[Jiro]

I have thymol and tartaric acid in a flask... i now pour in about 15mL dichloromethane and shake it... the thymol dissolves and tartaric acid does not... I pour 5mL of NaOH in it... shake it... everything is dissolved... now i put it in my separatory funnel and shake it.... it separates. the dichloromethane layer is now at the bottom i take it out...then i take the top layer out(put it in different flask)... i put the dichloromethane back in the separatory funnel and put in 5mL of NaOH again and repeat the same thing for the funnel 2 more times... I will note that when i repeated it there was some white percepitate forming in the top layer. in the last repeatition there seemed to be no perceptate but the top layer was opaque white color

I now have all the top layer stuff in a flask(milky white color)... i put in some Na²SO₄ to get water out... then i evaporate it out using a hot water bath at about 65degrees celcius... i then recouver a highly viscous liquid which is redish brown color... smells like thymol as well... strange...

I take my remaining solution (the bottom layer of before) and put in HCL in it now the solution PH is like 2.0. Reason for this was to push the presumed tartaric acid compound to dissolve  the dichloromethane which i put in afterwards and extraction using the seperatory funnel...

i now have my solution i put in some Na²SO₄ and watch the water clump up again then put it in the water bath and then... then the flask was empty when i came back but it smelled like thymol... the temp of water bath is like 65 degrees celcius.

What happened to my products???
I dont know for sure... but..
postulates: the -OH  in the thymol somehow polymerized? and the tartaric acid was unstable?tartaricacid possibly reacted in a way to oxidize the thymol to be such? And since the 2 flasks smelled the same suggest probable cross-contamination.

If you know what happened let me know thanks haha

[Jiro]

hmmm I hope i didnt get the bottom and top fractions mixed up... I might do this experiment and switch my neutral and acidic solutions around with the dichloromethane. In either case I will do this experiment again using ether instead of dichloromethane and see if my results are better... if it works i should understand better, as the boiling point of dichloromethane is ~60-70ish, of what is going on... and in this case the top fraction would be ether haha... I'll keep anybody reading this posted lol (probably nobody cares haha)

[Jiro]

With the ether the experiment was a repeat of the intial experiment. the tartaric acid did not dissolve in the ether.

Results: the presumed thymol compound now is a yellow liquid and less viscous than the intial result with a little bit of crystallization that right now can or can be thymol and has not yet been concluded...the color and viscosity makes sense since the ether's boiling point is much lower...and thus heat energy into it resulted in a lesser degree of  polymerization.

The other fraction, the now acidic one, which should have contained the tartaric acid did not seem to contain any. When ether was put into the separatory funnel along with the acidic solution containing tartaric acid it should have theoretically pushed the tartaric acid compound to the top ether fraction. After separation was complete and excess water removed(Na2SO4), the presumed ether solution containing tartaric acid was then put in water bath at 35degrees celcius to evaporate the ether to yield what was going to be tartaric acid. Unfortunetly nothing was obtained.

It was then postulated that the nature of the compound (tartaric acid) was the cause of the negative results. It's melting point is very high like ~170degrees and from literature it is a very polar molecule. Thus protonation(acidifying by using HCL in this case) did not have any effect in shifting it to the the ether fraction when applied. Therefore the tartaric acid should have been in the water fraction...

However, this was tested to be unconclusive as the water fraction was set to boil leaving presumed tartaric acid behind...what was found was some white clumps and powder presumed to be chlorine ions sodium ions and some Na2SO4 stuff i accidently put in before and hopefully some tartaric acid... however, from simple tests it was hard to determine whether or not it existed. water was put into the flask again and it dissolved everything, then acetone was put into it and for some reason looked like it dissolved water! then ethanol was put into it and now there was a clear separation of the 2 liquids... I believe the ethanol fraction preciptated out white chunks/powder again... powder this was then recovered and burned with the reason because tartaric acid should burn since it is an organic molecule but however the powder burned like sodium... no real disquishment...

Conclusion: This is not the best approach to extract these compounds! haha... well I have a feeling the tartaric acid is actually in with my thymol product... I only have access to TLC plates and no other tools to figure out stuff like that

[Jiro]

Conclusion: This is not the best approach to extract these compounds! haha... well I have a feeling the tartaric acid is actually in with my thymol product... I only have access to TLC plates and no other tools to figure out stuff like that

Sorry that was a bad conclusion. There is no way in hell that the tartaric acid would be in the nutral fraction containing the thymol because then it would have to be a-polar which it is totally not. So it must be in the acidic solution... and which the HCL did not have any effect on it so it must be in the water fraction not the ether.