Stability of solid rhenium catalysts for liquid-phase biomass valorization–various facets of catalyst deactivation and rhenium leaching
Tài liệu tham khảo
Herrmann, 1990, Essays über Metallorganische Chemie V. Stand und Aussichten der Rhenium-Chemie in der Katalyse, J. Organomet. Chem., 382, 1, 10.1016/0022-328X(90)85211-G
Gothe, 2021, Rhenium – a tuneable player in tailored hydrogenation catalysis, Eur. J. Inorg. Chem., 2021, 4043, 10.1002/ejic.202100459
Davenport, 1968, Advances in rhenium catalysts, Ind. Eng. Chem., 60, 10, 10.1021/ie50707a004
Margitfalvi, 1984, Role of rhenium in bimetallic reforming catalysts, React. Kinet. Catal. Lett., 24, 315, 10.1007/BF02093449
Jothimurugesan, 1985, Role of rhenium in Pt-Re-Al2O3 reforming catalysis—an integrated study, AIChE J., 31, 1997, 10.1002/aic.690311209
Hilmen, 1996, TPR study of the mechanism of rhenium promotion of alumina-supported cobalt Fischer-Tropsch catalysts, Catal. Lett., 38, 143, 10.1007/BF00806560
Bertole, 2004, Support and rhenium effects on the intrinsic site activity and methane selectivity of cobalt Fischer-Tropsch catalysts, J. Catal., 221, 191, 10.1016/j.jcat.2003.08.006
Mol, 1999, Olefin metathesis over supported rhenium oxide catalysts, Catal. Today, 51, 289, 10.1016/S0920-5861(99)00051-6
Lwin, 2014, Olefin metathesis by supported metal oxide catalysts, ACS Catal., 4, 2505, 10.1021/cs500528h
Sádaba, 2015, Deactivation of solid catalysts in liquid media: the case of leaching of active sites in biomass conversion reactions, Green Chem., 17, 4133, 10.1039/C5GC00804B
Alonso, 2012, Bimetallic catalysts for upgrading of biomass to fuels and chemicals, Chem. Soc. Rev., 41, 8075, 10.1039/c2cs35188a
Petersen, 2017, New motifs in deoxydehydration: beyond the realms of rhenium, Chem. Eur J., 23, 10235, 10.1002/chem.201701153
Tshibalonza, 2020, The deoxydehydration (DODH) reaction: a versatile technology for accessing olefins from bio-based polyols, Green Chem., 22, 4801, 10.1039/D0GC00689K
Vaidya, 2017, Review of hydrogen production by catalytic aqueous-phase reforming, ChemistrySelect, 2, 6563, 10.1002/slct.201700905
Tomishige, 2017, Selective hydrogenolysis and hydrogenation using metal catalysts directly modified with metal oxide species, Green Chem., 19, 2876, 10.1039/C7GC00620A
Nakagawa, 2018, Perspective on catalyst development for glycerol reduction to C3 chemicals with molecular hydrogen, Res. Chem. Intermed., 44, 3879, 10.1007/s11164-018-3481-2
Murphy, 2018, Foundational techniques for catalyst design in the upgrading of biomass-derived multifunctional molecules, Prog. Energy Combust. Sci., 67, 1, 10.1016/j.pecs.2018.01.003
Fasolini, 2019, Hydrogen from renewables: a case study of glycerol reforming, Catalysts, 9, 722, 10.3390/catal9090722
Fasolini, 2019, A short overview on the hydrogen production via aqueous phase reforming (APR) of cellulose, C6-C5 sugars and polyols, Catalysts, 9, 917, 10.3390/catal9110917
Shi, 2019, Valorization of biomass-derived small oxygenates: kinetics, mechanisms and site requirements of H 2 -involved hydrogenation and deoxygenation pathways over heterogeneous catalysts, ChemCatChem, 11, 1824, 10.1002/cctc.201801828
Kim, 2019, Recent advances in hydrodeoxygenation of biomass-derived oxygenates over heterogeneous catalysts, Green Chem., 21, 3715, 10.1039/C9GC01210A
Han, 2019, Catalytic conversion of lignocellulosic biomass into hydrocarbons: a mini review, Catal. Today, 319, 2, 10.1016/j.cattod.2018.05.013
Valentini, 2019, Formic acid, a biomass-derived source of energy and hydrogen for biomass upgrading, Energy Environ. Sci., 12, 2646, 10.1039/C9EE01747J
Jin, 2019, Nanostructured metal catalysts for selective hydrogenation and oxidation of cellulosic biomass to chemicals, Chem. Rec., 19, 1952, 10.1002/tcr.201800144
Tamura, 2020, Reduction of sugar derivatives to valuable chemicals: utilization of asymmetric carbons, Catal. Sci. Technol., 10, 3805, 10.1039/D0CY00654H
Tomishige, 2020, Taming heterogeneous rhenium catalysis for the production of biomass-derived chemicals, Chin. Chem. Lett., 31, 1071, 10.1016/j.cclet.2019.07.014
Dutta, 2020, Hydro(deoxygenation) reaction network of lignocellulosic oxygenates, ChemSusChem, 13, 2894, 10.1002/cssc.202000247
Zhang, 2020, Recent advances in the selective catalytic hydrodeoxygenation of lignin-derived oxygenates to arenes, Green Chem., 22, 1072, 10.1039/C9GC02762A
Nakagawa, 2020, Erythritol: another C4 platform chemical in biomass refinery, ACS Omega, 5, 2520, 10.1021/acsomega.9b04046
Wang, 2020, A review of conversion of lignocellulose biomass to liquid transport fuels by integrated refining strategies, Fuel Process, Technol., 208
Tomishige, 2020, Design of supported metal catalysts modified with metal oxides for hydrodeoxygenation of biomass-related molecules, Curr. Opin. Green Sustain. Chem., 22, 13, 10.1016/j.cogsc.2019.11.003
Xu, 2020, Reductive catalytic routes towards sustainable production of hydrogen, fuels and chemicals from biomass derived polyols, Renew. Sustain. Energy Rev., 127, 1, 10.1016/j.rser.2020.109852
Tamura, 2020, Recent developments of heterogeneous catalysts for hydrogenation of carboxylic acids to their corresponding alcohols, Asian J. Org. Chem., 9, 126, 10.1002/ajoc.201900667
Robinson, 2016, J. Will medlin, bifunctional catalysts for upgrading of biomass-derived oxygenates: a review, ACS Catal., 6, 5026, 10.1021/acscatal.6b00923
Bhowmik, 2020, Advances in solid catalysts for selective hydrogenolysis of glycerol to 1,3-propanediol, Catal. Rev., 1
Enjamuri, 2020, Solid catalysts for conversion of furfural and its derivatives to alkanediols, Catal. Rev., 62, 566, 10.1080/01614940.2020.1744327
Checa, 2020, Recent advances in glycerol catalytic valorization: a review, Catalysts, 10, 1279, 10.3390/catal10111279
Iriondo, 2020, Value-added bio-chemicals commodities from catalytic conversion of biomass derived furan-compounds, Catalysts, 10, 895, 10.3390/catal10080895
Yang, 2021, Production of biomass-derived monomers through catalytic conversion of furfural and hydroxymethylfurfural, Green Chem. Eng., 2, 158, 10.1016/j.gce.2020.11.001
Wan, 2021, Toward value-added dicarboxylic acids from biomass derivatives via thermocatalytic conversion, ACS Catal., 5, 2524, 10.1021/acscatal.0c05419
Yun, 2021, Advances in understanding the selective hydrogenolysis of biomass derivatives, ACS Catal., 11, 11193, 10.1021/acscatal.1c02866
Pipitone, 2022, A critical review on catalyst design for aqueous phase reforming, Int. J. Hydrogen Energy, 47, 151, 10.1016/j.ijhydene.2021.09.206
Tran, 2013, Conversion of glycerol to hydrogen rich gas, Chem. Soc. Rev., 42, 9454, 10.1039/c3cs60227c
Nakagawa, 2013, Catalytic reduction of biomass-derived furanic compounds with hydrogen, ACS Catal., 3, 2655, 10.1021/cs400616p
Nakagawa, 2014, Catalytic materials for the hydrogenolysis of glycerol to 1,3-propanediol, J. Mater. Chem. A., 2, 6688, 10.1039/C3TA15384C
Raju, 2015, Rhenium-catalyzed dehydration and deoxydehydration of alcohols and polyols: opportunities for the formation of olefins from biomass, ACS Catal., 5, 281, 10.1021/cs501511x
Pritchard, 2015, Heterogeneous and homogeneous catalysis for the hydrogenation of carboxylic acid derivatives: history, advances and future directions, Chem. Soc. Rev., 44, 3808, 10.1039/C5CS00038F
Coronado, 2016, A review of catalytic aqueous-phase reforming of oxygenated hydrocarbons derived from biorefinery water fractions, Int. J. Hydrogen Energy, 41, 11003, 10.1016/j.ijhydene.2016.05.032
Tomishige, 2014, Role of Re species and acid cocatalyst on Ir-ReOx/SiO2 in the C-O hydrogenolysis of biomass-derived substrates, Chem. Rec., 14, 1041, 10.1002/tcr.201402026
Wei, 2015, Elucidation of the roles of Re in aqueous-phase reforming of glycerol over Pt-Re/C catalysts, ACS Catal., 5, 7312, 10.1021/acscatal.5b01770
Chia, 2011, Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts, J. Am. Chem. Soc., 133, 12675, 10.1021/ja2038358
Liu, 2014, Performance and characterization of rhenium-modified Rh-Ir alloy catalyst for one-pot conversion of furfural into 1,5-pentanediol, Catal. Sci. Technol., 4, 2535, 10.1039/C4CY00161C
Chia, 2013, Bimetallic RhRe/C catalysts for the production of biomass-derived chemicals, J. Catal., 308, 226, 10.1016/j.jcat.2013.08.008
Kirilin, 2014, Aqueous phase reforming of xylitol over Pt-Re bimetallic catalyst: effect of the Re addition, Catal. Today, 223, 97, 10.1016/j.cattod.2013.09.020
Manyar, 2010, Highly selective and efficient hydrogenation of carboxylic acids to alcohols using titania supported Pt catalysts, Chem. Commun., 46, 6279, 10.1039/c0cc01365j
Hibbitts, 2014, Acid strength and bifunctional catalytic behavior of alloys comprised of noble metals and oxophilic metal promoters, J. Catal., 315, 48, 10.1016/j.jcat.2014.03.016
Falcone, 2015, Evidence for the bifunctional nature of Pt-Re catalysts for selective glycerol hydrogenolysis, ACS Catal., 5, 5679, 10.1021/acscatal.5b01371
Nakagawa, 2012, Solid acid co-catalyst for the hydrogenolysis of glycerol to 1,3-propanediol over Ir-ReOx/SiO2, Appl. Catal. Gen., 433–434, 128, 10.1016/j.apcata.2012.05.009
Leiva, 2017, Conversion of guaiacol over supported ReOx catalysts: support and metal loading effect, Catal. Today, 296, 228, 10.1016/j.cattod.2017.04.002
Leiva, 2015, Hydrodeoxygenation of 2-methoxyphenol over different Re active phases supported on SiO2 catalysts, Appl. Catal. Gen., 490, 71, 10.1016/j.apcata.2014.10.054
Toledo, 2019, Effect of Re content and support in the liquid phase conversion of furfural to furfuryl alcohol and 2-methyl furan over ReOx catalysts, Fuel, 242, 532, 10.1016/j.fuel.2019.01.090
Ghampson, 2017, Catalytic hydrodeoxygenation of anisole over Re-MoOx/TiO2 and Re-VOx/TiO2 catalysts, Appl. Catal. B Environ., 208, 60, 10.1016/j.apcatb.2017.02.047
Suknev, 2015, The nature of active sites in Pt-ReOX/TiO2 catalysts for selective hydrogenation of carboxylic acids to alcohols, J. Energy Chem., 24, 646, 10.1016/j.jechem.2015.09.003
Kunkes, 2008, The role of rhenium in the conversion of glycerol to synthesis gas over carbon supported platinum-rhenium catalysts, J. Catal., 260, 164, 10.1016/j.jcat.2008.09.027
Zhou, 2020, Enhanced catalytic transfer hydrogenation of biomass-based furfural into 2-methylfuran over multifunctional Cu–Re bimetallic catalysts, ACS Sustain. Chem. Eng., 8, 16624, 10.1021/acssuschemeng.0c06026
Ghampson, 2016, Phenol hydrodeoxygenation: effect of support and Re promoter on the reactivity of Co catalysts, Catal. Sci. Technol., 6, 7289, 10.1039/C6CY01038E
Di, 2017, Role of Re and Ru in Re-Ru/C bimetallic catalysts for the aqueous hydrogenation of succinic acid, Ind. Eng. Chem. Res., 56, 4672, 10.1021/acs.iecr.6b04875
Di, 2017, Influence of Re-M interactions in Re-M/C bimetallic catalysts prepared by a microwave-assisted thermolytic method on aqueous-phase hydrogenation of succinic acid, Catal. Sci. Technol., 7, 5212, 10.1039/C7CY01039G
Jin, 2019, Hydrothermal deoxygenation of triglycerides over carbon-supported bimetallic PtRe catalysts without an external hydrogen source, Mol. Catal., 474
Xi, 2018, Mechanistic study of the ceria supported, re-catalyzed deoxydehydration of vicinal OH groups, Catal. Sci. Technol., 8, 5740, 10.1039/C8CY01782D
Ota, 2016, Performance, structure, and mechanism of ReOx-Pd/CeO2 catalyst for simultaneous removal of vicinal OH groups with H2, ACS Catal., 6, 3213, 10.1021/acscatal.6b00491
Toyao, 2019, Mechanistic study of the selective hydrogenation of carboxylic acid derivatives over supported rhenium catalysts, Catal. Sci. Technol., 9, 5413, 10.1039/C9CY01404G
Toyao, 2017, Rhenium-loaded TiO2: a highly versatile and chemoselective catalyst for the hydrogenation of carboxylic acid derivatives and the N-methylation of amines using H2 and CO2, Chem. Eur J., 23, 14848, 10.1002/chem.201702801
Takeda, 2016, Hydrogenation of dicarboxylic acids to diols over Re-Pd catalysts, Catal. Sci. Technol., 6, 5668, 10.1039/C6CY00335D
Tapin, 2014, Influence of the Re introduction method onto Pd/TiO2 catalysts for the selective hydrogenation of succinic acid in aqueous-phase, Catal. Today, 235, 127, 10.1016/j.cattod.2014.02.018
Sharkey, 2019, Fundamental insights into deactivation by leaching during rhenium-catalyzed deoxydehydration, ACS Catal., 9, 11317, 10.1021/acscatal.9b02806
Sandbrink, 2016, ReOx/TiO2: a recyclable solid catalyst for deoxydehydration, ACS Catal., 6, 677, 10.1021/acscatal.5b01936
Sharkey, 2018, New solid oxo-rhenium and oxo-molybdenum catalysts for the deoxydehydration of glycols to olefins, Catal. Today, 310, 86, 10.1016/j.cattod.2017.05.090
Ota, 2015, Hydrodeoxygenation of vicinal OH groups over heterogeneous rhenium catalyst promoted by palladium and ceria support, Angew. Chem. Int. Ed., 127, 1897, 10.1002/anie.201410352
Wang, 2020, Tungsten–zirconia-supported rhenium catalyst combined with a deoxydehydration catalyst for the one-pot synthesis of 1,4-butanediol from 1,4-anhydroerythritol, React. Chem. Eng., 5, 1237, 10.1039/D0RE00085J
Denning, 2013, Deoxydehydration of glycols catalyzed by carbon-supported perrhenate, ChemCatChem, 5, 3567, 10.1002/cctc.201300545
Zhang, 2012, Correlation of Pt-Re surface properties with reaction pathways for the aqueous-phase reforming of glycerol, J. Catal., 287, 37, 10.1016/j.jcat.2011.11.015
Luo, 2016, Selective hydrogenolysis of glycerol to 1,3-propanediol over egg-shell type Ir-ReOx catalysts, RSC Adv., 6, 13600, 10.1039/C5RA24808F
Ohta, 2014, Selective hydrodeoxygenation of lignin-related 4-propylphenol into n-propylbenzene in water by Pt-Re/ZrO2 catalysts, Catal. Today, 234, 139, 10.1016/j.cattod.2014.01.022
Liu, 2017, Catalytic hydrodeoxygenation of high carbon furylmethanes to renewable jet-fuel ranged alkanes over a rhenium-modified iridium catalyst, ChemSusChem, 10, 3225, 10.1002/cssc.201700863
Li, 2016, Synergistic effect between Pd and Re on Pd-Re/SBA-15 catalysts and their catalytic behavior in glycerol hydrogenolysis, RSC Adv., 6, 38680, 10.1039/C6RA02758J
Toyao, 2017, TiO2-Supported Re as a general and chemoselective heterogeneous catalyst for hydrogenation of carboxylic acids to alcohols, Chem. Eur J., 23, 1001, 10.1002/chem.201604762
West, 2009, Catalytic conversion of biomass-derived carbohydrates to fuels and chemicals by formation and upgrading of mono-functional hydrocarbon intermediates, Catal. Today, 147, 115, 10.1016/j.cattod.2009.02.004
Deng, 2021, Efficient catalysts for the green synthesis of adipic acid from biomass, Angew. Chem. Int. Ed., 60, 4712, 10.1002/anie.202013843
Hammond, 2017, Intensification studies of heterogeneous catalysts: probing and overcoming catalyst deactivation during liquid phase operation, Green Chem., 19, 2711, 10.1039/C7GC00163K
Miceli, 2021, Recovery/reuse of heterogeneous supported spent catalysts, Catalysts, 11, 591, 10.3390/catal11050591
Bartholomew, 2001, Mechanisms of catalyst deactivation, Appl. Catal. Gen., 212, 17, 10.1016/S0926-860X(00)00843-7
Argyle, 2015, Heterogeneous catalyst deactivation and regeneration: a review, Catalysts, 5, 145, 10.3390/catal5010145
Besson, 2003, Deactivation of metal catalysts in liquid phase organic reactions, Catal. Today, 81, 547, 10.1016/S0920-5861(03)00153-6
Lange, 2015, Renewable feedstocks: the problem of catalyst deactivation and its mitigation, Angew. Chem. Int. Ed., 54, 13187, 10.1002/anie.201503595
Héroguel, 2015, Improving heterogeneous catalyst stability for liquid-phase biomass conversion and reforming, Chimia, 69, 582, 10.2533/chimia.2015.582
Huo, 2020, Bioprivileged molecules: integrating biological and chemical catalysis for biomass conversion, Annu. Rev. Chem. Biomol. Eng., 11, 63, 10.1146/annurev-chembioeng-101519-121127
Kunkes, 2008, Catalytic conversion of biomass to monofunctional hydrocarbons and targeted liquid-fuel classes, Science, 322, 417, 10.1126/science.1159210
Duan, 2014, Hydrothermally stable regenerable catalytic supports for aqueous-phase conversion of biomass, Catal. Today, 234, 66, 10.1016/j.cattod.2014.03.009
Godina, 2018, Sibunit-supported mono- and bimetallic catalysts used in aqueous-phase reforming of xylitol, Ind. Eng. Chem. Res., 57, 2050, 10.1021/acs.iecr.7b04937
Kim, 2013, Aqueous-phase hydrodeoxygenation of sorbitol: a comparative study of Pt/Zr phosphate and PtReOx/C, J. Catal., 304, 72, 10.1016/j.jcat.2013.03.022
Lee, 2018, Production of renewable C4–C6 monoalcohols from waste biomass-derived carbohydrate via aqueous-phase hydrodeoxygenation over Pt-ReOx/Zr-P, Process Saf. Environ. Prot., 115, 2, 10.1016/j.psep.2017.05.015
Xiao, 2016, Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/SiO2 + Ir-ReOx/SiO2 in a fixed-bed reactor, Green Chem., 18, 2175, 10.1039/C5GC02228B
Karanjkar, 2016, Effect of carbon supports on RhRe bifunctional catalysts for selective hydrogenolysis of tetrahydropyran-2-methanol, Catal. Sci. Technol., 6, 7841, 10.1039/C6CY01763K
Shozi, 2017, An investigation of Cu-Re-ZnO catalysts for the hydrogenolysis of glycerol under continuous flow conditions, Sustain. Energy Fuels, 1, 1437, 10.1039/C7SE00199A
Vardon, 2014, Hydrothermal catalytic processing of saturated and unsaturated fatty acids to hydrocarbons with glycerol for in situ hydrogen production, Green Chem., 16, 1507, 10.1039/c3gc41798k
Liu, 2016, Catalytic conversion of sorbitol to gasoline-ranged products without external hydrogen over Pt-modified Ir-ReOx/SiO2, Catal. Today, 269, 122, 10.1016/j.cattod.2015.10.023
Liu, 2018, Hydrogenolysis of glycerol with in-situ produced H2 by aqueous-phase reforming of glycerol using Pt-modified Ir-ReOx/SiO2 catalyst, Catal. Today, 303, 106, 10.1016/j.cattod.2017.07.025
Yan, 2019, Guaiacol demethoxylation catalyzed by Re2O7 in ethanol, Catal. Today, 1
Li, 2012, Direct catalytic conversion of glycerol to liquid-fuel classes over Ir-Re supported on W-doped mesostructured silica, Appl. Catal. Gen., 449, 163, 10.1016/j.apcata.2012.09.018
Mascal, 2014, Hydrodeoxygenation of the angelica lactone dimer, a cellulose-based feedstock: simple, high-yield synthesis of branched C7-C10 gasoline-like hydrocarbons, Angew. Chem. Int. Ed., 53, 1854, 10.1002/anie.201308143
Feng, 2014, Aqueous-phase hydrodeoxygenation of 4-propylphenol as a lignin model to n-propylbenzene over Re-Ni/ZrO2 catalysts, J. Mol. Catal. Chem., 388–389, 41, 10.1016/j.molcata.2013.09.025
Liu, 2018, Selective hydrodeoxygenation of vegetable oils and waste cooking oils to green diesel using a silica-supported Ir–ReOx bimetallic catalyst, ChemSusChem, 11, 1446, 10.1002/cssc.201800321
Park, 2018, Multifunctional cascade catalysis of itaconic acid hydrodeoxygenation to 3-Methyl-tetrahydrofuran, ACS Sustain. Chem. Eng., 6, 9394, 10.1021/acssuschemeng.8b01743
Alda-Onggar, 2018, Hydrodeoxygenation of isoeugenol over alumina-supported Ir, Pt, and Re catalysts, ACS Sustain. Chem. Eng., 6, 16205, 10.1021/acssuschemeng.8b03035
Bin Jung, 2018, Effective hydrodeoxygenation of lignin-derived phenols using bimetallic RuRe catalysts: effect of carbon supports, Catal. Today, 303, 191, 10.1016/j.cattod.2017.07.027
Liu, 2019, Renewable lubricants with tailored molecular architecture, Sci. Adv., 5
Zhou, 2020, Hydrodeoxygenation of ethyl stearate over Re-promoted Ru/TiO2 catalysts: rate enhancement and selectivity control by the addition of Re, Catal. Sci. Technol., 10, 222, 10.1039/C9CY01909J
Jeong, 2021, Investigation of the activity and selectivity of supported rhenium catalysts for the hydrodeoxygenation of 2-methoxyphenol, Catal. Today, 375, 164, 10.1016/j.cattod.2020.05.004
Koso, 2009, Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol, Chem. Commun., 2035, 10.1039/b822942b
Koso, 2009, Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO2, J. Catal., 267, 89, 10.1016/j.jcat.2009.07.010
Chen, 2010, Chemoselective hydrogenolysis of tetrahydropyran-2-methanol to 1,6-hexanediol over rhenium-modified carbon-supported rhodium catalysts, ChemCatChem, 2, 547, 10.1002/cctc.201000018
Amada, 2010, Hydrogenolysis of 1,2-propanediol for the production of biopropanols from glycerol, ChemSusChem, 3, 728, 10.1002/cssc.201000040
Nakagawa, 2010, Direct hydrogenolysis of glycerol into 1,3-propanediol over rhenium-modified iridium catalyst, J. Catal., 272, 191, 10.1016/j.jcat.2010.04.009
Shinmi, 2010, Modification of Rh/SiO2 catalyst for the hydrogenolysis of glycerol in water, Appl. Catal. B Environ., 94, 318, 10.1016/j.apcatb.2009.11.021
Amada, 2011, Reaction mechanism of the glycerol hydrogenolysis to 1,3-propanediol over Ir-ReOx/SiO2 catalyst, Appl. Catal. B Environ., 105, 117, 10.1016/j.apcatb.2011.04.001
Amada, 2012, Production of biobutanediols by the hydrogenolysis of erythritol, ChemSusChem, 5, 1991, 10.1002/cssc.201200121
Chen, 2013, One-pot conversion of sugar and sugar polyols to n-alkanes without C-C dissociation over the Ir-ReOx/SiO2 catalyst combined with H-ZSM-5, ChemSusChem, 6, 613, 10.1002/cssc.201200940
Liu, 2014, One-pot conversion of cellulose into n -hexane over the Ir-ReO x/SiO2 catalyst combined with HZSM-5, ACS Sustain. Chem. Eng., 2, 1819, 10.1021/sc5001463
Tamura, 2014, Promoting effect of Ru on Ir-ReOx/SiO2 catalyst in hydrogenolysis of glycerol, J. Mol. Catal. Chem., 388–389, 177, 10.1016/j.molcata.2013.09.015
Liu, 2014, One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir-ReOx/SiO2 bifunctional catalyst, Green Chem., 16, 617, 10.1039/C3GC41335G
Liu, 2015, Selective transformation of hemicellulose (xylan) into n-pentane, pentanols or xylitol over a rhenium-modified iridium catalyst combined with acids, Green Chem., 18, 165, 10.1039/C5GC02183A
Liu, 2015, Production of renewable hexanols from mechanocatalytically depolymerized cellulose by using Ir-ReOx/SiO2 catalyst, ChemSusChem, 8, 628, 10.1002/cssc.201403010
Deng, 2015, Ir-Re alloy as a highly active catalyst for the hydrogenolysis of glycerol to 1,3-propanediol, Catal. Sci. Technol., 5, 1540, 10.1039/C4CY01285B
Said, 2017, Selective C−O hydrogenolysis of erythritol over supported Rh-ReOx catalysts in the aqueous phase, ChemCatChem, 9, 2768, 10.1002/cctc.201700260
Li, 2018, Aqueous-phase hydrogenolysis of glycerol over Re promoted Ru catalysts encapuslated in porous silica nanoparticles, Nanomaterials, 8, 153, 10.3390/nano8030153
Sadier, 2019, Effect of carbon chain length on catalytic C–O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase, Appl. Catal. Gen., 586, 10.1016/j.apcata.2019.117213
Varghese, 2019, Synergistic contribution of the acidic metal oxide-metal couple and solvent environment in the selective hydrogenolysis of glycerol: a combined experimental and computational study using ReOx-Ir as the catalyst, ACS Catal., 9, 485, 10.1021/acscatal.8b03079
Liu, 2019, Highly active iridium–rhenium catalyst condensed on silica support for hydrogenolysis of glycerol to 1,3-propanediol, Appl. Catal. B Environ., 256, 10.1016/j.apcatb.2019.117775
Liu, 2019, Selective hydrogenolysis of glycerol to 1,3-propanediol over rhenium-oxide-modified iridium nanoparticles coating rutile titania support, ACS Catal., 10913, 10.1021/acscatal.9b03824
X. Li, B. Zhang, X. Pan, J. Ji, Y. Ren, H. Wang, N. Ji, Q. Liu, C. Li, One-Pot conversion of lignin into naphthenes catalyzed by a heterogeneous rhenium oxide-modified iridium compound, ChemSusChem. 13 (2020) 4409–4419. https://doi.org/10.1002/cssc.201903286.
Kong, 2020, Catalytic hydrotreatment of kraft lignin into aromatic alcohols over nickel-rhenium supported on niobium oxide catalyst, Bioresour. Technol., 299, 10.1016/j.biortech.2019.122582
Zhang, 2019, Cleavage of lignin C-O bonds over a heterogeneous rhenium catalyst through hydrogen transfer reactions, Green Chem., 21, 5556, 10.1039/C9GC01710K
Licursi, 2018, Cascade strategy for the tunable catalytic valorization of levulinic acid and γ-valerolactone to 2-methyltetrahydrofuran and alcohols, Catalysts, 8, 277, 10.3390/catal8070277
Hong, 2012, Hydrogenation of succinic acid to tetrahydrofuran (THF) over rhenium catalyst supported on H2SO4-treated mesoporous carbon, Appl. Catal. Gen., 415–416, 141, 10.1016/j.apcata.2011.12.022
Takeda, 2012, Selective hydrogenation of higher saturated carboxylic acids to alcohols using a ReOx–Pd/SiO2 catalyst, Catal. Sci. Technol., 2, 2221, 10.1039/c2cy20302b
Tamura, 2013, Rapid synthesis of unsaturated alcohols under mild conditions by highly selective hydrogenation, Chem. Commun., 49, 7034, 10.1039/c3cc41526k
Kang, 2014, Hydrogenation of succinic acid to γ-butyrolactone and 1,4-butanediol over mesoporous rhenium-copper-carbon composite catalyst, J. Mol. Catal. Chem., 395, 234, 10.1016/j.molcata.2014.08.032
Di, 2015, Hydrogenation of succinic acid over supported rhenium catalysts prepared by the microwave-assisted thermolytic method, Catal. Sci. Technol., 5, 2441, 10.1039/C5CY00004A
Kang, 2015, Hydrogenation of succinic acid to 1,4-butanediol over Re-Ru bimetallic catalysts supported on mesoporous carbon, Appl. Catal. Gen., 490, 153, 10.1016/j.apcata.2014.11.029
Takeda, 2015, Characterization of Re-Pd/SiO2 catalysts for hydrogenation of stearic acid, ACS Catal., 5, 7034, 10.1021/acscatal.5b01054
Liu, 2016, A sustainable process for the production of 2-methyl-1,4-butanediol by hydrogenation of biomass-derived itaconic acid, Catal. Today, 274, 88, 10.1016/j.cattod.2016.01.041
Liu, 2017, Supported nickel-rhenium catalysts for selective hydrogenation of methyl esters to alcohols, Chem. Commun., 53, 9761, 10.1039/C7CC04759B
Ullrich, 2018, Selective hydrogenation of carboxylic acids to alcohols or alkanes employing a heterogeneous catalyst, ACS Catal., 8, 785, 10.1021/acscatal.7b03484
Bal’zhinimaev, 2018, Highly selective/enantioselective Pt-ReOx/C catalyst for hydrogenation of L-malic acid at mild conditions, J. Energy Chem., 27, 903, 10.1016/j.jechem.2017.07.018
Di, 2019, Supported Co–Re bimetallic catalysts with different structures as efficient catalysts for hydrogenation of citral, ChemSusChem, 12, 807, 10.1002/cssc.201802744
Ly, 2020, In situ preparation of bimetallic ReOx-Pd/TiO2 catalysts for selective aqueous-phase hydrogenation of succinic acid to 1,4-butanediol, Catal. Today, 355, 75, 10.1016/j.cattod.2019.03.024
Tapin, 2020, Characterization by X-ray absorption spectroscopy of bimetallic Re–Pd/TiO2 catalysts efficient for selective aqueous-phase hydrogenation of succinic acid to 1,4-butanediol, Mater. Chem. Phys., 252, 10.1016/j.matchemphys.2020.123225
Wei, 2021, Low loading of CoRe/TiO 2 for efficient hydrodeoxygenation of levulinic acid to γ-valerolactone, ACS Sustain. Chem. Eng., 9, 10.1021/acssuschemeng.1c03380
Li, 2016, Highly selective deoxydehydration of tartaric acid over supported and unsupported rhenium catalysts with modified acidities, ChemSusChem, 9, 2774, 10.1002/cssc.201600865
Tazawa, 2016, Deoxydehydration with molecular hydrogen over ceria-supported rhenium catalyst with gold promoter, ACS Catal., 6, 6393, 10.1021/acscatal.6b01864
Nakagawa, 2018, Mechanistic study of hydrogen-driven deoxydehydration over ceria-supported rhenium catalyst promoted by Au nanoparticles, ACS Catal., 8, 584, 10.1021/acscatal.7b02879
Nijem, 2018, Bimetallic Pt-Re nanoporous networks: synthesis, characterization, and catalytic reactivity, J. Phys. Chem. C, 122, 24801, 10.1021/acs.jpcc.8b07863
Lin, 2019, Zirconia-supported rhenium oxide as an efficient catalyst for the synthesis of biomass-based adipic acid ester, Chem. Commun., 55, 11017, 10.1039/C9CC05413H
Jang, 2019, Deoxydehydration of biomass-derived polyols with a reusable unsupported rhenium nanoparticles catalyst, ACS Sustain. Chem. Eng., 7, 11438, 10.1021/acssuschemeng.9b01253
Cao, 2019, Direct synthesis of unsaturated sugars from methyl glycosides, ACS Catal., 9, 3725, 10.1021/acscatal.9b00589
Hočevar, 2021, H2-free Re-based catalytic dehydroxylation of aldaric acid to muconic and adipic acid esters, Angew. Chem. Int. Ed., 60, 1244, 10.1002/anie.202010035
I. Meiners, Y. Louven, R. Palkovits, Zeolite-supported rhenium catalysts for the deoxydehydration of 1,2-hexanediol to 1-hexene, ChemCatChem. 13 (2021) 2393–2397. https://doi.org/10.1002/cctc.202100277.
Tamura, 2018, Transformation of sugars into chiral polyols over a heterogeneous catalyst, Angew. Chem. Int. Ed., 57, 8058, 10.1002/anie.201803043
Wang, 2019, Preparation of highly active monometallic rhenium catalysts for selective synthesis of 1,4-butanediol from 1,4-anhydroerythritol, ChemSusChem, 12, 3615, 10.1002/cssc.201900900
Wang, 2018, One-pot catalytic selective synthesis of 1,4-butanediol from 1,4-anhydroerythritol and hydrogen, Green Chem., 20, 2547, 10.1039/C8GC00574E
Jang, 2021, A heterogeneous Pt-ReOx/C catalyst for making renewable adipates in one step from sugar acids, ACS Catal., 11, 95, 10.1021/acscatal.0c04158
Genuino, 2020, Catalytic hydrogenation of renewable levulinic acid to γ-valerolactone: insights into the influence of feed impurities on catalyst performance in batch and flow reactors, ACS Sustain. Chem. Eng., 8, 5903, 10.1021/acssuschemeng.9b07678
Metkar, 2015, Reactive distillation process for the production of furfural using solid acid catalysts, Green Chem., 17, 1453, 10.1039/C4GC01912A
Mortensen, 2014, Stability and resistance of nickel catalysts for hydrodeoxygenation: carbon deposition and effects of sulfur, potassium, and chlorine in the feed, Catal. Sci. Technol., 4, 3672, 10.1039/C4CY00522H
Schwartz, 2015, Inhibition of metal hydrogenation catalysts by biogenic impurities, Catal. Lett., 145, 15, 10.1007/s10562-014-1441-z
Zhang, 2008, Effect of biogenic fermentation impurities on lactic acid hydrogenation to propylene glycol, Bioresour. Technol., 99, 5873, 10.1016/j.biortech.2007.10.027
F.M. Harth, J. Celis, A. Taubert, S. Rössler, H. Wagner, M. Goepel, C. Wilhelm, R. Gläser, Ru/C-Catalyzed hydrogenation of aqueous glycolic acid from microalgae – influence of pH and biologically relevant additives, ChemistryOpen. 11 (2022) e20220005. https://doi.org/10.1002/open.202200050.
Schwartz, 2014, Engineering catalyst microenvironments for metal-catalyzed hydrogenation of biologically derived platform chemicals, Angew. Chem. Int. Ed., 53, 12718, 10.1002/anie.201407615
Binczarski, 2016, Biologically synthesized crude calcium lactate as a substrate for propylene glycol production, RSC Adv., 6, 92420, 10.1039/C6RA20722G
Pham Minh, 2010, Aqueous-phase hydrogenation of biomass-based succinic acid to 1,4-butanediol over supported bimetallic catalysts, Top. Catal., 53, 1270, 10.1007/s11244-010-9580-y
Al-Naji, 2020, Aqueous-phase hydrogenation of levulinic acid using formic acid as a sustainable reducing agent over Pt catalysts supported on mesoporous zirconia, ACS Sustain. Chem. Eng., 8, 393, 10.1021/acssuschemeng.9b05546
Al-Naji, 2020, Pentanoic acid from γ-valerolactone and formic acid using bifunctional catalysis, Green Chem., 22, 1171, 10.1039/C9GC02627D
Ruppert, 2016, Ru catalysts for levulinic acid hydrogenation with formic acid as a hydrogen source, Green Chem., 18, 2014, 10.1039/C5GC02200B
Guo, 2012, A mini-review on membrane fouling, Bioresour. Technol., 122, 27, 10.1016/j.biortech.2012.04.089
Albers, 2008, Carbonaceous deposits
Bartholomew, 1982, Carbon deposition in steam reforming and methanation, Catal. Rev., 24, 67, 10.1080/03602458208079650
Van Zandvoort, 2013, Formation, molecular structure, and morphology of humins in biomass conversion: influence of feedstock and processing conditions, ChemSusChem, 6, 1745, 10.1002/cssc.201300332
Ochoa, 2020, Coke formation and deactivation during catalytic reforming of biomass and waste pyrolysis products: a review, Renew. Sustain. Energy Rev., 119, 109600, 10.1016/j.rser.2019.109600
sintering, in: IUPAC Compend. Chem. Terminol., IUPAC, Research Triagle Park, NC, n.D. https://doi.org/10.1351/goldbook.S05704.
Trimm, 1991, 29
Hansen, 2013, Sintering of catalytic nanoparticles: particle migration or ostwald ripening?, Acc. Chem. Res., 46, 1720, 10.1021/ar3002427
German, 2009, Review: liquid phase sintering, J. Mater. Sci., 44, 1, 10.1007/s10853-008-3008-0
Mine, 2022, Experimental and theoretical investigation of metal–support interactions in metal-oxide-supported rhenium materials, J. Phys. Chem. C, 126, 4472, 10.1021/acs.jpcc.2c00955
Ro, 2018, Approaches for understanding and controlling interfacial effects in oxide-supported metal catalysts, ACS Catal., 8, 7368, 10.1021/acscatal.8b02071
van Deelen, 2019, Control of metal-support interactions in heterogeneous catalysts to enhance activity and selectivity, Nat. Catal., 2, 955, 10.1038/s41929-019-0364-x
She, 2012, Highly dispersed and active ReOx on alumina-modified SBA-15 silica for 2-butanol dehydration, ACS Catal., 2, 1020, 10.1021/cs2006444
Arnoldy, 1985, Temperature-Programmed Reduction of Al2O3-, SiO2-, and carbon-supported Re2O7 catalysts, J. Catal., 93, 231, 10.1016/0021-9517(85)90171-X
Canale, 2014, Deoxydehydration of glycerol to allyl alcohol catalyzed by rhenium derivatives, Catal. Sci. Technol., 4, 3697, 10.1039/C4CY00631C
Beamson, 2011, Selective hydrogenation of amides using bimetallic Ru/Re and Rh/Re catalysts, J. Catal., 278, 228, 10.1016/j.jcat.2010.12.009
Möller, 2011, Subcritical water as reaction environment: fundamentals of hydrothermal biomass transformation, ChemSusChem, 4, 566, 10.1002/cssc.201000341
Kruse, 2015, Water - a magic solvent for biomass conversion, J. Supercrit. Fluids, 96, 36, 10.1016/j.supflu.2014.09.038
Xiong, 2014, Hydrothermally stable heterogeneous catalysts for conversion of biorenewables, Green Chem., 16, 4627, 10.1039/C4GC01152J
Ravenelle, 2010, Stability of zeolites in hot liquid water, J. Phys. Chem. C, 114, 10.1021/jp104639e
Vjunov, 2015, Impact of aqueous medium on zeolite framework integrity, Chem. Mater., 27, 3533, 10.1021/acs.chemmater.5b01238
Prodinger, 2020, Recent progress to understand and improve zeolite stability in the aqueous medium, Pet. Chem., 60, 420, 10.1134/S0965544120040143
Zhang, 2015, Factors that determine zeolite stability in hot liquid water, J. Am. Chem. Soc., 137, 11810, 10.1021/jacs.5b07398
Ennaert, 2016, Potential and challenges of zeolite chemistry in the catalytic conversion of biomass, Chem. Soc. Rev., 45, 584, 10.1039/C5CS00859J
Pham, 2012, Improved hydrothermal stability of mesoporous oxides for reactions in the aqueous phase, Angew. Chem. Int. Ed., 51, 13163, 10.1002/anie.201206675
Lacheen, 2006, Structure and catalytic function of Re-oxo species grafted onto H-MFI zeolite by sublimation of Re2O7, J. Am. Chem. Soc., 128, 15082, 10.1021/ja065832x
Ma, 2010, Influence of catalyst pretreatment on catalytic properties and performances of Ru-Re/SiO2 in glycerol hydrogenolysis to propanediols, Catal. Today, 149, 148, 10.1016/j.cattod.2009.03.015
Sá, 2011, Evaluation of Pt and Re oxidation state in a pressurized reactor: difference in reduction between gas and liquid phase, Chem. Commun., 47, 6590, 10.1039/c1cc10895f
Rozmysłowicz, 2015, Selective hydrogenation of fatty acids to alcohols over highly dispersed ReOx/TiO2 catalyst, J. Catal., 328, 197, 10.1016/j.jcat.2015.01.003
Ly, 2015, Insights into the oxidation state and location of rhenium in Re-Pd/TiO2 catalysts for aqueous-phase selective hydrogenation of succinic acid to 1,4-butanediol as a function of palladium and rhenium deposition methods, ChemCatChem, 7, 2161, 10.1002/cctc.201500197
Kim, 2003, Chemistry of rhenium as an analogue of technetium: experimental studies of the dissolution of rhenium oxides in aqueous solutions, Radiochim. Acta, 91, 211, 10.1524/ract.91.4.211.19968
Rice, 1993, Nomenclature for liquid-liquid distribution (solvent extraction), Pure Appl. Chem., 65, 2373, 10.1351/pac199365112373
Eremin, 2017, Understanding active species in catalytic transformations: from molecular catalysis to nanoparticles, leaching, “Cocktails” of catalysts and dynamic systems, Coord. Chem. Rev., 346, 2, 10.1016/j.ccr.2016.12.021
Ciftci, 2014, Pt-Re synergy in aqueous-phase reforming of glycerol and the water-gas shift reaction, J. Catal., 311, 88, 10.1016/j.jcat.2013.11.011
Li, 2014, Glycerol hydrogenolysis to propanediols over supported Pd-Re catalysts, RSC Adv., 4, 5503, 10.1039/c3ra46134c
Baranowska, 2014, Effect of rhenium on ruthenium dispersion in the Ru-Re/γ-Al2O3 catalysts, Catal. Lett., 144, 447, 10.1007/s10562-013-1169-1
Daniel, 2010, X-Ray absorption spectroscopy of bimetallic Pt-Re catalysts for hydrogenolysis of glycerol to propanediols, ChemCatChem, 2, 1107, 10.1002/cctc.201000093
Pieck, 1996, Preparation of Pt-Re/Al2O3 catalysts by surface redox reactions I. Influence of operating variables on Re deposit in the presence of hydrochloric acid, Appl. Catal. Gen., 134, 319, 10.1016/0926-860X(95)00237-5
Bare, 2011, Experimental (XAS, STEM, TPR, and XPS) and theoretical (DFT) characterization of supported rhenium catalysts, J. Phys. Chem. C, 115, 5740, 10.1021/jp1105218
Haus, 2021, Correlating the synthesis, structure, and catalytic performance of Pt-Re/TiO2for the aqueous-phase hydrogenation of carboxylic acid derivatives, ACS Catal., 11, 5119, 10.1021/acscatal.0c05612
Cook, 1996, Toward nonoxidative routes to oxygenated organics: stereospecific deoxydehydration of diols and polyols to alkenes and allylic alcohols catalyzed by the metal oxo complex (C5Me5)ReO3, J. Am. Chem. Soc., 118, 9448, 10.1021/ja9620604
Ziegler, 2009, H2-driven deoxygenation of epoxides and diols to alkenes catalyzed by methyltrioxorhenium, Inorg. Chem., 48, 9998, 10.1021/ic901792b
Shiramizu, 2012, Deoxygenation of biomass-derived feedstocks: oxorhenium-catalyzed deoxydehydration of sugars and sugar alcohols, Angew. Chem. Int. Ed., 51, 8082, 10.1002/anie.201203877
Choe, 2010, Influence of rhenium speciation on the stability and activity of Re/Pd bimetal catalysts used for perchlorate reduction, Environ. Sci. Technol., 44, 4716, 10.1021/es100227z
Choe, 2014, X-Ray spectroscopic characterization of immobilized rhenium species in hydrated rhenium–palladium bimetallic catalysts used for perchlorate water treatment, J. Phys. Chem. C, 118, 11666, 10.1021/jp5006814
Pieck, 1996, Preparation of Pt-Re/Al2O3 catalysts by surface redox reactions II. Influence of the acid medium on Re deposition and Pt-Re interaction, Appl. Catal. Gen., 143, 283, 10.1016/0926-860X(96)00086-5
Zhao, 2002, The leaching and re-deposition of metal species from and onto conventional supported palladium catalysts in the Heck reaction of iodobenzene and methyl acrylate in N-methylpyrrolidone, J. Mol. Catal. Chem., 180, 211, 10.1016/S1381-1169(01)00436-8
Glasnov, 2009, Heterogeneous versus homogeneous palladium catalysts for ligandless Mizoroki-Heck reactions: a comparison of batch/microwave and continuous-flow processing, Chem. Eur J., 15, 1001, 10.1002/chem.200802200
Georg Nadler, 2000, Rhenium and rhenium compounds
Sheldon, 1998, Heterogeneous catalysts for liquid-phase oxidations: philosophers' stones or trojan horses?, Acc. Chem. Res., 31, 485, 10.1021/ar9700163
Huo, 2021, Improving hydrothermal stability of supported metal catalysts for biomass conversions: a review, ACS Catal., 11, 5248, 10.1021/acscatal.1c00197