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Author: Subject: Toluene to Aniline path
low.safety.standards
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[*] posted on 17-7-2018 at 05:53
Toluene to Aniline path


Hi guys,

New to the forum wanted to ask some input. I'm making hypergolic rocket fuel from Aniline and RFNA. The RFNA was made from Sulfuric Acid and Sodium Nitrate, I'm now moving to find a path from Toluene to Aniline. My idea so far is as follows.

1 - Oxidizing Toluene with Potassium Permanganate to get Benzoic Acid
2 - Neutralize Benzoic Acid with Sodium Hydroxide to get Sodium Benzoate
3 - Distill the Benzene from molten Sodium Benzoate and Sodium Hydroxide ('Organikum's Process')
4 - Nitrate the Benzene to get Nitrobenzene
5 - Reduce Nitrobenzene with Sn and HCl to get the Aniline.

This is the simplest path I found in terms of easy-to-find reagents.

Any inputs? Also, any idea of how much % I could mix aniline with another fuel and still have the hypergolic reaction?
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DavidJR
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[*] posted on 17-7-2018 at 07:01


Sodium benzoate is already readily available and very cheap (it's used as a preservative in food).



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CobaltChloride
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[*] posted on 17-7-2018 at 07:54


As DavidJR said, sodium benzoate is really easy to get. It can be found at supermarkets as a preservative. For a method of converting this to anilline without going through the toxic intermediate of benzene and doing the messy decarboxylation, check this thread out http://www.sciencemadness.org/talk/viewthread.php?tid=4201
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myristicinaldehyde
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[*] posted on 17-7-2018 at 08:30


If you want to use aniline for further reactions, and it is not an end-goal, a much easier route is purchasing acetanilide here and then deprotecting it.



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Loptr
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[*] posted on 17-7-2018 at 12:39


There is a route to aniline using benzoic acid, nitromethane, and polyphosphoric acid.

I know this paper mentions it, but I can't remember if its the one I have in mind.

https://pubs.acs.org/doi/abs/10.1021/jo01032a020?journalCode...




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[*] posted on 17-7-2018 at 13:52


The intermediate Benzotrichloride to get Benzoyl chloride from Toluene, which I think it's done by bubbling Cl2 under UV in Toluene, is super toxic, right? :/
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JJay
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[*] posted on 17-7-2018 at 14:02


It's not that toxic or nasty compared to chlorine gas or benzyl chloride, but it's fairly nasty and probably a carcinogen... definitely not something you want to breathe.



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[*] posted on 17-7-2018 at 14:13


Oh well, I might just try it when I get my fumehood.
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[*] posted on 21-7-2018 at 17:51


Tbh it would be easiest to just buy aniline, but you can als heat benzoic acid with urea to make benzamide, then do a Hoffman degradation.
https://en.wikipedia.org/wiki/Hofmann_rearrangement
https://smvideo.djr.pw/watch/141/synthesis-of-anthranilic-ac...
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[*] posted on 21-9-2018 at 12:03


Quote: Originally posted by TGSpecialist1  
Tbh it would be easiest to just buy aniline


That's what I ended up doing
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