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Author: Subject: The unfindable reference for Acetone Dicarboxylic Acid Anhydride
Johnny Windchimes
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[*] posted on 3-2-2020 at 05:46
The unfindable reference for Acetone Dicarboxylic Acid Anhydride


Good day,

I am on the hunt for a reference for the synthesis of 1,3 Acetone dicarboxylic acid anhydride from 1940. Findlay makes reference to it as well as Casale and a number of others. According to 1950's Findlay it yields "in excellent amounts"; that's the scientist equivalent of "BAD ASS DUDE!!!!111"


Here is the reference:

R. Kaushall, J. of Indian Chem. Soc., 17, 138 (1940).



Now, before anyone says UTFSE....

Google, sci-hub, my library at Uni.... cant find it. It definitely exists, but perhaps was never digitized? I've even emailed the current Indian Chem Society about it (no response for 2 weeks now, not wholly unexpected....)

Can anyone here locate this beast? I'd even take a copy in Hindi at this point....

Thanks to all who try!~

[Edited on 3-2-2020 by Johnny Windchimes]

[Edited on 3-2-2020 by Johnny Windchimes]
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Mush
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[*] posted on 3-2-2020 at 10:20


We have a section for article requests. Can you please contact Polverone or Woelen for access.
"References
Articles or books may be requested or shared in this forum. For access, please contact Polverone or woelen. "

It is def. offline.

Your Uni. should be able to get it for you for a small fee (about 5 USD) as an interlibary loan/request. If you are a student you should even have discount on loans.



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Johnny Windchimes
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[*] posted on 3-2-2020 at 11:26


Thanks I'll give that a go!
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wg48temp9
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[*] posted on 4-2-2020 at 05:08


Below is a more recent paper. Four steps 77% yield. What do you want it for?

Attachment: Acetone-Dicarboxylic-Acid-Anhydride.pdf (184kB)
This file has been downloaded 105 times

[Edited on 2/4/2020 by wg48temp9]




i am wg48 but not on my usual pc hence the temp handle.

Thank goodness for Fleming and the fungi.

Old codger' lives matters, wear a mask and help save them.
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Johnny Windchimes
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[*] posted on 4-2-2020 at 10:19


Hey there,

I'd very much like to stabilize it (it decomposes quickly as you may know) for storage. I've been having some issues with the various methods (From Kato 1966 & 1967 to Findlay 1950 and Casale 1987) and I think its basically my poor temperature control. That, and the ungodly "classic" synth via H2SO4 and Citric acid that I could barely handle....

Now, I do have a tube furnace and a quartz tube re: Garage Chemists SO3 Oleum synth, but I would LOVE to avoid that and have been using just 98% H2SO4 and Anhydrous Citric acid.

Oh how much hubris I had when I read 1899 Jerden and decided "pfffft I have vac distillation and a few fritted filters..... I need not a hydraulic press as per EVERY 'real' scientist who ever made 1,3 acetonedicarboxylic acid...."

Well a bunch of wasted time (days and days and days and days) later I got a nice stainless steel press and away we went.

Again, typical of my syntheses I ran out of time and came back to the quenched classic (albeit modified to avoid oleum and use instead Conc. H2SO4) reaction in the freezer and worked it up. Positive violet colour test with FeCl3 sol'n in H2O, so instead of taking the 15 minutes to do even a basic melting point on it, away we went to waste a liter of acetic anhydride.

I'm fairly sure I eventually made Citraconic Anhydride because it all melted at basically 3 - 6 degrees C. But thats a crazy guess based on a literature browse and not much else.


Onwards to the later Oxone and Cobalt & Tungstate catalyzed reactions (ragukumar2014; ordered those catalysts and awaiting their arrival), and finally ending with a slight modification of a Chinese patent (CN103288629B) involving H2O2 oxidation with a catalytic amount of conc. H2SO4 and we have a winner.

Prep scale for now as I don't want to waste any more Citric Acid, but a nice melting point of 134-136 C, and keeping it in a jar at room temp for even a few hours had it decompose into a yellow mess and build pressure in the jar (A la' Acetone and CO2).


So.... short story long, I'd like to store the next batch as the anhydride and I wanted to know what Dr. Kaushal[sic] had to say about it which spawned such rave reviews.

Cheers~!

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