clearly_not_atara
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Methanesulfonic acid from sodium cocoyl isethionate
Sodium cocoyl isethionate is available as a bulk powder for the new trend of homemade soap makers. Lucky for us, isethionates have excellent safety
and cleaning properties which means they’ll probably stick around.
The ester linkage is attacked by alkali, and this reaction is easy to carry out because the surfactant is highly soluble in water. Reflux is not a
good idea because soap is foamy but holding at 90 C for a few hours should yield a solution of isethionate.
Oxidizing isethionate with dichromate or permanganate should take it all the way to the carboxylate, which, having an alpha-EWG, should spontaneously
decarboxylate under acidic conditions.
The oxidation will not affect the lipid fraction from hydrolysis and is ideally carried out under alkaline conditions to ensure it doesn’t stop at
the aldehyde. So hydrolysis and oxidation can probably be performed in one pot.
[Edited on 04-20-1969 by clearly_not_atara]
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Nitrous2000
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methanesulfonic acid synthesis
anyone try this?
is it a viable route to methanesulfonic acid?
Nitrous
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Endo
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Nitrous,
Looks to me like the isethionate esters are all 'ethane' sulfonates. Hydrolysis of the ester linkage would yield you a ethane sulfonate which is not
the critter you are looking for.
Good Luck!
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clearly_not_atara
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Hey, give past me more credit than that. You lose one carbon atom to the decarboxylation. The hydrolysis product is 2-hydroxyethyl sulfonic acid. But
the negative charge on the sulfonate may interfere with hydrolysis.
[Edited on 04-20-1969 by clearly_not_atara]
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Sigmatropic
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I reckon oxidizing taurine with some form of bleach would be a better route to sulfoacetic acid.
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Nitrous2000
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thanks folks,
As usual, too good to be true... is...tgtbt
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Lionel Spanner
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Plus there is the possibility of the sulphonic acid group forming some kind of complex with the chromium or manganese, complicating the reaction.
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Texium
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Thread Moved
14-9-2023 at 11:58 |
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