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Topic: Desulfonation of sulfonate (rather than sulfonic acid)  (Read 2208 times)

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Offline Grasshopper

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Desulfonation of sulfonate (rather than sulfonic acid)
« on: December 10, 2014, 06:48:35 AM »
I have a polymer that contains aromatic groups in the chain; these have attached sodium sulfonate groups. I would like to lower the polymer's melting point, so am looking at trying to cleave off the sulfonate groups.

Can you 'desulfonate' sodium sulfonate by reflux in dilute sulphuric acid, as you would for aromatic sulfonic acids? I can't find literature examples of this...

Offline Grasshopper

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Re: Desulfonation of sulfonate (rather than sulfonic acid)
« Reply #1 on: December 11, 2014, 07:56:45 AM »
Actually, since writing this question I have thought of another question... since the sulphonate group is a worse nucleophile/base than carbonate, presumably it would be difficult to make sulphonic esters etc from this starting point, but is there an efficient way to replace the sodium with some bulky organic cation? This would presumably lower the melting point of the polymer...

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