Deoxydehydration of Biomass-Derived Polyols with a Reusable Unsupported Rhenium Nanoparticles Catalyst

Jang, Jun Hee; Sohn, Hyuntae; Camacho-Bunquin, Jeffrey; Yang, Dali; Park, Chan Y.; Delferro, Massimiliano; Abu-Omar, Mahdi M.

doi:10.1021/acssuschemeng.9b01253

Title: Deoxydehydration of Biomass-Derived Polyols with a Reusable Unsupported Rhenium Nanoparticles Catalyst

Journal Article · Wed May 29 00:00:00 EDT 2019 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.9b01253· OSTI ID:1559530

^[1]; Sohn, Hyuntae ^[2]; Camacho-Bunquin, Jeffrey ^[2]; Yang, Dali ^[2]; Park, Chan Y. ^[1];

^[2];

^[1]

Univ. of California, Santa Barbara, CA (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)

Oxorhenium catalysts effectively transform biomass derived polyols into corresponding alkenes, via deoxydehydration (DODH) with a secondary alcohol as a hydrogen donor. This report describes the preparation of unsupported rhenium oxide nanoparticles (ReO_x NPs), their use as DODH heterogeneous catalyst, and changes in the speciation and structure of Re during catalysis leading to a mechanism for DODH by a heterogeneous catalyst. The unsupported nanoparticles catalyze various polyols transformation to produce alkenes with high efficiency and recyclability. X-ray spectroscopy analysis shows the structure of as-prepared ReO_x NPs is similar to perrhenate with oxidation state between Re(VI) and Re(VII). Under reaction conditions and post catalysis, the ReOx NPs are reduced by approximately two oxidation units. Kinetic isotope effect demonstrates that dissociation of a C-H bond during reduction of ReO_x NPs by 3-octanol is part of the rate-determining step. Based on all experimental observations, the mechanism of DODH catalysis with unsupported ReO_x NPs involving a Re(VII)/Re(V) redox-pair is introduced.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

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

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1559530

Journal Information:: ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 13; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 19 works

Citation information provided by
Web of Science

References (36)

Chemicals from Biomass Dodds, D. R.; Gross, R. A. Science, Vol. 318, Issue 5854 https://doi.org/10.1126/science.1146356	journal	November 2007
Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols Shiramizu, Mika; Toste, F. Dean Angewandte Chemie International Edition, Vol. 51, Issue 32 https://doi.org/10.1002/anie.201203877	journal	July 2012
Deoxydehydration of glycerol to allyl alcohol catalyzed by rhenium derivatives Canale, Valentino; Tonucci, Lucia; Bressan, Mario Catal. Sci. Technol., Vol. 4, Issue 10 https://doi.org/10.1039/C4CY00631C	journal	January 2014
Rhenium-Catalyzed Dehydration and Deoxydehydration of Alcohols and Polyols: Opportunities for the Formation of Olefins from Biomass Raju, Suresh; Moret, Marc-Etienne; Klein Gebbink, Robertus J. M. ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501511x	journal	November 2014
Vanadium-catalyzed deoxydehydration of glycols Chapman, Garry; Nicholas, Kenneth M. Chemical Communications, Vol. 49, Issue 74 https://doi.org/10.1039/c3cc44656e	journal	January 2013
Molybdenum-Catalyzed Conversion of Diols and Biomass-Derived Polyols to Alkenes Using Isopropyl Alcohol as Reductant and Solvent Dethlefsen, Johannes R.; Lupp, Daniel; Teshome, Ayele ACS Catalysis, Vol. 5, Issue 6 https://doi.org/10.1021/acscatal.5b00427	journal	May 2015
Bifunctional Catalysts for Upgrading of Biomass-Derived Oxygenates: A Review Robinson, Allison M.; Hensley, Jesse E.; Medlin, J. Will ACS Catalysis, Vol. 6, Issue 8 https://doi.org/10.1021/acscatal.6b00923	journal	July 2016
Toward Nonoxidative Routes to Oxygenated Organics: Stereospecific Deoxydehydration of Diols and Polyols to Alkenes and Allylic Alcohols Catalyzed by the Metal Oxo Complex (C ₅ Me ₅ )ReO ₃ Cook, Gerald K.; Andrews, Mark A. Journal of the American Chemical Society, Vol. 118, Issue 39 https://doi.org/10.1021/ja9620604	journal	January 1996
Catalytic Deoxydehydration of Diols to Olefins by using a Bulky Cyclopentadiene-based Trioxorhenium Catalyst Raju, Suresh; Jastrzebski, Johann T. B. H.; Lutz, Martin ChemSusChem, Vol. 6, Issue 9 https://doi.org/10.1002/cssc.201300364	journal	July 2013
H ₂ -Driven Deoxygenation of Epoxides and Diols to Alkenes Catalyzed by Methyltrioxorhenium Ziegler, Jeanette E.; Zdilla, Michael J.; Evans, Andrew J. Inorganic Chemistry, Vol. 48, Issue 21 https://doi.org/10.1021/ic901792b	journal	November 2009
Mechanism of the MeReO ₃ -Catalyzed Deoxygenation of Epoxides Bi, Siwei; Wang, Jiayong; Liu, Lingjun Organometallics, Vol. 31, Issue 17 https://doi.org/10.1021/om300485w	journal	August 2012
Oxorhenium-catalyzed deoxydehydration of glycols and epoxides Davis, Jacqkis; Srivastava, Radhey S. Tetrahedron Letters, Vol. 55, Issue 30 https://doi.org/10.1016/j.tetlet.2014.05.044	journal	July 2014
Rhenium-Catalyzed Deoxydehydration of Glycols by Sulfite Vkuturi, Saidi; Chapman, Garry; Ahmad, Irshad Inorganic Chemistry, Vol. 49, Issue 11 https://doi.org/10.1021/ic100467p	journal	June 2010
Sulfite-Driven, Oxorhenium-Catalyzed Deoxydehydration of Glycols Ahmad, Irshad; Chapman, Garry; Nicholas, Kenneth M. Organometallics, Vol. 30, Issue 10 https://doi.org/10.1021/om2001662	journal	May 2011
Mechanism of Sulfite-Driven, MeReO ₃ -Catalyzed Deoxydehydration of Glycols Liu, Peng; Nicholas, Kenneth M. Organometallics, Vol. 32, Issue 6 https://doi.org/10.1021/om301251z	journal	February 2013
Rhenium-Catalyzed Didehydroxylation of Vicinal Diols to Alkenes Using a Simple Alcohol as a Reducing Agent Arceo, Elena; Ellman, Jonathan A.; Bergman, Robert G. Journal of the American Chemical Society, Vol. 132, Issue 33 https://doi.org/10.1021/ja103436v	journal	August 2010
Rhenium-Catalyzed Transfer Hydrogenation and Deoxygenation of Biomass-Derived Polyols to Small and Useful Organics Yi, Jing; Liu, Shuo; Abu-Omar, Mahdi M. ChemSusChem, Vol. 5, Issue 8 https://doi.org/10.1002/cssc.201200138	journal	June 2012
Mechanism of MTO-Catalyzed Deoxydehydration of Diols to Alkenes Using Sacrificial Alcohols Liu, Shuo; Senocak, Aysegul; Smeltz, Jessica L. Organometallics, Vol. 32, Issue 11 https://doi.org/10.1021/om400127z	journal	March 2013
Mechanism of the Methyltrioxorhenium-Catalyzed Deoxydehydration of Polyols: A New Pathway Revealed Qu, Shuanglin; Dang, Yanfeng; Wen, Mingwei Chemistry - A European Journal, Vol. 19, Issue 12 https://doi.org/10.1002/chem.201204001	journal	February 2013
Expanding the Scope of Biomass-Derived Chemicals through Tandem Reactions Based on Oxorhenium-Catalyzed Deoxydehydration Shiramizu, Mika; Toste, F. Dean Angewandte Chemie International Edition, Vol. 52, Issue 49 https://doi.org/10.1002/anie.201307564	journal	November 2013
Highly Efficient Chemical Process To Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium-Catalyzed Deoxydehydration Li, Xiukai; Wu, Di; Lu, Ting Angewandte Chemie, Vol. 126, Issue 16 https://doi.org/10.1002/ange.201310991	journal	March 2014
Rhenium-Catalyzed Deoxydehydration of Diols and Polyols Dethlefsen, Johannes R.; Fristrup, Peter ChemSusChem, Vol. 8, Issue 5 https://doi.org/10.1002/cssc.201402987	journal	December 2014
Deoxydehydration of Glycols Catalyzed by Carbon-Supported Perrhenate Denning, Alana L.; Dang, Huong; Liu, Zhimin ChemCatChem, Vol. 5, Issue 12 https://doi.org/10.1002/cctc.201300545	journal	August 2013
Highly Selective Deoxydehydration of Tartaric Acid over Supported and Unsupported Rhenium Catalysts with Modified Acidities Li, Xiukai; Zhang, Yugen ChemSusChem, Vol. 9, Issue 19 https://doi.org/10.1002/cssc.201600865	journal	August 2016
ReO _x /TiO ₂ : A Recyclable Solid Catalyst for Deoxydehydration Sandbrink, Lennart; Klindtworth, Elisabeth; Islam, Husn-Ubayda ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b01936	journal	December 2015
Deoxydehydration with Molecular Hydrogen over Ceria-Supported Rhenium Catalyst with Gold Promoter Tazawa, Shuhei; Ota, Nobuhiko; Tamura, Masazumi ACS Catalysis, Vol. 6, Issue 10 https://doi.org/10.1021/acscatal.6b01864	journal	August 2016
Direct Conversion of Glycerol to Allyl Alcohol Over Alumina-Supported Rhenium Oxide Kon, Yoshihiro; Araque, Marcia; Nakashima, Takuya ChemistrySelect, Vol. 2, Issue 30 https://doi.org/10.1002/slct.201702070	journal	October 2017
Role of Re Species and Acid Cocatalyst on Ir-ReO _x /SiO ₂ in the C-O Hydrogenolysis of Biomass-Derived Substrates : Hydrogenolysis of Biomass-Derived Substrates Tomishige, Keiichi; Tamura, Masazumi; Nakagawa, Yoshinao The Chemical Record, Vol. 14, Issue 6 https://doi.org/10.1002/tcr.201402026	journal	August 2014
Mechanistic Study of Hydrogen-Driven Deoxydehydration over Ceria-Supported Rhenium Catalyst Promoted by Au Nanoparticles Nakagawa, Yoshinao; Tazawa, Shuhei; Wang, Tianmiao ACS Catalysis, Vol. 8, Issue 1 https://doi.org/10.1021/acscatal.7b02879	journal	December 2017
A Reusable Unsupported Rhenium Nanocrystalline Catalyst for Acceptorless Dehydrogenation of Alcohols through γ-C-H Activation Yi, Jing; Miller, Jeffrey T.; Zemlyanov, Dmitry Y. Angewandte Chemie, Vol. 126, Issue 3 https://doi.org/10.1002/ange.201307665	journal	November 2013
X-ray Spectroscopic Characterization of Immobilized Rhenium Species in Hydrated Rhenium–Palladium Bimetallic Catalysts Used for Perchlorate Water Treatment Choe, Jong Kwon; Boyanov, Maxim I.; Liu, Jinyong The Journal of Physical Chemistry C, Vol. 118, Issue 22 https://doi.org/10.1021/jp5006814	journal	May 2014
The Oxidation of Rhenium and Identification of Rhenium Oxides During Catalytic Partial Oxidation of Ethylene: An In-Situ XPS Study Greiner, Mark T.; Rocha, Tulio C. R.; Johnson, Benjamin Zeitschrift für Physikalische Chemie, Vol. 228, Issue 4-5 https://doi.org/10.1515/zpch-2014-0002	journal	January 2014
ATHENA , ARTEMIS , HEPHAESTUS : data analysis for X-ray absorption spectroscopy using IFEFFIT Ravel, B.; Newville, M. Journal of Synchrotron Radiation, Vol. 12, Issue 4 https://doi.org/10.1107/S0909049505012719	journal	June 2005
New Motifs in Deoxydehydration: Beyond the Realms of Rhenium Petersen, Allan R.; Fristrup, Peter Chemistry – A European Journal, Vol. 23, Issue 43 https://doi.org/10.1002/chem.201701153	journal	June 2017
Ammonium perrhenate at 295 and 135 K Kruger, G. J.; Reynhardt, E. C. Acta Crystallographica Section B, Vol. 34, Issue 1 https://doi.org/10.1107/S0567740878002721	journal	January 1978
Elemental Reductants for the Deoxydehydration of Glycols Michael McClain, J.; Nicholas, Kenneth M. ACS Catalysis, Vol. 4, Issue 7 https://doi.org/10.1021/cs500461v	journal	May 2014

Cited By (1)

Recent Advances in the Deoxydehydration of Vicinal Diols and Polyols Donnelly, Liam J.; Thomas, Stephen P.; Love, Jason B. Chemistry – An Asian Journal, Vol. 14, Issue 21 https://doi.org/10.1002/asia.201901274	journal	October 2019

Similar Records

Mechanistic study of the ceria supported, re-catalyzed deoxydehydration of vicinal OH groups

Journal Article · Mon Jan 01 00:00:00 EST 2018 · Catalysis Science and Technology · OSTI ID:1559530

Xi, Yongjie; Yang, Wenqiang; Ammal, Salai Cheettu; +3 more

Catalytic Deoxydehydration of Carbohydrates and Polyols to Chemicals and Fuels

Technical Report · Fri Jan 15 00:00:00 EST 2016 · OSTI ID:1559530

Nicholas, Kenneth M.

Deoxydehydration and Catalytic Transfer Hydrogenation: New Strategy to Valorize Tartaric Acid and Succinic Acid to γ-Butyrolactone and Tetrahydrofuran

Journal Article · Thu Dec 03 00:00:00 EST 2020 · Energies · OSTI ID:1559530

Jang, Jun Hee; Abu-Omar, Mahdi M.

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
deoxydehydration
glycerol
heterogeneous catalysis
mechanism
rhenium
unsupported nanoparticle

Title: Deoxydehydration of Biomass-Derived Polyols with a Reusable Unsupported Rhenium Nanoparticles Catalyst

Citation Formats

References (36)

Cited By (1)

Similar Records

Related Subjects