Thermoresponsive block copolymer supported Pt nanocatalysts for base-free aerobic oxidation of 5-hydroxymethyl-2-furfural
Huaxin Qu, Jie Deng, Bei Wang, Lezi Ouyang, Yong Tang, Kai Yu, Lan-Lan Lou, Shuangxi Liu
Thermoresponsive block copolymer supported Pt nanocatalysts for base-free aerobic oxidation of 5-hydroxymethyl-2-furfural
A base-free catalytic system for the aerobic oxidation of 5-hydroxymethyl-2-furfural was exploited by using Pt nanoparticles immobilized onto a thermoresponsive poly(acrylamide-co-acrylonitrile)-b-poly(N-vinylimidazole) block copolymer, with an upper critical solution temperature of about 45 °C. The Pt nanocatalysts were well-dispersed and highly active for the base-free oxidation of 5-hydroxymethyl-2-furfural by molecular oxygen in water, affording high yields of 2,5-furandicarboxylic acid (up to>99.9%). The imidazole groups in the block copolymer were conducive to the improvement of catalytic performance. Moreover, the catalysts could be easily separated and recovered based on their thermosensitivity by cooling the reaction system below the upper critical solution temperature. Good stability and reusability were observed over these copolymer-immobilized catalysts with no obvious decrease in catalytic activity in the five consecutive cycles.
aerobic oxidation / base-free / 5-hydroxymethyl-2-furfural / Pt nanoparticle / thermoresponsive block copolymer
[1] |
Besson M, Gallezot P, Pinel C. Conversion of biomass into chemicals over metal catalysts. Chemical Reviews, 2014, 114(3): 1827–1870
CrossRef
Google scholar
|
[2] |
Li C, Zhao X, Wang A, Huber G W, Zhang T. Catalytic transformation of lignin for the production of chemicals and fuels. Chemical Reviews, 2015, 115(21): 11559–11624
CrossRef
Google scholar
|
[3] |
Liu B, Zhang Z. Catalytic conversion of biomass into chemicals and fuels over magnetic catalysts. ACS Catalysis, 2016, 6(1): 326–338
CrossRef
Google scholar
|
[4] |
Zhang Z, Song J, Han B. Catalytic transformation of lignocellulose into chemicals and fuel products in ionic liquids. Chemical Reviews, 2017, 117(10): 6834–6880
CrossRef
Google scholar
|
[5] |
Zhang Z, Huber G W. Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chemical Society Reviews, 2018, 47(4): 1351–1390
CrossRef
Google scholar
|
[6] |
van Putten R J, van der Waal J C, de Jong E, Rasrendra C B, Heeres H J, de Vries J G. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chemical Reviews, 2013, 113(3): 1499–1597
CrossRef
Google scholar
|
[7] |
Xu C, Paone E, Rodríguez-Padrón D, Luque R, Mauriello F. Recent catalytic routes for the preparation and the upgrading of biomass derived furfural and 5-hydroxymethylfurfural. Chemical Society Reviews, 2020, 49(13): 4273–4306
CrossRef
Google scholar
|
[8] |
Tong X, Ma Y, Li Y. Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes. Applied Catalysis A, General, 2010, 385(1–2): 1–13
CrossRef
Google scholar
|
[9] |
Werpy T, Petersen G. Top Value Added Chemicals from Biomass: Volume I—Results of Screening for Potential Candidates from Sugars and Synthesis Gas. US DOE Report, 2004
|
[10] |
Eerhart A J J E, Faaij A P C, Patel M K. Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance. Energy & Environmental Science, 2012, 5(4): 6407–6422
CrossRef
Google scholar
|
[11] |
Sajid M, Zhao X, Liu D. Production of 2,5-furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF): recent progress focusing on the chemical-catalytic routes. Green Chemistry, 2018, 20(24): 5427–5453
CrossRef
Google scholar
|
[12] |
Chen C, Wang L, Zhu B, Zhou Z, El-Hout S I, Yang J, Zhang J. 2,5-Furandicarboxylic acid production via catalytic oxidation of 5-hydroxymethylfurfural: catalysts, processes and reaction mechanism. Journal of Energy Chemistry, 2021, 54: 528–554
CrossRef
Google scholar
|
[13] |
Albonetti S, Lolli A, Morandi V, Migliori A, Lucarelli C, Cavani F. Conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylicacid over Au-based catalysts: optimization of active phase and metal-support interaction. Applied Catalysis B: Environmental, 2015, 163: 520–530
CrossRef
Google scholar
|
[14] |
Cai J, Ma H, Zhang J, Song Q, Du Z, Huang Y, Xu J. Gold nanoclusters confined in a supercage of Y zeolite for aerobic oxidation of HMF under mild conditions. Chemistry-A European Journal, 2013, 19(42): 14215–14223
CrossRef
Google scholar
|
[15] |
Liu Y, Ma H Y, Lei D, Lou L L, Liu S, Zhou W, Wang G C, Yu K. Active oxygen species promoted catalytic oxidation of 5-hydroxymethyl-2-furfural on facet-specific Pt nanocrystals. ACS Catalysis, 2019, 9(9): 8306–8315
CrossRef
Google scholar
|
[16] |
Yu K, Lei D, Feng Y, Yu H, Chang Y, Wang Y, Liu Y, Wang G C, Lou L L, Liu S, Zhou W. The role of Bi-doping in promoting electron transfer and catalytic performance of Pt/3DOM-Ce1−xBixO2−δ. Journal of Catalysis, 2018, 365: 292–302
CrossRef
Google scholar
|
[17] |
Rass H A, Essayem N, Besson M. Selective aerobic oxidation of 5-HMF into 2,5-furandicarboxylic acid with Pt catalysts supported on TiO2- and ZrO2-based supports. ChemSusChem, 2015, 8(7): 1206–1217
CrossRef
Google scholar
|
[18] |
Yang J, Yu H, Wang Y, Qi F, Liu H, Lou L L, Yu K, Zhou W, Liu S. Effect of the oxygen coordination environment of Ca-Mn oxides on the catalytic performance of Pd supported catalysts for aerobic oxidation of 5-hydroxymethyl-2-furfural. Catalysis Science & Technology, 2019, 9(23): 6659–6668
CrossRef
Google scholar
|
[19] |
Lei D, Yu K, Li M R, Wang Y, Wang Q, Liu T, Liu P, Lou L L, Wang G, Liu S. Facet effect of single-crystalline Pd nanocrystals for aerobic oxidation of 5-hydroxymethyl-2-furfural. ACS Catalysis, 2017, 7(1): 421–432
CrossRef
Google scholar
|
[20] |
Zhang Z, Zhen J, Liu B, Lv K, Deng K. Selective aerobic oxidation of the biomass-derived precursor 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under mild conditions over a magnetic palladium nanocatalyst. Green Chemistry, 2015, 17(2): 1308–1317
CrossRef
Google scholar
|
[21] |
Xie J, Nie J, Liu H. Aqueous-phase selective aerobic oxidation of 5-hydroxymethylfurfural on Ru/C in the presence of base. Chinese Journal of Catalysis, 2014, 35(6): 937–944
CrossRef
Google scholar
|
[22] |
Villa A, Schiavoni M, Campisi S, Veith G M, Prati L. Pd-modified Au on carbon as an effective and durable catalyst for the direct oxidation of HMF to 2,5-furandicarboxylic acid. ChemSusChem, 2013, 6(4): 609–612
CrossRef
Google scholar
|
[23] |
Gui Z, Cao W, Saravanamurugan S, Riisager A, Chen L, Qi Z. Efficient aerobic oxidation of 5-hydroxymethylfurfural in aqueous media with Au-Pd supported on zinc hydroxycarbonate. ChemCatChem, 2016, 8(23): 3636–3643
CrossRef
Google scholar
|
[24] |
Gupta N K, Nishimura S, Takagaki A, Ebitani K. Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure. Green Chemistry, 2011, 13(4): 824–827
CrossRef
Google scholar
|
[25] |
Gao T, Gao T, Fang W, Cao Q. Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid in water by hydrotalcite-activated carbon composite supported gold catalyst. Molecular Catalysis, 2017, 439: 171–179
CrossRef
Google scholar
|
[26] |
Ferraz C P, Zieliński M, Pietrowski M, Heyte S, Dumeignil F, Rossi L M, Wojcieszak R. Influence of support basic sites in green oxidation of biobased substrates using Au-promoted catalysts. ACS Sustainable Chemistry & Engineering, 2018, 6(12): 16332–16340
CrossRef
Google scholar
|
[27] |
Wang Y, Yu K, Lei D, Si W, Feng Y, Lou L L, Liu S. Basicity-tuned hydrotalcite-supported Pd catalysts for aerobic oxidation of 5-hydroxymethyl-2-furfural under mild conditions. ACS Sustainable Chemistry & Engineering, 2016, 4(9): 4752–4761
CrossRef
Google scholar
|
[28] |
Gao Z, Xie R, Fan G, Yang L, Li F. Highly efficient and stable bimetallic AuPd over La-doped Ca-Mg-Al layered double hydroxide for base-free aerobic oxidation of 5-hydroxymethylfurfural in water. ACS Sustainable Chemistry & Engineering, 2017, 5(7): 5852–5861
CrossRef
Google scholar
|
[29] |
Bonincontro D, Lolli A, Villa A, Prati L, Dimitratos N, Veith G M, Chinchilla L E, Botton G A, Cavani F, Albonetti S. AuPd-nNiO as an effective catalyst for the base-free oxidation of HMF under mild reaction conditions. Green Chemistry, 2019, 21(15): 4090–4099
CrossRef
Google scholar
|
[30] |
Wan X, Zhou C, Chen J, Deng W, Zhang Q, Yang Y, Wang Y. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2,5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au-Pd alloy nanoparticles. ACS Catalysis, 2014, 4(7): 2175–2185
CrossRef
Google scholar
|
[31] |
Zhou C, Deng W, Wan X, Zhang Q, Yang Y, Wang Y. Functionalized carbon nanotubes for biomass conversion: the base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over platinum supported on a carbon nanotube catalyst. ChemCatChem, 2015, 7(18): 2853–2863
CrossRef
Google scholar
|
[32] |
Yi G, Teong S P, Zhang Y. Base-free conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Ru/C catalyst. Green Chemistry, 2016, 18(4): 979–983
CrossRef
Google scholar
|
[33] |
Guan W, Zhang Y, Wei Y, Li B, Feng Y, Yan C, Huo P, Yan Y. Pickering HIPEs derived hierarchical porous nitrogen-doped carbon supported bimetallic AuPd catalyst for base-free aerobic oxidation of HMF to FDCA in water. Fuel, 2020, 278: 118362
CrossRef
Google scholar
|
[34] |
Han X, Li C, Guo Y, Liu X, Zhang Y, Wang Y. N-doped carbon supported Pt catalyst for base-free oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid. Applied Catalysis A, General, 2016, 526: 1–8
CrossRef
Google scholar
|
[35] |
Artz J, Palkovits R. Base-free aqueous-phase oxidation of 5-hydroxymethylfurfural over ruthenium catalysts supported on covalent triazine frameworks. ChemSusChem, 2015, 8(22): 3832–3838
CrossRef
Google scholar
|
[36] |
Gao T, Chen J, Fang W, Cao Q, Su W, Dumeignil F. Ru/MnxCe1Oy catalysts with enhanced oxygen mobility and strong metal-support interaction: exceptional performances in 5-hydroxymethylfurfural base-free aerobic oxidation. Journal of Catalysis, 2018, 368: 53–68
CrossRef
Google scholar
|
[37] |
Mishra D K, Lee H J, Kim J, Lee H S, Cho J K, Suh Y W, Yi Y, Kim Y J. MnCo2O4 spinel supported ruthenium catalyst for air-oxidation of HMF to FDCA under aqueous phase and base-free conditions. Green Chemistry, 2017, 19(7): 1619–1623
CrossRef
Google scholar
|
[38] |
Han X, Geng L, Guo Y, Jia R, Liu X, Zhang Y, Wang Y. Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over a Pt/C–O–Mg catalyst. Green Chemistry, 2016, 18(6): 1597–1604
CrossRef
Google scholar
|
[39] |
Ke C, Li M, Fan G, Yang L, Li F. Pt nanoparticles supported on nitrogen-doped-carbon-decorated CeO2 for base-free aerobic oxidation of 5-hydroxymethylfurfural. Chemistry, an Asian Journal, 2018, 13(18): 2714–2722
CrossRef
Google scholar
|
[40] |
Siankevich S, Savoglidis G, Fei Z, Laurenczy G, Alexander D T L, Yan N, Dyson P J. A novel platinum nanocatalyst for the oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under mild conditions. Journal of Catalysis, 2014, 315: 67–74
CrossRef
Google scholar
|
[41] |
Liguori F, Barbaro P, Calisi N. Continuous-flow oxidation of HMF to FDCA by resin-supported platinum catalysts in neat water. ChemSusChem, 2019, 12(12): 2558–2563
CrossRef
Google scholar
|
[42] |
Bawa P, Pillay V, Choonara Y E, du Toit L C. Stimuli-responsive polymers and their applications in drug delivery. Biomedical Materials, 2009, 4(2): 022001
CrossRef
Google scholar
|
[43] |
Cheng W, Gu L, Ren W, Liu Y. Stimuli-responsive polymers for anti-cancer drug delivery. Materials Science and Engineering C, 2015, 45: 600–608
CrossRef
Google scholar
|
[44] |
Trzebicka B, Szweda R, Kosowski D, Szweda D, Otulakowski Ł, Haladjova E, Dworak A. Thermoresponsive polymer-peptide/protein conjugates. Progress in Polymer Science, 2017, 68: 35–76
CrossRef
Google scholar
|
[45] |
Mackenzie K J, Francis M B. Recyclable thermoresponsive polymer-cellulase bioconjugates for biomass depolymerization. Journal of the American Chemical Society, 2013, 135(1): 293–300
CrossRef
Google scholar
|
[46] |
Lou L L, Qu H, Yu W, Wang B, Ouyang L, Liu S, Zhou W. Covalently immobilized lipase on a thermoresponsive polymer with an upper critical solution temperature as an efficient and recyclable asymmetric catalyst in aqueous media. ChemCatChem, 2018, 10(5): 1166–1172
CrossRef
Google scholar
|
[47] |
Zhang J, Zhang M, Tang K, Verpoort F, Sun T. Polymer-based stimuli-responsive recyclable catalytic systems for organic synthesis. Small, 2014, 10(1): 32–46
CrossRef
Google scholar
|
[48] |
Tan R, Dong Y, Peng M, Zheng W, Yin D. Thermoresponsive chiral salen Mn(III) complexes as efficient and reusable catalysts for the oxidative kinetic resolution of secondary alcohols in water. Applied Catalysis A, General, 2013, 458: 1–10
CrossRef
Google scholar
|
[49] |
Yu W, Lou L L, Yu K, Li S, Shi Y, Liu S. Pt nanoparticles stabilized by thermosensitive polymer as effective and recyclable catalysts for asymmetric hydrogenation of ethyl pyruvate. RSC Advances, 2016, 6(57): 52500–52508
CrossRef
Google scholar
|
[50] |
Kong L, Zhao J, Cheng T, Lin J, Liu G. A polymer-coated rhodium/diamine-functionalized silica for controllable reaction switching in enantioselective tandem reduction-actonization of ethyl 2-acylarylcarboxylates. ACS Catalysis, 2016, 6(4): 2244–2249
CrossRef
Google scholar
|
[51] |
Hou L, Wu P. Understanding the UCST-type transition of P(AAm-co-AN) in H2O and D2O: dramatic effects of solvent isotopes. Soft Matter, 2015, 11(35): 7059–7065
CrossRef
Google scholar
|
[52] |
Davis S E, Zope B N, Davis R J. On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts. Green Chemistry, 2012, 14(1): 143–147
CrossRef
Google scholar
|
[53] |
Davis S E, Ide M S, Davis R J. Selective oxidation of alcohols and aldehydes over supported metal nanoparticles. Green Chemistry, 2013, 15(1): 17–45
CrossRef
Google scholar
|
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〈 | 〉 |