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Author: Subject: Oxalic Acid from Skunk Cabbage
DFliyerz
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[*] posted on 16-4-2015 at 09:57
Oxalic Acid from Skunk Cabbage


The "greenbelt" behind my house is plagued by lots of Western Skunk Cabbage, which is known for having calcium oxalate crystals in it which makes it poisonous. I was thinking that it might be possible to extract oxalic acid (which could then be purified by turning it back into calcium oxalate) by steeping the leaves in a dilute solution of hydrochloric acid to turn the calcium oxalate into oxalic acid, adding calcium chloride to the filtered solution to precipitate out calcium oxalate while leaving most of the other contaminants in solution, and then either using the calcium oxalate or turning it back into oxalic acid with hydrochloric acid. If needed the oxalic acid could be separated from the calcium chloride in solution by dissolving everything in ethanol (since oxalic acid is much more soluble in ethanol than calcium chloride), or acetone, although I haven't found whether or not oxalic acid is soluble in acetone. Yes, I know I could just go buy oxalic acid, but I like finding impractical routes to chemicals just because I can!

[Edited on 4-16-2015 by DFliyerz]
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Bert
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[*] posted on 16-4-2015 at 11:38


You might have a cheaper/easier result from sawdust and mixed alkalis.

http://thesis.library.caltech.edu/487/

But hey, if it looks more interesting to do a plant extraction, by all means! Please do report your results.




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DFliyerz
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[*] posted on 16-4-2015 at 12:43


Quote: Originally posted by Bert  
You might have a cheaper/easier result from sawdust and mixed alkalis.

http://thesis.library.caltech.edu/487/

But hey, if it looks more interesting to do a plant extraction, by all means! Please do report your results.


I'd probably do that method instead, but I don't have any potassium hydroxide! (I'm doing a small batch from potassium carbonate/calcium hydroxide, but again; it's very small.)
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[*] posted on 16-4-2015 at 15:06


Could the same be attempted with rhubarb leaves?
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[*] posted on 16-4-2015 at 20:39


There are good extractions for rhubarb, just do a Google search. Hydrochloric acid may improve the mobility of calcium oxalate but it will not improve the oxalate solubility. The calcium oxalate is still not very soluble.
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[*] posted on 16-4-2015 at 21:21


Next time I grow (or see) rhubarb, I might give this a go.
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[*] posted on 17-4-2015 at 03:36


Your procedure sounds like it would work, but I would recommend adding calcium carbonate instead of calcium chloride to re-precipitate calcium oxalate; this will ensure neither hydrochloric acid nor oxalic acid remain in solution.

Scrolling down far enough on this page, you'll find that oxalic acid is insoluble in acetone, but it is very soluble in ethanol.

For a few other DIY routes to oxalic acid, check out this page: http://www.henriettes-herb.com/eclectic/kings/acidum-oxal.ht...




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