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Topic: Silica dissolving during column chromatography  (Read 30635 times)

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Offline uglepik

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Silica dissolving during column chromatography
« on: July 20, 2011, 04:39:21 AM »
I've recently run some flash columns using chloroform:methanol:water:acetic acid mixtures as eluant. Usually with ratios in this range:

CHCl3: 60-90%
MeOH: 10-30%
H2O: 1-4%
AcOH: 1-3%

A typical eluant would like this: CHCl3:MeOH:H2O:AcOH (80:20:2:1)

Now I have, based on some odd elemental analysis with consistently low ratios for each element, begun to wonder whether such mixtures will dissolve silica and thereby transfer it to your (supposedly) purified product.

Does anyone have any knowledge or experience regarding this? If it happens? To what extent it happens? How to prevent it? Or how to get rid of the silica once it's there?

Most of my compounds are not soluble in neat organic solvents, but need added acid (formic acid, TFA).

Thanks in advance!
Andreas

Offline ATMyller

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Re: Silica dissolving during column chromatography
« Reply #1 on: July 20, 2011, 04:53:50 AM »
Silica (SiO2) is very diffucult to dissolve and requiers either hydrofluoric acid or concetrated hot alkali like NaOH and should not happen with the used eluent.

On the other hand TFA might be able to dissolve silica, but I'm not familiar enough with it to say for certain.
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Offline helenn

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Re: Silica dissolving during column chromatography
« Reply #2 on: July 20, 2011, 06:08:32 AM »
Greater than 15 % MeOH solutions can dissolve silica, I've seen it happen, you don't get a lot, but it is visible when you evaporate the solvent.

Offline discodermolide

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Re: Silica dissolving during column chromatography
« Reply #3 on: July 20, 2011, 07:53:29 AM »
I've recently run some flash columns using chloroform:methanol:water:acetic acid mixtures as eluant. Usually with ratios in this range:

CHCl3: 60-90%
MeOH: 10-30%
H2O: 1-4%
AcOH: 1-3%

A typical eluant would like this: CHCl3:MeOH:H2O:AcOH (80:20:2:1)

Now I have, based on some odd elemental analysis with consistently low ratios for each element, begun to wonder whether such mixtures will dissolve silica and thereby transfer it to your (supposedly) purified product.

Does anyone have any knowledge or experience regarding this? If it happens? To what extent it happens? How to prevent it? Or how to get rid of the silica once it's there?

Most of my compounds are not soluble in neat organic solvents, but need added acid (formic acid, TFA).

Thanks in advance!
Andreas
Run a sulphate ash test on your products, this will indicate the inorganic content of the material
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Offline Babcock_Hall

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Re: Silica dissolving during column chromatography
« Reply #4 on: July 20, 2011, 09:13:00 AM »
I have also heard that methanol in high enough concentrations will dissolve silica.  If the product can be redissolved in an organic solvent that does not contain methanol, the silica should fall back out.

Offline fledarmus

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Re: Silica dissolving during column chromatography
« Reply #5 on: July 20, 2011, 05:38:44 PM »
Yes, high percentages of methanol in chloroform in dichloromethane can dissolve silica gel. Using a straight chloroform/methanol mixture, I find that 20% methanol is usually okay, and I have pushed it to 25%. but I wouldn't go any higher than that and expect not to find silica gel in the product. As Babcock_Hall says, redissolving the product in acetonitrile, ethyl acetate, or even DMF if you have the vacuum pump to rotovap it back off, will allow you to filter out the silica gel if you absolutely have to go that high.

I don't know what the addition of water and acetic acid would do, but I would expect that it would make it easier to dissolve the silica gel.

Chloroform:Ethyl Acetate:Acetic Acid mixtures might allow you to get a more polar solvent system without dissolving silica gel - I've never had a problem with silica gel dissolving in any other solvent I've tried.

Offline rucik5

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Re: Silica dissolving during column chromatography
« Reply #6 on: July 20, 2011, 05:49:12 PM »
The only thing I can add is that I've seen silica dissolving when using 100% EtOAc as eluent. Re-dissolving stuff in a small amount of DCM and filtering seems a fairly good way around it.

Offline uglepik

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Re: Silica dissolving during column chromatography
« Reply #7 on: July 21, 2011, 09:51:30 AM »
Okay guys, good answers. I guess I'll have to deal with a bit of silica in some of my products  :-\

Offline opsomath

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Re: Silica dissolving during column chromatography
« Reply #8 on: July 21, 2011, 02:05:40 PM »
Contrary to other posts, it doesn't take that much polarity to dissolve _small_ amounts of silica. Hexane-ether mixes can pick up a little, especially if you are concentrating extremely large amounts of solvent relative to the amount of material coming through (trying to isolate a very faint band).

Offline Honclbrif

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Re: Silica dissolving during column chromatography
« Reply #9 on: July 21, 2011, 03:47:26 PM »
Someone seriously needs to do an in depth investigation into the solubility of silica in organic solvents. I've heard everything from "no more than 10% MeOH" to "MeOH doesn't dissolve new silica, only dissolved silica gel made through an older process" to opsomath's comment in this thread. I don't know who or what to trust anymore and its getting frustrating.
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Offline uglepik

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Re: Silica dissolving during column chromatography
« Reply #10 on: July 21, 2011, 04:36:29 PM »
Someone seriously needs to do an in depth investigation into the solubility of silica in organic solvents. I've heard everything from "no more than 10% MeOH" to "MeOH doesn't dissolve new silica, only dissolved silica gel made through an older process" to opsomath's comment in this thread. I don't know who or what to trust anymore and its getting frustrating.

Can it really be that such a study has never been done? It sure would be interesting information... And not too hard to do I suppose.

Offline Robert Kerr

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Re: Silica dissolving during column chromatography
« Reply #11 on: September 03, 2015, 02:31:25 PM »
This is an old topic for this forum … but considering the answers, and the number of views, I felt I had to respond before too many people start believing some of these answers.

Silica gel does not dissolve in organic solvents alone.

Methanol does not dissolve silica gel.

If you have silica gel in your products recovered after chromatography, it is because the Silica gel of … for example, 43-75 microns … ALSO has a lot of what are called ‘fines’.  Fines are particles of silica very much smaller than the stated size formed after sizing.  This happens because silica gel particles are not that strong and break up fairly easily.  These smaller particles cannot be retained by the frit at the end of the column, and therefore wind up in small amounts in chromatographic eluent.  After evaporation of the solvent, the substance of interest is still there, and so are the silica gel fines.

Silica gel does not dissolve in organic solvents alone.

Methanol does not dissolve silica gel.

Offline TheMantis

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Re: Silica dissolving during column chromatography
« Reply #12 on: September 13, 2015, 04:40:57 PM »
if you are going to use an eluent that polar then you may want to consider using a reverse phase column.

Offline deranjit

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Re: Silica dissolving during column chromatography
« Reply #13 on: March 21, 2017, 10:24:05 PM »
I was using MeOH + water (vol:vol = 1:4) as eluent and found that some of the silica was coming out with the eluent. So, initially I thought it could be the MeOH dissolving silica particles. Thereafter, I prepared a different silica column where I used only water as eluent, I found the same was repeated, some particles came out with the eluent. So, I continued to flush using water as eluent till the clean and transparent water came out of the column. This gave me the understanding that there are finer silica particles which are much smaller than the specified sizes by the manufacturer.

Offline rolnor

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Re: Silica dissolving during column chromatography
« Reply #14 on: March 22, 2017, 07:00:36 AM »
This is an old topic for this forum … but considering the answers, and the number of views, I felt I had to respond before too many people start believing some of these answers.

Silica gel does not dissolve in organic solvents alone.

Methanol does not dissolve silica gel.

If you have silica gel in your products recovered after chromatography, it is because the Silica gel of … for example, 43-75 microns … ALSO has a lot of what are called ‘fines’.  Fines are particles of silica very much smaller than the stated size formed after sizing.  This happens because silica gel particles are not that strong and break up fairly easily.  These smaller particles cannot be retained by the frit at the end of the column, and therefore wind up in small amounts in chromatographic eluent.  After evaporation of the solvent, the substance of interest is still there, and so are the silica gel fines.

Silica gel does not dissolve in organic solvents alone.

Methanol does not dissolve silica gel.

How can you be so sure?

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