Bio-Based Chemicals: Selective Aerobic Oxidation of Tetrahydrofuran-2,5-dimethanol to Tetrahydrofuran-2,5-dicarboxylic Acid Using Hydrotalcite-Supported Gold Catalysts

Qingqing Yuan, Kevin Hiemstra, Tim G. Meinds, Ibrahim Chaabane, Zhenchen Tang, Leon Rohrbach, Wilbert Vrijburg, Tiny Verhoeven, Emiel J. M. Hensen, Siebe van der Veer, Paolo P. Pescarmona, Hero J. Heeres, Peter J. Deuss*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

14 Citaten (Scopus)
396 Downloads (Pure)

Samenvatting

A new, sustainable catalytic route for the synthesis of tetrahydrofuran-2,5-dicarboxylic acid (THFDCA), a compound with potential application in polymer industry, is presented starting from the bio-based platform chemical 5-(hydroxymethyl)furfural (HMF). This conversion was successfully achieved via oxidation of tetrahydrofuran-2,5-dimethanol (THFDM) over hydrotalcite (HT)-supported gold nano-particle catalysts (similar to 2 wt %) in water. THFDM was readily obtained with high yield (>99%) from HMF at a demonstrated 20 g scale by catalytic hydrogenation. The highest yield of THFDCA (91%) was achieved after 7 h at 110 degrees C under 30 bar air pressure and without addition of a homogeneous base. Additionally, Au-Cu bimetallic catalysts supported on HT were prepared and showed enhanced activity at lower temperature compared to the monometallic gold catalysts. In addition to THFDCA, the intermediate oxidation product with one alcohol and one carboxylic acid group (5-hydroxymethyl tetrahydrofuran-2-carboxylic acid, THFCA) was identified and isolated from the reactions. Further investigations indicated that the gold nanoparticle size and basicity of HT supports significantly influence the performance of the catalyst and that sintering of gold nanoparticles was the main pathway for catalyst deactivation. Operation in a continuous setup using one of the Au-Cu catalysts revealed that product adsorption and deposition also contributes to a decrease in catalyst performance.

Originele taal-2English
Pagina's (van-tot)4647-4656
Aantal pagina's19
TijdschriftACS Sustainable Chemistry & Engineering
Volume7
Nummer van het tijdschrift5
DOI's
StatusPublished - 4-mrt-2019

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