Sciencemadness Discussion Board

Sulfonation of styrene

akre - 21-1-2004 at 11:58

I'm going to try sulfonate poly(styrene). I was thinking of using sulfuric acid and sulfuryl chloride (Cl2O2S). Am I right if I assume that the reaction:
Cl2O2S + H2SO4 <-> SO2 + 2 HCl + SO3
takes place?

guaguanco - 21-1-2004 at 13:09

Quote:
Originally posted by akre
I'm going to try sulfonate poly(styrene). I was thinking of using sulfuric acid and sulfuryl chloride (Cl2O2S). Am I right if I assume that the reaction:
Cl2O2S + H2SO4 <-> SO2 + 2 HCl + SO3
takes place?

I would actually expect that mixture to equilibrate with Chlorosulfonic acid.

(Repaired links)
You might want to look at:
http://wwwsoc.nii.ac.jp/jsac/analsci/pdfs/a17_1117.pdf
http://ecl.web.psi.ch/Publications/iface_pub/EActa_02
http://www.physics.nus.edu.sg/~phyjiwei/ChemMat2002.pdf

[Edited on 22-1-2004 by guaguanco]

blip - 22-1-2004 at 15:32

Don't you mean:
http://www.physics.nus.edu.sg/~phyjiwei/ChemMat2002.pdf
I can't figure out what's wrong with the middle one though.

akre - 31-1-2004 at 14:04

Do you mean the reaction would be:
SO2Cl2 + H2SO4 <-> HClO3S + HCl + SO3

or just
SO2Cl2 + H2SO4 <-> 2 HClO3S

what is causing the fumes when dripping sulfuryl chloride into sulfuric acid? The water in the sulfuric acid?

[Edited on 31-1-2004 by akre]

guaguanco - 1-2-2004 at 23:50

Yes, you're generating a certain amount of HCl unless the H2SO4 is anhydrous.

Note that H2SO4 is a perfectly good sulfonating agent in it's own right, although there's nothing wrong with chlorosulfonic acid. Take your pick.

akre - 2-2-2004 at 04:16

I've read somewhere sulfonation with sulfuric acid requires high temperatures and long reaction times as opposed to chlorosulfonic acid.

Nosferatu - 17-2-2004 at 03:21

Quote:
Originally posted by akre
I've read somewhere sulfonation with sulfuric acid requires high temperatures and long reaction times as opposed to chlorosulfonic acid.


For sulfonation, oleum works better, and it's more fun to work with. :cool:

http://www.disobey.com/horror/movie_media/nosferatu/download...

[Edited on 17-2-2004 by Nosferatu]