numos - 9-3-2014 at 16:53
I have a feeling this question has been asked here before because it seems like a common occurrence, but I tried some keywords and did not find any
similarities.
I did a standard chloroform preparation as I had done many times before, adding 2.5ml of acetone to 100ml of 8.0% bleach, then separating the lower
layer.
I don't know what went wrong today, I think I added the acetone too quickly, as the solution did heat up, not hot, just warm as it was in an ice bath.
However as I placed in the sep funnel, I didn't get a clear layer, it was brown, I'm keeping it in a different vial for now. I know that it does not
smell like chloroform, some traces maybe, but it smells like acetone.
So was it the heat that caused it? What is this substance now?
Oscilllator - 9-3-2014 at 17:08
I don't know what the substance is, but I can tell you it probably wasn't the heat that caused it. I have made chloroform by this method in a RBF with
a condensor, and the solution heated up enough it started refluxing. The chloroform was perfectly clear.
Did your bleach have additives such as perfume? If so, its possible you just conducted a chloroform extraction of said perfume, and this is what is
colouring your chloroform.
numos - 9-3-2014 at 17:52
This might be it, this was a new bottle of bleach that I opened, same brand, same concentration, different Lot #...
Bleach company needs to get they consistency up to date. -.-
BromicAcid - 9-3-2014 at 18:21
There are all sorts of impurities in chloroform produced this way. Distill it, problem solved.
TheChemiKid - 10-3-2014 at 07:13
Yes, I had discolored chloroform once. After distillation, it was a clear liquid.
Tsjerk - 10-3-2014 at 09:39
It is more common to get impurities than not to have them in oxidative environments
numos - 12-3-2014 at 19:41
Ok, so I found out what the problem was... it was the first time I used a DIY overhead stirrer, and the "rod" I used was made of a mystery plastic,
upon examination I found that the submerged part had become quite corroded. It was a small amount of chloroform, so I figured I'd just make a new
batch.
Anyways... I've conveniently encountered a different problem...
If you look at the picture I've uploaded you can see two layers. Both are "chloroform" synthesized the same way through the haloform
reaction.
The top layer I made a few weeks ago and the bottom I made today. When I added today's batch to the bottle they separated! Apart from these three
reactions I have never seen, made, smelled, or used any chloroform so I'm having an identification problem.
I'll describe both layers. The top layer was made a while ago, smells very sweet and good even, but has no effect when sniffed. It is also somewhat
cloudy. The bottom layer smells kind of like acetone but it's unique enough for me to know it isn't acetone, it does, however bring that stingy
[cooling] sensation you get when you inhale. This layer is clear, and made me go major woozy when inhaled.
So I'm think the bottom layer is the chloroform but Wikipedia describes chloroform as "sweet-smelling" and the bottom layer is definitely not sweet
when the top one is. Maybe my sense of smell is off...?
I'm still feeling woozy, so please excuse the grammar and word choice.
Edit: I didn't realize this is a different topic, sorry 
, feel free to move it if
necessary.
[Edited on 3-13-2014 by numos]
woelen - 12-3-2014 at 23:31
The bottom layer must be chloroform. Chloroform is a very dense liquid, it will sink to the bottom. However, the chloroform most likely will be very
impure.
The top layer probably mostly is water, with some chloroform in it (chloroform is quite soluble in water). Any acetone impurity will go into the
bottom chloroform layer and this can explain why the top layer smells less of acetone than the bottom layer.
Acetone and chloroform can react further at high pH to chlorobutanol, a compound with formula CH3CH(OH)(CCl3)CH3, which can make you feel very drowsy
(it is a known sleeping agent and is still used in some travelling pills to alleviate the symptoms of travelling sickness). This compound has a lovely
smell and gives a strong sense of cooling of your throat. I once made this in the pure form and I found it very attractive to sniff this compound. I
was feeling drowsy at that time as well.