SuperOxide
Hazard to Others
Posts: 487
Registered: 24-7-2019
Location: Devils Anus
Member Is Offline
|
|
Is it possible to synthesize phthalic acid [or anhydride] from phthalimide?
I'm well familiar with the synthesis of phthalic anhydride from phthalate based plasticizers, which I have done a few times. And I know that's easily
turned into phthalimide using urea or ammonia. However, I was looking to see if there's a known synthesis procedure for going the other direction? I
have a decent amount of phthalimide, and there are a few reactions I'd like to try that need phthalic acid/anhydride, and I don't want to have to
purchase them or make them again from scratch if I can just use the phthalimide I have on hand that's just been sitting on the shelf collecting dust.
I did look around, and either my Google fu isn't what it use to be, or there isn't too much out there about this.
Thanks.
|
|
|
Oxy
Hazard to Others
Posts: 140
Registered: 1-12-2020
Member Is Offline
|
|
Carboxylic acids can be synthesised from amides by hydrolysis in acidic or basic conditions.
basic conditions will produce salt but it's pretty easy to convert it to acid
[Edited on 7-6-2021 by Oxy]
|
|
|
SuperOxide
Hazard to Others
Posts: 487
Registered: 24-7-2019
Location: Devils Anus
Member Is Offline
|
|
Quote: Originally posted by Oxy  | Carboxylic acids can be synthesised from amides by hydrolysis in acidic or basic conditions.
basic conditions will produce salt but it's pretty easy to convert it to acid |
Thanks, Oxy. This looks right: http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch22/ch22-2... - I'll give that as hot.
[Edited on 7-6-2021 by SuperOxide]
|
|
|
zed
International Hazard
Posts: 2284
Registered: 6-9-2008
Location: Great State of Jefferson, City of Portland
Member Is Offline
Mood: Semi-repentant Sith Lord
|
|
Hydrolysis of Phthalimide might not be really easy.
I'd look for a published procedure.
|
|
|
Triflic Acid
Hazard to Others
Posts: 486
Registered: 27-9-2020
Member Is Offline
Mood: Slowly Oxidizing into Oblivion
|
|
Amide hydrolysis is generally a pain. Might be worth trying http://www.sciencemadness.org/talk/viewthread.php?tid=79854
There wasn't a fire, we just had an uncontrolled rapid oxidation event at the power plant.
|
|
|
SuperOxide
Hazard to Others
Posts: 487
Registered: 24-7-2019
Location: Devils Anus
Member Is Offline
|
|
Yeahhh, I did a little more research, it looks like it would be better to just re-make the phthalates, or buy some.
As always, thanks for the input.
|
|
|
clearly_not_atara
International Hazard
Posts: 2799
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
If you have hydrazine handy, phthalimide rapidly converts to the cyclic hydrazide. Then oxidizing this gives a 2,3-diazanaphthoquinone that should
easily undergo acidic hydrolysis. Nothing is easier than buying more, of course.
|
|
|
SuperOxide
Hazard to Others
Posts: 487
Registered: 24-7-2019
Location: Devils Anus
Member Is Offline
|
|
| Quote: Originally posted by clearly_not_atara | | If you have hydrazine handy, phthalimide rapidly converts to the cyclic hydrazide. Then oxidizing this gives a 2,3-diazanaphthoquinone that should
easily undergo acidic hydrolysis. Nothing is easier than buying more, of course. |
Yeah, I saw this when I was researching the reaction. I don't have any hydrazine handy at the moment, though that's on my to-do list (maybe this weekend).
I may do it anyways (on a smaller scale) just as an experiment to learn about the reaction a bit.
[Edited on 8-6-2021 by SuperOxide]
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
