Sciencemadness Discussion Board

Sulphonation of Hydro Quinone

truchem2k - 12-12-2016 at 08:51

Hi every buddy

I am doing the sulphonation of HydroQuinone with H2SO4 without using solvents but not getting proper sulphonation. have any synthesis root without using solvents or any specific condition.

Boffis - 12-12-2016 at 10:21

Have you tried the reaction? If so what happened to make you think it hasn't worked?

truchem2k - 15-12-2016 at 08:18

Thanks Boffis for interest

I had tried with H2SO4 at 48 Temp but getting hard lumps after some time. and about 3% of un sulphonated HydroQuinone reported by HPLC also find some disulphonic product.

Eddygp - 16-12-2016 at 05:28

Quote: Originally posted by truchem2k  
Thanks Boffis for interest

I had tried with H2SO4 at 48 Temp but getting hard lumps after some time. and about 3% of un sulphonated HydroQuinone reported by HPLC also find some disulphonic product.


Well there you are, it's not deactivating enough so further sulfonation occurs. Since stoichiometry is not really an option, I'm not sure how I would approach this, unless you want to do what you did, separate fractions, desulfonate and join the unsulfonated and desulfonated fractions, resulfonate, repeat, repeat... which is tiring. In other words, reversible so not the end of the world, but still, one would rather have either a better plan or a robot.

[Edited on 16-12-2016 by Eddygp]

Tsjerk - 16-12-2016 at 13:23

Maybe you can think of a system where the sulfuric acid is always the least available reagent, as in adding the sulfuric slowly to a suspension / solution of hydroquinone, in a inert liquid.

UC235 - 17-12-2016 at 16:19

Organic chemistry isn't stoichiometric. settle for modest sulfonation to exclude disulfonation, extract reaction mix with water and use NaCl or KCl to salt out product as with the production of sodium naphthalenesulfonate detailed elsewhere on this forum for production of 2-ethoxynaphthalene.

Consider using chlorosulfonic acid instead.

[Edited on 18-12-2016 by UC235]