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Author: Subject: Synthesis of thioacetone?
panajotovicn
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[*] posted on 1-1-2018 at 14:27
Synthesis of thioacetone?


Hi,
I was just wondering if it would be possible to synthesise C3H6S (thioacetone) form acetone and hydrogen sulfide under catalyst - aluminium chloride?
Yes/no? And, any other way?
Thanks.

[Edited on 1-1-2018 by panajotovicn]
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[*] posted on 1-1-2018 at 17:49


However Wikipedia supports your theory, I didn't find any workup treating about reacting acetone, H2S and AlCl3.

There are a few methods to produce thioacetone that can be found on Google. An interesting way is reacting acetone with PSCl3 and Triethylamine using water as a solvent and microwave radiation:

Thioacetone.jpg - 19kB

But while I was researching about Alprazolam synthesis, I found a preparation described at a Patent that covers the substitution step of the oxigen molecule of a ketone for sulfur, using phosphorus pentasulfide in an easier workup way:

Sulfur replacement of Ketones with P4S10.jpg - 143kB

I hope it helps!





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j_sum1
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[*] posted on 1-1-2018 at 18:13


Don't do it man!
http://blogs.sciencemag.org/pipeline/archives/2009/06/11/thi...
Quote:
“Recently we found ourselves with an odour problem beyond our worst expectations. During early experiments, a stopper jumped from a bottle of residues, and, although replaced at once, resulted in an immediate complaint of nausea and sickness from colleagues working in a building two hundred yards away. Two of our chemists who had done no more than investigate the cracking of minute amounts of trithioacetone found themselves the object of hostile stares in a restaurant and suffered the humiliation of having a waitress spray the area around them with a deodorant. The odours defied the expected effects of dilution since workers in the laboratory did not find the odours intolerable … and genuinely denied responsibility since they were working in closed systems. To convince them otherwise, they were dispersed with other observers around the laboratory, at distances up to a quarter of a mile, and one drop of either acetone gem-dithiol or the mother liquors from crude trithioacetone crystallisations were placed on a watch glass in a fume cupboard. The odour was detected downwind in seconds.”




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clearly_not_atara
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[*] posted on 1-1-2018 at 23:21


As far as I know this molecule defeats all known containment procedures; there is no reported way of producing thioacetone without causing severe discomfort to everyone in a kilometer radius. So this is one of the worst syntheses you could attempt: it cannot succeed by any reasonable measure of "success".



[Edited on 04-20-1969 by clearly_not_atara]
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Radium212
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[*] posted on 2-1-2018 at 03:00


Yeah, I'd avoid thioacetone. Have you heard of the Freiburg incident, where an entire block of the city had to be evacuated due to the stench from some accidentally produced in a soap factory. If you're making some kind of stinkbomb maybe just use cadaverine or putrescine.
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[*] posted on 2-1-2018 at 03:48


I agree with the other members of this Forum that said it's a horrible stink chemical reagent.

But I think my duty here is just analyse the chemical reactions and the ways to do that with the better yields and in an OTC manner. Who knows if you're intending to make exactly thioacetone or another thioketone?

People here often ask for a synthesis or a product that's not always is the real target of their questions. I'm used to see that, here, in this Forum.

If you want to know how to substitute the oxigen molecule of a ketone by sulfur, the way is follow the directions I've given. But If you really just want to produce thioacetone to do a revenge against your enemies, like a skunk does, you're on the right way:D

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PirateDocBrown
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[*] posted on 2-1-2018 at 09:58


For a stink bomb, it'd be best to have a device that can make it in situ, like from two reactants that combine with each other.
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[*] posted on 2-1-2018 at 14:21


I suggest doing it microchemistry style in an ampoule. Seeing as it's a stink bomb you're not looking for something pure, just disgusting.
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[*] posted on 3-1-2018 at 11:54


I suggest using cadaverine or putrescine for a stink bomb.
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Tellurium
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[*] posted on 9-1-2018 at 04:02


You can use Acetone with some HCl and bubble H2S gas into this mixture. This will produce the trimer: Trithioacetone.
I already done this and even the trimer stinks terrible when concentrated, got a tiny drop of the liquid onto my hand and even days later people were complaining about the smell.:D But please don't try to crack the Trithioacetone to thioacetone - that stuff is far far worse!:o
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[*] posted on 9-1-2018 at 07:26


If you're looking for something stinky or strange smelling, I'd suggest going with Phenyl Isocyanide. Its toxicity is very low, and the synthesis is very simple. It requires the following:
An Erlenmeyer flask
Equal amounts of both Aniline and Chloroform
Ethanol + Water in a 80/20 or 90/10 ratio (the less water the better, but enough to enable the reaction)
and finally, a smaller amount of Sodium Hydroxide (the amount depends on how much Aniline and Chloroform you use)
Dissolve the Aniline in the EtOH/H2O solvent, and dissolve the Sodium Hydroxide in to this. Add the Chloroform all at once, and stir to dissolve. Put a thermometer in the flask, make a hole for the thermometer in some Saran wrap, and seal the top of the flask with it. Heat-seal the wrap with a hairdryer or Heat gun on low heat. Gently warm the mixture to between 20-26 C for half an hour. You could distill the PhNC off under vacuum if you wanted to, just make sure your ventilation system is top of the line, or you live way out there, like me. It's nauseatingly pungent, and in the words of some, described as "highly specific, almost overpowering', 'horrible', and 'extremely distressing" (this was the description of other, more volatile Isocyanides, but this goes for Phenyl as well).




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James Nilep
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[*] posted on 9-1-2018 at 08:34


I have attempted the H2S Acetone method before using a hydrochloric acid catalyst with a large excess of acetone on a relatively small scale, but it didn’t seem to yield any trithioacetone, just a smelly solution of H2S, although I did not attempt to crack the trimer, after all I didn’t want the whole neighborhood to potentially vomit simultaneously
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[*] posted on 9-1-2018 at 12:34


Every time I've made H2S, it's been by accident. I'm not sure how one might make it deliberately. However, the accidental syntheses have typically involved dissolving metal reduction of sulfate, or the reaction of metal with sulfur and subsequent acid hydrolysis. It's kind of hard to tell how much is being produced though, just because it stinks a similar amount no matter how much or how little is produced.



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