Jump to main content
Jump to site search

Issue 8, 2017
Previous Article Next Article

Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines

Author affiliations

Abstract

Glutamic acid is a promising renewable platform molecule which is abundantly available in biomass waste streams; it is also efficiently manufactured by fermentation. Here we report the reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines. In order to recycle nitrogen in an industrially relevant co-product, glutamic acid was modified to N,N-dimethylglutamic acid by a mild reductive alkylation with Pd/C. Subsequently, selective C–N hydrogenolysis in methanol resulted in dimethyl glutarate and trimethylamine. A wide screening of transition metals (Pt, Pd, Rh and Ru) immobilized on various supports showed that the highest yields of dimethyl glutarate were obtained with Pt/TiO2. An FTIR study and kinetic experiments on metal-loaded and unloaded supports demonstrate that the interplay between the metal and the moderate acidity of the support results in the excellent C–N hydrogenolysis activity and selectivity. Finally, reaction parameter optimization resulted in 81% yield of dimethyl glutarate with 1 wt% Pt/TiO2 at 225 °C, 30 bar H2 after 8 h.

Graphical abstract: Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 22 Nov 2016, accepted on 14 Feb 2017 and first published on 14 Feb 2017


Article type: Paper
DOI: 10.1039/C6GC03222B
Citation: Green Chem., 2017,19, 1866-1876
  •   Request permissions

    Metal-catalyzed reductive deamination of glutamic acid to bio-based dimethyl glutarate and methylamines

    F. De Schouwer, T. Cuypers, L. Claes and D. E. De Vos, Green Chem., 2017, 19, 1866
    DOI: 10.1039/C6GC03222B

Search articles by author