Dimethyl Fumarate → Dimethyl Succinate

HRID 1379888Notes

Reaction equation

HRID 1379888 reaction equation
[CH3:1][CH:2]1[CH2:10][CH:9]=[C:8]2[CH:4]([C:5](=[O:12])[O:6][C:7]2=[O:11])[CH2:3]1.[C:13]([O:21][CH3:22])(=[O:20])/[CH:14]=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].C(OC)(=O)/C=C/C(OC)=O>>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][C:5]2=[O:12].[C:13]([O:21][CH3:22])(=[O:20])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 637568Dimethyl FumarateHCID 5271565Dimethyl maleate2×HCID 22445707HCID 22445707, compound

Product 2

HCID 7820Dimethyl SuccinateHCID 880694-Methylphthalic anhydride

Procedure

10 ml/hour of a solution of 1 mol of 5-methyl-tetrahydroisobenzofuran-1,3-dione and 2 mol of dimethyl maleate were pumped at 200° C. into the top of a trickle-phase reactor filled with 100 ml of catalyst in tablet form (5% by weight palladium-on-aluminium oxide). The conversion of the dimethyl maleate after passage through the reactor was 100%. No dimethyl fumarate could be detected in the product mixture leaving the reactor. 5-Methylisobenzofuran-1,3-dione and dimethyl succinate had been formed with selectivities of over 95% and over 97% respectively. The conversion of the dehydrogenation was 99.8%. The catalyst showed no signs of deactivation after 500 hours of operation.

Workup

  1. customleaving the reactor

Sources & evidence

ORD record
ord-381dc97d1e8449a88a854f5edccc856a
Source dataset
uspto-grants-1997_09
Patent number
US05672719

Reaction notes

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