Volume 125, Issue 44 pp. 11713-11717

Zuschrift

A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions^†

Xingyu Wang,

Xingyu Wang

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)

Search for more papers by this author

Dr. Roberto Rinaldi,

Corresponding Author

Dr. Roberto Rinaldi

[email protected]

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)Search for more papers by this author

Xingyu Wang,

Xingyu Wang

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)

Search for more papers by this author

Dr. Roberto Rinaldi,

Corresponding Author

Dr. Roberto Rinaldi

[email protected]

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim (Ruhr) (Germany)Search for more papers by this author

First published: 12 September 2013

https://doi.org/10.1002/ange.201304776

Citations: 49

^†

The funds for this research were provided by the Alexander von Humboldt Foundation (Sofja Kovalevskaja Award 2010). This work was performed as part of the Cluster of Excellence “Tailor-Made Fuels from Biomass”, funded by the German Federal and State Governments to promote science and research at German universities. We are indebted to Jan Geboers and Katrina Hong for meaningful discussions.

Share a link

Email
Wechat
Bluesky

Graphical Abstract

Ausweg gefunden: Die Umwandlung von Lignin in niedrigsiedende Arene anstatt hochsiedender Phenole könnte eine enorme Vereinfachung konventioneller Raffinerieprozesse bedeuten. Ein neuer Prozess für die Depolymerisation von Lignin mit gleichzeitiger Umwandlung von Phenolen in Arene wird beschrieben. Die Methode bietet auch einen allgemeinen Zugang zur Veredelung von Bioölen zu Arenen unter milden Bedingungen.

Supporting Information

References

1“Top Value-Added Chemicals from Biomass, Volume II—Results of Screening for Potential Candidates from Biorefinery Lignin”: J. E. Holladay, J. F. White, J. J. Bozell, D. Johnson, available from http://www1.eere.energy.gov/bioenergy/pdfs/pnnl-16983.pdf. In this insightful report, the conversion of lignin into simple arenes is highlighted as “very desirable, and is perhaps the most challenging and complex of the lignin technology barriers” (on page 26, section “8. Aromatic Chemicals”).
Google Scholar
2J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 2010, 110, 3552.
10.1021/cr900354u
CAS PubMed Web of Science® Google Scholar
3“The Structural Chemistry of Phenols”: M. Kaftory in PATAI′S Chemistry of Functional Groups, Wiley, Hoboken, 2009, DOI: .
Google Scholar
4
4aT. Q. Hu, G. R. Cairns, B. R. James, Holzforschung 2000, 54, 127;
10.1515/HF.2000.022
CAS Web of Science® Google Scholar
4bW. Lonsky, H. Traitler, K. Kratzl, J. Chem. Soc. Perkin Trans. 1 1975, 169;
10.1039/p19750000169
CAS Web of Science® Google Scholar
4cA. Mori, T. Mizusaki, T. Ikawa, T. Maegawa, Y. Monguchi, H. Sajiki, Tetrahedron 2007, 63, 1270;
10.1016/j.tet.2006.11.060
CAS Web of Science® Google Scholar
4dW. J. Musliner, J. W. Gates, J. Am. Chem. Soc. 1966, 88, 4271;
10.1021/ja00970a037
CAS Web of Science® Google Scholar
4eW. J. Musliner, J. W. Gates, Org. Synth. 1988, 50-9, 150;
Web of Science® Google Scholar
4fM. Pailer, E. Gossinge, Monatsh. Chem. 1969, 100, 1613;
10.1007/BF00900179
CAS Web of Science® Google Scholar
4gH. Sajiki, A. Mori, T. Mizusaki, T. Ikawa, T. Maegawa, K. Hirota, Org. Lett. 2006, 8, 987;
10.1021/ol060045q
CAS PubMed Web of Science® Google Scholar
4hE. Vowinkel, H. J. Baese, Chem. Ber. Recl. 1974, 107, 1213;
10.1002/cber.19741070417
CAS Web of Science® Google Scholar
4iE. Vowinkel, C. Wolff, Chem. Ber. Recl. 1974, 107, 907.
10.1002/cber.19741070318
CAS Web of Science® Google Scholar
5R. Rinaldi, X. Wang, European Patent Pending, 2012.
Google Scholar
6X. Wang, R. Rinaldi, Energy Environ. Sci. 2012, 5, 8244.
10.1039/c2ee21855k
CAS Web of Science® Google Scholar
7X. Wang, R. Rinaldi, ChemSusChem 2012, 5, 1455.
10.1002/cssc.201200040
CAS PubMed Web of Science® Google Scholar
8
8aJ. M. Nichols, L. M. Bishop, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2010, 132, 12554;
10.1021/ja106101f
CAS PubMed Web of Science® Google Scholar
8bA. G. Sergeev, J. F. Hartwig, Science 2011, 332, 439;
10.1126/science.1200437
CAS PubMed Web of Science® Google Scholar
8cS. Enthaler, M. Weidauer, Chem. Eur. J. 2012, 18, 1910;
10.1002/chem.201103677
CAS PubMed Web of Science® Google Scholar
8dS. K. Hanson, R. Wu, L. A. P. Silks, Angew. Chem. 2012, 124, 3466;
10.1002/ange.201107020
Web of Science® Google Scholar
Angew. Chem. Int. Ed. 2012, 51, 3410;
10.1002/anie.201107020
CAS PubMed Web of Science® Google Scholar
8eP. Kelley, S. Lin, G. Edouard, M. W. Day, T. Agapie, J. Am. Chem. Soc. 2012, 134, 5480;
10.1021/ja300326t
CAS PubMed Web of Science® Google Scholar
8fA. Wu, B. O. Patrick, E. Chung, B. R. James, Dalton Trans. 2012, 41, 11093.
10.1039/c2dt31065a
CAS PubMed Web of Science® Google Scholar
9A. G. Sergeev, J. D. Webb, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 20226.
10.1021/ja3085912
CAS PubMed Web of Science® Google Scholar
10T. H. Parsell, B. C. Owen, I. Klein, T. M. Jarrell, C. L. Marcum, L. J. Haupert, L. M. Amundson, H. I. Kenttaemaa, F. Ribeiro, J. T. Miller, M. M. Abu-Omar, Chem. Sci. 2013, 4, 806.
10.1039/C2SC21657D
CAS Web of Science® Google Scholar
11
11aE. A. Capanema, M. Y. Balakshin, J. F. Kadla, J. Agric. Food Chem. 2004, 52, 1850;
10.1021/jf035282b
CAS PubMed Web of Science® Google Scholar
11bE. A. Capanema, M. Y. Balakshin, J. F. Kadla, J. Agric. Food Chem. 2005, 53, 9639.
10.1021/jf0515330
CAS PubMed Web of Science® Google Scholar
12
12aC. Zhao, J. He, A. A. Lemonidou, X. Li, J. A. Lercher, J. Catal. 2011, 280, 8;
10.1016/j.jcat.2011.02.001
CAS Web of Science® Google Scholar
12bC. Zhao, Y. Kou, A. A. Lemonidou, X. Li, J. A. Lercher, Angew. Chem. 2009, 121, 4047;
10.1002/ange.200900404
Web of Science® Google Scholar
Angew. Chem. Int. Ed. 2009, 48, 3987;
10.1002/anie.200900404
CAS PubMed Web of Science® Google Scholar
12cC. Zhao, Y. Kou, A. A. Lemonidou, X. Li, J. A. Lercher, Chem. Commun. 2010, 46, 412.
10.1039/B916822B
CAS PubMed Web of Science® Google Scholar
13
13aP. M. Mortensen, J. D. Grunwaldt, P. A. Jensen, K. G. Knudsen, A. D. Jensen, Appl. Catal. A 2011, 407, 1;
10.1016/j.apcata.2011.08.046
CAS Web of Science® Google Scholar
13bS. Vasireddy, B. Morreale, A. Cugini, C. Song, J. J. Spivey, Energy Environ. Sci. 2011, 4, 311;
10.1039/C0EE00097C
CAS Web of Science® Google Scholar
13cT. D. Matson, K. Barta, A. V. Iretskii, P. C. Ford, J. Am. Chem. Soc. 2011, 133, 14090;
10.1021/ja205436c
CAS PubMed Web of Science® Google Scholar
13dJ. Wildschut, M. Iqbal, F. H. Mahfud, I. Melian-Cabrera, R. H. Venderbosch, H. J. Heeres, Energy Environ. Sci. 2010, 3, 962.
10.1039/b923170f
CAS Web of Science® Google Scholar

Citing Literature

Volume125, Issue44

October 25, 2013

Pages 11713-11717

This is the

German version

of Angewandte Chemie.

Note for articles published since 1962:

Do not cite this version alone.

Take me to the International Edition version with citable page numbers, DOI, and citation export.

We apologize for the inconvenience.

A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions^†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions†

Graphical Abstract

Supporting Information

References

Citing Literature

References

Related

Information

A Route for Lignin and Bio-Oil Conversion: Dehydroxylation of Phenols into Arenes by Catalytic Tandem Reactions^†