Catalytic Carbonylation of Acrylic Acid to Succinic Anhydride

Alternative sources for polymeric materials have been sought in the past few years to reduce our dependence on fossil feedstock. We report the catalytic carbonylation of acrylic acid, a platform chemical that can be bio-sourced, as a new pathway toward the formation of a useful monomer to polyesters, namely succinic anhydride. The novel system reported herein tackles the difficult carbonylation of unsaturated carboxylic acids through the utilization of an Earth-abundant metal catalyst, [Co-2(CO)(8)], in presence of a bidentate ligand, 1,2-bis(dicyclohexylphosphino)ethane (dcpe), and H-2. We investigated the influence of the reaction conditions through the variations of metal, ligand, temperature, pressure, and gas composition. The carbonylative ring-closure of acrylic acid was successfully obtained in high yield and selectivity toward the formation of succinic anhydride using mild conditions (90 & DEG;C and 16 bar of CO/H-2 95 : 5).

Automated summary

In order to reduce our reliance on fossil feedstock, alternative sources for polymeric materials have been sought in recent years. This study presents a new approach to the formation of a useful monomer for polyesters, succinic anhydride, through the catalytic carbonylation of bio-sourced acrylic acid. The use of an Earth-abundant metal catalyst, [Co-2(CO)(8)], along with a bidentate ligand, 1,2-bis(dicyclohexylphosphino)ethane (dcpe), and H-2, successfully tackles the challenging carbonylation of unsaturated carboxylic acids.