Frontiers of Chemical Science and Engineering >
Conversion of phenol to cyclohexane in the aqueous phase over Ni/zeolite bi-functional catalysts
Received date: 07 Jan 2020
Accepted date: 05 Mar 2020
Published date: 15 Apr 2021
Copyright
A series of Ni/HZSM-5 and Ni/HIM-5 bi-functional catalysts were synthesized and applied to the aqueous-phase hydrodeoxygenation (HDO) of phenol. The Ni dispersibility and particle sizes were shown to be directly related to the porosity and crystal sizes of the parent zeolites, which further influenced the catalytic performances. The large pores and small crystal sizes of the parent zeolites were beneficial for dispersing Ni and forming small Ni particles, and the corresponding Ni/zeolite catalyst exhibited a higher phenol conversion and selectivity towards hydrocarbons. Importantly, the Ni/HIM-5 bi-functional catalyst exhibited a high activity (98.3%) and high selectivity for hydrocarbons (98.8%) when heated at 220°C for 1 h and is thus a new potential catalyst for the HDO of phenolics to form hydrocarbons in the aqueous phase.
Jimei Zhang , Fuping Tian , Junwen Chen , Yanchun Shi , Hongbin Cao , Pengge Ning , Shanshan Sun , Yongbing Xie . Conversion of phenol to cyclohexane in the aqueous phase over Ni/zeolite bi-functional catalysts[J]. Frontiers of Chemical Science and Engineering, 2021 , 15(2) : 288 -298 . DOI: 10.1007/s11705-020-1932-y
| 1 |
Zhang X H, Zhang Q, Wang T J, Ma L L, Yu Y X, Chen L G. Hydrodeoxygenation of lignin-derived phenolic compounds to hydrocarbons over Ni/SiO2-ZrO2 catalysts. Bioresource Technology, 2013, 134: 73–80
|
| 2 |
Wang G H, Cao Z W, Gu D, Pfänder N, Swertz A C, Spliethoff B, Bongard H J, Weidenthaler C, Schmidt W, Rinaldi R, Schüth F. Nitrogen-doped ordered mesoporous carbon supported bimetallic PtCo nanoparticles for upgrading of biophenolics. Angewandte Chemie International Edition, 2016, 55(31): 8850–8855
|
| 3 |
Yu Z Q, Wang Y, Sun Z C, Li X, Wang A J, Camaioni D M, Lercher J A. Ni3P as a high-performance catalytic phase for the hydrodeoxygenation of phenolic compounds. Green Chemistry, 2018, 20(3): 609–619
|
| 4 |
Chheda J N, Huber G W, Dumesic J A. Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angewandte Chemie International Edition, 2007, 46(38): 7164–7183
|
| 5 |
Mei Q Q, Shen X J, Liu H Z, Han B X. Selectively transform lignin into value-added chemicals. Chinese Chemical Letters, 2019, 30(1): 15–24
|
| 6 |
Song W J, He Y Y, Lai S T, Lai W K, Yi X D, Yang W M, Jiang X M. Selective hydrodeoxygenation of lignin phenols to alcohols in aqueous phase over hierarchical Nb2O5-supported Ni Catalyst. Green Chemistry, 2020, 22(5): 1662–1670
|
| 7 |
Mortensen P M, Grunwaldt J D, Jensen P A, Jensen A D. Screening of catalysts for hydrodeoxygenation of phenol as a model compound for bio-oil. ACS Catalysis, 2013, 3(8): 1774–1785
|
| 8 |
Gutierrez A, Kaila R K, Honkela M L, Slioor R, Krause A O I. Hydrodeoxygenation of guaiacol on noble metal catalysts. Catalysis Today, 2009, 147(3-4): 239–246
|
| 9 |
Furimsky E. Catalytic hydrodeoxygenation. Applied Catalysis A, General, 2000, 199(2): 147–190
|
| 10 |
Zhang X H, Tang W W, Zhang Q, Wang T J, Ma L L. Hydrodeoxygenation of lignin-derived phenoic compounds to hydrocarbon fuel over supported Ni-based catalysts. Applied Energy, 2018, 227: 73–79
|
| 11 |
Yung M M, Foo G S, Sievers C. Role of Pt during hydrodeoxygenation of biomass pyrolysis vapors over Pt/HBEA. Catalysis Today, 2018, 302: 151–160
|
| 12 |
He Z, Wang X Q. Highly selective catalytic hydrodeoxygenation of guaiacol to cyclohexane over Pt/TiO2 and NiMo/Al2O3 catalysts. Frontiers of Chemical Science and Engineering, 2014, 8(3): 369–377
|
| 13 |
He S B, Boom J, van der Gaast R, Seshan K. Hydro-pyrolysis of lignocellulosic biomass over alumina supported Platinum, Mo2C and WC catalysts. Frontiers of Chemical Science and Engineering, 2018, 12(1): 155–161
|
| 14 |
Mao L Y, Li Y X, Zhang Z C. Upgrading of derived pyrolysis vapors for the production of biofuels from corncobs. Frontiers of Chemical Science and Engineering, 2018, 12(1): 50–58
|
| 15 |
Shao Y, Xia Q E, Dong L, Liu X H, Han X, Parker S F, Cheng Y Q, Daemen L L, Ramirez-Cuesta A J, Yang S H, Wang Y. Selective production of arenes via direct lignin upgrading over a niobium-based catalyst. Nature Communications, 2017, 8(201): 1–9
|
| 16 |
Yoosuk B, Tumnantong D, Prasassarakich P. Unsupported MoS2 and CoMoS2 catalysts for hydrodeoxygenation of phenol. Chemical Engineering Science, 2012, 79: 1–7
|
| 17 |
Song W J, Zhou S J, Hu S H, Lai W K, Lian Y X, Wang J Q, Yang W M, Wang M Y, Wang P, Jiang X M. Surface engineering of CoMoS nanosulfide for hydrodeoxygenation of lignin-derived phenols to arenes. ACS Catalysis, 2019, 9(1): 259–268
|
| 18 |
Liu G L, Robertson A W, Li M M J, Kuo W C H, Darby M T, Muhieddine M H, Lin Y C, Suenaga K, Stamatakis M, Warner J H, Tsang S C E. MoS2 monolayer catalyst doped with isolated Co atoms for the hydrodeoxyganetion reaction. Nature Chemistry, 2017, 9(8): 1–7
|
| 19 |
Zhao C, Kou Y, Lemonidou A A, Li X B, Lercher J A. Highly selective catalytic conversion of phenolic bio-oil to alkanes. Angewandte Chemie International Edition, 2009, 48(22): 3987–3990
|
| 20 |
Zhao C, He J Y, Lemonidou A A, Li X B, Lercher J A. Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. Journal of Catalysis, 2011, 280(1): 8–16
|
| 21 |
Zhao C, Lercher J A. Selective hydrodeoxygenation of lignin-derived phenolic monomers and dimers to cycloalkanes on Pd/C and HZSM-5 catalysts. ChemCatChem, 2011, 4(1): 64–68
|
| 22 |
Zhao C, Kasakov S, He J Y, Lercher J A. Comparison of kinetics, activity and stability of Ni/HZSM-5 and Ni/Al2O3-HZSM-5 for phenol hydrodeoxygenation. Journal of Catalysis, 2012, 296: 12–23
|
| 23 |
Robinson A M, Hensley J E, Medlin J W. Bifunctional catalysts for upgrading of biomass-derived oxygenates: A review. ACS Catalysis, 2016, 6(8): 5026–5043
|
| 24 |
He J Y, Zhao C, Lercher J A. Impact of solvent for individual steps of phenol hydrodeoxygenation with Pd/C and HZSM-5 as catalysts. Journal of Catalysis, 2014, 309: 362–375
|
| 25 |
Song W J, Liu Y S, Baráth E, Zhao C, Lercher J A. Synergistic effects of Ni and acid sites for hydrogenation and C‒O bond cleavage of substituted phenols. Green Chemistry, 2015, 17(2): 1204–1218
|
| 26 |
Zhao C, Yu Y Z, Jentys A, Lercher J A. Understanding the impact of aluminum oxide binder on Ni/HZSM-5 for phenol hydrodeoxygenation. Applied Catalysis B: Environmental, 2013, 132: 282–292
|
| 27 |
Pichler C M, Gu D, Joshi H, Schuth F. Influence of preparation method and doping of zirconium oxide onto the material characteristics and catalytic activity for the HDO reaction in nickel on zirconium oxide catalysts. Journal of Catalysis, 2018, 365: 367–375
|
| 28 |
Yang F F, Liu D, Zhao Y T, Wang H, Han J Y, Ge Q F, Zhu X L. Size dependence of vapor phase hydrodeoxygenation of m-cresol on Ni/SiO2 catalysts. ACS Catalysis, 2018, 8(3): 1672–1682
|
| 29 |
Shi Y C, Xing E H, Cao Y Y, Liu M J, Wu K J, Yang M D, Wu Y L. Tailoring product distribution during upgrading of palmitic acid over bi-functional metal/zeolite catalysts. Chemical Engineering Science, 2017, 166: 262–273
|
| 30 |
Cao Y Y, Shi Y C, Liang J M, Wu Y L, Huang S B, Wang J L, Yang M D, Hu H S. High iso-alkanes production from palmitic acid over bi-functional Ni/H-ZSM-22 catalysts. Chemical Engineering Science, 2017, 158: 188–195
|
| 31 |
Sankaranarayanan T M, Berenguer A, Ochoa-Hernandez C, Moreno I, Jana P, Coronado J M, Serrano D P, Pizarro P. Hydrodeoxygenation of anisole as bio-oil model compound over supported Ni and Co catalysts: Effect of metal and support properties. Catalysis Today, 2015, 243: 163–172
|
| 32 |
Shi Y C, Xing E H, Zhang J M, Xie Y B, Zhao H, Sheng Y X, Cao H B. Temperature-dependent selectivity of hydrogenation/hydrogenolysis during phenol conversion over Ni catalysts. ACS Sustainable Chemistry & Engineering, 2019, 7(10): 9464–9473
|
| 33 |
Jo S K. Weakly-bound hydrogen on defected Pt (111). Surface Science, 2015, 635: 99–107
|
| 34 |
de Souza P M, Rabelo-Neto R C, Borges L E P, Jacobs G, Davis B H, Resasco D E, Noronha F B. Hydrodeoxygenation of phenol over Pd catalysts effect of support on reaction mechanism and catalyst deactivation. ACS Catalysis, 2017, 7(3): 2058–2073
|
| 35 |
de Souza P M, Rabelo-Neto R C, Borges L E P, Jacobs G, Davis B H, Sooknoi T, Resasco D E, Noronha F B. Role of keto intermediates in the hydrodeoxygenation of phenol over Pd on oxophilic supports. ACS Catalysis, 2015, 5(2): 1318–1329
|
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