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Author: Subject: Isolating adipic acid
DraconicAcid
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[*] posted on 26-6-2013 at 14:03
Isolating adipic acid


Adipic acid is fairly soluble in water, and I'm trying to think of a way to get it out of solution without resorting to liquid-liquid extraction (which I don't have the glassware for). Anyone know if there are any insoluble salts of this acid?



Please remember: "Filtrate" is not a verb.
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plante1999
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[*] posted on 26-6-2013 at 14:19


I guess calcium would do the trick, as it generally form insoluble salt with organic acids, but I may be wrong.



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DraconicAcid
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[*] posted on 26-6-2013 at 14:28


Quote: Originally posted by plante1999  
I guess calcium would do the trick, as it generally form insoluble salt with organic acids, but I may be wrong.

Calcium adipate was the one ion that I was able to find out is soluble in water.

There's a patent online that states " Unlike succinic acid, calcium succinate is relatively insoluble in water when compared with calcium adipate. Calcium succinate has a solubility at 25° C. of only 1.26%, and the solubility at this temperature is a peak solubility with lower solubilities at higher and lower temperatures. "

http://www.freepatentsonline.com/4423018.html




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[*] posted on 26-6-2013 at 14:39


I can't answer your question directly, but here's some forum experience making adipic acid in case you haven't seen it:

http://www.sciencemadness.org/talk/viewthread.php?tid=3173#p...

I made mine using a procedure in Brewster (1961). Here's the applicable excerpt:

"Acidify the hot filtrate with con HCl and allow it to stand in a bath of ice water for 15-20 minutes. Collect the crystals of adipic acid by suction filtration...."

The expected yield was 3g. I did a double batch and obtained 6.2g. I used 10.6mL of cyclohexanone. So you can calculate my yield if desired.





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DraconicAcid
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[*] posted on 26-6-2013 at 14:59


Yeah, the standard prep is either from permanganate, or from hot nitric acid (this has gone volcano on me more than once). I wanted to try to bleach oxidation of an alcohol, and it seemed that adipic acid would be the easiest product to isolate....until I realized how much solution it would take. Bother.

A few patents claim that it can be precipitated as a urea adduct....hmmm.

http://www.google.com/patents/US4146730

[Edited on 26-6-2013 by DraconicAcid]




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[*] posted on 26-6-2013 at 15:11


Quote: Originally posted by DraconicAcid  
liquid-liquid extraction (which I don't have the glassware for).

<em>Seriously</em>, you don't have two beakers‽




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DraconicAcid
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[*] posted on 26-6-2013 at 15:15


Well, I don't have a sep funnel.

<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: removed unnecessary quoting]

[Edited on 7/8/13 by bfesser]




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[*] posted on 26-6-2013 at 15:20


Sorry, guys- I just remembered that work-related stuff is forbidden from sciencemadness, and this is meant towards a lab I'm developing for my students. Feel free to close the thread.



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[*] posted on 26-6-2013 at 15:25


Quote: Originally posted by DraconicAcid  
Well, I don't have a sep funnel.


Take a narrow and tall measuring cylinder and use a syringe to suck out the layer.

<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: removed unnecessary quoting]

[Edited on 7/8/13 by bfesser]
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[*] posted on 27-6-2013 at 06:48


Quote: Originally posted by DraconicAcid  
Sorry, guys- I just remembered that work-related stuff is forbidden from sciencemadness, and this is meant towards a lab I'm developing for my students. Feel free to close the thread.


I wouldn't think that items of more general interest would be a problem here, but the site http://www.chemicalforums.com/ does have a lot of questions relating to teaching labs, graduate work, and work related questions, if that helps.

It is a similar site with a different mix of threads, but nicely complementary to this forum.
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[*] posted on 27-6-2013 at 17:35


You seem to have lost interest, but lead adipate is insoluble, if it is of any use to someone else: http://link.springer.com/article/10.1007/BF02641149
http://www.sciencedirect.com/science/article/pii/00399140688...



[Edited on 28-6-2013 by sonogashira]
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