Hydrodeoxygenation of phenolic compounds to cycloalkanes over supported nickel phosphides

Yu, Zhiquan; Wang, Anjie; Liu, Shan; Yao, Yunlong; Sun, Zhichao; Li, Xiang; Liu, Yingya; Wang, Yao; Camaioni, Donald M.; Lercher, Johannes A.

doi:10.1016/j.cattod.2018.05.012

Title: Hydrodeoxygenation of phenolic compounds to cycloalkanes over supported nickel phosphides

Journal Article · Mon May 07 00:00:00 EDT 2018 · Catalysis Today

DOI:https://doi.org/10.1016/j.cattod.2018.05.012· OSTI ID:1437025

Yu, Zhiquan ^[1]; Wang, Anjie ^[1]; Liu, Shan ^[1]; Yao, Yunlong ^[1]; Sun, Zhichao ^[1]; Li, Xiang ^[1]; Liu, Yingya ^[1]; Wang, Yao ^[1]; Camaioni, Donald M. ^[2]; Lercher, Johannes A. ^[2]

Dalian Univ. of Technology, Dalian (China)
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

SiO₂, HZSM-5 and Al₂O₃ were used to support nickel phosphides to prepare hydrodeoxygenation (HDO) catalysts. The nickel loading was kept at 20 wt% while the Ni/P molar ratio was varied among 3, 2, and 1 in the preparation by incipient wetness impregnation. XRD characterization revealed that Ni₃P, Ni₁₂P₅, and Ni₂P as the major crystal phases were obtained at Ni/P ratio of 3, 2, and 1, respectively, on SiO₂ and HZSM-5. When Al₂O₃ was used as the support, nickel metal rather than nickel phosphides was generated. Among SiO₂-supported nickel phosphides, Ni₃P exhibited highest hydrogenation activity and catalytic performance in phenol HDO. Ni₃P/HZSM-5 showed the high catalytic performance in HDO of phenol as well as catechol and o-cresol, with Ni₃P as the hydrogenation site and the acid sites in HZSM-5 zeolite as the dehydration site. In conclusion, the strong acidity in HZSM-5 also facilitated the isomerization of cycloalkanes at elevated temperatures.

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Research Organization:: Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-76RL01830; 21073022; 21173033; 21473017; 21603024; U1162203; U1508205; 2016YFE01069800

OSTI ID:: 1437025

Journal Information:: Catalysis Today, Vol. 319; ISSN 0920-5861

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 40 works

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References (44)

Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
A review of catalytic upgrading of bio-oil to engine fuels Mortensen, P. M.; Grunwaldt, J.-D.; Jensen, P. A. Applied Catalysis A: General, Vol. 407, Issue 1-2, p. 1-19 https://doi.org/10.1016/j.apcata.2011.08.046	journal	November 2011
Influence of oxygen-, nitrogen-, and sulfur-containing compounds on the hydrodeoxygenation of phenols over sulfided cobalt-molybdenum/.gamma.-alumina and nickel-molybdenum/.gamma.-alumina catalysts Laurent, Etienne; Delmon, Bernard Industrial & Engineering Chemistry Research, Vol. 32, Issue 11 https://doi.org/10.1021/ie00023a013	journal	November 1993
Historical Developments in Hydroprocessing Bio-oils Elliott, Douglas C. Energy & Fuels, Vol. 21, Issue 3, p. 1792-1815 https://doi.org/10.1021/ef070044u	journal	May 2007
Hydrodeoxygenation of guaiacol as model compound for pyrolysis oil on transition metal phosphide hydroprocessing catalysts Zhao, H. Y.; Li, D.; Bui, P. Applied Catalysis A: General, Vol. 391, Issue 1-2 https://doi.org/10.1016/j.apcata.2010.07.039	journal	January 2011
Production of Phenol and Cresol from Guaiacol on Nickel Phosphide Catalysts Supported on Acidic Supports Ted Oyama, S.; Onkawa, Tatsuki; Takagaki, Atsushi Topics in Catalysis, Vol. 58, Issue 4-6 https://doi.org/10.1007/s11244-015-0361-5	journal	March 2015
Support Effects of Ni2P Catalysts on the Hydrodeoxygenation of Guaiacol: In Situ XAFS Studies Moon, Ji-Sue; Lee, Yong-Kul Topics in Catalysis, Vol. 58, Issue 4-6 https://doi.org/10.1007/s11244-015-0362-4	journal	March 2015
Atmospheric Hydrodeoxygenation of Guaiacol over Alumina-, Zirconia-, and Silica-Supported Nickel Phosphide Catalysts Wu, Shin-Kuan; Lai, Po-Chen; Lin, Yu-Chuan ACS Sustainable Chemistry & Engineering, Vol. 1, Issue 3 https://doi.org/10.1021/sc300157d	journal	February 2013
Highly selective hydrodeoxygenation of anisole, phenol and guaiacol to benzene over nickel phosphide Li, Yunhua; Fu, Juan; Chen, Binghui RSC Advances, Vol. 7, Issue 25 https://doi.org/10.1039/C7RA00989E	journal	January 2017
Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes Zhao, Chen; He, Jiayue; Lemonidou, Angeliki A. Journal of Catalysis, Vol. 280, Issue 1 https://doi.org/10.1016/j.jcat.2011.02.001	journal	May 2011
Hydrodeoxygenation of Phenols to Form Cyclohexanes Catalyzed by Pt/H‐beta in Ester Solvents under Mild Conditions Ohta, Hidetoshi; Kong, Weihu; Yamamoto, Kentaro ChemistrySelect, Vol. 2, Issue 15 https://doi.org/10.1002/slct.201700696	journal	May 2017
Low temperature hydrodeoxygenation of phenols under ambient hydrogen pressure to form cyclohexanes catalysed by Pt nanoparticles supported on H-ZSM-5 Ohta, Hidetoshi; Yamamoto, Kentaro; Hayashi, Minoru Chemical Communications, Vol. 51, Issue 95 https://doi.org/10.1039/C5CC05607A	journal	January 2015
Catalytic Hydrodeoxygenation of Bio-oil Model Compounds over Pt/HY Catalyst Lee, Heejin; Kim, Hannah; Yu, Mi Jin Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep28765	journal	June 2016
Nickel and cobalt phosphides as effective catalysts for oxygen removal of dibenzofuran: role of contact time, hydrogen pressure and hydrogen/feed molar ratio Infantes-Molina, A.; Gralberg, E.; Cecilia, J. A. Catalysis Science & Technology, Vol. 5, Issue 6 https://doi.org/10.1039/C5CY00282F	journal	January 2015
Nickel Phosphides Supported on HZSM-5 for Catalytic Hydrodeoxygenation of Eugenol: Effect of Phosphorus Content Qi, Jingbo; Tang, Si-Fu; Sun, Yuanyuan ChemistrySelect, Vol. 2, Issue 25 https://doi.org/10.1002/slct.201701391	journal	August 2017
Ni ₃ P as a high-performance catalytic phase for the hydrodeoxygenation of phenolic compounds Yu, Zhiquan; Wang, Yao; Sun, Zhichao Green Chemistry, Vol. 20, Issue 3 https://doi.org/10.1039/C7GC03262E	journal	January 2018
Directly converting CO2 into a gasoline fuel Wei, Jian; Ge, Qingjie; Yao, Ruwei Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms15174	journal	May 2017
Dehydration of Alcohols on Aluminum Oxide Knözinger, H. Angewandte Chemie International Edition in English, Vol. 7, Issue 10 https://doi.org/10.1002/anie.196807911	journal	October 1968
Gas phase dehydration of C6 alcohols promoted by Y zeolite and supported nafion catalysts Park, Colin; Keane, Mark A. Journal of Molecular Catalysis A: Chemical, Vol. 166, Issue 2 https://doi.org/10.1016/S1381-1169(00)00474-X	journal	February 2001
Reaction path analysis for 1-butanol dehydration in H-ZSM-5 zeolite: Ab initio and microkinetic modeling John, Mathew; Alexopoulos, Konstantinos; Reyniers, Marie-Françoise Journal of Catalysis, Vol. 330 https://doi.org/10.1016/j.jcat.2015.07.005	journal	October 2015
Dehydration of 1-Octadecanol over H-BEA: A Combined Experimental and Computational Study Song, Wenji; Liu, Yuanshuai; Baráth, Eszter ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b01217	journal	January 2016
Metal Phosphides: Preparation, Characterization and Catalytic Reactivity Prins, Roel; Bussell, Mark E. Catalysis Letters, Vol. 142, Issue 12 https://doi.org/10.1007/s10562-012-0929-7	journal	November 2012
Hydrodeoxygenation of guaiacol over Ni2P/SiO2–reaction mechanism and catalyst deactivation Lan, Xuefang; Hensen, Emiel J. M.; Weber, Thomas Applied Catalysis A: General, Vol. 550 https://doi.org/10.1016/j.apcata.2017.10.018	journal	January 2018
Hydrodeoxygenation of m-cresol over nickel and nickel phosphide based catalysts. Influence of the nature of the active phase and the support Gonçalves, Vinicius O. O.; de Souza, Priscilla M.; Cabioc’h, Thierry Applied Catalysis B: Environmental, Vol. 219 https://doi.org/10.1016/j.apcatb.2017.07.042	journal	December 2017
Atmospheric Hydrodeoxygenation of Guaiacol over Nickel Phosphide Catalysts: Effect of Phosphorus Composition Wu, Shin-Kuan; Lai, Po-Chen; Lin, Yu-Chuan Catalysis Letters, Vol. 144, Issue 5 https://doi.org/10.1007/s10562-014-1231-7	journal	March 2014
Effects of P/Ni ratio and Ni content on performance of γ-Al 2 O 3 -supported nickel phosphides for deoxygenation of methyl laurate to hydrocarbons Zhang, Zhena; Tang, Mingxiao; Chen, Jixiang Applied Surface Science, Vol. 360 https://doi.org/10.1016/j.apsusc.2015.10.182	journal	January 2016
Preparation of Ni 2 P/Al 2 O 3 by temperature-programmed reduction of a phosphate precursor with a low P/Ni ratio Li, Xiang; Feng, Jianpeng; Guo, Jingyu Journal of Catalysis, Vol. 334 https://doi.org/10.1016/j.jcat.2015.11.007	journal	February 2016
Catalytic deoxygenation of methyl laurate as a model compound to hydrocarbons on nickel phosphide catalysts: Remarkable support effect Shi, Heng; Chen, Jixiang; Yang, Yan Fuel Processing Technology, Vol. 118 https://doi.org/10.1016/j.fuproc.2013.08.010	journal	February 2014
From nanoparticles to hierarchical structures: Controlling the morphology of zeolite beta Petushkov, Anton; Merilis, Giorvanni; Larsen, Sarah C. Microporous and Mesoporous Materials, Vol. 143, Issue 1 https://doi.org/10.1016/j.micromeso.2011.02.012	journal	August 2011
Hydroprocessing of soybean oil on nickel-phosphide supported catalysts Zarchin, Ruby; Rabaev, Moshe; Vidruk-Nehemya, Roxana Fuel, Vol. 139 https://doi.org/10.1016/j.fuel.2014.09.053	journal	January 2015
Reversibility of the Modification of HZSM-5 with Phosphate Anions Derewinski, Miroslaw; Sarv, Priit; Sun, Xianyong The Journal of Physical Chemistry C, Vol. 118, Issue 12 https://doi.org/10.1021/jp4053677	journal	March 2014
Hydroconversion of methyl laurate on bifunctional Ni 2 P/AlMCM-41 catalyst prepared via in situ phosphorization using triphenylphosphine Zhao, Sha; Zhang, Zhena; Zhu, Kongying Applied Surface Science, Vol. 404 https://doi.org/10.1016/j.apsusc.2017.02.016	journal	May 2017
Facile Preparation of Ni ₂ P with a Sulfur-Containing Surface Layer by Low-Temperature Reduction of Ni ₂ P ₂ S ₆ Tian, Song; Li, Xiang; Wang, Anjie Angewandte Chemie International Edition, Vol. 55, Issue 12 https://doi.org/10.1002/anie.201510599	journal	February 2016
Role of sulfur in hydrotreating catalysis over nickel phosphide Duan, X.; Teng, Y.; Wang, A. Journal of Catalysis, Vol. 261, Issue 2 https://doi.org/10.1016/j.jcat.2008.12.003	journal	January 2009
Density functional theory study on crystal nickel phosphides Ren, Jun; Wang, Jian-guo; Li, Jun-fen Journal of Fuel Chemistry and Technology, Vol. 35, Issue 4 https://doi.org/10.1016/S1872-5813(07)60029-2	journal	August 2007
Spatial and electronic structure of the Ni3P surface Zhou, Liangcai; Kong, Yi; Du, Yong Applied Surface Science, Vol. 256, Issue 24 https://doi.org/10.1016/j.apsusc.2010.06.038	journal	October 2010
Effect of a second metal (Co, Fe, Mo and W) on performance of Ni2P/SiO2 for hydrodeoxygenation of methyl laurate Pan, Zhengyi; Wang, Rijie; Nie, Ziyang Journal of Energy Chemistry, Vol. 25, Issue 3 https://doi.org/10.1016/j.jechem.2016.02.007	journal	May 2016
Silica deposition as an approach for improving the hydrothermal stability of an alumina support during glycerol aqueous phase reforming Liu, Fang; Okolie, Chukwuemeka; Ravenelle, Ryan M. Applied Catalysis A: General, Vol. 551 https://doi.org/10.1016/j.apcata.2017.11.025	journal	February 2018
Influence of CS 2 on performance of Ni 2 P/SiO 2 for deoxygenation of methyl laurate as a model compound to hydrocarbons: Simultaneous investigation on catalyst deactivation Zheng, Zheng; Li, Ming-Feng; Chu, Yang Fuel Processing Technology, Vol. 134 https://doi.org/10.1016/j.fuproc.2015.02.002	journal	June 2015
Nanosized Metal Phosphides Embedded in Nitrogen-Doped Porous Carbon Nanofibers for Enhanced Hydrogen Evolution at All pH Values Wang, Min-Qiang; Ye, Cui; Liu, Heng Angewandte Chemie International Edition, Vol. 57, Issue 7 https://doi.org/10.1002/anie.201710150	journal	January 2018
Hydrodeoxygenation of lignin model compounds over a copper chromite catalyst Deutsch, Keenan L.; Shanks, Brent H. Applied Catalysis A: General, Vol. 447-448 https://doi.org/10.1016/j.apcata.2012.09.047	journal	December 2012
Kinetics of the hydrodeoxygenation of cresol isomers over Ni2P/SiO2: Proposals of nature of deoxygenation active sites based on an experimental study Gonçalves, Vinicius O. O.; de Souza, Priscilla M.; da Silva, Victor Teixeira Applied Catalysis B: Environmental, Vol. 205 https://doi.org/10.1016/j.apcatb.2016.12.051	journal	May 2017
Catalytic Hydrodeoxygenation of Methyl-Substituted Phenols: Correlations of Kinetic Parameters with Molecular Properties Massoth, F. E.; Politzer, P.; Concha, M. C. The Journal of Physical Chemistry B, Vol. 110, Issue 29 https://doi.org/10.1021/jp057332g	journal	July 2006
Hydrogenation of o-cresol on platinum catalyst: Catalytic experiments and first-principles calculations Li, Yaping; Liu, Zhimin; Xue, Wenhua Applied Surface Science, Vol. 393 https://doi.org/10.1016/j.apsusc.2016.10.028	journal	January 2017

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