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Precious Metals

Atomically dispersed ruthenium hydride on beta zeolite as catalysts for the isomerization of muconates


  • Vercammen, J. et al. Shape-selective C–H activation of aromatics to biarylic compounds using molecular palladium in zeolites. Nat. Catal. 3, 1002–1009 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Lange, J.-P. Performance metrics for sustainable catalysis in industry. Nat. Catal. 4, 186–192 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Brandi, F., Khalil, I., Antonietti, M. & Al-Naji, M. Continuous-flow production of isosorbide from aqueous-cellulosic derivable feed over sustainable heterogeneous catalysts. ACS Sustain. Chem. Eng. 9, 927–935 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Dusselier, M., Van Wouwe, P., Dewaele, A., Makshina, E. & Sels, B. F. Lactic acid as a platform chemical in the biobased economy: the role of chemocatalysis. Energy Environ. Sci. 6, 1415–1442 (2013).

    Article 
    CAS 

    Google Scholar
     

  • te Molder, T. D. J., Kersten, S. R. A., Lange, J.-P. & Ruiz, M. P. From woody biomass to ethylene glycol: inorganics removal boosts the yield. Ind. Eng. Chem. Res. 60, 13515–13522 (2021).

    Article 

    Google Scholar
     

  • Van Praet, S., Preegel, G., Rammal, F. & Sels, B. F. One-pot consecutive reductive amination synthesis of pharmaceuticals: from biobased glycolaldehyde to hydroxychloroquine. ACS Sustain. Chem. Eng. 10, 6503–6508 (2022).

    Article 

    Google Scholar
     

  • Schutyser, W. et al. Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem. Soc. Rev. 47, 852–908 (2018).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Sun, Z. et al. Complete lignocellulose conversion with integrated catalyst recycling yielding valuable aromatics and fuels. Nat. Catal. 1, 82–92 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Liao, Y. et al. A sustainable wood biorefinery for low-carbon footprint chemicals production. Science 367, 1385–1390 (2020).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Dusselier, M., Mascal, M. & Sels, B. F. in Selective Catalysis for Renewable Feedstocks and Chemicals (ed. Nicholas, K.) 1–40 (Springer Cham, 2014).

  • Lange, J.-P. Towards circular carbo-chemicals – the metamorphosis of petrochemicals. Energy Environ. Sci. 14, 4358–4376 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Gao, C., Ma, C. & Xu, P. Biotechnological routes based on lactic acid production from biomass. Biotechnol. Adv. 29, 930–939 (2011).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Araji, N. et al. Synthesis of maleic and fumaric acids from furfural in the presence of betaine hydrochloride and hydrogen peroxide. Green Chem. 19, 98–101 (2017).

    Article 
    CAS 

    Google Scholar
     

  • Yu, Q. et al. A sustainable system for maleic acid synthesis from biomass-derived sugar. J. Chem. Technol. Biotechnol. 95, 751–757 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Kang, S., Fu, J. & Zhang, G. From lignocellulosic biomass to levulinic acid: a review on acid-catalyzed hydrolysis. Renew. Sustain. Energy Rev. 94, 340–362 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Xu, W.-P. et al. Conversion of levulinic acid to valuable chemicals: a review. J. Chem. Technol. Biotechnol. 96, 3009–3024 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Schwartz, T. J., Shanks, B. H. & Dumesic, J. A. Coupling chemical and biological catalysis: a flexible paradigm for producing biobased chemicals. Curr. Opin. Biotechnol. 38, 54–62 (2016).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Shanks, B. H. & Keeling, P. L. Bioprivileged molecules: creating value from biomass. Green Chem. 19, 3177–3185 (2017).

    Article 
    CAS 

    Google Scholar
     

  • Shanks, B. H. & Broadbelt, L. J. A robust strategy for sustainable organic chemicals utilizing bioprivileged molecules. ChemSusChem 12, 2970–2975 (2019).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Khalil, I., Quintens, G., Junkers, T. & Dusselier, M. Muconic acid isomers as platform chemicals and monomers in the biobased economy. Green Chem. 22, 1517–1541 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Briou, B., Améduri, B. & Boutevin, B. Trends in the Diels–Alder reaction in polymer chemistry. Chem. Soc. Rev. 50, 11055–11097 (2021).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Maniar, D. et al. Enzymatic synthesis of muconic acid-based polymers: trans, trans-dimethyl muconate and trans, β-dimethyl hydromuconate. Polymers 13, 2498 (2021).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Zhang, H., Jiang, H., Zhang, Y., Zhang, N. & Xiong, R. Ferroelectric lithography in single‐component organic enantiomorphic ferroelectrics. Angew. Chem. Int. Ed. 61, e202200135 (2022).

    Article 
    CAS 

    Google Scholar
     

  • Carter, P. et al. Bioenabled platform to access polyamides with built-in target properties. J. Am. Chem. Soc. 22, 9548–9553 (2022).

    Article 

    Google Scholar
     

  • He, J. et al. Zirconium phosphate supported copper catalyst for selective oxidation of phenol to cis, cis-muconic acid. Appl. Catal. A 664, 119351 (2023).

    Article 
    CAS 

    Google Scholar
     

  • Klein, B. C. et al. Economics and global warming potential of a commercial-scale delignifying biorefinery based on co-solvent enhanced lignocellulosic fractionation to produce alcohols, sustainable aviation fuels, and co-products from biomass. Energy Environ. Sci. 17, 1202–1215 (2024).

    Article 
    CAS 

    Google Scholar
     

  • Ling, C. et al. Muconic acid production from glucose and xylose in Pseudomonas putida via evolution and metabolic engineering. Nat. Commun. 13, 4925 (2022).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Shiramizu, M. & Toste, F. D. Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration. Angew. Chem. Int. Ed. 52, 12905–12909 (2013).

    Article 
    CAS 

    Google Scholar
     

  • Saraçi, E., Wang, L., Theopold, K. H. & Lobo, R. F. Bioderived muconates by cross‐metathesis and their conversion into terephthalates. ChemSusChem 11, 773–780 (2018).

    Article 
    PubMed 

    Google Scholar
     

  • Quintens, G., Vrijsen, J., Adriaensens, P., Vanderzande, D. & Junkers, T. Muconic acid esters as bio-based acrylate mimics. Polym. Chem. 10, 5555–5563 (2019).

    Article 
    CAS 

    Google Scholar
     

  • Carraher, J. M., Pfennig, T., Rao, R. G., Shanks, B. H. & Tessonnier, J. P. cis,cis-Muconic acid isomerization and catalytic conversion to biobased cyclic-C6-1,4-diacid monomers. Green Chem. 19, 3042–3050 (2017).

    Article 
    CAS 

    Google Scholar
     

  • Lu, R. et al. Production of diethyl terephthalate from biomass-derived muconic acid. Angew. Chem. Int. Ed. 55, 249–253 (2016).

    Article 
    CAS 

    Google Scholar
     

  • Rammal, F., Gaumont, A. C. & Lakhdar, S. Metal-free visible-light-mediated aromatization of 1,2-dihydronaphthalenes. Eur. J. Org. Chem. 2020, 1482–1485 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Carraher, J. M. et al. Solvent-driven isomerization of cis,cis-muconic acid for the production of specialty and performance-advantaged cyclic biobased monomers. Green Chem. 22, 6444–6454 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Gopalakrishnan, D. K., Bhardwaj, S., Kumar, S., Karmakar, T. & Vaitla, J. Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides with diazo compounds and acetals. Chem. Commun. 60, 3846–3849 (2024).

    Article 
    CAS 

    Google Scholar
     

  • Grundmann, C. Zur kenntnis der oxydation von phenolen mit peressigsäure. Ber. Dtsch. Chem. Ges. 69, 1755–1757 (1936).

    Article 

    Google Scholar
     

  • Settle, A. E. et al. Iodine-catalyzed Isomerization of dimethyl muconate. ChemSusChem 11, 1768–1780 (2018).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Frost, J. W., Miermont, A., Schweitzer, D. & Bui, V. Preparation of trans, trans muconic acid and trans, trans muconates. US patent US0314243 A1 (2010).

  • Bui, V., MacRae, D. & Schweitzer, D. Methods for producing isomers of muconic acid and muconate salts. US patent US0030215 (2013).

  • Tessonnier, J. P., Carraher, J. M., Pfennig, T. & Shanks, B. Isomerization of muconic acid. US patent US9957218 B2 (2018).

  • Khalil, I. et al. Solvent-driven isomerization of muconates in DMSO: reaction mechanism and process sustainability. Green Chem. 26, 5852–5861 (2024).

    Article 
    CAS 

    Google Scholar
     

  • Peeters, E. et al. Tandem reduction–reoxidation augments the catalytic activity of Sn-beta zeolites by redispersion and respeciation of SnO2 clusters. Chem. Mater. 33, 9366–9381 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Kerstens, D. et al. Fast and selective solvent-free branching of unsaturated fatty acids with hierarchical ZSM-5. ACS Sustain. Chem. Eng. 9, 4357–4362 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Shah, M. A. et al. Catalytic amination of lactic acid using Ru–zeolites. Dalton Trans. 51, 10773–10778 (2022).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Philippaerts, A. et al. Design of Ru–zeolites for hydrogen-free production of conjugated linoleic acids. ChemSusChem 4, 757–767 (2011).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Yue, C. J., Liu, Y. & He, R. Olefins isomerization by hydride-complexes of ruthenium. J. Mol. Catal. Chem. 259, 17–23 (2006).

    Article 
    CAS 

    Google Scholar
     

  • Wang, A., Li, J. & Zhang, T. Heterogeneous single-atom catalysis. Nat. Rev. Chem. 2, 65–81 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Ge, L. et al. Synergistic catalysis of Ru single-atoms and zeolite boosts high-efficiency hydrogen storage. Appl. Catal. B 319, 121958 (2022).

    Article 
    CAS 

    Google Scholar
     

  • Matthiesen, J. E., Carraher, J. M., Vasiliu, M., Dixon, D. A. & Tessonnier, J. P. Electrochemical conversion of muconic acid to biobased diacid monomers. ACS Sustain. Chem. Eng. 4, 3575–3585 (2016).

    Article 
    CAS 

    Google Scholar
     

  • Qiu, J.-Z. et al. Pure siliceous zeolite-supported Ru single-atom active sites for ammonia synthesis. Chem. Mater. 31, 9413–9421 (2019).

    Article 
    CAS 

    Google Scholar
     

  • Tekin, K., Hao, N., Karagoz, S. & Ragauskas, A. J. Ethanol: a promising green solvent for the deconstruction of lignocellulose. ChemSusChem 11, 3559–3575 (2018).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Yang, H. et al. Isolated single‐atom ruthenium anchored on beta zeolite as an efficient heterogeneous catalyst for styrene epoxidation. ChemNanoMat 6, 1647–1651 (2020).

    Article 
    CAS 

    Google Scholar
     

  • Sun, R. et al. Heterogeneous catalysts for CO2 hydrogenation to formic acid/formate: from nanoscale to single atom. Energy Environ. Sci. 14, 1247–1285 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Ghoreishian, S. M., Shariati, K., Huh, Y. S. & Lauterbach, J. Recent advances in ammonia synthesis over ruthenium single-atom-embedded catalysts: a focused review. Chem. Eng. J. 467, 143533 (2023).

    Article 
    CAS 

    Google Scholar
     

  • Mon, M. et al. Stabilized Ru[(H2O)6]3+ in confined spaces (MOFs and zeolites) catalyzes the imination of primary alcohols under atmospheric conditions with wide scope. ACS Catal. 8, 10401–10406 (2018).

    Article 
    CAS 

    Google Scholar
     

  • Wang, D. & Astruc, D. The golden age of transfer hydrogenation. Chem. Rev. 115, 6621–6686 (2015).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Capeletti, M. R., Balzano, L., de la Puente, G., Laborde, M. & Sedran, U. Synthesis of acetal (1,1-diethoxyethane) from ethanol and acetaldehyde over acidic catalysts. Appl. Catal. A 198, L1–L4 (2000).

    Article 
    CAS 

    Google Scholar
     

  • Hao, W. et al. Ru-catalyzed enantioselective hydrogenation of 2-pyridyl-substituted alkenes and substrate-mediated H/D exchange. ACS Catal. 12, 1150–1160 (2022).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Kita, Y., Kuwabara, M., Yamadera, S., Kamata, K. & Hara, M. Effects of ruthenium hydride species on primary amine synthesis by direct amination of alcohols over a heterogeneous Ru catalyst. Chem. Sci. 11, 9884–9890 (2020).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar
     

  • Wachs, I. E. & Bañares, M. A. (eds) Springer Handbook of Advanced Catalyst Characterization (Springer Cham, 2023).

  • Wang, X. & Andrews, L. Infrared spectra and theoretical calculations for Fe, Ru, and Os metal hydrides and dihydrogen complexes. J. Phys. Chem. A 113, 551–563 (2009).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Settle, A. E. et al. Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds. Green Chem. 19, 3468–3492 (2017).

    Article 
    CAS 

    Google Scholar
     

  • Shang, Y., Xu, X., Gao, B., Wang, S. & Duan, X. Single-atom catalysis in advanced oxidation processes for environmental remediation. Chem. Soc. Rev. 50, 5281–5322 (2021).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • Devos, J. et al. Engineering low-temperature ozone activation of zeolites: process specifics, possible mechanisms and hybrid activation methods. Chem. Eng. J. 431, 133862 (2022).

    Article 
    CAS 

    Google Scholar
     

  • Zavala‐Sanchez, L., Khalil, I., Oliviero, L., Paul, J. & Maugé, F. Structure and quantification of edge sites of WS2/Al2O3 catalysts coupling IR/CO spectroscopy and DFT calculations. ChemCatChem 12, 2066–2076 (2020).

    Article 

    Google Scholar
     

  • Emeis, C. A. Determination of integrated molar extinction coefficients for infrared absorption bands of pyridine adsorbed on solid acid catalysts. J. Catal. 141, 347–354 (1993).

    Article 
    CAS 

    Google Scholar
     

  • Devos, J., Robijns, S., Van Goethem, C., Khalil, I. & Dusselier, M. Interzeolite conversion and the role of aluminum: toward generic principles of acid site genesis and distributions in ZSM-5 and SSZ-13. Chem. Mater. 33, 2516–2531 (2021).

    Article 
    CAS 

    Google Scholar
     

  • Ravel, B. & Newville, M. ATHENA, ARTEMIS, HEPHAESTUS: data analysis for X-ray absorption spectroscopy using IFEFFIT. J. Synchrotron Radiat. 12, 537–541 (2005).

    Article 
    CAS 
    PubMed 

    Google Scholar
     

  • te Velde, G. et al. Chemistry with ADF. J. Comput. Chem. 22, 931–967 (2001).

    Article 

    Google Scholar
     

  • Martini, A. et al. PyFitIt: the software for quantitative analysis of XANES spectra using machine-learning algorithms. Comput. Phys. Commun. 250, 107064 (2020).

    Article 
    CAS 

    Google Scholar
     



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