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Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers

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Abstract

The production of monomers from bio-based platform chemicals shows great potential to reduce the chemical industry's demand for fossil resources. We herein present a two-step approach, which yields N-vinyl-2-pyrrolidone monomers from bio-based carboxylic acids, such as itaconic and levulinic acid. A highly active, heterogeneous palladium catalyst facilitating the reductive amidation of itaconic acid (TOF = 950 molPyr·molPd_surface−1 h−1) as well as the reductive amination of levulinic acid (TOF = 4000 molPyr·molPd_surface−1 h−1) was designed. Especially the reductive amidation of itaconic acid to 3- and 4-methyl-2-pyrrolidone was found to be structure sensitive. A clear trend between Pd particle size and catalyst activity could be shown by the synthesis of Pd/C catalysts with varying Pd particle sizes. The vinylation of the synthesized methyl-2-pyrrolidones with acetylene was tested using common industrial conditions (10–18 bar acetylene, 150 °C, KOH catalyst, no solvent). Similar to the industrial vinylation of 2-pyrrolidone, good yields of up to 80% N-vinyl-methyl-2-pyrrolidone were received. Therefore, and due to the excellent maximum yield of methyl-2-pyrrolidones in reductive amidation (95 mol%), the envisioned process can be a promising drop-in technology, directly replacing fossil resources in the production of an established monomer class.

Graphical abstract: Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers

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Supplementary files

Article information


Submitted
24 Mar 2020
Accepted
13 Jun 2020
First published
15 Jun 2020

Green Chem., 2020, Advance Article
Article type
Paper

Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers

Y. Louven, M. O. Haus, M. Konrad, J. P. Hofmann and R. Palkovits, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC01043J

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