Sciencemadness Discussion Board

Recrystallization, solubility of glacial acids.

semiconductive - 2-1-2024 at 14:03

I'm just doing some physical chemistry experiments at the moment, and am curious about what is more likely to recrystallize in a non-water system.

I'll describe what I've done, my reasoning, and I would appreciate any comments pointing out where I likely have made a mistake.

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I bought some sodium saccharine, which turns out to carry water of crystallization.
Saccharine is a weak acid, so I think the sodium might be removable by exposure to a stronger acid. At the same time, by boiling it in an acid and refluxing I figure the water could be driven off.

So, I tried an experiment

roughly 1CC dry measure of NaSaccharine, in 4CC's glacial acetic acid.
I heated it until it fully dissolved using a soldering iron (25W) in a glass test tube.
The grains of sodium saccharine cause bubbling/boiling until all of it is dissolved. Once dissolved, the boiling point rapidly rises and bumping occurs. Can easily erupt out of test tube.

When I allow to cool, roughly the same amount of crystals form (volume wise) as initially added as Na:Sacc. I think this means that the solubility of saccharine in glacial acetic acid is low, when cold.

Acetic acid will absorb water, but the molecular weight of acetic acid + water is lower than that of acetic acid bonded to saccharine; so I expect the acetic acid to co-boil with water leaving a continuously stronger solution of saccharine in acetic acid.

When re-heating, a second time, the solution does not boil during the dissolution of the crystals. I think this is a good sign that the water of crystallization, originally in the saccharine, has transferred into the acetic acid. I boil the system down until only 1CC of liquid remains. Then I add 2cc's of fresh glacial acetic acid again.

Hopefully, the remaining solution is now very close to anhydrous.

I am not sure how to get the sodium to separate from the saccharine.
I know if I add a stronger acid, such as formic acid, that the sodium ought to prefer the formic acid over the saccharine. But, I am not sure which will want to go into solution more -- the saccharine, or the sodium formate.

It occurrs to me that MgSO4, cooked to dryness, will not dissolve in glacial acetic acid. Perhaps I could use it as a dessicant, and because it is highly polar, I would expect it to cause any traces of water or small polar molecules (Na:Formate), to stick to it. Adding 1/2CC of dry powder sinks to the bottom of the tube. It increases the rate of re-crystallization when cooling the tube, remarkably.

The entire tube rapidly fills with crystals when cooling, and the liquid tends to become colloidal when heated to boiling with MgSO4 present.

I begin adding formic acid drop wise, re-heating and cooling the tube, in particular I begin to heat the top of the tube (rather than the bottom) and place the bottom of the tube on a cold metal surface in order to encourage crystallization to start from the bottom of the test tube. I also cap the tube with a rubber bung to reduce heat loss from the top.

After several small additions of formic acid (7 drops/ cycle of heating recrystallizing), I notice that a significant amout of the saccharine no longer crystallizes out. I have roughly 1/2CC of crystals forming, AND the remaining solution becomes clear after several cycles of heating the remaining liquid and cooling it again. ( But, if I heat the bottom of the test tube, the entire thing becomes colloidal again. )

So, I have a situation where roughly 1CC of dry saccharine powder now re-crystallizes into 1/2cc of crystals. Upon careful heat cycling while leaving a few crystals un-dissolved on bottom of tube, I can get the remaining solution to turn clear.

Now, I am not sure what is crystallizing out and what is remaining in solution.
I have been told that during crystallization, substances tend to separate since crystals do not like to include multiple different chemicals.

I am hoping that saccharine (being a bigger molecule, less polar), is more likely to remain in solution than sodium formate will. Would you expect this to happen, but if not, why not?

Thanks. (Curious.)