Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase

Liu, Shiwei; Han, Jing; Wu, Qiong; Bian, Bing; Li, Lu; Yu, Shitao; Song, Jie; Zhang, Cong; Ragauskas, Arthur J.

doi:10.1007/s10562-019-02852-1

Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase

Journal Article · Thu Jun 06 00:00:00 EDT 2019 · Catalysis Letters

DOI:https://doi.org/10.1007/s10562-019-02852-1· OSTI ID:1665977

^[1]; Han, Jing ^[1]; Wu, Qiong ^[1]; Bian, Bing ^[2]; Li, Lu ^[1]; Yu, Shitao ^[1]; Song, Jie ^[3]; Zhang, Cong ^[1]; ^[4]

Qingdao Univ. of Science and Technology (China)
Shandong Univ. of Science and Technology, Qingdao (China)
Univ. of Michigan, Ann Arbor, MI (United States)
Univ. of Tennessee, Knoxville, TN (United States)

Cyclohexanone is an important intermediate in the manufacture of polyamides in chemical industry, but direct selective hydrogenation of phenol to cyclohexanone under mild conditions is a challenge. Hydrogenation of phenol to cyclohexanone has been investigated in the presence of the composite catalytic system of Pd/C-heteropoly acid. 100% conversion of phenol and 93.6% selectivity of cyclohexanone were achieved within 3 h under 80 °C and 1.0 MPa hydrogen pressure. It has been found that a synergetic effect of Pd/C and heteropoly acid enhanced the catalytic performance of the composite catalytic system which suppressed the hydrogenation of cyclohexanone to cyclohexanol.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1665977

Journal Information:: Catalysis Letters, Journal Name: Catalysis Letters Journal Issue: 9 Vol. 149; ISSN 1011-372X

Publisher:: SpringerCopyright Statement

Country of Publication:: United States

Language:: English

References (29)

Selective hydrogenation of cinnamaldehyde using Pd catalysts supported on Mg/Al mixed oxides: Influence of the Pd incorporation method Martínez-Ortiz, María J.; de la Rosa-Guzmán, Miguel A.; Vargas-García, Jorge R. The Canadian Journal of Chemical Engineering, Vol. 96, Issue 1 https://doi.org/10.1002/cjce.22946	journal	August 2017
Improved (Photo)catalytic Propene Hydration in a Gas/Solid System by Using Heteropolyacid/Oxide Composites: Electron Paramagnetic Resonance, Acidity, and Role of Water: Improved (Photo)catalytic Propene Hydration in a Gas/Solid System by Using Heteropolyacid/Oxide Composites: Electron Paramagnetic Resonance, Acidity, García-López, Elisa I.; Marcì, Giuseppe; Pomilla, Francesca R. European Journal of Inorganic Chemistry, Vol. 2017, Issue 13 https://doi.org/10.1002/ejic.201601396	journal	April 2017
Polymer synthesis by solid-acid catalyst based on heteropolyacid ammonium salt Morinaga, Hisatoyo; Nakajima, Lisa; Nishioka, Yoshihito Polymer Bulletin, Vol. 73, Issue 2 https://doi.org/10.1007/s00289-015-1498-x	journal	August 2015
Air-promoted selective hydrogenation of phenol to cyclohexanone at low temperature over Pd-based nanocatalysts Guo, Qing; Mo, Shiguang; Liu, Pengxin Science China Chemistry, Vol. 60, Issue 11 https://doi.org/10.1007/s11426-017-9095-4	journal	August 2017
Liquid phase selective hydrogenation of furfural on Raney nickel modified by impregnation of salts of heteropolyacids Baijun, Liu; Lianhai, Lu; Bingchun, Wang Applied Catalysis A: General, Vol. 171, Issue 1 https://doi.org/10.1016/S0926-860X(98)00081-7	journal	June 1998
Pd–heteropoly acid as a bifunctional heterogeneous catalyst for one-pot conversion of citronellal to menthol da Silva Rocha, Kelly A.; Robles-Dutenhefner, Patricia A.; Sousa, Edesia M. B. Applied Catalysis A: General, Vol. 317, Issue 2 https://doi.org/10.1016/j.apcata.2006.10.019	journal	February 2007
Aqueous phase electrocatalysis and thermal catalysis for the hydrogenation of phenol at mild conditions Song, Yang; Gutiérrez, Oliver Y.; Herranz, Juan Applied Catalysis B: Environmental, Vol. 182 https://doi.org/10.1016/j.apcatb.2015.09.027	journal	March 2016
Selective hydrogenation of phenol to cyclohexanone over Pd@CN (N-doped porous carbon): Role of catalyst reduction method Hu, Shuo; Yang, Guangxin; Jiang, Hong Applied Surface Science, Vol. 435 https://doi.org/10.1016/j.apsusc.2017.11.181	journal	March 2018
Highly selective hydrogenation of phenol and derivatives over Pd catalysts supported on SiO2 and γ-Al2O3 in aqueous media Cheng, Ling; Dai, Qiguang; Li, Hua Catalysis Communications, Vol. 57 https://doi.org/10.1016/j.catcom.2014.07.006	journal	December 2014
One-step semi-continuous cyclohexanone production via hydrogenation of phenol in a submerged ceramic membrane reactor Jiang, Hong; Qu, Zhengyan; Li, Ying Chemical Engineering Journal, Vol. 284 https://doi.org/10.1016/j.cej.2015.09.037	journal	January 2016
Selective hydrogenation of phenol by phosphotungstic acid modified Pd/Ce-AlO x catalyst in high-temperature water system Guan, Qingqing; Zeng, Yanhua; Shen, Junjun Chemical Engineering Journal, Vol. 299 https://doi.org/10.1016/j.cej.2016.03.105	journal	September 2016
12-Molybdophosphoric acid supported on titania: A highly active and selective heterogeneous catalyst for the transesterification of dimethyl carbonate and phenol Wang, Songlin; Tang, Rongzhi; Zhang, Yuanzhuo Chemical Engineering Science, Vol. 138 https://doi.org/10.1016/j.ces.2015.08.005	journal	December 2015
Rational synthesis of core-shell Fe3O4@thermally crosslinked PANI nanostructures based on a PVP-mediated in-situ polymerization strategy: Towards a stable catalyst support for 12-tungstophosphoric acid Fang, Lining; Wang, Ge; Guo, Wanchun Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 533 https://doi.org/10.1016/j.colsurfa.2017.07.060	journal	November 2017
Isomerisation of n-hexane over bifunctional Pt-heteropoly acid catalyst: Enhancing effect of gold Alazman, Abdulrahman; Belic, Domagoj; Kozhevnikova, Elena F. Journal of Catalysis, Vol. 357 https://doi.org/10.1016/j.jcat.2017.11.001	journal	January 2018
Insights into deactivation mechanism of Pd@CN catalyst in the liquid-phase hydrogenation of phenol to cyclohexanone Hu, Shuo; Zhang, Xiang; Qu, Zhengyan Journal of Industrial and Engineering Chemistry, Vol. 53 https://doi.org/10.1016/j.jiec.2017.05.004	journal	September 2017
Highly selective hydrogenation of phenol to cyclohexanol over nano silica supported Ni catalysts in aqueous medium He, J.; Lu, X. -H.; Shen, Y. Molecular Catalysis, Vol. 440 https://doi.org/10.1016/j.mcat.2017.07.016	journal	October 2017
Redox properties of Keggin-type heteropolyacid (HPA) catalysts: effect of counter-cation, heteroatom, and polyatom substitution Song, In K.; Barteau, Mark A. Journal of Molecular Catalysis A: Chemical, Vol. 212, Issue 1-2 https://doi.org/10.1016/j.molcata.2003.10.040	journal	April 2004
A Side-Stream Catalysis/Membrane Filtration System for the Continuous Liquid-Phase Hydrogenation of Phenol over Pd@CN to Produce Cyclohexanone Qu, Zhengyan; Hu, Shuo; Jiang, Hong Industrial & Engineering Chemistry Research, Vol. 56, Issue 41 https://doi.org/10.1021/acs.iecr.7b03043	journal	October 2017
Enhanced Selectivity of Phenol Hydrogenation in Low-Pressure CO ₂ over Supported Pd Catalysts Liu, Tianzhu; Zhou, Hu; Han, Bingbing ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 12 https://doi.org/10.1021/acssuschemeng.7b02974	journal	November 2017
Synthesis of ketones from biomass-derived feedstock Meng, Qinglei; Hou, Minqiang; Liu, Huizhen Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms14190	journal	January 2017
Selective hydrogenation of phenol and related derivatives Zhong, Jiawei; Chen, Jinzhu; Chen, Limin Catal. Sci. Technol., Vol. 4, Issue 10 https://doi.org/10.1039/C4CY00583J	journal	January 2014
Selective phenol hydrogenation to cyclohexanone over alkali–metal-promoted Pd/TiO ₂ in aqueous media Zhou, Hu; Han, Bingbing; Liu, Tianzhu Green Chemistry, Vol. 19, Issue 15 https://doi.org/10.1039/C7GC01318C	journal	January 2017
Decoration of chitosan microspheres with Brønsted heteropolyacids and Lewis ion Ti: trifunctional catalysts for esterification to biodiesel Tong, Tong; Li, Yiming; Hou, Rui RSC Advances, Vol. 7, Issue 67 https://doi.org/10.1039/C7RA07479D	journal	January 2017
Synergistic catalysis of nano-Pd and nano rare-earth oxide/AC: complex nanostructured catalysts fabricated by a photochemical route for selective hydrogenation of phenol Zhang, Yanji; Zhou, Jicheng; Si, Jiaqi RSC Advances, Vol. 7, Issue 86 https://doi.org/10.1039/C7RA09917G	journal	January 2017
Using One Rotary Blood Pump to Produce Separate Pulsatile Circulations in the Upper and Lower Halves of the Body Isoyama, Takashi; Abe, Yusuke; Chinzei, Tsuneo Artificial Organs, Vol. 24, Issue 8 https://doi.org/10.1046/j.1525-1594.2000.06592.x	journal	August 2000
Heteropoly acid supported on activated natural clay-catalyzed synthesis of 3,4-dihydropyrimidinones/thiones through Biginelli reaction under solvent-free conditions Selvakumar, Karuppaiah; Shanmugaprabha, Thangamariyappan; Kumaresan, Murugan Synthetic Communications, Vol. 48, Issue 2 https://doi.org/10.1080/00397911.2017.1396614	journal	December 2017
Heteropoly acid supported on activated natural clay-catalyzed synthesis of 3,4-dihydropyrimidinones/thiones through Biginelli reaction under solvent-free conditions Selvakumar, Karuppaiah; Shanmugaprabha, Thangamariyappan; Kumaresan, Murugan Taylor & Francis https://doi.org/10.6084/m9.figshare.5734746	text	January 2017
Heteropoly acid supported on activated natural clay-catalyzed synthesis of 3,4-dihydropyrimidinones/thiones through Biginelli reaction under solvent-free conditions Selvakumar, Karuppaiah; Shanmugaprabha, Thangamariyappan; Kumaresan, Murugan Taylor & Francis https://doi.org/10.6084/m9.figshare.5734746.v1	text	January 2017
Liquid-phase Hydrogenation of Phenol to Cyclohexanone over Supported Palladium Catalysts Fan, Lihui; Zhang, Luyang; Shen, Yanming Bulletin of Chemical Reaction Engineering & Catalysis, Vol. 11, Issue 3 https://doi.org/10.9767/bcrec.11.3.575.354-362	journal	October 2016

Cited By (1)

Polarized Catalytic Polymer Nanofibers Lolla, Dinesh; Abutaleb, Ahmed; Kashfipour, Marjan A. Materials, Vol. 12, Issue 18 https://doi.org/10.3390/ma12182859	journal	September 2019

Similar Records

Highly selective hydrogenation of phenol to cyclohexanone over a Pd-loaded N-doped carbon catalyst derived from chitosan

Journal Article · Fri Dec 31 19:00:00 EST 2021 · Journal of Colloid and Interface Science · OSTI ID:1820750

Impact of solvent for individual steps of phenol hydrodeoxygenation with Pd/C and HZSM-5 as catalysts

Journal Article · Tue Dec 31 23:00:00 EST 2013 · Journal of Catalysis · OSTI ID:1234794

Carbon-supported platinum alloy catalysts for phenol hydrogenation for making industrial chemicals

Conference · Thu Jul 01 00:00:00 EDT 1999 · OSTI ID:20082355

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase

Citation Formats

References (29)

Cited By (1)

Similar Records

Related Subjects