Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds

Settle, Amy E.; Berstis, Laura; Rorrer, Nicholas A.; Roman-Leshkov, Yuriy; Beckham, Gregg T.; Richards, Ryan M.; Vardon, Derek R.

doi:10.1039/C7GC00992E

Title: Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds

Journal Article · Wed May 17 00:00:00 EDT 2017 · Green Chemistry

DOI:https://doi.org/10.1039/C7GC00992E· OSTI ID:1374130

Settle, Amy E. ^[1]; Berstis, Laura ^[2]; Rorrer, Nicholas A. ^[2]; Roman-Leshkov, Yuriy ^[3];

^[2];

^[1];

^[2]

National Renewable Energy Lab. (NREL), Golden, CO (United States); Colorado School of Mines, Golden, CO (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)

In this tutorial review, we provide an overview of heterogeneous Diels–Alder catalysis for the production of lignocellulosic biomass-derived aromatic compounds. Diels–Alder reactions afford an extremely selective and efficient route for carbon–carbon cycloadditions to produce intermediates that can readily undergo subsequent dehydration or dehydrogenation reactions for aromatization. As a result, catalysis of Diels–Alder reactions with biomass-derived dienes and dienophiles has seen a growth of interest in recent years; however, significant opportunities remain to (i) tailor heterogeneous catalyst materials for tandem Diels–Alder and aromatization reactions, and (ii) utilize biomass-derived dienes and dienophiles to access both conventional and novel aromatic monomers. As such, this review discusses the mechanistic aspects of Diels–Alder reactions from both an experimental and computational perspective, as well as the synergy of Brønsted–Lewis acid catalysts to facilitate tandem Diels–Alder and aromatization reactions. Heterogeneous catalyst design strategies for Diels–Alder reactions are reviewed for two exemplary solid acid catalysts, zeolites and polyoxometalates, and recent efforts for targeting direct replacement aromatic monomers from biomass are summarized. In conclusion, we point out important research directions for progressing Diels–Alder catalysis to target novel, aromatic monomers with chemical functionality that enables new properties compared to monomers that are readily accessible from petroleum.

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Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office (BETO); USDOE Office of Energy Efficiency and Renewable Energy (EERE), NREL Laboratory Directed Research and Development (LDRD); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1374130

Report Number(s):: NREL/JA-5100-68713; GRCHFJ

Journal Information:: Green Chemistry, Vol. 19, Issue 15; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 169 works

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Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N -Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes Parisotto, Stefano; Palagi, Lorenzo; Prandi, Cristina Chemistry - A European Journal, Vol. 24, Issue 21 https://doi.org/10.1002/chem.201800765	journal	March 2018
Catalytic Transformation of Cellulose and Its Derivatives into Functionalized Organic Acids Li, Shi; Deng, Weiping; Wang, Shanshan ChemSusChem, Vol. 11, Issue 13 https://doi.org/10.1002/cssc.201800440	journal	June 2018
Production of Plant Phthalate and its Hydrogenated Derivative from Bio-Based Platform Chemicals Lu, Rui; Lu, Fang; Si, Xiaoqin ChemSusChem, Vol. 11, Issue 10 https://doi.org/10.1002/cssc.201800646	journal	April 2018
Boosting biomass valorisation. Synergistic design of continuous flow reactors and water-tolerant polystyrene acid catalysts for a non-stop production of esters Trombettoni, Valeria; Sciosci, Daniele; Bracciale, Maria Paola Green Chemistry, Vol. 20, Issue 14 https://doi.org/10.1039/c8gc00824h	journal	January 2018
Heterogeneous (de)chlorination-enabled control of reactivity in the liquid-phase synthesis of furanic biofuel from cellulosic feedstock Li, Hu; Wang, Changhong; Xu, Yufei Green Chemistry, Vol. 22, Issue 3 https://doi.org/10.1039/c9gc04092g	journal	January 2020
Rhodium-terpyridine catalyzed redox-neutral depolymerization of lignin in water Liu, Yuxuan; Li, Changzhi; Miao, Wang Green Chemistry, Vol. 22, Issue 1 https://doi.org/10.1039/c9gc03057c	journal	January 2020
Improving the production of maleic acid from biomass: TS-1 catalysed aqueous phase oxidation of furfural in the presence of γ-valerolactone Rodenas, Y.; Mariscal, R.; Fierro, J. L. G. Green Chemistry, Vol. 20, Issue 12 https://doi.org/10.1039/c8gc00857d	journal	January 2018
Production of Terephthalic Acid from Corn Stover Lignin Song, Song; Zhang, Jiaguang; Gözaydın, Gökalp Angewandte Chemie, Vol. 131, Issue 15 https://doi.org/10.1002/ange.201814284	journal	February 2019
Synthesis of Renewable meta ‐Xylylenediamine from Biomass‐Derived Furfural Scodeller, Ivan; Mansouri, Samir; Morvan, Didier Angewandte Chemie, Vol. 130, Issue 33 https://doi.org/10.1002/ange.201803828	journal	August 2018
Selective Production of Renewable para -Xylene by Tungsten Carbide Catalyzed Atom-Economic Cascade Reactions Dai, Tao; Li, Changzhi; Li, Lin Angewandte Chemie International Edition, Vol. 57, Issue 7 https://doi.org/10.1002/anie.201710074	journal	January 2018
Production of Terephthalic Acid from Corn Stover Lignin Song, Song; Zhang, Jiaguang; Gözaydın, Gökalp Angewandte Chemie International Edition, Vol. 58, Issue 15 https://doi.org/10.1002/anie.201814284	journal	April 2019
Sorbitol Cyclodehydration to Isosorbide Catalyzed by Acidic Carbon Obtained from Reaction By‐Product Zhang, Yi; Chen, Tong; Zhang, Gang ChemistrySelect, Vol. 5, Issue 5 https://doi.org/10.1002/slct.201904251	journal	February 2020
1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes Yao, Yongqi; Yang, Wen; Lin, Qifu Organic Chemistry Frontiers, Vol. 6, Issue 19 https://doi.org/10.1039/c9qo00660e	journal	January 2019

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