timsong (Newbee)
11-18-01 21:52
No 238085
      GBL via Succinic Acid  Bookmark   

Gamma Butyrolactone via Succinic acid.

Ref :-

Succinic has a strong tendancy to form closed-ring derivatives. Thus on distillation it is converted into the cyclic succinic anhydride.

Succinic anhydride gives gamma butyrolactone on reduction.

CH2-CO                  CH2-CH2
!         \                 !           \
!          O  }Redu}    !            O
!         /                 !           /
CH2-CO                  CH2-CO


Can anybody give me anymore information on this and the methods used for reduction ?
 
 
 
 
    terbium
(Old P2P Cook)
11-18-01 23:28
No 238101
      Re: GBL via Succinic Acid  Bookmark   

Succinic anhydride gives gamma butyrolactone on reduction.

Can anybody give me anymore information on this and the methods used for reduction ?


Well, you are the person who made the assertion. Where did you get your information?
 
 
 
 
    moo
(Hive Bee)
11-18-01 23:51
No 238112
      Re: GBL via Succinic Acid  Bookmark   

This has been mentioned here at the Hive earlier. Also 5th edition of March's Advanced Organic Chemistry mentions reduction of cyclic anhydrides to lactones by zinc and acetic acid but gives only references on more advanced catalytic methods. The catalysts seemed a little exotic, I think some contained cobalt but cannot remember more because I was looking for references on the zinc reduction.

understanding is everything
 
 
 
 
    timsong
(Newbee)
11-19-01 00:24
No 238121
      Re: GBL via Succinic Acid  Bookmark   

I just read about this in an 1947 organic chemistry book by Paul Karrer. Unfortunately it does not go into any more details than I have posted. I was hoping that information from other sources/people might build a more detailed picture of this route.

I have tried distilling succinic acid that I obtained from a wine making shop, but I just ended up with a brown mess with a dirty kind of oil smell. And even if I did manange to obtain succinic anhydride what would be the best thing to reduce it with ?
 
 
 
 
    encopo
(Hive Bee)
11-19-01 03:38
No 238195
      Re: GBL via Succinic Acid  Bookmark   

Have a look at my posts on n-butane -> maleic anhydride
-> THF/GBL -> GHB.
We need someone to figure out a nicer version of the butane
oxidation. (maybe I'll get around to it).

Don't mind me. I'm mentally ill.
 
 
 
 
    terbium
(Old P2P Cook)
11-19-01 07:28
No 238287
      Re: GBL via Succinic Acid  Bookmark   

From Freifelder:
... the pattern seen in the hydrogenation of succinic anhydride. Reduction with copper chromite at 250 and 200 atm gave only 29% of butyrolactone because of the severe conditons (66a). Under more moderate conditions hydrogenation with palladium on carbon or on alumina in ethyl acetate at 35-100 and 16-75 atm gave an 80-94% yield of lactone (66b). Reduction at atmospheric pressure (65) or at 2-3 atm (2) required a large amount of platinum oxide, 10-15% by weight. Some butyric acid was obttained in addition to the butyrolactone.

2. Unpublished work by the author.
65. McCrindle, Overton, Raphael, J. Chem. Soc., 1962, 4798.
66. (a) Wojcik and Adkins, J. Am. Chem. Soc., 55, 4939 (1933); (b) Franco-Filipasic, Koyler and Borks, Jr., U.S. Patent 3,113,138 (1963)

 
 
 
 
    Aurelius
(Hive Bee)
11-19-01 07:31
No 238289
      Re: GBL via Succinic Acid  Bookmark   

aurelius would rather put up with the low yeild (succinic acid is easily avail) and not have to use precious metal catalyst or obtain butyric acid as a byproduct (stench)
 
 
 
 
    Elementary
(Hive Bee)
01-30-02 15:23
No 262731
      Re: GBL via Succinic Acid  Bookmark   

Patent US6297389

A process for the production of gamma-butyrolactone. Starting from maleic and/or succinic anhydride the conversion takes place in the presence of a catalyst composed of copper oxide and zinc oxide


One day I'll understand everything !