An experimental and theoretical study of glycerol oxidation to 1,3-dihydroxyacetone over bimetallic Pt-Bi catalysts

Xiao, Yang; Greeley, Jeffrey; Varma, Arvind; Zhao, Zhi-Jian; Xiao, Guomin

doi:10.1002/aic.15418

Title: An experimental and theoretical study of glycerol oxidation to 1,3-dihydroxyacetone over bimetallic Pt-Bi catalysts

Journal Article · 25 July 2016 · AIChE Journal

DOI: https://doi.org/10.1002/aic.15418 · OSTI ID:1461651

Xiao, Yang ^[1]; Greeley, Jeffrey ^[1]; Varma, Arvind ^[1]; Zhao, Zhi-Jian ^[2]; Xiao, Guomin ^[3]

Purdue Univ., West Lafayette, IN (United States). School of Chemical Engineering
Purdue Univ., West Lafayette, IN (United States). School of Chemical Engineering; Tianjin Univ., Tianjin (China). Collaborative Innovation Center of Chemical Science and Engineering
Southeast Univ., Nanjing (China). School of Chemistry and Chemical Engineering

It is important to utilize glycerol, the main by-product of biodiesel, to manufacture value-added chemicals such as 1,3-dihydroxyacetone (DHA). In the present work, the performance of five different catalysts (Pt-Bi/AC, Pt-Bi/ZSM-5, Pt/MCM-41, Pt-Bi/MCM-41, and Pt/Bi-doped-MCM-41) was investigated experimentally, where Pt-Bi/MCM-41 was found to exhibit the highest DHA yield. To better understand the experimental results and to obtain insight into the reaction mechanism, density functional theory (DFT) computations were conducted to provide energy barriers of elementary steps. Both experimental and calculated results show that for high DHA selectivity, Bi should be located in an adatom-like configuration Pt, rather than inside Pt. A favorable pathway and catalytic cycle of DHA formation were proposed based on the DFT results. A cooperative effect, between Pt as the primary component and Bi as a promoter, was identified for DHA formation. Both experimental and theoretical considerations demonstrate that Pt-Bi is efficient to convert glycerol to DHA selectively.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC) Center (NERSC).

Sponsoring Organization:: USDOE

OSTI ID:: 1461651

Journal Information:: AIChE Journal, Vol. 63, Issue 2; ISSN 0001-1541

Publisher:: American Institute of Chemical EngineersCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 53 works

Citation information provided by
Web of Science

References (60)

Investigation of Synthesizing MCM-41/ZSM-5 Composites Huang, Limin; Guo, Wanping; Deng, Peng The Journal of Physical Chemistry B, Vol. 104, Issue 13 https://doi.org/10.1021/jp990861y	journal	April 2000
Theoretical study on the leaching of palladium in a CO atmosphere Chang, Chun-Ran; Zhao, Zhi-Jian; Köhler, Klaus Catalysis Science & Technology, Vol. 2, Issue 11 https://doi.org/10.1039/c2cy20441j	journal	January 2012
Handbook of Heterogeneous Catalysis https://doi.org/10.1002/9783527610044	book	March 2008
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Molecular-level descriptions of surface chemistry in kinetic models using density functional theory Gokhale, Amit A.; Kandoi, Shampa; Greeley, Jeffrey P. Chemical Engineering Science, Vol. 59, Issue 22-23 https://doi.org/10.1016/j.ces.2004.09.038	journal	November 2004
Ethylidyne Formation from Ethylene over Pt(111): A Mechanistic Study from First-Principle Calculations Zhao, Zhi-Jian; Moskaleva, Lyudmila V.; Aleksandrov, Hristiyan A. The Journal of Physical Chemistry C, Vol. 114, Issue 28 https://doi.org/10.1021/jp100612y	journal	June 2010
Catalytic routes for the conversion of biomass into liquid hydrocarbon transportation fuels Serrano-Ruiz, Juan Carlos; Dumesic, James A. Energy Environ. Sci., Vol. 4, Issue 1 https://doi.org/10.1039/C0EE00436G	journal	January 2011
Selective Oxidation of Cinnamyl Alcohol to Cinnamaldehyde with Air over Bi-Pt/Alumina Catalysts Mallat, T.; Bodnar, Z.; Hug, P. Journal of Catalysis, Vol. 153, Issue 1 https://doi.org/10.1006/jcat.1995.1115	journal	April 1995
The role of bismuth in the SOHIO process Hanna, T. Coordination Chemistry Reviews, Vol. 248, Issue 5-6 https://doi.org/10.1016/j.ccr.2003.10.001	journal	March 2004
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
A new optimizer using particle swarm theory Eberhart, R.; Kennedy, J. MHS'95. Proceedings of the Sixth International Symposium on Micro Machine and Human Science https://doi.org/10.1109/MHS.1995.494215	conference	January 1995
Activation of Hydrogen on Zeolites: Kinetics and Mechanism of n-Heptane Cracking on H-ZSM-5 Zeolites Under High Hydrogen Pressure Meusinger, J.; Corma, A. Journal of Catalysis, Vol. 152, Issue 1 https://doi.org/10.1006/jcat.1995.1072	journal	March 1995
Crystal structure and structure-related properties of ZSM-5 Olson, D. H.; Kokotailo, G. T.; Lawton, S. L. The Journal of Physical Chemistry, Vol. 85, Issue 15 https://doi.org/10.1021/j150615a020	journal	July 1981
Value-added uses for crude glycerol--a byproduct of biodiesel production Yang, Fangxia; Hanna, Milford A.; Sun, Runcang Biotechnology for Biofuels, Vol. 5, Issue 1 https://doi.org/10.1186/1754-6834-5-13	journal	January 2012
Selective oxidation of glycerol on a platinum-bismuth catalyst Kimura, Hiroshi; Tsuto, Keiichi; Wakisaka, Tatsushi Applied Catalysis A: General, Vol. 96, Issue 2 https://doi.org/10.1016/0926-860X(90)80011-3	journal	March 1993
High-throughput screening of monometallic catalysts for aqueous-phase hydrogenation of biomass-derived oxygenates Lee, Jechan; Xu, Ye; Huber, George W. Applied Catalysis B: Environmental, Vol. 140-141 https://doi.org/10.1016/j.apcatb.2013.03.031	journal	August 2013
Advances in Mesoporous Molecular Sieve MCM-41 Zhao, Xiu S.; Lu, G. Q. (Max); Millar, Graeme J. Industrial & Engineering Chemistry Research, Vol. 35, Issue 7 https://doi.org/10.1021/ie950702a	journal	January 1996
A dimer method for finding saddle points on high dimensional potential surfaces using only first derivatives Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 111, Issue 15 https://doi.org/10.1063/1.480097	journal	October 1999
On a Theory of the van der Waals Adsorption of Gases Brunauer, Stephen; Deming, Lola S.; Deming, W. Edwards Journal of the American Chemical Society, Vol. 62, Issue 7 https://doi.org/10.1021/ja01864a025	journal	July 1940
Selective oxidation of glycerol in a base-free aqueous solution over different sized Pt catalysts Liang, Dan; Gao, Jing; Wang, Junhua Catalysis Communications, Vol. 10, Issue 12 https://doi.org/10.1016/j.catcom.2009.04.023	journal	June 2009
High-precision sampling for Brillouin-zone integration in metals Methfessel, M.; Paxton, A. T. Physical Review B, Vol. 40, Issue 6 https://doi.org/10.1103/PhysRevB.40.3616	journal	August 1989
The Brønsted–Evans–Polanyi relation and the volcano curve in heterogeneous catalysis Bligaard, T.; Nørskov, J. K.; Dahl, S. Journal of Catalysis, Vol. 224, Issue 1 https://doi.org/10.1016/j.jcat.2004.02.034	journal	May 2004
Synthesis of an ultralarge pore titanium silicate isomorphous to MCM-41 and its application as a catalyst for selective oxidation of hydrocarbons Corma, A.; Navarro, M. T.; Pariente, J. P�rez Journal of the Chemical Society, Chemical Communications, Issue 2 https://doi.org/10.1039/c39940000147	journal	January 1994
A density functional theory analysis of trends in glycerol decomposition on close-packed transition metal surfaces Liu, Bin; Greeley, Jeffrey Physical Chemistry Chemical Physics, Vol. 15, Issue 17 https://doi.org/10.1039/c3cp44088e	journal	January 2013
Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism Kresge, C. T.; Leonowicz, M. E.; Roth, W. J. Nature, Vol. 359, Issue 6397, p. 710-712 https://doi.org/10.1038/359710a0	journal	October 1992
Effect of nickel incorporation on the acidity and stability of HZSM-5 zeolite in the MTO process Valle, B.; Alonso, A.; Atutxa, A. Catalysis Today, Vol. 106, Issue 1-4 https://doi.org/10.1016/j.cattod.2005.07.132	journal	October 2005
Decomposition Pathways of Glycerol via C–H, O–H, and C–C Bond Scission on Pt(111): A Density Functional Theory Study Liu, Bin; Greeley, Jeffrey The Journal of Physical Chemistry C, Vol. 115, Issue 40 https://doi.org/10.1021/jp202923w	journal	September 2011
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Modeling of Adsorption and Desorption in Pores of Simple Geometry Using Molecular Dynamics Sarkisov, L.; Monson, P. A. Langmuir, Vol. 17, Issue 24 https://doi.org/10.1021/la015521u	journal	November 2001
Selective Oxidation of Methanol to Dimethoxymethane over Mesoporous Al-P-V-O Catalysts Chen, Shuang; Meng, Yali; Zhao, Yujun AIChE Journal, Vol. 59, Issue 7 https://doi.org/10.1002/aic.14033	journal	March 2013
New methods for the oxidation of aldehydes to carboxylic acids and esters Corey, Elias J.; Gilman, Norman W.; Ganem, B. E. Journal of the American Chemical Society, Vol. 90, Issue 20 https://doi.org/10.1021/ja01022a059	journal	September 1968
Special points for Brillouin-zone integrations Monkhorst, Hendrik J.; Pack, James D. Physical Review B, Vol. 13, Issue 12, p. 5188-5192 https://doi.org/10.1103/PhysRevB.13.5188	journal	June 1976
Oxidation of glycerol using supported Pt, Pd and Au catalysts Carrettin, Silvio; McMorn, Paul; Johnston, Peter Physical Chemistry Chemical Physics, Vol. 5, Issue 6 https://doi.org/10.1039/b212047j	journal	February 2003
Self-assembled ultrathin nanotubes on diamond (100) surface Lu, Shaohua; Wang, Yanchao; Liu, Hanyu Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4666	journal	April 2014
First-principles study of CO oxidation on bismuth-promoted Pt(111) surfaces Kapur, Neeti; Shan, Bin; Hyun, Jangsuk Molecular Simulation, Vol. 37, Issue 8 https://doi.org/10.1080/08927022.2010.543978	journal	July 2011
Transesterification for biodiesel production catalyzed by combined lipases: Optimization and kinetics Liu, Yun; Yan, Yunjun; Hu, Fang AIChE Journal, Vol. 56, Issue 6 https://doi.org/10.1002/aic.12090	journal	November 2009
Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium Kresse, G.; Hafner, J. Physical Review B, Vol. 49, Issue 20, p. 14251-14269 https://doi.org/10.1103/PhysRevB.49.14251	journal	May 1994
Density Functional Theory in Surface Science and Heterogeneous Catalysis Nørskov, J. K.; Scheffler, M.; Toulhoat, H. MRS Bulletin, Vol. 31, Issue 9 https://doi.org/10.1557/mrs2006.175	journal	September 2006
Selective Oxidation of Glycerol to Dihydroxyacetone over Pt−Bi/C Catalyst: Optimization of Catalyst and Reaction Conditions Hu, Wenbin; Knight, Daniel; Lowry, Brian Industrial & Engineering Chemistry Research, Vol. 49, Issue 21 https://doi.org/10.1021/ie1005096	journal	November 2010
Critical review on the current scenario and significance of crude glycerol resulting from biodiesel industry towards more sustainable renewable energy industry Ayoub, Muhammad; Abdullah, Ahmad Zuhairi Renewable and Sustainable Energy Reviews, Vol. 16, Issue 5 https://doi.org/10.1016/j.rser.2012.01.054	journal	June 2012
Platinum−Bismuth-Catalyzed Oxidation of Glycerol: Kinetics and the Origin of Selective Deactivation Worz, N.; Brandner, A.; Claus, P. The Journal of Physical Chemistry C, Vol. 114, Issue 2 https://doi.org/10.1021/jp909412h	journal	December 2009
Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation Perdew, John P.; Chevary, J. A.; Vosko, S. H. Physical Review B, Vol. 46, Issue 11 https://doi.org/10.1103/PhysRevB.46.6671	journal	September 1992
Catalytic applications of MCM-41 with different pore sizes in selected liquid phase reactions Choi, J. S.; Kim, D. J.; Chang, S. H. Applied Catalysis A: General, Vol. 254, Issue 2 https://doi.org/10.1016/S0926-860X(03)00485-X	journal	November 2003
Bismuth-containing MCM-41: synthesis, characterization, and catalytic behavior in liquid-phase oxidation of cyclohexane Qian, G.; Ji, D.; Lu, G. Journal of Catalysis, Vol. 232, Issue 2 https://doi.org/10.1016/j.jcat.2005.03.024	journal	June 2005
A review of current technology for biodiesel production: State of the art Aransiola, E. F.; Ojumu, T. V.; Oyekola, O. O. Biomass and Bioenergy, Vol. 61, p. 276-297 https://doi.org/10.1016/j.biombioe.2013.11.014	journal	February 2014
Reversible work transition state theory: application to dissociative adsorption of hydrogen Mills, Gregory; Jónsson, Hannes; Schenter, Gregory K. Surface Science, Vol. 324, Issue 2-3 https://doi.org/10.1016/0039-6028(94)00731-4	journal	February 1995
Density Functional Theory Study of Selectivity Considerations for C–C Versus C–O Bond Scission in Glycerol Decomposition on Pt(111) Liu, Bin; Greeley, Jeffrey Topics in Catalysis, Vol. 55, Issue 5-6 https://doi.org/10.1007/s11244-012-9806-2	journal	May 2012
Catalytic hydrothermal liquefaction of D . tertiolecta for the production of bio-oil over different acid/base catalysts Chen, Yu; Wu, Yulong; Ding, Ranran AIChE Journal, Vol. 61, Issue 4 https://doi.org/10.1002/aic.14740	journal	February 2015
Adsorption of Gases in Multimolecular Layers Brunauer, Stephen; Emmett, P. H.; Teller, Edward Journal of the American Chemical Society, Vol. 60, Issue 2, p. 309-319 https://doi.org/10.1021/ja01269a023	journal	February 1938
Hydrocracking of Vacuum Gasoil on the Novel Mesoporous MCM-41 Aluminosilicate Catalyst Corma, A.; Martinez, A.; Martinezsoria, V. Journal of Catalysis, Vol. 153, Issue 1 https://doi.org/10.1006/jcat.1995.1104	journal	April 1995
Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points Henkelman, Graeme; Jónsson, Hannes The Journal of Chemical Physics, Vol. 113, Issue 22 https://doi.org/10.1063/1.1323224	journal	December 2000
Gas-phase dehydration of glycerol over ZSM-5 catalysts Kim, Yong Tae; Jung, Kwang-Deog; Park, Eun Duck Microporous and Mesoporous Materials, Vol. 131, Issue 1-3 https://doi.org/10.1016/j.micromeso.2009.11.037	journal	June 2010
First-Principles Atomistic Thermodynamics for Oxidation Catalysis: Surface Phase Diagrams and Catalytically Interesting Regions Reuter, Karsten; Scheffler, Matthias Physical Review Letters, Vol. 90, Issue 4 https://doi.org/10.1103/PhysRevLett.90.046103	journal	January 2003
Studies on mesoporous materials Chen, Cong-Yan; Li, Hong-Xin; Davis, Mark E. Microporous Materials, Vol. 2, Issue 1 https://doi.org/10.1016/0927-6513(93)80058-3	journal	December 1993
Mesoporous redox molecular sieves analogous to MCM-41 Carvalho, Wagner A.; Varaldo, Paula B.; Wallau, Martin Zeolites, Vol. 18, Issue 5-6 https://doi.org/10.1016/S0144-2449(97)00031-6	journal	May 1997
Selective oxidation of glycerol to glyceric acid using a gold catalyst in aqueous sodium hydroxide Carrettin, Silvio; McMorn, Paul; Johnston, Peter Chemical Communications, Issue 7 https://doi.org/10.1039/b201112n	journal	March 2002
Hydrogen-oxygen titration method for the measurement of supported platinum surface areas Benson, J. Journal of Catalysis, Vol. 4, Issue 6 https://doi.org/10.1016/0021-9517(65)90271-X	journal	December 1965
DFT studies for cleavage of C$z.sbnd;C and C$z.sbnd;O bonds in surface species derived from ethanol on Pt(111) Alcala, R. Journal of Catalysis, Vol. 218, Issue 1 https://doi.org/10.1016/S0021-9517(03)00090-3	journal	August 2003
Identification of surface intermediates during ethylidyne formation on Pt(111) by calculation of infrared intensities and deuterium isotope shifts Zhao, Zhi-Jian; Greeley, Jeffrey P. Surface Science, Vol. 640 https://doi.org/10.1016/j.susc.2015.01.022	journal	October 2015
Selective oxidation of glycerol on a platinum-bismuth catalyst by using a fixed bed reactor Kimura, Hiroshi Applied Catalysis A: General, Vol. 105, Issue 2 https://doi.org/10.1016/0926-860X(93)80245-L	journal	November 1993

Cited By (6)

Effects of the Synthesis Method and Promoter Content on Bismuth‐Modified Platinum Catalysts in the Electro‐oxidation of Glycerol and Formic Acid Ning, Xiaomei; Zhou, Xiaosong; Luo, Jin ChemElectroChem, Vol. 6, Issue 6 https://doi.org/10.1002/celc.201900043	journal	February 2019
Nanostructured Metal Catalysts for Selective Hydrogenation and Oxidation of Cellulosic Biomass to Chemicals Jin, Xin; Fang, Tianqi; Wang, Jinyao The Chemical Record, Vol. 19, Issue 9 https://doi.org/10.1002/tcr.201800144	journal	November 2018
Deactivation and regeneration of in situ formed bismuth-promoted platinum catalyst for the selective oxidation of glycerol to dihydroxyacetone Ning, Xiaomei; Zhan, Liang; Wang, Hongjuan New Journal of Chemistry, Vol. 42, Issue 23 https://doi.org/10.1039/c8nj04513e	journal	January 2018
Efficient production of dihydroxyacetone from glycerol over a Pt/CeO ₂ -ZrO ₂ -Bi ₂ O ₃ /SBA-16 catalyst Choi, Pil-Gyu; Nunotani, Naoyoshi; Imanaka, Nobuhito Journal of Asian Ceramic Societies, Vol. 6, Issue 4 https://doi.org/10.1080/21870764.2018.1533444	journal	October 2018
Promoting Role of Bismuth on Hydrotalcite-Supported Platinum Catalysts in Aqueous Phase Oxidation of Glycerol to Dihydroxyacetone Xue, Wenjie; Wang, Zenglong; Liang, Yu Catalysts, Vol. 8, Issue 1 https://doi.org/10.3390/catal8010020	journal	January 2018
Navigating Glycerol Conversion Roadmap and Heterogeneous Catalyst Selection Aided by Density Functional Theory: A Review Liu, Bin; Gao, Feng Catalysts, Vol. 8, Issue 2 https://doi.org/10.3390/catal8020044	journal	January 2018