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Rhodanide
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[*] posted on 18-12-2017 at 06:22
Aniline Nitrate


Hi all, last night I thought I'd try making Aniline Nitrate by addition of Aniline to concentrated HNO3. My Aniline is a few months old, and therefore orange. Upon addition of Aniline to a roughly 50% solution of HNO3 in water, I was left with a clear solution, and no crystals like I was expecting. I added roughly 10mLs of WFNA to the solution, which formed an intermediate, blue oxidized Aniline compound. Upon addition of 2 more mLs of Aniline, I got a nice thick crop of red crystals, which I vacuum filtered. According to the synthesis, I should have just gotten colorless Aniline Nitrate when the two initial reactants were combined. Instead, I had to modify the synth to get any precipitate. Also, why is my precipitate red? A strongly-colored byproduct?
I'm a bit confused.
Thanks,
-R/T

P.S. I got the synthesis from the PrepChem synthesis of Diazobenzene Nitrate.

[Edited on 18-12-2017 by Tetra]




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PirateDocBrown
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[*] posted on 18-12-2017 at 06:33


Never add aniline to any sort of nitric acid. You are lucky you didn't blow yourself up.

Your dilution and the possible degradation of your reagent are likely the only things that saved you.

Aniline and WFNA are hypergolic, and detonate on contact.



Attachment: Chemical_Incompatibilities.pdf (484kB)
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[Edited on 12/18/17 by PirateDocBrown]
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Rhodanide
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[*] posted on 18-12-2017 at 10:01


Quote: Originally posted by PirateDocBrown  
Never add aniline to any sort of nitric acid. You are lucky you didn't blow yourself up.

Your dilution and the possible degradation of your reagent are likely the only things that saved you.

Aniline and WFNA are hypergolic, and detonate on contact.





[Edited on 12/18/17 by PirateDocBrown]



I don't ever plan on trying that. However, my Nitric acid was 50% at first, so the WFNA only added to that. I didn't START with WFNA.




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[*] posted on 18-12-2017 at 10:18


I remember one of our Organic chem lecturers explaining that, if you want to nitrate aniline you need to acetylate it first ( or something). His comment was that without that first step you either got a fire, or "road mending material."
I doubt aniline forms a stable nitrate (and I'm using a pretty loose definition of "stable")
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[*] posted on 19-12-2017 at 06:19


Quote: Originally posted by unionised  
I remember one of our Organic chem lecturers explaining that, if you want to nitrate aniline you need to acetylate it first ( or something). His comment was that without that first step you either got a fire, or "road mending material."
I doubt aniline forms a stable nitrate (and I'm using a pretty loose definition of "stable")


Bitumen: Now with Aniline Nitrate!
But really, when they say that in the synthesis that you're supposed to get a white precipitate, are they just taking the piss or is it actually possible?




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[*] posted on 19-12-2017 at 08:55


You have fuming nitric acid? So try nitration of dimethylanaline instead. Tetryl is more fun.

Tetryl from Dimethylanaline video

You put fuming nitric acid and analine in the same container and DID NOT intend to start a fire?

Download this from the Library here and READ IT before you lose your eyebrows.

Ignition! An Informal History of Rocket Propellants

http://library.sciencemadness.org/library/index.html

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The Chemistry of Powder and Explosives




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[*] posted on 19-12-2017 at 10:06


Quote: Originally posted by Bert  
You have fuming nitric acid? So try nitration of dimethylanaline instead. Tetryl is more fun.

Tetryl from Dimethylanaline video

You put fuming nitric acid and analine in the same container and DID NOT intend to start a fire?

Download this from the Library here and READ IT before you lose your eyebrows.

Ignition! An Informal History of Rocket Propellants

http://library.sciencemadness.org/library/index.html

While you are about it, download this too:

The Chemistry of Powder and Explosives


I do not have Dimethylaniline.
As for the WFNA, I don't see what all the confusion is about.

Firstly, I DID NOT start with pure WFNA. Aniline was added to FIFTY PERCENT (50%) Nitric acid. ONLY AFTER, was a small splash of WFNA added to the solution of Aniline Nitrate, to increase the acid concentration. After that, there was only slight exotherm, but no more than adding NaOH to water.

Hope this clears things up, and no, I know damn well enough not to add a fuel, an Amine even, to WFNA. I don't have a death wish, hahaha.




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[*] posted on 19-12-2017 at 13:22


Quote:
I do not have Dimethylaniline. 


You have analine. Do you have methanol and sulfuric acid?

Quote:
As for the WFNA, I don't see what all the confusion is about.


Most of us saw the words fuming nitric acid and analine in the same procedure and assumed your lab would look like this?

Which nitroanaline were you trying to synthesize?




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[*] posted on 22-12-2017 at 21:54


Quote: Originally posted by Bert  
Quote:
I do not have Dimethylaniline. 


You have analine. Do you have methanol and sulfuric acid?

Quote:
As for the WFNA, I don't see what all the confusion is about.


Most of us saw the words fuming nitric acid and analine in the same procedure and assumed your lab would look like this?

Which nitroanaline were you trying to synthesize?


I love that video.
Anyways, I was going off of this procedure: http://www.prepchem.com/synthesis-diazobenzene-nitrate/
I do have those things. Didn't know that was all which was required. Huh.




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[*] posted on 22-12-2017 at 22:44


There's a slight confusion here. You are trying to make aniline nitrate the salt (PhNH3+NO3-), not to nitrate aniline.

The reason why you did not observe any product is very likely down to solubility. Aniline surely gets protonated, it's just that the solubility limit of aniline nitrate was not reached and the salt did not crash out. Actually aniline nitrate is very soluble in water! Cool the solution down and see if you get any crystallization, if not, increase the aniline concentration. Do not try to evaporate the solution to dryness, heating a mixture like this can easily lead to a severe runaway. I would also go for a smaller scale just in case.

[Edited on 23-12-2017 by kavu]
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[*] posted on 23-12-2017 at 08:33


May I ask why you are interested in aniline nitrate, I do find some references to this in older books on dye chemistry.





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[*] posted on 23-12-2017 at 09:48


It should be possible to make it
"The crystals of anilinium nitrate, C6H8N+·NO3−, were obtained by slow evaporation of an aqueous solution. "
https://www.researchgate.net/publication/233851807_Structura...
but I doubt it's very stable.
This is interesting (and quite pretty)
shodhganga.inflibnet.ac.in/bitstream/10603/86766/17/17_chapter%208.pdf
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[*] posted on 23-12-2017 at 10:16


I think that rather than using nitric acid, salt metathesis of aniline sulfate with calcium nitrate should prevent redox and nitration reactions even at high concentration.



[Edited on 04-20-1969 by clearly_not_atara]
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