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Author: Subject: Substitute solvent for p-aminophenol (instead of EtOEt?)
thors.lab
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[*] posted on 22-12-2019 at 06:35
Substitute solvent for p-aminophenol (instead of EtOEt?)


Hi,

I'm looking at performing this reaction involving the preparation of p-aminophenol from nitrobenzene.

The procedure calls for the use of diethyl ether to extract the product from an aqueous solution, followed by distillation. Is there a cheap substitute for this? I was looking at maybe ethyl acetate, but that stuff is pretty pricey. Pubchem says p-aminophenol is slightly soluble in toluene, but considering it's "practically insoluble in benzene" I'm not sure it would be enough for a good extraction.

As a side note, I was looking to avoid EtOEt because unfortunately, I don't have the equipment to extract EtOEt efficiently from something like car starter fluid. I don't have a very efficient condenser (standard 200mm or 300mm liebig) and my vigreux won't be here on time before I have to go back to my uni dorm. That being said, does anybody think a simple distillation setup with a 200/300mm liebig (can't remember the exact length right now) would be sufficient to recover at least a reasonable amount of ether?

Thanks,

Thor

[Edited on 22-12-2019 by thors.lab]




Please check out my latest video: Synthesizing Nitrobenzene, and the last one:
Making Nitric Acid.
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stephill92
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[*] posted on 22-12-2019 at 06:58


I've found that Walmart (at least for me) sells the highest percent of ether to heptane, and its mostly just those two. I'm sure if you just use a simple distillation setup you'll get a good enough separation but you'll probably want to get more than one can.
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[*] posted on 22-12-2019 at 06:59


Even a short liebig should work provided you use ice cold water and proceed slowly. A long liebig would only allow you to distill the ether faster, it would NOT condense more ether.

You can find ethyl acetate in nail polish remover (distill to purify it if you want).
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[*] posted on 22-12-2019 at 08:12


I have a feeling that the para amino phenol would react with ethyl acetate.The reaction may be too slow to matter, but it's easiest to use ether.

Just a thought; if the material extracts into ether, how well does it extract into the ether/ heptane mixture?
You might be able to do without the distillation
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thors.lab
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[*] posted on 22-12-2019 at 16:00


Quote: Originally posted by unionised  
I have a feeling that the para amino phenol would react with ethyl acetate.The reaction may be too slow to matter, but it's easiest to use ether.

Just a thought; if the material extracts into ether, how well does it extract into the ether/ heptane mixture?
You might be able to do without the distillation


I was wondering this myself. Most likely I don’t think the heptane would affect it too much but I was afraid a significant portion of the EtOEt would covaporize with the propellants and other low boiling compounds when I tried to remove it from the bottle.




Please check out my latest video: Synthesizing Nitrobenzene, and the last one:
Making Nitric Acid.
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S.C. Wack
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[*] posted on 22-12-2019 at 16:07


There is some high boiler in there. I think the heptane would affect solubility a lot because there's a lot of it. It's easy to separate even so given the bp difference.



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