Oxidation of Cyclohexene Catalyzed by Nanoporous Au(Ag) in Liquid Phase

Dou, Jian; Tang, Yu; Nguyen, Luan; Tong, Xiao; Thapa, Prem S.; Tao, Franklin Feng

doi:10.1007/s10562-016-1883-6

Oxidation of Cyclohexene Catalyzed by Nanoporous Au(Ag) in Liquid Phase

Journal Article · Thu Dec 22 00:00:00 EST 2016 · Catalysis Letters

DOI:https://doi.org/10.1007/s10562-016-1883-6· OSTI ID:1438210

Dou, Jian ^[1]; Tang, Yu ^[1]; Nguyen, Luan ^[1]; Tong, Xiao ^[2]; Thapa, Prem S. ^[3]; Tao, Franklin Feng ^[4]

Univ. of Kansas, Lawrence, KS (United States). Dept. of Chemical and Petroleum Engineering
Brookhaven National Lab. (BNL), Upton, NY (United States). Center for Functional Nanomaterials
Univ. of Kansas, Lawrence, KS (United States). Microscopy and Analytical Imaging Lab.
Univ. of Kansas, Lawrence, KS (United States). Dept. of Chemical and Petroleum Engineering. Dept. of Chemistry

Nanoporous gold with minor silver content has been identified as a new type of gold based catalyst for selective oxidation of cyclohexene with molecular oxygen in liquid. By oxidation of the leached nanoporous gold foils in ozone, the minor silver content was oxidized in this paper to form silver oxide nanoclusters on the surface of nanoporous gold. With further treatment in methanol, the surface silver oxide was reduced and surface alloy was formed on gold ligaments. Both nanoporous gold treated with ozone only and the one with ozone and then methanol are very active for selective oxidation of cyclohexene with molecular oxygen in liquid of cyclohexene with a turn-over-frequency (TOF) of 0.55–0.99 molecules per surface Au atom per second under a solvent-free and initiator- free condition. The total selectivity for production of 2-cyclohexene-1-one, 2-cyclohexene-1-ol, and cyclohexene oxide was increased from 57.5 % to 80.8 % by an additional treatment of nanoporous gold in methanol after activation in zone. Finally, the correlation of catalytic selectivity for the production of the three products and corresponding surface chemistry of ligament suggests that (1) the formed Au–Ag alloy surface is favorable for the formation of 2-cyclohexen-1-one, 2-cyclohexene-1-ol, and cyclohexene oxide and (2) the surface silver oxide is favorable for the production of cyclohexenyl hydroperoxide.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States); Energy Frontier Research Centers (EFRC) (United States). Integrated Mesoscale Architectures for Sustainable Catalysis (IMASC); Univ. of Kansas, Lawrence, KS (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0012573; SC0012704

OSTI ID:: 1438210

Report Number(s):: BNL--205655-2018-JAAM

Journal Information:: Catalysis Letters, Journal Name: Catalysis Letters Journal Issue: 2 Vol. 147; ISSN 1011-372X

Publisher:: SpringerCopyright Statement

Country of Publication:: United States

Language:: English

References (67)

Gold Catalysis Hashmi, A. Stephen K.; Hutchings, Graham J. Angewandte Chemie International Edition, Vol. 45, Issue 47 https://doi.org/10.1002/anie.200602454	journal	December 2006
Gold Catalysts: Nanoporous Gold Foams Zielasek, Volkmar; Jürgens, Birte; Schulz, Christian Angewandte Chemie International Edition, Vol. 45, Issue 48 https://doi.org/10.1002/anie.200602484	journal	December 2006
On the Role of Residual Ag in Nanoporous Au Catalysts for CO Oxidation: A Combined Microreactor and TAP Reactor Study Wang, L. C.; Zhong, Y.; Widmann, D. ChemCatChem, Vol. 4, Issue 2 https://doi.org/10.1002/cctc.201100297	journal	December 2011
Oxidative Coupling of Alcohols and Amines over Bimetallic Unsupported Nanoporous Gold: Tailored Activity through Mechanistic Predictability Wichmann, Andre; Bäumer, Marcus; Wittstock, Arne ChemCatChem, Vol. 7, Issue 1 https://doi.org/10.1002/cctc.201402843	journal	November 2014
X-ray photoelectron spectroscopic binding energy shifts due to matrix in alloys and small supported metal particles Kim, K. S.; Winograd, N. Chemical Physics Letters, Vol. 30, Issue 1 https://doi.org/10.1016/0009-2614(75)85505-9	journal	January 1975
Ruthenium catalyzed epoxidations: mechanistic and synthetic aspects Barf, G. A.; Sheldon, R. A. Journal of Molecular Catalysis A: Chemical, Vol. 102, Issue 1 https://doi.org/10.1016/1381-1169(95)00089-5	journal	September 1995
Instability of gold oxide Au2O3 Tsai, Hungchun; Hu, Emily; Perng, Kuoguang Surface Science, Vol. 537, Issue 1-3 https://doi.org/10.1016/S0039-6028(03)00640-X	journal	July 2003
Oxidation of a polycrystalline silver foil by reaction with ozone Waterhouse, G. I. N.; Bowmaker, G. A.; Metson, J. B. Applied Surface Science, Vol. 183, Issue 3-4 https://doi.org/10.1016/S0169-4332(01)00561-X	journal	November 2001
The direct epoxidation of higher olefins using molecular oxygen Monnier, John R. Applied Catalysis A: General, Vol. 221, Issue 1-2 https://doi.org/10.1016/S0926-860X(01)00799-2	journal	November 2001
Oxovanadium(IV) complexes as homogeneous catalyst—aerobic epoxidation of olefins Mohebbi, Sajjad; Boghaei, Davar M.; Sarvestani, Ali Hossien Applied Catalysis A: General, Vol. 278, Issue 2 https://doi.org/10.1016/j.apcata.2004.10.005	journal	January 2005
Efficient allylic oxidation of cyclohexene catalyzed by immobilized Schiff base complex using peroxides as oxidants Mukherjee, Sanghamitra; Samanta, Sujit; Roy, Bidhan Chandra Applied Catalysis A: General, Vol. 301, Issue 1 https://doi.org/10.1016/j.apcata.2005.11.015	journal	February 2006
A “one-pot” synthesis of adipic acid from cyclohexene under mild conditions with new bifunctional Ti-AlSBA mesostructured catalysts Lapisardi, Grégory; Chiker, Fatima; Launay, Franck Catalysis Communications, Vol. 5, Issue 6 https://doi.org/10.1016/j.catcom.2004.03.005	journal	June 2004
Interplay of theoretical calculations and experiments for a study of catalysis by gold Okumura, Mitsutaka; Haruta, Masatake Catalysis Today, Vol. 259 https://doi.org/10.1016/j.cattod.2015.05.006	journal	January 2016
Superior catalytic properties in aerobic oxidation of olefins over Au nanoparticles on pyrrolidone-modified SBA-15 Wang, Liang; Wang, Hong; Hapala, Prokop Journal of Catalysis, Vol. 281, Issue 1 https://doi.org/10.1016/j.jcat.2011.03.029	journal	July 2011
Solvent-free allylic oxidation of alkenes with O2 mediated by Fe- and Cr-MIL-101 Skobelev, Igor Y.; Sorokin, Alexander B.; Kovalenko, Konstantin A. Journal of Catalysis, Vol. 298 https://doi.org/10.1016/j.jcat.2012.11.003	journal	February 2013
Catalysis on nanoporous gold–silver systems: Synergistic effects toward oxidation reactions and influence of the surface composition Déronzier, Thierry; Morfin, Franck; Lomello, Marc Journal of Catalysis, Vol. 311 https://doi.org/10.1016/j.jcat.2013.12.001	journal	March 2014
Thin-sheet microfibrous-structured nanoporous gold/Al fiber catalysts for oxidative coupling of methanol to methyl formate Zhang, Qiaofei; Li, Yakun; Zhang, Li Journal of Catalysis, Vol. 317 https://doi.org/10.1016/j.jcat.2014.06.004	journal	August 2014
Exploiting basic principles to control the selectivity of the vapor phase catalytic oxidative cross-coupling of primary alcohols over nanoporous gold catalysts Wang, Lu-Cun; Stowers, Kara J.; Zugic, Branko Journal of Catalysis, Vol. 329 https://doi.org/10.1016/j.jcat.2015.04.022	journal	September 2015
Low-temperature CO oxidation over unsupported nanoporous gold catalysts with active or inert oxide residues Duan, Huimei; Xu, Caixia Journal of Catalysis, Vol. 332 https://doi.org/10.1016/j.jcat.2015.08.014	journal	December 2015
Gold on thiol-functionalized magnetic mesoporous silica sphere catalyst for the aerobic oxidation of olefins Fang, Yiyun; Chen, Yuanzhe; Li, Xinzhe Journal of Molecular Catalysis A: Chemical, Vol. 392 https://doi.org/10.1016/j.molcata.2014.04.032	journal	October 2014
Determination of Organic Peroxides by Iodine Liberation Procedures. Mair, R. D.; Graupner, A. J. Analytical Chemistry, Vol. 36, Issue 1 https://doi.org/10.1021/ac60207a061	journal	January 1964
Oxidation of Olefins with Hydrogen Peroxide Catalyzed by Bismuth Salts: A Mechanistic Study Kuznetsov, Maxim L.; Rocha, Bruno G. M.; Pombeiro, Armando J. L. ACS Catalysis, Vol. 5, Issue 6 https://doi.org/10.1021/acscatal.5b00077	journal	May 2015
Ozone-Activated Nanoporous Gold: A Stable and Storable Material for Catalytic Oxidation Personick, Michelle L.; Zugic, Branko; Biener, Monika M. ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00330	journal	June 2015
Nanoporous Gold: Understanding the Origin of the Reactivity of a 21st Century Catalyst Made by Pre-Columbian Technology Biener, Juergen; Biener, Monika M.; Madix, Robert J. ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01586	journal	September 2015
Switchable Alkene Epoxidation/Oxidative Cleavage with H ₂ O ₂ /NaHCO ₃ : Efficient Heterogeneous Catalysis Derived from Biosourced Eco-Mn Escande, Vincent; Petit, Eddy; Garoux, Laetitia ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 11 https://doi.org/10.1021/acssuschemeng.5b00561	journal	October 2015
Catalysis by Unsupported Skeletal Gold Catalysts Wittstock, Arne; Bäumer, Marcus Accounts of Chemical Research, Vol. 47, Issue 3 https://doi.org/10.1021/ar400202p	journal	November 2013
Metal-Catalyzed Epoxidations of Alkenes with Hydrogen Peroxide Lane, Benjamin S.; Burgess, Kevin Chemical Reviews, Vol. 103, Issue 7 https://doi.org/10.1021/cr020471z	journal	July 2003
Cyclohexene Epoxidation with Cyclohexyl Hydroperoxide: A Catalytic Route to Largely Increase Oxygenate Yield from Cyclohexane Oxidation Hereijgers, Bart P. C.; Parton, Rudy F.; Weckhuysen, Bert M. ACS Catalysis, Vol. 1, Issue 10 https://doi.org/10.1021/cs200354c	journal	August 2011
Establishing a Au Nanoparticle Size Effect in the Oxidation of Cyclohexene Using Gradually Changing Au Catalysts Donoeva, Baira G.; Ovoshchnikov, Daniil S.; Golovko, Vladimir B. ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs400701j	journal	November 2013
Surface Characterization Study of the Thermal Decomposition of AgO Weaver, Jason F.; Hoflund, Gar B. The Journal of Physical Chemistry, Vol. 98, Issue 34 https://doi.org/10.1021/j100085a035	journal	August 1994
Selective Oxidation of Styrene on an Oxygen-Covered Au(111) Deng, Xingyi; Friend, Cynthia M. Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja0557031	journal	December 2005
Low Temperature CO Oxidation over Unsupported Nanoporous Gold Xu, Caixia; Su, Jixin; Xu, Xiaohong Journal of the American Chemical Society, Vol. 129, Issue 1, p. 42-43 https://doi.org/10.1021/ja0675503	journal	January 2007
Achieving Optimum Selectivity in Oxygen Assisted Alcohol Cross-Coupling on Gold Xu, Bingjun; Madix, Robert J.; Friend, Cynthia M. Journal of the American Chemical Society, Vol. 132, Issue 46 https://doi.org/10.1021/ja106706v	journal	November 2010
Toward Controlled Modification of Nanoporous Gold. A Detailed Surface Science Study on Cleaning and Oxidation Schaefer, A.; Ragazzon, D.; Wittstock, A. The Journal of Physical Chemistry C, Vol. 116, Issue 7 https://doi.org/10.1021/jp207638t	journal	February 2012
Nanoporous Gold-Supported Ceria for the Water–Gas Shift Reaction: UHV Inspired Design for Applied Catalysis Shi, Junjie; Schaefer, Andreas; Wichmann, Andre The Journal of Physical Chemistry C, Vol. 118, Issue 50 https://doi.org/10.1021/jp505433a	journal	July 2014
Density Functional Theory (DFT) Studies of CO Oxidation over Nanoporous Gold: Effects of Residual Ag and CO Self-Promoting Oxidation Wang, Pu; Tang, Xianqiong; Tang, Jian The Journal of Physical Chemistry C, Vol. 119, Issue 19 https://doi.org/10.1021/jp5124376	journal	May 2015
Investigation of Halide-Induced Aggregation of Au Nanoparticles into Spongelike Gold Zhang, Zhiqiang; Li, Haiwen; Zhang, Feng Langmuir, Vol. 30, Issue 10 https://doi.org/10.1021/la4046447	journal	March 2014
ALD Functionalized Nanoporous Gold: Thermal Stability, Mechanical Properties, and Catalytic Activity Biener, Monika M.; Biener, Juergen; Wichmann, Andre Nano Letters, Vol. 11, Issue 8 https://doi.org/10.1021/nl200993g	journal	August 2011
Atomic Observation of Catalysis-Induced Nanopore Coarsening of Nanoporous Gold Fujita, Takeshi; Tokunaga, Tomoharu; Zhang, Ling Nano Letters, Vol. 14, Issue 3 https://doi.org/10.1021/nl403895s	journal	February 2014
Tunable gold catalysts for selective hydrocarbon oxidation under mild conditions Hughes, Mathew D.; Xu, Yi-Jun; Jenkins, Patrick Nature, Vol. 437, Issue 7062 https://doi.org/10.1038/nature04190	journal	October 2005
Selective oxidation with dioxygen by gold nanoparticle catalysts derived from 55-atom clusters Turner, Mark; Golovko, Vladimir B.; Vaughan, Owain P. H. Nature, Vol. 454, Issue 7207 https://doi.org/10.1038/nature07194	journal	August 2008
Sponge-like nanoporous single crystals of gold Khristosov, Maria Koifman; Bloch, Leonid; Burghammer, Manfred Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms9841	journal	November 2015
Hierarchical Nanoporous Gold-Platinum with Heterogeneous Interfaces for Methanol Electrooxidation Xiao, Shuang; Xiao, Fei; Hu, Yuan Scientific Reports, Vol. 4, Issue 1 https://doi.org/10.1038/srep04370	journal	March 2014
Mesoporous gold sponges: electric charge-assisted seed mediated synthesis and application as surface-enhanced Raman scattering substrates Yi, Zao; Luo, Jiangshan; Tan, Xiulan Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep16137	journal	November 2015
Different morphologies of silver nanoparticles as catalysts for the selective oxidation of styrene in the gas phase Chimentão, R. J.; Kirm, I.; Medina, F. Chem. Commun., Issue 7 https://doi.org/10.1039/B400762J	journal	January 2004
Highly selective epoxidation of styrene using a transition metal–aluminium( iii ) complex containing the [MeAl(2-py) ₃ ] ⁻ anion (2-py = 2-pyridyl) Alvarez, Carmen Soria; García, Felipe; Humphrey, Simon M. Chem. Commun., Issue 2 https://doi.org/10.1039/B413488E	journal	January 2005
On the theoretical understanding of the unexpected O ₂ activation by nanoporous gold Fajín, José L. C.; Cordeiro, M. Natália D. S.; Gomes, José R. B. Chem. Commun., Vol. 47, Issue 29 https://doi.org/10.1039/C1CC12166A	journal	January 2011
One-step electrochemical fabrication of nanoporous gold wire arrays from ionic liquid Hsieh, Yi-Ting; Sun, I-Wen Chem. Commun., Vol. 50, Issue 2 https://doi.org/10.1039/C3CC46061D	journal	January 2014
Dispersing Pt atoms onto nanoporous gold for high performance direct formic acid fuel cells Wang, Rongyue; Liu, Jianguo; Liu, Pan Chem. Sci., Vol. 5, Issue 1 https://doi.org/10.1039/C3SC52792A	journal	January 2014
One-pot fabrication of yolk–shell nanospheres with ultra-small Au nanoparticles for catalysis Yao, Yi; Zhang, Xiaoming; Peng, Juan Chemical Communications, Vol. 51, Issue 18 https://doi.org/10.1039/C4CC10237A	journal	January 2015
Initiator-free hydrocarbon oxidation using supported gold nanoparticles Alshammari, Hamed; Miedziak, Peter J.; Davies, Thomas E. Catal. Sci. Technol., Vol. 4, Issue 4 https://doi.org/10.1039/C4CY00088A	journal	January 2014
Correlation of the structure and applications of dealloyed nanoporous metals in catalysis and energy conversion/storage Qiu, H. -J.; Xu, Hai-Tao; Liu, Li Nanoscale, Vol. 7, Issue 2 https://doi.org/10.1039/C4NR05778C	journal	January 2015
Atomic layer-by-layer construction of Pd on nanoporous gold via underpotential deposition and displacement reaction Yan, Xuejiao; Xiong, Haiyan; Bai, Qingguo RSC Advances, Vol. 5, Issue 25 https://doi.org/10.1039/C4RA17014H	journal	January 2015
Tailoring metal–oxide interfaces of inverse catalysts of TiO ₂ /nanoporous-Au under hydrogen oxidation Qadir, Kamran; Quynh, Bui Thi Phuong; Lee, Hyosun Chemical Communications, Vol. 51, Issue 47 https://doi.org/10.1039/C5CC02832A	journal	January 2015
Highly efficient heterogeneous aerobic cross-dehydrogenative coupling via C–H functionalization of tertiary amines using a nanoporous gold skeleton catalyst Ho, Hon Eong; Ishikawa, Yoshifumi; Asao, Naoki Chemical Communications, Vol. 51, Issue 64 https://doi.org/10.1039/C5CC04856G	journal	January 2015
Mesoporous TUD-1 supported indium oxide nanoparticles for epoxidation of styrene using molecular O ₂ Rahman, Sumbul; Farooqui, Saleem A.; Rai, Aditya RSC Advances, Vol. 5, Issue 58 https://doi.org/10.1039/C5RA03400K	journal	January 2015
Preparation of SnO ₂ /graphene nanocomposite and its application to the catalytic epoxidation of alkenes with H ₂ O ₂ Liu, Min; Wang, Xiaozhong; Chen, Yingqi RSC Advances, Vol. 5, Issue 75 https://doi.org/10.1039/C5RA11285K	journal	January 2015
Preparation of mesoporous titanosilicate with isolated Ti active centers for cyclohexene oxidation Gupta, S.; Vinod, C. P.; Jagadeesan, D. RSC Advances, Vol. 5, Issue 112 https://doi.org/10.1039/C5RA18044A	journal	January 2015
Green oxidation with aqueous hydrogen peroxide Noyori, Ryoji; Aoki, Masao; Sato, Kazuhiko Chemical Communications, Issue 16 https://doi.org/10.1039/b303160h	journal	January 2003
Silver residues as a possible key to a remarkable oxidative catalytic activity of nanoporous gold Moskaleva, Lyudmila V.; Röhe, Sarah; Wittstock, Arne Physical Chemistry Chemical Physics, Vol. 13, Issue 10 https://doi.org/10.1039/c0cp02372h	journal	January 2011
Design of an in-house ambient pressure AP-XPS using a bench-top X-ray source and the surface chemistry of ceria under reaction conditions Tao, Franklin (Feng) Chemical Communications, Vol. 48, Issue 32 https://doi.org/10.1039/c2cc17715c	journal	January 2012
Unsupported nanoporous gold for heterogeneous catalysis Zhang, Xiaomei; Ding, Yi Catalysis Science & Technology, Vol. 3, Issue 11 https://doi.org/10.1039/c3cy00241a	journal	January 2013
Immobilized Cu(ii) and Co(ii) salen complexes on graphene oxide and their catalytic activity for aerobic epoxidation of styrene Li, Zhifang; Wu, Shujie; Ding, Hong New Journal of Chemistry, Vol. 37, Issue 5 https://doi.org/10.1039/c3nj00099k	journal	January 2013
Ductile-brittle transition in random porous Au Li, Rong; Sieradzki, K. Physical Review Letters, Vol. 68, Issue 8 https://doi.org/10.1103/PhysRevLett.68.1168	journal	February 1992
Oxidation of gold by ultraviolet light and ozone at 25 °C King, David E. Journal of Vacuum Science & Technology A: Vacuum, Surfaces, and Films, Vol. 13, Issue 3 https://doi.org/10.1116/1.579869	journal	May 1995
Oxidation-Resistant Gold-55 Clusters Boyen, H. -G. Science, Vol. 297, Issue 5586 https://doi.org/10.1126/science.1076248	journal	August 2002
Nanoporous Gold Catalysts for Selective Gas-Phase Oxidative Coupling of Methanol at Low Temperature Wittstock, A.; Zielasek, V.; Biener, J. Science, Vol. 327, Issue 5963 https://doi.org/10.1126/science.1183591	journal	January 2010

Cited By (1)

Dealloyed Nanoporous Gold Catalysts: From Macroscopic Foams to Nanoparticulate Architectures Li, Guangfang Grace; Wang, Hui ChemNanoMat, Vol. 4, Issue 9 https://doi.org/10.1002/cnma.201800161	journal	May 2018

Similar Records

Process for catalytically oxidizing cycloolefins, particularly cyclohexene

Patent · Thu Dec 31 23:00:00 EST 1992 · OSTI ID:868949

Selective oxidation of olefins over transition metal-exchanged zeolite Y. [Cyclohexen and 1,4-cyclohexadiene]

Book · Sun Dec 31 23:00:00 EST 1978 · OSTI ID:6053680

Mechanistic Studies of the Oxidation of Cyclohexene to 2-Cyclohexen-1-one over ALD Prepared Titania Supported Vanadia

Journal Article · Wed May 20 20:00:00 EDT 2020 · Journal of Physical Chemistry. C · OSTI ID:2480863

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
catalysis
cyclohexene
gold
liquid phase
oxidation processes and reactions

Oxidation of Cyclohexene Catalyzed by Nanoporous Au(Ag) in Liquid Phase

Citation Formats

References (67)

Cited By (1)

Similar Records

Related Subjects