MagicJigPipe
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Diisobutyl Dicarboxylate Esters
My Mom went to the auctions the other day and came back with (amongst many other things) 2 cans of Sealed Air -Instapak Port Cleaner. They contain:
Diisobutyl glutarate (CAS 71195-64-7), diisobutyl adipate (CAS 141-04-8), diisobutyl succinate (CAS 925-06-4) and carbon dioxide propellant.
For some reason when I looked up the MSDS for the cleaner it claimed to contain gamma-butyrolactone! I assume it was an old MSDS and they simply
changed their formula as per the list 1 status of the lactone.
Anyway, my question is, does anyone know what these solvents can be used for in the lab? Are they worthless? I find them interesting because I have
never heard of them before.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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not_important
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Dieasters are decent solvents, but as esters they are relatively reactive, and they have high boiling points. This mixture, possibly with a different
ratio of esters, is sold as DBE-IB, used in coatings as a slow evaporating (tail) potion of the solvent base, helping form continuous films without
pinholes.
The acids themselves could be useful, as could be the isobutyl alcohol. Succinic acid can be converted to the cyclic imide, which is reacted with Cl2
or Br2 to give NCS or NBS (N-ChloroSuccinimide, N-BromoSuccinimide)- useful halogenating agents (Wiki has an OK write-up).
here's the MSDS
Attachment: Instapak Port Cleaner.pdf (60kB)
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MagicJigPipe
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Yes, isobutanol. That's not something I hear about too often and would love to have some if not for anything than to just be able to say I have it.
Thanks for the info!
Separating the acids would prove difficult wouldn't it? I think my best bet would be to keep the acids mixed or discard them.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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not_important
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All depends, as they have their uses.
If you've the equipment to fractionally distill under reduced pressure, then you could fractionate the esters.
If not, then you can use other physical properties to separate them. Glutaric acid is 10 times as soluble in water as succinic, and about 40 times
more soluble than adipic; fractional crystallization should give decent separation.
Take the free acids and drop them in toluene or xylene along with a few mole-percent of boric acid. Arraign for slow distillation of the
aromatic-water azeotrope, distill that off with return of the solvent to the pot. Succinic and glutaric acids for cyclic esters, adipic does not
although it can form polymeric esters. The anhydrides have much different physical properties than the dibasic acid, some research should give you
enough information to separate succinic anhydride from adipic acids and its oligimers.
Di-esters of adipic acid can undergo a Dieckmann condensation to give the cyclopentane b-ketoester. This is useful synthetically, or can be
decarboxylated to cyclopentanone, which can be transformed into cyclopentanol, cyclopentene, cyclopentane, and indirectly into cyclopentadiene.
Glutaric acid can be reacted with ammonia, the heated to give glutarimide which with some effort can be made into piperidine or pyridine.
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chemrox
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I'm using high boiling esters to charge my manostat.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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