mayko
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Odd sulfurous substances...
A couple months ago, I made a solution of sulfur in aqueous sodium hydroxide as an anodizing solution. I was doing some qualitative experiments with
it, and noticed that when acetone was added, a green immiscible layer formed. Several small washes of acetone were made, then pipetted off and
combined. This concentrated version was red, but when diluted became green, then light blue.
This sounds like some sort of polysulfide perhaps? I don't think it's cloudy enough to be a colloid, but the very dilute light blue looks a bit like
suspended sulfur.
The second observation came from many years ago when I was a kid with a basement lab and some ether. As I remember it, mixing sulfur, ether, and
ammonia would produce a red, smelly liquid which I tentatively identified as ammonium polysulfide. Embarassingly, I just finished failing to reproduce
this result with engine starter spray.
If you have any idea what is going on in either case, or can confirm/deny the second observation, I'm quite curious 
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AndersHoveland
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Sulfur can actually be dissolved in basic solution to form thiosulfate and sulfides/polysulfides.
I am not sure, but it might be possible the sulfur is somehow oxidizing the acetone through its tautomer. Bromine, for example, will spontaneously
slowly react with acetone after a few minutes to form bromoacetone.
I'm not saying let's go kill all the stupid people...I'm just saying lets remove all the warning labels and let the problem sort itself out.
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Random
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I guess thioacetone wasnt formed since they evacuated the town after some lab produced it..
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mayko
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I hadn't heard about that, but apparently yeah, it's pretty stinky:
http://pipeline.corante.com/archives/2009/06/11/things_i_wont_work_with_thioacetone.php
The acetone-based substance has a definite smell, definitely sulfurous, reminds me of propane/natural gas additive. It's pretty faint though, wouldn't
make a good stink bomb let alone clear a town
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AndersHoveland
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Here is something else to consider. Iodine can react with acetone to form iodoacetone. But sulfur is actually a stronger oxidizer than elemental
iodine, at least in the absence of water.
For example, when heated in a sealed tube, iodine did not react with hydrogen sulfide, and similarly sulfur was able to oxidize anhydrous hydrogen
iodide.
http://www.sciencemadness.org/talk/viewthread.php?tid=17604
So if iodine can react with acetone, there is good reason to believe that sulfur can oxidize acetone also, although it would probably require a little
acid to catalyze the tautomerization of the acetone for the reaction to proceed.
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Random
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Who knows maybe thioacetone bad smell is exaggerated among chemists, but one thing is true, it is one of worse things you could make for your
neighbours.
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Adas
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I've just made that green thing today, it smells like a thiol (so I assume it is a thiol), but the smell is very mild compared to other thiols. I
assume that it can be acetone thiol - CH3-C(O)-CH2-SH or something similar.
In the picture, you can clearly see the layer with Na-polysulfides and a chunk of unreacted sulfur, the upper layer is acetone with that green thing
dissolved in it. When I tried to ozonize these 2 phases, the upper one got evaporated completely, and only the aqueous layer remained.
Rest In Pieces!
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woelen
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Interesting stuff. Do thiols really have such strong colors? I have no personal experience with them, but I thought they were colorless liquids or
white solids.
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Adas
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Quote: Originally posted by woelen  | | Interesting stuff. Do thiols really have such strong colors? I have no personal experience with them, but I thought they were colorless liquids or
white solids. |
This may be an exception, it may be caused by both carbonyl and thiol groups near eachother interacting somehow. The green solution even looks like a
suspension sometimes, but, as I said, this stuff is volatile and evaporates together with acetone. Green color is quite spectacular in this type of
reactions, IMO.
Rest In Pieces!
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blogfast25
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| Quote: Originally posted by woelen | | Do thiols really have such strong colors? I have no personal experience with them, but I thought they were colorless liquids or white solids.
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They're also known as mercaptans. Ring a bell?
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DraconicAcid
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There's a picture of methanethiol in the "pretty pictures" thread; it's perfectly colourless. I've worked with thiophenol, which was also colourless
(but not odourless).
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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blogfast25
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I actually misread 'color' for odour. Says something about how our minds work, I think...
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woelen
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The human brains
is a funny thing. I indeed was talking about color. I know of the strong odour of this kind of compounds.
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