Maleic Anhydride → 1,2,3,4-Cyclobutanetetracarboxylic dianhydride

HRID 611437Notes

Reaction equation

HRID 611437 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1>[Hg].C(OCC)(=O)C>[CH:3]12[C:4](=[O:5])[O:6][C:1](=[O:7])[CH:2]1[CH:3]1[C:4](=[O:5])[O:6][C:1](=[O:7])[CH:2]12

Participants

4

Reactant 1

HCID 7923Maleic Anhydride

Product 1

HCID 1072801,2,3,4-Cyclobutanetetracarboxylic dianhydrideYield 100%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 1 liter-glass flask equipped with a 500 W moderate-pressure mercury lamp, 100 g (1.02 M) of maleic anhydride and 1 kg of ethyl acetate were placed and mixed to provide a homogeneous solution. Under stirring in an agron atmosphere, the solution was irradiated with light by using the mercury lamp for 8 hours at 20° C. to precipitate a crystal. After the reaction, the crystal was recovered by filtration to obtain 3.3 g of cyclobutanetetracarboxylic dianhydride (100% trans form).

Workup

  1. additionmixed
  2. customto provide a homogeneous solution
  3. customthe solution was irradiated with light
  4. customfor 8 hours
  5. customat 20° C.
  6. customto precipitate a crystal
  7. customAfter the reaction
  8. filtrationthe crystal was recovered by filtration

Sources & evidence

ORD record
ord-7e8636e3b437432283c323dab4460fe3
Source dataset
uspto-grants-1999_12
Patent number
US06001276

Reaction notes

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