Selective Hydrogenation of 5‐Ethoxymethylfurfural over Alumina‐Supported Heterogeneous Catalysts

Ras, Erik‐Jan; Maisuls, Sergio; Haesakkers, Paul; Gruter, Gert‐Jan M.; Rothenberg, Gadi

doi:10.1002/adsc.200900526

Cited by 66 publications

(59 citation statements)

References 18 publications

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“…It can serve as a precursor to numerous products and chemical intermediates relevant to the fuel, polymer, and pharmaceutical industries [4][5][6][7][8][9]. Selective hydrogenation gives a fuel additive with combustion properties similar to ethanol, and superior diesel miscibility [10]. Biodiesel and jet fuel may be synthesized by hydrogenating the aldol-condensation products of HMF [5,6].…”

Section: Introductionmentioning

confidence: 99%

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

et al. 2010

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Solid catalysts based on SBA-15 silica were designed for the conversion of fructose to 5-hydroxymethylfurfural (HMF). The catalysts incorporate thioether groups that may promote the tautomerization of fructose to its furanose form, as well as sulfonic acid groups to catalyze its dehydration. The materials were characterized by elemental analysis, X-ray diffraction, N 2 adsorption/ desorption, and solid-state 13 C and 29 Si CP/MAS NMR spectroscopy. Functional groups incorporated into mesoporous silica by co-condensation are more robust under the reaction conditions (water at 180°C) than those grafted onto a non-porous silica. The bifunctional mesoporous catalyst achieved a selectivity for HMF of 74% at 66% fructose conversion.

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Section: Introductionmentioning

confidence: 99%

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

et al. 2010

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“…The samples are collected in the liquid phase and analyzed offline using GC (Varian #CP9205 column, FID detector). A detailed description of the equipment used and the catalyst synthesis methodology is published elsewhere [9].…”

Section: Resultsmentioning

confidence: 99%

“…The results are discussed in terms of mechanistic implications and process conditions, using data mining techniques to highlight general trends and explain their chemical meaning. We recently reported the hydrogenation of 1 over alumina supported catalysts [9]. The key results of the alumina-based catalysts are compared here with the silica-based results in terms of major trends.…”

Section: Introductionmentioning

confidence: 99%

Understanding Catalytic Biomass Conversion Through Data Mining

2010

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Catalytic conversion of biomass is a key challenge that we chemists face in the twenty-first century. Worldwide, research is conducted into obtaining bulk chemicals, polymers and fuels. Our project centres on glucose valorisation via furfural derivatives using catalytic hydrogenation. We present here new results for a set of 48 bimetallic catalysts supported on silica, and demonstrate the application of data mining tools to identify major trends in the data. These results are combined with a full factorial data set for the hydrogenation of 5-ethoxymethylfurfural over alumina-supported transition metal catalysts. All the catalysts in the combined datasets were synthesized and tested for performance under identical conditions. This, combined with the fact that no combinations of metals were left out, enables the use of advanced data mining tools. The paper describes the data and highlights the relevant trends from a chemist's viewpoint.

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“…Therefore, we turned to solid catalysts, which are both cheaper and easier to separate. 28 Here, we describe the efficient solid acid catalysed acetoxylation of LA to 2-APA. Subsequent pyrolysis can yield AA in high efficiency, regenerating acetic acid in the process (eqn (1)).…”

Section: -13mentioning

confidence: 99%

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

et al. 2015

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Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid Beerthuis, R.; Granollers, M.; Brown, D.R.; Salavagione, H.J.; Rothenberg, G.; Shiju, N.R. Published in: RSC Advances DOI:10.1039/c4ra12695eLink to publication Citation for published version (APA):Beerthuis, R., Granollers, M., Brown, D. R., Salavagione, H. J., Rothenberg, G., & Shiju, N. R. (2015). Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. RSC Advances, 5(6), 4103-4108. DOI: 10.1039/c4ra12695e General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.

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Selective Hydrogenation of 5‐Ethoxymethylfurfural over Alumina‐Supported Heterogeneous Catalysts

Cited by 66 publications

References 18 publications

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural

Understanding Catalytic Biomass Conversion Through Data Mining

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

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