PdPb-Catalyzed Decarboxylation of Proline to Pyrrolidine: Highly Selective Formation of a Biobased Amine in Water

© 2016 American Chemical Society. Amino acids have huge potential as platform chemicals in the biobased industry. Pd-catalyzed decarboxylation is a very promising route for the valorization of these natural compounds derived from protein waste or fermentation. We report that the highly abundant and nonessential amino acid L-proline is very reactive in the Pd-catalyzed decarboxylation. Full conversions are obtained with Pd/C and different Pd/MeOx catalysts; this allowed the identification of the different side reactions and the mapping of the reaction network. Due to the high reactivity of pyrrolidine, the selectivity for pyrrolidine was initially low. By carefully modifying Pd/ZrO2 with Pb in a controlled mannervia two incipient wetness impregnation stepsthe selectivity increased remarkably. Finally, a thorough investigation of the reaction parameters resulted in an increased activity of this modified catalyst and an even further enhanced selectivity under a low H2 pressure of 4 bar at 235 °C in water. This results in a very selective and sustainable production route for the highly interesting pyrrolidine.

Jaar van publicatie:2016

BOF-keylabel:ja

IOF-keylabel:ja

BOF-publication weight:6

CSS-citation score:1

Authors from:Higher Education

Toegankelijkheid:Open