Chemical Forums

Please login or register.

Login with username, password and session length

Sponsored links

Pages: [1]   Go Down

Author Topic: Purifying an compound containing a tosylate nad a tosylate side product  (Read 460 times)

0 Members and 1 Guest are viewing this topic.

ZidaneTribal

  • Very New Member
  • *
  • Mole Snacks: +0/-0
  • Offline Offline
  • Posts: 2

Greetings,

I've synthezized a functionalized polymer with tosylate groups. Due to excess ethanol formed during the the reaction, my tosylate chloride reagent reacted with that ethanol forming a side product. Purification was done by precipitation but the side product couldn't be removed. Is recommended to run a column over Al2O3 to remove the side product? I'm not sure if the tosylate will tolerate purification by column chromatography. What are your suggestions?
Logged

Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Mole Snacks: +198/-14
  • Offline Offline
  • Posts: 3094
Re: Purifying an compound containing a tosylate nad a tosylate side product
« Reply #1 on: November 20, 2017, 02:02:21 AM »

I am not sure of the answer to your question.  Do you think that your material would tolerate some type of size exclusion chromatography?
Logged

ZidaneTribal

  • Very New Member
  • *
  • Mole Snacks: +0/-0
  • Offline Offline
  • Posts: 2
Re: Purifying an compound containing a tosylate nad a tosylate side product
« Reply #2 on: November 20, 2017, 05:27:08 AM »

I am not sure of the answer to your question.  Do you think that your material would tolerate some type of size exclusion chromatography?

That's a good suggestion. But I'd like to run it as simple as possible. I fear that my tosylate groups will gone after column chromatography. Did ever purify a tosylate compound with column?
Logged

wildfyr

  • Chemist
  • Full Member
  • *
  • Mole Snacks: +49/-5
  • Offline Offline
  • Posts: 453
Re: Purifying an compound containing a tosylate nad a tosylate side product
« Reply #3 on: November 20, 2017, 06:34:36 AM »

Yes, tosylates can handle a column just fine. I've never tried a alumina column with it, just a standard silica column.

However, polymers usually smear all over the column, so pay close attention to your TLC.

You should try precipitating or redissolving in various solvents and see if you can't get purification that way. For instance, tosyl ethanol is probably soluble in diethyl ether, but polymers tend to have terrible ether solubility.
Logged

phth

  • Chemist
  • Full Member
  • *
  • Mole Snacks: +24/-4
  • Offline Offline
  • Posts: 373
Re: Purifying an compound containing a tosylate nad a tosylate side product
« Reply #4 on: November 21, 2017, 10:49:49 AM »

Run a 2D TLC plate to assess if it will decompose on alumina or silica.  Like Wildfyr said it will only be minor decomposition if any i.e. 10-20% loss. 
Logged
Pages: [1]   Go Up
 

Mitch Andre Garcia's Chemical Forums 2003-Present.

Page created in 0.06 seconds with 24 queries.