But then again I'd never had really large patches of skin nitrated..
Any sufficiently advanced technology is indistinguishable from magic.
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KonkreteRocketry
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Or maybe like this..
Thermal decomp of Cu(NO3)2(H2O)3.
Get 3 H2O, 4 NO2, 1 O2, and 2CuO.
Collect the gas, the NO2 and O2.
Collect the CuO left over.
Pass the NO2 and O2 gas into a glass of distilled water.
NO2 + H2O = HNO3.
Put CuO into HNO3.
Get Anhydrous copper nitrate 
NO2 + H2O Get HNO3.
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AndersHoveland
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Putting CuO into HNO3 will not make anyhydrous copper nitrate.
CuO + 2 HNO3 --> Cu(NO3)2 · H2O
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Motherload
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CuO + N2O4 should work or 2X NO2
I don't know how vigorously the reaction would take place. Probably try it with a 100 mg of CuO with lots of cooling to keep the N2O4 liquid as I am
certain the reaction will be exothermic and will need lots of ventilation.
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DraconicAcid
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Not to mention that the nitric acid itself is rarely anhydrous (the concentrated stuff we use in the lab is 70% nitric acid, the rest water).
Cite: Aldrich Catalogue, 2012-2014, p 1901-1902.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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KonkreteRocketry
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| Quote: Originally posted by DraconicAcid |
Not to mention that the nitric acid itself is rarely anhydrous (the concentrated stuff we use in the lab is 70% nitric acid, the rest water).
Cite: Aldrich Catalogue, 2012-2014, p 1901-1902. |
Uummmm ok, but pure HNO3 does give Anhydrous Cu(NO3)2 right ?
Copper, silver compounds have a lot of reactions :p
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DraconicAcid
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Probably not, because one of the products of the reaction is water. Whether or not anhydrous nitric acid would be sufficiently hygroscopic to absorb
that water is beyond me, but I have my doubts that your plans of passing NO2 through a glass of distilled water will give you the anhydrous result you
crave.
[Edited on 22-2-2013 by DraconicAcid]
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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plante1999
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Here is my unscusceful try at making anhydrous copper nitrate. I also tested liquid nitrogen oxide dissolution in conc. nitric acid, as a preparation
for my Ostwald reactor project.
Here is my set-up at making liquid nitrogen oxides. I used a snow/ conc. HCl mixture to make the cooling bath, it dropped to -40 Celsius. The NOx
generator contain copper, 40% HNO3 and is quite cold at -5 degree Celsius. As you can see I now have ground glass!
Here is the liquid NOx:
Just after adding the copper, but it didn't reacted:
Because it didn't reacted, I dessided to test nitrogen oxide solubility, I added 1 ml of 70%+ nitric acid to the liquid NOx, you can see the nitric
acid in the round bottom flask next to the beaker:
And this is my extremly concentrated nitric acid and the copper piece (I only have one ground glass stopper, and it was used for the nitric acid):
I may re-try this, but using gaseous NOx on hot copper.
I never asked for this.
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DraconicAcid
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Cool (or cold). The intense blue of the NOx is presumably due to N2O3, which Cotton and Wilkinson assured me was blue (NO2 being red-brown and N2O4
being colourless). I made it once by holding a chunk of dry ice over some copper reacting with nitric acid- it was soon covered in a blue frost.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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