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Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.7b07801· OSTI ID:1464155
 [1];  [1];  [1];  [2];  [3];  [3];  [4];  [1]
  1. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; BASF Corporation, Berkeley, CA (United States). California Research Alliance (CARA)
  2. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
  3. BASF SE, Ludwigshafen (Germany)
  4. BASF Corp., Fremont, CA (United States); BASF Corporation, Berkeley, CA (United States). California Research Alliance (CARA)
The development of a system for the operationally simple, scalable conversion of polyhydroxylated biomass into industrially relevant feedstock chemicals is described. This system includes a bimetallic Pd/Re catalyst in combination with hydrogen gas as a terminal reductant and enables the high-yielding reduction of sugar acids. This procedure has been applied to the synthesis of adipate esters, precursors for the production of Nylon-6,6, in excellent yield from biomass-derived sources.
Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
BASF Corporation; National Science Foundation (NSF) (United States); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1464155
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 40 Vol. 139; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (60)

Deoxygenation of Biomass-Derived Feedstocks: Oxorhenium-Catalyzed Deoxydehydration of Sugars and Sugar Alcohols journal July 2012
Expanding the Scope of Biomass-Derived Chemicals through Tandem Reactions Based on Oxorhenium-Catalyzed Deoxydehydration 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 journal March 2014
Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support journal December 2014
Mechanistic Study on Oxorhenium-Catalyzed Deoxydehydration and Allylic Alcohol Isomerization journal April 2016
Green building blocks for bio-based plastics journal January 2014
Deoxydehydration of Glycols Catalyzed by Carbon-Supported Perrhenate journal August 2013
In Situ Spectroscopic Investigation of the Rhenium-Catalyzed Deoxydehydration of Vicinal Diols journal March 2015
Catalytic Processes for the Technical Use of Natural Fats and Oils journal May 2008
To the Core of Autocatalysis in Cyclohexane Autoxidation journal May 2006
Useful Products from Complex Starting Materials: Common Chemicals from Biomass Feedstocks journal April 2010
Mechanism of the Methyltrioxorhenium-Catalyzed Deoxydehydration of Polyols: A New Pathway Revealed journal February 2013
Mechanistic Insights into the Rhenium-Catalyzed Alcohol-To-Olefin Dehydration Reaction journal August 2013
Renewability is not Enough: Recent Advances in the Sustainable Synthesis of Biomass-Derived Monomers and Polymers journal June 2016
Rhenium-Catalyzed Transfer Hydrogenation and Deoxygenation of Biomass-Derived Polyols to Small and Useful Organics journal June 2012
Catalytic Deoxydehydration of Glycols with Alcohol Reductants journal March 2013
Catalytic Deoxydehydration of Diols to Olefins by using a Bulky Cyclopentadiene-based Trioxorhenium Catalyst journal July 2013
Rhenium-Catalyzed Deoxydehydration of Diols and Polyols journal December 2014
Selective Deoxygenation of Biomass-Derived Bio-oils within Hydrogen-Modest Environments: A Review and New Insights journal July 2016
Highly Selective Deoxydehydration of Tartaric Acid over Supported and Unsupported Rhenium Catalysts with Modified Acidities journal August 2016
Supported Molybdenum Catalysts for the Deoxydehydration of 1,4-Anhydroerythritol into 2,5-Dihydrofuran journal March 2017
Dioxomolybdenum(VI) Complexes with Acylpyrazolonate Ligands: Synthesis, Structures, and Catalytic Properties journal May 2013
Abatement of N2O emissions produced in the adipic acid industry journal May 1994
Deoxydehydration of Polyols book January 2014
Selective Hydrogenolysis of C–O Bonds Using the Interaction of the Catalyst Surface and OH Groups book January 2014
Catalysts for Fatty Alcohol Production from Renewable Resources journal October 2016
Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst journal June 2001
Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes journal September 2010
Alkane production from biomass: chemo-, bio- and integrated catalytic approaches journal December 2015
Production of Fuels and Chemicals from Biomass: Condensation Reactions and Beyond journal July 2016
Metabolic engineering strategies to bio-adipic acid production journal June 2017
Green chemistry, catalysis and valorization of waste biomass journal October 2016
Ionic liquid-mediated deoxydehydration reactions: Green synthetic process for bio-based adipic acid journal August 2017
DFT Studies on the Mechanism of the Vanadium-Catalyzed Deoxydehydration of Diols journal February 2016
Synthesis of Cyclopentadienyl-Based Trioxo-rhenium Complexes and Their Use as Deoxydehydration Catalysts journal June 2016
Molybdenum-Catalyzed Conversion of Diols and Biomass-Derived Polyols to Alkenes Using Isopropyl Alcohol as Reductant and Solvent journal May 2015
ReO x /TiO 2 : A Recyclable Solid Catalyst for Deoxydehydration journal December 2015
Carbon Monoxide (CO)- and Hydrogen-Driven, Vanadium-Catalyzed Deoxydehydration of Glycols journal February 2016
Performance, Structure, and Mechanism of ReO x –Pd/CeO 2 Catalyst for Simultaneous Removal of Vicinal OH Groups with H 2 journal April 2016
Deoxydehydration with Molecular Hydrogen over Ceria-Supported Rhenium Catalyst with Gold Promoter journal August 2016
Rhenium-Catalyzed Dehydration and Deoxydehydration of Alcohols and Polyols: Opportunities for the Formation of Olefins from Biomass journal November 2014
Efficient Heterogeneous Catalytic Reduction of Perchlorate in Water journal March 2007
Rhenium-Catalyzed Deoxydehydration of Glycols by Sulfite journal June 2010
H 2 -Driven Deoxygenation of Epoxides and Diols to Alkenes Catalyzed by Methyltrioxorhenium journal November 2009
Transiting from Adipic Acid to Bioadipic Acid. 1, Petroleum-Based Processes journal December 2014
Transiting from Adipic Acid to Bioadipic Acid. Part II. Biosynthetic Pathways journal January 2015
Environmentally compatible synthesis of adipic acid from D-glucose journal January 1994
Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions journal January 1994
Kinetic Isotope Effects in Cycloreversion of Rhenium (V) Diolates journal April 2002
Rhenium-Catalyzed Didehydroxylation of Vicinal Diols to Alkenes Using a Simple Alcohol as a Reducing Agent journal August 2010
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 journal January 1996
Are There Metal Oxides That Prefer a [2 + 2] Addition over a [3 + 2] Addition to Olefins? Theoretical Study of the Reaction Mechanism of LReO 3 Addition (L = O - , Cl, Cp) to Ethylene 1 journal March 1999
Mechanism of Sulfite-Driven, MeReO 3 -Catalyzed Deoxydehydration of Glycols journal February 2013
Emerging catalytic processes for the production of adipic acid journal January 2013
Bioprivileged molecules: creating value from biomass journal January 2017
In situ generation of resin-supported Pd nanoparticles under mild catalytic conditions: a green route to highly efficient, reusable hydrogenation catalysts journal January 2012
Vanadium-catalyzed deoxydehydration of glycols journal January 2013
Catalytic Synthesis of γ-Alkoxy-α-keto Esters journal February 2011
Valorization of Biomass: Deriving More Value from Waste journal August 2012
Nylon Production: An Unknown Source of Atmospheric Nitrous Oxide journal February 1991

Cited By (17)

Local generation of hydrogen for enhanced photothermal therapy journal October 2018
Production of Hexaric Acids from Biomass journal July 2019
Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate journal May 2018
Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst journal July 2018
Nylon Intermediates from Bio‐Based Levulinic Acid journal March 2019
Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate journal May 2018
Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst journal July 2018
Nylon Intermediates from Bio‐Based Levulinic Acid journal March 2019
Recent Advances in the Deoxydehydration of Vicinal Diols and Polyols journal October 2019
Single‐Site Molybdenum Catalyst for the Synthesis of Fumarate journal July 2019
Catalytic Transformation of Cellulose and Its Derivatives into Functionalized Organic Acids journal June 2018
Preparation of Highly Active Monometallic Rhenium Catalysts for Selective Synthesis of 1,4‐Butanediol from 1,4‐Anhydroerythritol journal July 2019
Perspective on catalyst development for glycerol reduction to C3 chemicals with molecular hydrogen journal May 2018
Adipic acid production catalyzed by a combination of a solid acid and an iodide salt from biomass-derived tetrahydrofuran-2,5-dicarboxylic acid journal January 2018
One-pot catalytic selective synthesis of 1,4-butanediol from 1,4-anhydroerythritol and hydrogen journal January 2018
Zirconia-supported rhenium oxide as an efficient catalyst for the synthesis of biomass-based adipic acid ester journal January 2019
N,N,O-Coordinated tricarbonylrhenium precatalysts for the aerobic deoxydehydration of diols and polyols journal January 2020

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