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 (Corresponding author)

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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 nanoparticle catalysts (∼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 °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-2Engels
Pagina's (van-tot)4647-4656
Aantal pagina's10
TijdschriftACS Sustainable Chemistry & Engineering
Volume7
Nummer van het tijdschrift5
DOI's
StatusGepubliceerd - 4 mrt 2019

Vingerafdruk

hydrotalcite
Dicarboxylic Acids
Gold
gold
catalyst
oxidation
Oxidation
Catalysts
Acids
acid
Furfural
Nanoparticles
Carboxylic acids
Catalyst supports
carboxylic acid
Furaldehyde
Catalyst deactivation
Alkalinity
Carboxylic Acids
Hydrogenation

Citeer dit

Yuan, Qingqing ; Hiemstra, Kevin ; Meinds, Tim G. ; Chaabane, Ibrahim ; Tang, Zhenchen ; Rohrbach, Leon ; Vrijburg, Wilbert ; Verhoeven, Tiny ; Hensen, Emiel J.M. ; van der Veer, Siebe ; Pescarmona, Paolo P. ; Heeres, Hero J. ; Deuss, Peter J. / Bio-based chemicals : Selective aerobic oxidation of tetrahydrofuran-2,5-dimethanol to tetrahydrofuran-2,5-dicarboxylic acid using hydrotalcite-supported gold catalysts. In: ACS Sustainable Chemistry & Engineering. 2019 ; Vol. 7, Nr. 5. blz. 4647-4656.
@article{64821cd8bb89463ea5d9b83e2192d405,
title = "Bio-based chemicals: Selective aerobic oxidation of tetrahydrofuran-2,5-dimethanol to tetrahydrofuran-2,5-dicarboxylic acid using hydrotalcite-supported gold catalysts",
abstract = "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 nanoparticle catalysts (∼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 °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.",
keywords = "Gold catalysts, Hydrotalcite, Oxidation catalysis, Renewable chemicals, Tetrahydrofuran-2,5-dimethanol",
author = "Qingqing Yuan and Kevin Hiemstra and Meinds, {Tim G.} and Ibrahim Chaabane and Zhenchen Tang and Leon Rohrbach and Wilbert Vrijburg and Tiny Verhoeven and Hensen, {Emiel J.M.} and {van der Veer}, Siebe and Pescarmona, {Paolo P.} and Heeres, {Hero J.} and Deuss, {Peter J.}",
year = "2019",
month = "3",
day = "4",
doi = "10.1021/acssuschemeng.8b03821",
language = "English",
volume = "7",
pages = "4647--4656",
journal = "ACS Sustainable Chemistry & Engineering",
issn = "2168-0485",
publisher = "American Chemical Society",
number = "5",

}

Bio-based chemicals : Selective aerobic oxidation of tetrahydrofuran-2,5-dimethanol to tetrahydrofuran-2,5-dicarboxylic acid using hydrotalcite-supported gold catalysts. / Yuan, Qingqing; Hiemstra, Kevin; Meinds, Tim G.; Chaabane, Ibrahim; Tang, Zhenchen; Rohrbach, Leon; Vrijburg, Wilbert; Verhoeven, Tiny; Hensen, Emiel J.M.; van der Veer, Siebe; Pescarmona, Paolo P.; Heeres, Hero J.; Deuss, Peter J. (Corresponding author).

In: ACS Sustainable Chemistry & Engineering, Vol. 7, Nr. 5, 04.03.2019, blz. 4647-4656.

Onderzoeksoutput: Bijdrage aan tijdschriftTijdschriftartikelAcademicpeer review

TY - JOUR

T1 - Bio-based chemicals

T2 - Selective aerobic oxidation of tetrahydrofuran-2,5-dimethanol to tetrahydrofuran-2,5-dicarboxylic acid using hydrotalcite-supported gold catalysts

AU - Yuan, Qingqing

AU - Hiemstra, Kevin

AU - Meinds, Tim G.

AU - Chaabane, Ibrahim

AU - Tang, Zhenchen

AU - Rohrbach, Leon

AU - Vrijburg, Wilbert

AU - Verhoeven, Tiny

AU - Hensen, Emiel J.M.

AU - van der Veer, Siebe

AU - Pescarmona, Paolo P.

AU - Heeres, Hero J.

AU - Deuss, Peter J.

PY - 2019/3/4

Y1 - 2019/3/4

N2 - 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 nanoparticle catalysts (∼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 °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.

AB - 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 nanoparticle catalysts (∼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 °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.

KW - Gold catalysts

KW - Hydrotalcite

KW - Oxidation catalysis

KW - Renewable chemicals

KW - Tetrahydrofuran-2,5-dimethanol

UR - http://www.scopus.com/inward/record.url?scp=85061894632&partnerID=8YFLogxK

U2 - 10.1021/acssuschemeng.8b03821

DO - 10.1021/acssuschemeng.8b03821

M3 - Article

AN - SCOPUS:85061894632

VL - 7

SP - 4647

EP - 4656

JO - ACS Sustainable Chemistry & Engineering

JF - ACS Sustainable Chemistry & Engineering

SN - 2168-0485

IS - 5

ER -