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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: baum0372 on July 17, 2014, 11:48:30 PM

Title: Acidity of Molecular Sieves
Post by: baum0372 on July 17, 2014, 11:48:30 PM
Has anyone ever noticed if molecular sieves are slightly acidic?  I require some dry DMF and am concerned that the acidic residue from the sieves may affect the purity of the solvent.

I have the suspicion that sieves are slightly acidic, as I tried to make some dry ethyl vinyl ether by storing over 4Å sieves, and within a few hours the solution was noticeably more viscous, and after 2-3 days, the solution was a gel.  I suspect the vinyl ether polymerized due to acid in the sieves.

Anyone else had problems with sieves?
Title: Re: Acidity of Molecular Sieves
Post by: kamiyu on July 18, 2014, 04:47:20 AM
Your post made me recall one fact about molecular seive, that soem site in the seive is super acidic (more acidic than pure H2SO4)

Not sure if my memory is right, tough.
Title: Re: Acidity of Molecular Sieves
Post by: Arkcon on July 18, 2014, 06:19:34 AM
Your post made me recall one fact about molecular seive, that soem site in the seive is super acidic (more acidic than pure H2SO4)

Not sure if my memory is right, tough.

I'd like you to come up with a definitive reference for this fact as well.  As I understand it, molecular sieves are basically expanded refractory materials, generally, clays or zeolites.  http://en.wikipedia.org/wiki/Molecular_sieve  They might be slightly basic, but more acidic than sulfuric seems very far fetched.
Title: Re: Acidity of Molecular Sieves
Post by: willug on July 18, 2014, 07:42:05 AM
Reminds me of this post at Daniel Sejer's 'Curley Arrow' blog;

http://curlyarrow.blogspot.co.uk/2010/04/anhydrous-solvents-part-3-acetone-and.html
Title: Re: Acidity of Molecular Sieves
Post by: kamiyu on July 18, 2014, 07:44:44 AM
1) I am sorry I cannot come up with a reference about the acidity of molecular sieve. What I wanted to say was I once (many years ago) heard that MS can be super acidic.

2) Indeed, you can google the information with "molecular sieve superacid" or "molecular sieve acidic". I think you can get pretty much information there
Title: Re: Acidity of Molecular Sieves
Post by: TheUnassuming on July 19, 2014, 04:20:11 PM
Mol sieves are generally considered to be "basic", though you could argue perhaps that its not acting as a traditional base but simply absorbing protons.  From the general absorbent idea they could perhaps be acidic if they absorbed hydroxide ions as well.  That said, I've only observed them acting functionally as a base.
Title: Re: Acidity of Molecular Sieves
Post by: wildfyr on August 04, 2014, 01:48:01 PM
For one thing, I know you can't dry acetone over sieves because it causes aldol condensation