Hellhound
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DMS from DMSO?
Is there an effective route to obtain DMS from DMSO?
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BromicAcid
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From the usual DMSO reference (Technical Bulletin Reaction Solvent Dimethyl Sulfoxide) | Quote: | DMSO is reduced to dimethyl sulfide, CH3SCH3, by a number of strong reducing agents, including aluminum hydrides and boranes. Mercaptans reduce
acidified DMSO and are oxidized to the disulfides:
2RSH + CH3SOCH3 --(acid)--> RSSR + CH3SCH3 + H2O |
The bulletin is avalible online in PDF format from
Gaylord Chemical Corporation, although this is the entry on reduction of DMSO the references are avalible there as well as other interesting
information.
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Hellhound
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Oh,man,thanks,but i mean dimethylsulphate.
I just noticed this mess in using "DMS" abbreviation for both dimethylsulphate and dimethylsulfide.
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BromicAcid
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I have never read a procedure to prepare dimethyl sulfate from dimethyl sulfoxide though in another thread on dimethyl sulfate (where this should have
been posted in the first place) I referenced a pecular phenomenon where a woman using large amounts of DMSO to control althritis supposedly gave off a
poisonous gas when the EMS unit came for her, and it has been postulated that the combination of oxygen therapy and some other factors may have come
together to allow for her body and the oxygen to convert the dimethyl sulfoxide to dimethyl sulfate, interesting huh?
However that seems a little far fetched to do in a lab, in order to get dimethyl sulfate you would have to oxidize the bonds in between the sulfur and
the carbon atoms, something that seems a little difficult to do/unrealalistic. In the paper I referenced above the folowing information is give on
oxidation of DMSO: | Quote: | | DMSO reacts with strong oxidizing agents to give dimethyl sulfone, CH3SO2CH3. Ozone gives a good yield of the sulfone. Dichromate oxidation and
permanganate oxidation have been used for quantitative determination of DMSO. |
All the oxidation procedures
mentioned thereafter in the paper give dimethyl sulfone or halogenated derivatives of it, sorry.
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Sandmeyer
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There is no practical way to do this from DMSO. My opinion is unless DMS can't be purchased it should not be made, and since it is used
exclusively for methylations then methyliodide is an excellent substitute and can easily be made from methanol, its synthesis has been a subject of at
least 2 threads here.
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DDTea
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| Quote: | Originally posted by Sandmeyer
There is no practical way to do this from DMSO. My opinion is unless DMS can't be purchased it should not be made, and since it is used
exclusively for methylations then methyliodide is an excellent substitute and can easily be made from methanol, its synthesis has been a subject of at
least 2 threads here. |
If you're talking about toxicity, it's worth noting that Methyl Iodide is also a Vesicant, Carcinogen, and a poison. However, in the lab,
it is still much more preferred than Dimethyl Sulfate.
The only advantage to Dimethyl Sulfate over Methyl Iodide that I can is that it is cheaper and more suitable for industrial manufacturing. In the
lab, though, this should not be a problem.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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