shivam
Harmless
Posts: 28
Registered: 26-10-2015
Location: GJ, India
Member Is Offline
Mood: Curious
|
|
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..
|
|
|
woelen
Super Administrator
Posts: 8014
Registered: 20-8-2005
Location: Netherlands
Member Is Offline
Mood: interested
|
|
It can be used to make nitrobenzene, which has interesting optic properties:
https://en.wikipedia.org/wiki/Kerr_effect
|
|
|
deltaH
Dangerous source of unreferenced speculation
Posts: 1663
Registered: 30-9-2013
Location: South Africa
Member Is Offline
Mood: Heavily protonated
|
|
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]
|
|
|
morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
Magpie
lab constructor
Posts: 5939
Registered: 1-11-2003
Location: USA
Member Is Offline
Mood: Chemistry: the subtle science.
|
|
Make chlorobenzene via a Sandmeyer reaction.
Diazotize and make phenol.
The single most important condition for a successful synthesis is good mixing - Nicodem
|
|
|
karlos³
International Hazard
Posts: 1520
Registered: 10-1-2011
Location: yes!
Member Is Offline
Mood: oxazolidinic 8)
|
|
Make phenylhydrazine and use it to do a fischer indole synthesis maybe?
Or is that the diazotization reaction you´ve did?
|
|
|
shivam
Harmless
Posts: 28
Registered: 26-10-2015
Location: GJ, India
Member Is Offline
Mood: Curious
|
|
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??
|
|
|
karlos³
International Hazard
Posts: 1520
Registered: 10-1-2011
Location: yes!
Member Is Offline
Mood: oxazolidinic 8)
|
|
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
|
|
|
morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
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
|
|
|
shivam
Harmless
Posts: 28
Registered: 26-10-2015
Location: GJ, India
Member Is Offline
Mood: Curious
|
|
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]
|
|
|
morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
It should work without FeCl3. And on the other hand I don´t find FeCl3 as effective catalyst in water solution
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
