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

Abstract

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.

Authors:
 [1];  [2];  [2];  [3]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [2]
  1. National Renewable Energy Lab. (NREL), Golden, CO (United States); Colorado School of Mines, Golden, CO (United States)
  2. National Renewable Energy Lab. (NREL), Golden, CO (United States)
  3. Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States); Energy Frontier Research Centers (EFRC) (United States). Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B); 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) (SC-22)
OSTI Identifier:
1374130
Report Number(s):
NREL/JA-5100-68713
Journal ID: ISSN 1463-9262; GRCHFJ
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Volume: 19; Journal Issue: 15; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; catalysis; lignocellosic biomass; aromatic compounds

Citation Formats

Settle, Amy E., Berstis, Laura, Rorrer, Nicholas A., Roman-Leshkov, Yuriy, Beckham, Gregg T., Richards, Ryan M., and Vardon, Derek R. Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds. United States: N. p., 2017. Web. doi:10.1039/C7GC00992E.
Settle, Amy E., Berstis, Laura, Rorrer, Nicholas A., Roman-Leshkov, Yuriy, Beckham, Gregg T., Richards, Ryan M., & Vardon, Derek R. Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds. United States. doi:10.1039/C7GC00992E.
Settle, Amy E., Berstis, Laura, Rorrer, Nicholas A., Roman-Leshkov, Yuriy, Beckham, Gregg T., Richards, Ryan M., and Vardon, Derek R. Wed . "Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds". United States. doi:10.1039/C7GC00992E. https://www.osti.gov/servlets/purl/1374130.
@article{osti_1374130,
title = {Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds},
author = {Settle, Amy E. and Berstis, Laura and Rorrer, Nicholas A. and Roman-Leshkov, Yuriy and Beckham, Gregg T. and Richards, Ryan M. and Vardon, Derek R.},
abstractNote = {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.},
doi = {10.1039/C7GC00992E},
journal = {Green Chemistry},
number = 15,
volume = 19,
place = {United States},
year = {2017},
month = {5}
}

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