Sciencemadness Discussion Board - preparation of succinic anhydride

preparation of succinic anhydride

Magpie - 4-10-2019 at 14:16

Succinic anhydride was prepared today using the procedure in Fieser's "Experiments in Organic Chemistry," p.104. One mole of succinic acid (SA) reacts with one mole of acetic anhydride (AA) to form one mole of succinic anhydride plus 2 moles of acetic acid.

15g of SA was added to a 100 ml rbf followed by 25g of AA. As I was unable to synthesize SA from glutamate I bought it (100g for ~$13 from Himedia). These components were heated with a steam bath under reflux protected by a CaCl2 guard tube. The SA just sat on the bottom of the rbf even with vigorous shaking. I eventually added a mag stirrer to get them mixing. It might have been better to add the SA to the AA. After a few minutes the mix turned clear. I heated/mixed it for another 1/2 hr per procedure.

The mix was allowed to cool whereupon nice crystals formed. The rbf was then placed in an ice bath to promote further crystallization. The crystals were then washed onto a vacuum filter paper with a little ether and allowed to air dry for a few hours. The mp was 119°, Fieser: 119-120°C. The yield was 10.2g, Fieser: 10-11g.

Any comments or questions will be gladly entertained.

succinic acid refluxing with aa.JPG - 122kB

[Edited on 4-10-2019 by Magpie]

CharlieA - 4-10-2019 at 16:39

Very nice write up. And kudos to you for characterizing your product with a mp. This gives a lot of credibility to the prep. I would only add the molar quantities of reactants and products, and the mp of the starting SA (I'm too lazy, to look it up.)

All in all, a very good, professional report. The very best part is your measurement of the product's melting point. So many reports that I read here, do not characterize the product quantitatively; or at least they don't report the characterization if it was done.

AvBaeyer - 4-10-2019 at 18:26

Magpie,

Great to see you back in action. Your absence has been noticeable. As usual you present a nice description of your preparation as well as characterization. Well done.

As an aside, some time back I made succinic anhydride by refluxing the acid in toluene with a catalytic amount of p-toluenesulfonic acid in conjunction with a Dean-Stark trap. It worked well also. At the time I did not have enough acetic anhydride to use the Fieser procedure.

AvB

Metacelsus - 5-10-2019 at 07:00

Looks good!

Any plans for future experiments using the succinic anhydride?

Boffis - 5-10-2019 at 07:13

Nice work once again Magpie. Succinic anhydride is a useful compound.

I would be interested in the details of your experiment AvBaeyer. I presume this is another azeotropic removal of water liberated by the reversible thermal dehydration of succinic acid.

Magpie - 5-10-2019 at 10:48

Quote: Originally posted by Metacelsus

Looks good!

Any plans for future experiments using the succinic anhydride?

None. I'll be looking for something interesting.

Thanks to the others for the compliments. This really is a very easy synthesis, just something to get me going again.

[Edited on 5-10-2019 by Magpie]

Metacelsus - 5-10-2019 at 13:28

Quote: Originally posted by Magpie

Quote: Originally posted by Metacelsus

Looks good!

Any plans for future experiments using the succinic anhydride?

Maybe you could make succinimide (and NBS). But I think you can start from the acid + ammonia for that, instead of the anhydride.

Or if you have hydroxylamine you could make N-hydroxylsuccinimide: http://www.prepchem.com/synthesis-of-n-hydroxysuccinimide/

[Edited on 2019-10-5 by Metacelsus]

John paul III - 6-10-2019 at 05:50

Is there an incentive to use this method over the thermal method considering it requires precious acetic anhydride?

[Edited on 6-10-2019 by John paul III]

[Edited on 6-10-2019 by John paul III]