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Author: Subject: Separating Phthalic Acid & Salicylic Acid
NotBismuth
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[*] posted on 29-5-2019 at 03:24
Separating Phthalic Acid & Salicylic Acid


All I could find was that they're both soluble in boiling water. Would just decomposing Salicylic Acid be the feasible way? Thanks in advance :D
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DraconicAcid
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[*] posted on 29-5-2019 at 07:04


Partially, it depends on the mixture. If you have mostly one contaminated with a small amount of the other, recrystallizing it a few times from water may be sufficient. If it's more of a 50:50 mix, then it will be more challenging. Chromatography might work. You might find that their sodium or potassium salts have sufficiently different solubilities in alcohol or acetone to separate the two.



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[*] posted on 29-5-2019 at 07:10


Well the Phthalic Acid would be the dominant - the Salicylic Acid is formed from the Ester Hydrolysis of a Sodium Salicylate catalyst. Thanks! :]

[Edited on 29-5-2019 by NotBismuth]
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TGSpecialist1
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[*] posted on 29-5-2019 at 11:38


Calcium phtalate is insoluble.
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[*] posted on 29-5-2019 at 12:24


Quote: Originally posted by TGSpecialist1  
Calcium phtalate is insoluble.

Calcium salicylate has a solubility of 2.3 g/100 mL. That should be enough to remove a small amount of salicylic acid.




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[*] posted on 29-5-2019 at 12:33


You could first convert the acids to sodium salts then add just enough CaCl2 to selectively precipitate calcium phtalate.
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[*] posted on 29-5-2019 at 13:16


This book: https://books.google.ca/books?id=KPyLb5f-p4EC&pg=PA224&a...

says that both calcium phthalate and calcium salicylate are insoluble.

Some other possibilities.....
Zinc salicylate is very soluble, zinc phthalate is not (according to the above book).

To precipitate calcium phthalate, you need to remove both the hydrogens from phthalic acid; to precipitate calcium salicylate, you only need to remove one. if you kept the pH at 4, you'd convert all the salicylic acid into salicylate, but all the phthalic acid would be the hydrogen phthalate ion (which might not precipitate with calcium- you'd need to find the Ksp values for the compound to determine it theoretically).




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[*] posted on 29-5-2019 at 17:24


Phthalic acid pKas = 2.89; 5.51
Salicylic acid pKas = 3.0; 13.4
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[*] posted on 29-5-2019 at 20:59


Quote: Originally posted by TGSpecialist1  
Phthalic acid pKas = 2.89; 5.51
Salicylic acid pKas = 3.0; 13.4

Yes, so if you adjust the pH to about 4, you'll take one H+ off of both acids. However, for the purposes of precipitating out any salts, the second hydrogen on salicylic acid can be ignored, and we can treat it as a monoprotic acid.




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[*] posted on 30-5-2019 at 06:36


What?! These Chemicals are allowed in Singapore?!:o



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[*] posted on 2-6-2019 at 20:14


Quote: Originally posted by fusso  
What?! These Chemicals are allowed in Singapore?!:o


Just need to source Diethyl Phthalate solvent from Glowsticks and hydrolyse it to Phthalic Acid. Seeing that this is just a proof of concept & efficiency isn't a priority, it would make more sense to proceed VIA the acid catalysed approach. HCl can either be obtained through distillation of toilet cleaner or from the reaction of Sulfuric Acid & Salt. Sulfuric Acid can easily be obtained from Car Battery or just burning Sulfur and bubbling the Dioxide into Hydrogen Peroxide :¶

P.S. I'm using Glowsticks as the source because I'd also need the Phenol from it - probably to make Phenolphthalein

[Edited on 3-6-2019 by NotBismuth]
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