Zeolite-encaged gold catalysts for the oxidative condensation of furfural

Abstract

The oxidative condensation between renewable furfural and fatty alcohols is a crucial avenue for producing high-quality liquid fuels and valuable furan derivatives. The selectivity control in this reaction process remains a significant challenge. Herein, we report the strategy of confining well dispersed gold species within ZSM-5 structure to construct highly active Au@ZSM-5 zeolite catalysts for the oxidative condensation of furfural. Characterization results and spectroscopy analyses demonstrate the efficient encapsulation of isolated and cationic Au clusters in zeolite structure. Au@ZSM-5(K) catalyst shows remarkable performance with 69.7% furfural conversion and 90.2% furan-2-acrolein selectivity as well as good recycle stability. It is revealed that the microstructure of ZSM-5 zeolite can significantly promote oxidative condensation activity through confinement effects. This work presents an explicit example of constructing zeolite encaged noble metal catalysts toward targeted chemical transformations.

Graphical abstract

Keywords

zeolite / encapsulation / gold / oxidative condensation / furfural

References

[1] Bozell J J , Petersen G R . Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “top 10” revisited. Green Chemistry, 2010, 12(4): 539–554

[2] Fatih Demirbas M . Current technologies for biomass conversion into chemicals and fuels. Energy Sources. Part A, Recovery, Utilization, and Environmental Effects, 2006, 28(13): 1181–1188

[3] Suttibak S , Sriprateep K , Pattiya A . Production of bio-oil via fast pyrolysis of cassava rhizome in a fluidised-bed reactor. Energy Procedia, 2012, 14: 668–673

[4] Alonso D M , Bond J Q , Dumesic J A . Catalytic conversion of biomass to biofuels. Green Chemistry, 2010, 12(9): 1493–1513

[5] Taylor M J , Durndell L J , Isaacs M A , Parlett C M A , Wilson K , Lee A F , Kyriakou G . Highly selective hydrogenation of furfural over supported Pt nanoparticles under mild conditions. Applied Catalysis B: Environmental, 2016, 180: 580–585

[6] MenegazzoFSignorettoMPinnaFManzoliMAinaVCerratoGBoccuzziF. Oxidative esterification of renewable furfural on gold-based catalysts: which is the best support? Journal of Catalysis, 2014, 309: 241–247

[7] Brandolese A , Ragno D , Di Carmine G , Bernardi T , Bortolini O , Giovannini P P , Pandoli O G , Altomare A , Massi A . Aerobic oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid and its derivatives by heterogeneous NHC-catalysis. Organic & Biomolecular Chemistry, 2018, 16(46): 8955–8964

[8] Choudhary H , Nishimura S , Ebitani K . Highly efficient aqueous oxidation of furfural to succinic acid using reusable heterogeneous acid catalyst with hydrogen peroxide. Chemistry Letters, 2012, 41(4): 409–411

[9] Nguyen Thanh D , Kikhtyanin O , Ramos R , Kothari M , Ulbrich P , Munshi T , Kubička D . Nanosized TiO₂—A promising catalyst for the aldol condensation of furfural with acetone in biomass upgrading. Catalysis Today, 2016, 277: 97–107

[10] Taarning E , Nielsen I S , Egeblad K , Madsen R , Christensen C H . Chemicals from renewables: aerobic oxidation of furfural and hydroxymethylfurfural over gold catalysts. ChemSusChem, 2008, 1(1): 75–78

[11] Li H , Riisager A , Saravanamurugan S , Pandey A , Sangwan R S , Yang S , Luque R . Carbon-increasing catalytic strategies for upgrading biomass into energy-intensive fuels and chemicals. ACS Catalysis, 2018, 8(1): 148–187

[12] Zhang X , Xu S , Li Q , Zhou G , Xia H . Recent advances in the conversion of furfural into bio-chemicals through chemo- and bio-catalysis. RSC Advances, 2021, 11(43): 27042–27058

[13] Li X , Jia P , Wang T . Furfural: a promising platform compound for sustainable production of C4 and C5 chemicals. ACS Catalysis, 2016, 6(11): 7621–7640

[14] Luo Y , Li Z , Li X , Pandey A , Sangwan R S , Yang S , Luque R . The production of furfural directly from hemicellulose in lignocellulosic biomass: a review. Catalysis Today, 2019, 319: 14–24

[15] Xia H , Xu S , Hu H , An J , Li C . Efficient conversion of 5-hydroxymethylfurfural to high-value chemicals by chemo- and bio-catalysis. RSC Advances, 2018, 8(54): 30875–30886

[16] Fang Q , Qin Z X , Shi Y , Liu F , Barkaoui S , Abroshan H , Li G , Qin Z , Shi Y , Liu F . . Au/NiO composite: a catalyst for one-pot cascade conversion of furfural. ACS Applied Energy Materials, 2019, 2(4): 2654–2661

[17] Tong X , Liu Z , Yu L , Li Y . A tunable process: catalytic transformation of renewable furfural with aliphatic alcohols in the presence of molecular oxygen. Chemical Communications, 2015, 51(17): 3674–3677

[18] Tong X , Liu Z , Hu J , Liao S . Au-catalyzed oxidative condensation of renewable furfural and ethanol to produce furan-2-acrolein in the presence of molecular oxygen. Applied Catalysis A, General, 2016, 510: 196–203

[19] Gao Y , Tong X , Zhang H . A selective oxidative valorization of biomass-derived furfural and ethanol with the supported gold catalysts. Catalysis Today, 2020, 355: 238–245

[20] Monti E , Ventimiglia A , Soto C A G , Martelli F , Rodríguez-Aguado E , Cecilia J A , Maireles-Torres P , Ospitali F , Tabanelli T , Albonetti S . . Oxidative condensation/esterification of furfural with ethanol using preformed Au colloidal nanoparticles. Impact of stabilizer and heat treatment protocols on catalytic activity and stability. Molecular Catalysis, 2022, 528: 112438

[21] Sankar M , He Q , Engel R V , Sainna M A , Logsdail A J , Roldan A , Willock D J , Agarwal N , Kiely C J , Hutchings G J . Role of the support in gold-containing nanoparticles as heterogeneous catalysts. Chemical Reviews, 2020, 120(8): 3890–3938

[22] Zhang Y , Cui X , Shi F , Deng Y . Nano-gold catalysis in fine chemical synthesis. Chemical Reviews, 2012, 112(4): 2467–2505

[23] Ishida T , Taketoshi A , Haruta M . Gold nanoparticles for oxidation reactions: critical role of supports and Au particle size. Topics in Organometallic Chemistry, 2020, 66: 1–48

[24] Liu L , Corma A . Confining isolated atoms and clusters in crystalline porous materials for catalysis. Nature Reviews. Materials, 2021, 6(3): 244–263

[25] Schauermann S , Nilius N , Shaikhutdinov S , Freund H J . Nanoparticles for heterogeneous catalysis: new mechanistic insights. Accounts of Chemical Research, 2013, 46(8): 1673–1681

[26] Chen M S , Goodman D W . The structure of catalytically active gold on titania. Science, 2004, 306(5694): 252–255

[27] Majimel J , Lamirand-Majimel M , Moog I , Feral-Martin C , Tréguer-Delapierre M . Size-dependent stability of supported gold nanostructures onto ceria: an HRTEM study. Journal of Physical Chemistry C, 2009, 113(21): 9275–9283

[28] Yusuf S , Jiao F . Effect of the support on the photocatalytic water oxidation activity of cobalt oxide nanoclusters. ACS Catalysis, 2012, 2(12): 2753–2760

[29] Prati L , Villa A . Gold colloids: from quasi-homogeneous to heterogeneous catalytic systems. Accounts of Chemical Research, 2014, 47(3): 855–863

[30] Chai Y , Liu S , Zhao Z , Gong J , Dai W , Wu G , Guan N , Li L . Selectivity modulation of encapsulated palladium nanoparticles by zeolite microenvironment for biomass catalytic upgrading. ACS Catalysis, 2018, 8(9): 8578–8589

[31] Gao M , Gong Z , Weng X , Shang W , Chai Y , Dai W , Wu G , Guan N , Li L . Methane combustion over palladium catalyst within the confined space of MFI zeolite. Chinese Journal of Catalysis, 2021, 42(10): 1689–1699

[32] Shang W , Gao M , Chai Y , Wu G , Guan N , Li L . Stabilizing isolated rhodium cations by MFI zeolite for heterogeneous methanol carbonylation. ACS Catalysis, 2021, 11(12): 7249–7256

[33] Farshi A , Shaiyegh F , Burogerdi S H , Dehgan A . FCC process role in propylene demands. Petroleum Science and Technology, 2011, 29(9): 875–885

[34] Yan H T , Le Van Mao R . Hybrid catalysts used in the catalytic steam cracking process (CSC): influence of the pore characteristics and the surface acidity properties of the ZSM-5 zeolite-based component on the overall catalytic performance. Applied Catalysis A, General, 2010, 375(1): 63–69

[35] Farshi A , Abri H R . The addition of ZSM-5 to a fluid catalytic cracking catalyst for increasing olefins in fluid catalytic cracking light gas. Petroleum Science and Technology, 2012, 30(12): 1285–1295

[36] Ying F , Wang S , Au C T , Lai S Y . Effect of the oxidation state of gold on the complete oxidation of isobutane on Au/CeO₂ catalysts. Gold Bulletin, 2010, 43(4): 241–251

[37] Zhang M , Liu Q , Long H , Sun L , Murayama T , Qi C . Insights into Au nanoparticle size and chemical state of Au/ZSM-5 catalyst for catalytic cracking of n-octane to increase propylene production. Journal of Physical Chemistry C, 2021, 125(29): 16013–16023

[38] Huang H , Ye W , Song C , Liu Y , Zhang X , Shan Y , Ge Y , Zhang S , Lu R . Confinement of Au³⁺-rich clusters by using silicalite-1 for selective solvent-free oxidation of toluene. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2021, 9(26): 14710–14721

[39] Boccuzzi F , Chiorino A . FTIR study of carbon monoxide oxidation and scrambling at room temperature over copper supported on ZnO and TiO₂. Journal of Physical Chemistry, 1996, 100(9): 3617–3624

[40] Boccuzzi F , Chiorino A , Manzoli M . FTIR study of the electronic effects of CO adsorbed on gold nanoparticles supported on titania. Surface Science, 2000, 454(1): 942–946

[41] Boccuzzi F , Chiorino A . FTIR study of CO oxidation on Au/TiO₂ at 90 K and room temperature. An insight into the nature of the reaction centers. Journal of Physical Chemistry B, 2000, 104(23): 5414–5416

[42] Minicò S , Scirè S , Crisafulli C , Visco A M , Galvagno S . Galvagno S. FT-IR study of Au/Fe₂O₃ catalysts for CO oxidation at low temperature. Catalysis Letters, 1997, 47(3): 273–276

[43] Chen H , Li Z , Qin Z , Kim H J , Abroshan H , Li G . Silica-encapsulated gold nanoclusters for efficient acetylene hydrogenation to ethylene. ACS Applied Nano Materials, 2019, 2(5): 2999–3006

[44] Simakov A , Tuzovskaya I , Pestryakov A , Bogdanchikova N , Gurin V , Avalos M , Farías M H . On the nature of active gold species in zeolites in CO oxidation. Applied Catalysis A, General, 2007, 331(1): 121–128

[45] Yang N , Pattisson S , Douthwaite M , Zeng G , Zhang H , Ma J , Hutchings G J . Influence of stabilizers on the performance of Au/TiO₂ catalysts for CO oxidation. ACS Catalysis, 2021, 11(18): 11607–11615

RIGHTS & PERMISSIONS

Higher Education Press