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

Journal Article · · Journal of the American Chemical Society
 [1];  [1];  [1];  [2];  [3];  [3];  [4]; ORCiD logo [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:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); BASF Corporation
Grant/Contract Number:
AC02-05CH11231; CHE-1413862; 53093
OSTI ID:
1464155
Journal Information:
Journal of the American Chemical Society, Vol. 139, Issue 40; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 51 works
Citation information provided by
Web of Science

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Cited By (18)

Recent Advances in the Deoxydehydration of Vicinal Diols and Polyols journal October 2019
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
Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst journal July 2018
Nylon Intermediates from Bio‐Based Levulinic Acid journal March 2019
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
Catalytic Transformation of Cellulose and Its Derivatives into Functionalized Organic Acids journal June 2018
Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate journal May 2018
Local generation of hydrogen for enhanced photothermal therapy journal October 2018
N,N,O-Coordinated tricarbonylrhenium precatalysts for the aerobic deoxydehydration of diols and polyols journal January 2020
Production of Hexaric Acids from Biomass journal July 2019
Single‐Site Molybdenum Catalyst for the Synthesis of Fumarate 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
Local generation of hydrogen for enhanced photothermal therapy journal October 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
Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst journal July 2018
Nylon Intermediates from Bio‐Based Levulinic Acid journal March 2019