shivam
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A lot of leftover Aniline
Hey guys,
I have seen here a thousand procedures and interesting reactions through which aniline can be synthesized. Well, I already have a liter of lab grade
aniline left from a small diazotization reaction that i wanted to run.
So are there any other uses of it? Please list any synthesis that involves USING UP the aniline, rather than making it...
I'll appreciate any help..
Thanks..
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woelen
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It can be used to make nitrobenzene, which has interesting optic properties:
https://en.wikipedia.org/wiki/Kerr_effect
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deltaH
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Make polyaniline, fascinating conductive polymeric material: https://en.wikipedia.org/wiki/Polyaniline
Make indophenol dyes with it's oxidative coupling to phenol.
Make Nigrosin, a pitch black dye used to make ink: https://en.wikipedia.org/wiki/Nigrosin
You'd need to prepare woelen's suggested nitrobenzene for that, but also use aniline and aniline hydrochloride, looks like a perfect
way to use it up and you can sell the ink afterwards 
[Edited on 26-11-2015 by deltaH]
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morsagh
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Very nice is identification of furfural, if you don´t have any just heat up wood with 12% HCl. Just mix acetic acid, furfural and aniline and you
should get nice violet colour. If you try, take a photo please.
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Magpie
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Make chlorobenzene via a Sandmeyer reaction.
Diazotize and make phenol.
The single most important condition for a successful synthesis is good mixing - Nicodem
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karlos³
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Make phenylhydrazine and use it to do a fischer indole synthesis maybe?
Or is that the diazotization reaction you´ve did?
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shivam
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Diazotization was for having a go at making some phenol.
Making phenylhydrazine sounds cool, i guess i can synthesize skattol by Fischer indole synthesis.
On the other hand, how's this for a synthesis :
Aniline -> precipitating tribromo aniline by bromine water -> diazotization and hydrolysis to get tribromo phenol -> reaction with oxalyl
chloride to get Bis(2,4,6 tribromophenol) oxalate
Theoretically, should TBPO work instead of TCPO [ Bis(2,4,56 trichlorophenol) oxalate ] for chemiluminescence??
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karlos³
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Yes it would work.
That is a very nice experiment and makes a lot of fun.
Here´s a reference for using tribromophenyloxalate: http://www.google.com/patents/US20080185562
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morsagh
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It is easier to produce tribromophenol than tribromoaniline so it is better to do sandmeyer first and than just mix phenol with bromine water, you´ll
get better yelds
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shivam
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Yeah! Sounds good.
If it works with bromine water, then IMO, bubbling chlorine gas in an acidified phenol solution should suffice for making trichlorophenol. Does it
work that way, or not??
I think it shouldn't need any catalyst, although, adding a few crystals of FeCl3would be nice. just in case merely bubbling chlorine isn't
enough.
Any views on that??
[Edited on 28-11-2015 by shivam]
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morsagh
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It should work without FeCl3. And on the other hand I don´t find FeCl3 as effective catalyst in water solution
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