Adas
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I made a thiol in my garden
Hello guys! Today I was trying to make thioacetone (bad idea, I know) but I made a thiol instead. 
I think that this experiment might be of some interest, since it is very easy to do in your own garden. Anybody can make thiols this way.
Here's what I did:
1. I prepared a test tube with acetone + HCl
2. I tried to light up a mixture of Al + S, but I failed. Even though, I dropped it into the test tube where the Al was slowly reacting with the HCl
(and thus probably reducing the acetone?)
3. I made another Al + S mixture and lit it up with KNO3 + sugar.
4. I divided the product into smaller pieces to fit in the test tube.
5. I put them in the test tube and heated with lighter.
6. I was heating the test tube periodically.
7. At first, only H2S was coming off, but after some time, I realised that there was no more H2S, but rather a thiol smell.
8. After some more time, there was absolutely no H2S.
I think that I made quite a lot of it. I even gassed my house with it a little bit, so I had to get rid of it.
What are your thoughts?
I think that at first, the acetone has been reduced and then the IPA reacted with H2S, HCl was a catalyst.
Thanks for your time.
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Nicodem
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Thread Moved
6-3-2013 at 07:13 |
SM2
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Try replacing your carbonyl (acetone) with a simple alcohol, methanol. If your hypothesis is correct, you will end up with a gas smelling like it
came directly out of tony sopranos ass. Careful, these thiols/mercaptans are highly toxic. Best of luck!
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Adas
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What the... :O I wasn't careful at all with it... What are the symptoms of poisoning? I didn't notice anything...
EDIT: "At very high concentrations it is highly toxic and affects the central nervous system." - Very high concentrations would be too unpleasant so I
assume I am OK.
[Edited on 6-3-2013 by Adas]
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Adas
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Phosphorus sulphide and thiol preparation
Hello guys.
My red P (and other chems) finally arrived from Poland. It is not bad quality.
This is good news for all of you that have red P and want to make some thiols.
Experiment:
I put some P into a test tube, then some sulfur. I heated it above a candle in order to make P4S10. When some of the mixture
melted, there were some *pops* of flame coming out of the red P, but nothing spectacular. After this, the heat of the reaction melted all the sulfur,
then it solidified and the reaction was complete. I heated the bottom of the test tube again to make sure it all reacted, but I just saw some tiny
bubbles so I stopped it.
Next, I dropped one drop of acetone in the test tube, just to see if it makes any thioacetone, but I only observed a thiolic smell (maybe iPr-SH), as
in my previous experiment.
Then I dropped in a few drops of ethanol. Immediately, ethane thiol was created.
I believe that the reaction is: P4S10 + 10 Et-OH -----> P4O10 + 10 Et-SH
I hope that I brought something positive to you by this experiment.
I got the idea from Wikipedia.
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Nicodem
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According to what kind of characterization?
| Quote: | | I believe that the reaction is: P4S10 + 10 Et-OH -----> P4O10 + 10 Et-SH |
That reaction does not make much sense. What kind of a mechanism would allow for such an outcome? What is the reference?
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Adas
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| Quote: | Due to hydrolysis by atmospheric moisture, P4S10 evolves H2S, thus P4S10 is associated with a rotten egg odour. Aside from H2S, hydrolysis of P4S10
gives phosphoric acid:
P4S10 + 16 H2O → 4 H3PO4 + 10 H2S
Other mild nucleophiles react with P4S10, including alcohols and amines. |
| Quote: | | In organic chemistry P4S10 is used as a thionation reagent. |
All from the wikipedia article. Please read the reference more carefully the next time.
Thanks.
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bfesser
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 Show some respect. <strong>Nicodem</strong> is not responsible for the poor quality of and lack of
meaningful citation in your post. Wikipedia is <em>never</em> to be used as a primary source (coming from me, that's saying <em>a
lot</em> .
Just because the Wikipedia article makes a claim, doesn't mean your experiment follows said claim. What conclusive (not smell) evidence do you have
that the expected reaction took place and produced the desired product? Also, don't flood the forum with multiple topics on the same subject.
[Edited on 7/12/13 by bfesser]
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bfesser
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Threads Merged
12-7-2013 at 08:28 |
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Interesting...I love me some smelly molecules  .
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Adas
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I didn't mean to say anything disrecpectful, sorry. I wasn't able find any better refference. But for your question: "What conclusive (not smell)
evidence do you have that the expected reaction took place and produced the desired product?" - What else could it be? Ethanol has got only ONE
reactive group (-OH). I know what thiols smell like. It couldn't be anything else. If yes, please correct me.
To my experiment: After letting it stand for a while, I poured in some H2O2, the solution turned milky with oil floating on the top (according to Wiki, the oil was diethyl disulfide). After some time, however, the hydrogen peroxide started reacting with the unreacted phosphorus and all the
thiol has been boiled out of the solution, while the oil was still present. It smelled like rotten cabbage or similar. Definitely different from the
thiol.
<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: removed
unnecessary quote(s)]
[Edited on 7/12/13 by bfesser]
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bfesser
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A good starting place is the list of <a href="http://en.wikipedia.org/wiki/Phosphorus_pentasulfide#References"
target="_blank">references</a> <img src="../scipics/_wiki.png" /> at the bottom of <em>every</em> Wikipedia article.
<a href="http://en.wikipedia.org/wiki/Methanethiol" target="_blank">Methanethiol</a> <img src="../scipics/_wiki.png" /> smells like
rotten cabbage.
<a href="http://en.wikipedia.org/wiki/Ethanethiol#Odor" target="_blank">Ethanethiol</a> <img src="../scipics/_wiki.png" /> has been
described as smelling like " leeks, onions or cooked cabbage, but is quite distinct."
[Edited on 7/12/13 by bfesser]
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Nicodem
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It was because I read that more carefully than you, that I asked you for the reference. There is nothing in that Wikipedia entry that supports your
claims about the reaction equation that you gave above. It says that P4S10 can be used as a thionation reagent. You say that
your attempt at the thionation reaction failed (did you even follow a published procedure at all?). Then you say that it reacted with the ethanol
trough an unreferenced reaction that seems anything but likely. I'm not saying that some small amount of ethanthiol can't form by the reaction of
P4S10 with ethanol under proper reaction conditions, but I can't see how that could be the main product under conditions you
applied, and even much less how this could ever occur trough such an unlikely reaction as you claimed.
| Quote: | | Other mild nucleophiles react with P4S10, including alcohols and amines. |
Where does it say it forms ethanthiol with ethanol?
| Quote: | | I wasn't able find any better refference. But for your question: "What conclusive (not smell) evidence do you have that the expected reaction took
place and produced the desired product?" - What else could it be? |
This is a science forum. You can't come here and insult us with such anti-scientific declarations like: "What else could it be?". The scientific
method is not some sort of masturbation! Leave the wishful thinking for the more appropriate fantasies.
| Quote: | | To my experiment: After letting it stand for a while, I poured in some H2O2, the solution turned milky with oil floating on the top (according to
Wiki, the oil was diethyl disulfide). |
Again you are blatantly abusing and manipulating Wikipedia. It says nothing about your "oil floating on the top" being diethyl disulfide. Start using
proper references, not some secondary sources, and use them correctly. Don't make up claims that are not there.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Adas
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So maybe I didn't understand the Wiki articles well enough?
What if somebody came with a new discovery, but couldn't find any references just because it was new? I was just trying to share my
experiments and experiences.
Some people post reactions that are absolutely wrong without reference, and even they do not receive such critics as I do. I don't understand this..
I am trying to use my knowledge and logics in figuring out my reactions, not just blind references, but I am starting to think that this forum just
requires the references. I am trying to do things in different ways as other people do, and you are criticising it. Sorry for using my brain and
creativity too much.
[Edited on 12-7-2013 by Adas]
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Nicodem
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Maybe you should make an effort and read the articles where there is actual support for claims and ideas. Relying on secondary literature is naive,
particularly such fragmented reviews like those on Wikipedia. Wikipedia reviews are useful for pursuing knowledge because you can follow the
references given there, but they are not useful as source of knowledge itself.
| Quote: | | What if somebody came with a new discovery, but couldn't find any references just because it was new? I was just trying to share my
experiments and experiences. |
Well, that is easy. First you need to prove that you came up with a discovery, which means you need to find a whole lot of references on the topic.
Next, chemistry is an experimental science which means that its most authoritative scientific reference is the experimental. This is why primary
literature needs to include the experimental data in order to classify as such.
The experimental is a detailed description of the experiment that includes the exact procedure written in such a way to be easily reproduced by a
person skilled in the art. This must then be followed by all the required evidence in support of any conclusion. In practice this evidence most
commonly consists of the characterization data (analytical data, derivatizations data, physical properties, organoleptic observations, etc.) and the
relevant measurements of physical changes.
| Quote: | | Some people post reactions that are absolutely wrong without reference, and even they do not receive such critics as I do. I don't understand this..
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Some people are just not worth the effort.
| Quote: | | I am trying to use my knowledge and logics in figuring out my reactions, not just blind references, but I am starting to think that this forum just
requires the references. I am trying to do things in different ways as other people do, and you are criticising it. Sorry for using my brain and
creativity too much. |
Creativity without rules is not creative at all. Just think about it, consider your limitations and tell me how on earth can you figure out what is
going on in your reactions without references? Science is a building-up process, not a digging-your-head-in-the-dirt process.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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simba
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You probably made some thiols afterall, but the question is 'how much did you make?'. These things are noticeable even at the tiniest amounts, and
saying any useful amount was produced in this process, judging only by the smell of the reaction mixture, does not sound very wise. Especially when
you don't even have a valid explanation to how it was formed.
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