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Author: Subject: Solubility of bases in acetophenone
sonogashira
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[*] posted on 2-12-2009 at 07:16
Solubility of bases in acetophenone


Hi. I had asked a related question in the short questions thread but without any response, so maybe I can ask here to see if it is through oversight rather than not knowing.

I would like to know if anyone has had success with dissolving bases in acetophenone. My intention is as a base for quaternary salt formation - but I won't repeat myself here.

I do not have enough solvent to do sample experiments so I am hoping someone has practical experience with this. Preferably simple (inorganic) bases would be best for me because I do not have very many chemicals. Thanks and sorry for the repetition but it would be nice to resolve the problem as it has stopped my experiments for now...
Best wishes

[Edited on 2-12-2009 by sonogashira]

[Edited on 2-12-2009 by sonogashira]
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stateofhack
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[*] posted on 2-12-2009 at 07:48


If you let me know which bases, i can do it for you :) I have a few hundred mls of acetophenone that i don't use, i wouldn't mind :)

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sonogashira
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[*] posted on 2-12-2009 at 09:46


Hey, thanks very much! That is very kind! ;)

From what little I could find the usual bases used are NaOH, Na2CO3 and K2CO3 (but in water or alcohol) - so if you could try these that would be great!

It may be I will need to add some alcohol too but an idea of the solubility in pure acetophenone would be helpful.

Aside from that some organic bases seem to work but these I don't have and so would rather use the inorganic.

So yes, if you could try those 3 it would be very helpful!
I hope to have time on Friday and the weekend so if for then it would be nice!

Thanks again! :)


[Edited on 2-12-2009 by sonogashira]
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stateofhack
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[*] posted on 2-12-2009 at 11:19


No worries,

I was thinking of trying the followng:

NaOH+MeOH
NaOH+ H2O
Na2CO3 + MeOH
Na2CO3 + H2O

Un-fortunantly i am all out of K2CO3 :(

The way i was thinking is of trying this is to dissolve 500 mg of the base in either water or MeOH ( i will a mixture of both too i think) and then attempt to dissolve it in acetophenone. I will try and get some sort of table and some pictures.

Also my Merck index list is as an Hypnotic?! Anyone heard of this?!
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sonogashira
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[*] posted on 2-12-2009 at 12:01


No need to go to too much trouble! (Unless it interests you :))

It would also be interesting to know if they dissolve in acetophenone to any extent without carrier solvent. Maybe the carbonate has the best chance... But the experiment sounds fine and would be very useful to me, so thank you and best of luck!

Oh and yes - it is a sedative/hypnotic. I tried it twice I think but the taste/smell is very unpleasant... and the smell lingers for a long time (mostly near the floor I noticed). I have a paper in fact which a kind person from here provided and I will attach. It has no pleasant effects like alcohol or ether... and the breath smells quite bad too which could annoy a partner! More like diphenhydramine sleeping pills (but more natural effect).

(And it is fine, I have no potassium carbonate either!)

Attachment: Cases Illustrating the Sedative Effects of Acetophenone.pdf (720kB)
This file has been downloaded 519 times

[Edited on 2-12-2009 by sonogashira]
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stateofhack
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[*] posted on 2-12-2009 at 12:38


Hello,

So this is what i got:

500 mg NaOH+ 2 mls H2O: Two layers formed, appear to mix with hard stirring but separate after.
500 mg NaOH+ 2 mls MeOH: Dissolves fine, doesnt take long to be fully intimatly mixed.

500 mg NaOH+ 1 mls MeOH + 1 mls H2O: Small droplets
formed, but not two distinct layers.
500 mg Na2CO3+ 2 mls H2O: Two layers formed, appear to mix with hard stirring but separate after.

500mg Na2CO3+ 2 mls EtOH: Dissolves fine, takes a little long to get everything nicely mixed.
500 mg Na2CO3+ 1 ml H2O + 1 ml MeOH: Small droplets formed, but not two distince layers.

500 mg NaOH+ 2 mls IPA: One layer, easy mixing and didn't take long.
500 mg Na2CO3+ 2 mls IPA: NaCO3 didnt dissolve well, droplets formed with white residue at the bottom.

Your in luck ;) I Just saw your post and tried to dissolve some of the carbonate in acetophenone with no solvents, it is still stirring but it doesn't seem to be working ( over 90 % of it is still there and its been going for a 5-10 min already)

Take note that i always used 3 mls of acetophenone in every test. Stirred at RT (23 C).

All solvents are stored dried under 4A mol sieves, so they should be pretty dry i think.
I have no idea what are your next step but i think that NaOH in IPA is your best bet OR Na2CO3 in EtOH (but EtOH is expensive...)and thanks for the paper!

Thanks hope it helps a little!

[Edited on 2-12-2009 by stateofhack]

[Edited on 2-12-2009 by stateofhack]
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sonogashira
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[*] posted on 2-12-2009 at 12:57


Thanks, that is a great help - very kind of you!
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stateofhack
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[*] posted on 2-12-2009 at 13:23


No worries glad to help, also i think that using butanol with Na2CO3 might be a good option. No idea tho as i am waiting on some butanol to arrive :(
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