Sciencemadness Discussion Board

aniline hydrochloride -->aniline

DrRoboto - 21-8-2011 at 17:04

Hi all, I just acquired some aniline hydrochloride, I am in need of some aniline, I would like to know how to generate it from the former chemical.

Thanks,

Dr. Roboto

[Edited on 22-8-2011 by DrRoboto]

redox - 21-8-2011 at 17:25

Add a stoichimetric amount of a strong base.

C6H5NH3Cl + NaOH ---> C6H5NH2 + NaCl + H20

Add 40 grams of sodium hydroxide to 129 grams of anilinium chloride in water. Decant off the organic layer of aniline, and enjoy!

Best regards,
Redox

[Edited on 22-8-2011 by redox]

ThatchemistKid - 22-8-2011 at 08:45

Aniline is pretty toxic, what exactly are you using it for? If you do not know how to free Aniline from its hydrochloride salt, what are you about to try to do with the aniline?

DrRoboto - 23-8-2011 at 15:55

I already tried what redox suggested before asking, it just appears that I have a very contaminated batch because it is very old and the above rxn did not work. Anyway, what's a sunset for? What's a rainbow for? What's the positrac on a '73 Plymouth for?

redox - 23-8-2011 at 15:57

Quote: Originally posted by DrRoboto  
I already tried what redox suggested before asking, it just appears that I have a very contaminated batch because it is very old and the above rxn did not work. Anyway, what's a sunset for? What's a rainbow for? What's the positrac on a '73 Plymouth for?


I'm not sure what you mean with those hypothetical questions, but what happened when you added the base? Did you observe any change?

Bot0nist - 23-8-2011 at 19:42

Joe Dirt...?
Don't cancerize your mullet man.

DrRoboto - 23-8-2011 at 20:27

Quote: Originally posted by redox  
Quote: Originally posted by DrRoboto  
I already tried what redox suggested before asking, it just appears that I have a very contaminated batch because it is very old and the above rxn did not work. Anyway, what's a sunset for? What's a rainbow for? What's the positrac on a '73 Plymouth for?


I'm not sure what you mean with those hypothetical questions, but what happened when you added the base? Did you observe any change?


Well, the Aniline HCl was very dark, apparently it was very old and therefore impure. It came from a Sergent Welch bottle that was VERY old. The material did not even dissolve completely in a generous quantity of distilled water, so I disposed of it.

TerryFlamingo - 23-8-2011 at 21:19

Did you make any attempt to purify or reduce the contamination of the sample you had prior to disposal?

DrRoboto - 23-8-2011 at 22:09

Quote: Originally posted by TerryFlamingo  
Did you make any attempt to purify or reduce the contamination of the sample you had prior to disposal?

Nope, since there was no way to do that reliably. I didn't want to be working with mystery substances.

drago57 - 23-8-2011 at 22:49

I've worked a fair bit with aniline for my project. It does go very dark brown, even opaque black if it's been kicking around for a long time. But it cleans up very nicely, you'll recover most of your original volume if you vacuum distill it from a little CaH2. Takes 3-4 months for the brown colour to begin to return unless you do things like store it in the fridge under Ar.

DrRoboto - 24-8-2011 at 11:15

Quote: Originally posted by drago57  
I've worked a fair bit with aniline for my project. It does go very dark brown, even opaque black if it's been kicking around for a long time. But it cleans up very nicely, you'll recover most of your original volume if you vacuum distill it from a little CaH2. Takes 3-4 months for the brown colour to begin to return unless you do things like store it in the fridge under Ar.

What I meant was, The aniline HCl (not aniline) consists of dark greenish black crystals (sources say it should be white to white with greenish tint). These crystals only seem to be partly soluble in a generous volume of water.