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Author: Subject: Aniline
benzal
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[*] posted on 24-8-2008 at 13:25
Aniline


Hi All, ive been reading the boards for quite a while and this is a great forum.

Does anyone has any experience preparing aniline by destructive distillation of Indogo. Indigo can be had cheaply from many places online no questions asked, its a dye, and it should be a very simple process, much more than going through nitrobenzene. Just heat condense the vapour and redistill. Im waiting on some new glassware at the moment (dont ask) so anyone tried it?

It seems there are no other posts on this topic and aniline can be a very useful chemical and if its that easy...... What do you all think?
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Sauron
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[*] posted on 24-8-2008 at 15:21


You have trouble buying aniline?

Why?

And if so, how are you gpomg tp use such aniline as you might obtain from indigo? Because if you can't buy aniline you can't buy LOTS of things.

All seems rather illogical to me.

[Edited on 25-8-2008 by Sauron]




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[*] posted on 24-8-2008 at 15:30


Maybe it has to do with the fact that Anilne can be an expensive compound to ship due to it being a self pack and a packing group II in the USA. Usually it goes out in its own poison pack box and costs $$$ just for shipping. Aniline is a useful chemical but with the days of Mom and Pop chemistry stores behind us, picking up reagent chemicals, at least here in the US can be a daunting task.



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[*] posted on 24-8-2008 at 16:01


Quote:
Just heat condense the vapour and redistill. Im waiting on some new glassware at the moment (dont ask) so anyone tried it?


The references say it works better heating together with KOH.
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[*] posted on 24-8-2008 at 16:29


Sauron, its just another synth to get a decent chemical like Benzene or sodium or something. The reason I posted is because of the seeming simplicity of the reaction and also in some countries you cant order ANYTHING without owning a business, so yeah I cant get LOTS of things lol, but Indigo dye is available from many online craft stores. Shockwave, I wanted to include that but forgot. Destructive distillation would be so easy though, you could use the same apparatus as used to produce Benzene from Benzoic acid. (excuse my spelling)
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[*] posted on 24-8-2008 at 19:26


A lot of these old reactions that refer to the preparation of aniline by the destructive distillation of indigo etc ignore the yield and the clean up required.
A lot of these reactions were important as they proved a structural relationship between say indigo and aniline.
Before spectroscopy, structural determination of organic compounds was an incredibly difficult task so this stuff really did matter.
If yoiu want to make aniline from OTC materials today then the sodium benzoate -> benzene -> nitrobenzene -> aniline route is the way to go.
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[*] posted on 24-8-2008 at 20:14


Not only are the yields likely to be low, with a number of other products, but I think you may find that the dye is not pure but rather diluted with an inert substance.

Another route is benzoic acid => benzamide => aniline (via Hoffmann rearrangement)
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[*] posted on 24-8-2008 at 20:17


Once more I am grateful not to be residing in the good old US of A where such idiocy prevails.



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[*] posted on 7-9-2008 at 20:48


Hmmmm. Seems to me that acetanilide can probably be shipped without a problem. It's a solid and it's much less toxic than aniline.

Is it still a non-prescription pain killer? You might be able to buy some OTC at your local drugstore. No muss, no fuss, just hydrolyse it, and then treat it with caution. Aniline as the free amine is reported to be pretty poisonous, so I wouldn't try using it as suntan oil.

How much aniline do you actually need?

Whoops, I'm noticing how long ago your post was, and about now....I'm concluding that you probably don't need it anymore.

Oh well, it's all grist for the mill.

[Edited on 7-9-2008 by zed]
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