Electrochemical Lignin Degradation in Ionic Liquids on Ternary Mixed Metal Electrodes
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Daniel Rauber
Abstract
Lignin is the second most abundant natural polymer and a promissing feedstock for the generation of renewable aromatic chemicals. We present an fundamental approach for the electrocatalytic cleavage of lignin dissolved in a recoverable, inexpensive ionic liquid using mixed metal oxide electrodes of different compositions. The distribution of depolymerization products generated by electrochemical oxidation were analyzed by means of mass spectrometry. The distribution and yield of the cracked species was found to depended strongly on the implemented metal catalyst and therefore offers the potential to tailor the amount and composition of the low molecular weight cleavage products. This approach could help to provide a more sustainable valorization of lignin for the potential production of high value aromatic compounds due to synergistic effects.
Acknowledgements
This work was supported by the German Research Foundation (DFG) under grant number HE 2403/19-1/VO 1355/4-1. DAV acknowledges general research support by the Alfried Krupp von Bohlen und Halbach-Stiftung. We thank Reiner Wintringer and Verlaine Fossog for technical support.
References
1. B. M. Upton, A. M. Kasko, Chem. Rev. 116 (2016) 2275.10.1021/acs.chemrev.5b00345Suche in Google Scholar PubMed
2. S. Laurichesse, L. Avérous, Prog. Polym. Sci. 39 (2014) 1266.10.1016/j.progpolymsci.2013.11.004Suche in Google Scholar
3. A. J. Ragauskas, G. T. Beckham, M. J. Biddy, R. Chandra, F. Chen, M. F. Davis, B. H. Davison, R. A. Dixon, P. Gilna, M. Keller, P. Langan, A. K. Naskar, J. N. Saddler, T. J. Tschaplinski, G. A. Tuskan, C. E. Wyman, Science 344 (2014) 1246843.10.1126/science.1246843Suche in Google Scholar PubMed
4. C. Li, X. Zhao, A. Wang, G. W. Huber, T. Zhang, Chem. Rev. 115 (2015) 11559.10.1021/acs.chemrev.5b00155Suche in Google Scholar PubMed
5. V. L. Pardini, C. Z. Smith, J. H. P. Utley, R. R. Vargas, H. Viertler, J. Org. Chem. 56 (1991) 7305.10.1021/jo00026a022Suche in Google Scholar
6. K. Stärk, N. Taccardi, A. Bösmann, P. Wasserscheid, ChemSusChem. 3 (2010) 719.10.1002/cssc.200900242Suche in Google Scholar PubMed
7. J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 110 (2010) 3552.10.1021/cr900354uSuche in Google Scholar PubMed
8. S.-H. Li, S. Liu, J. C. Colmenares, Y.-J. Xu, Green Chem. 18 (2016) 594.10.1039/C5GC02109JSuche in Google Scholar
9. S. Jia, B. J. Cox, X. Guo, Z. C. Zhang, J. G. Ekerdt, ChemSusChem. 3 (2010) 1078.10.1002/cssc.201000112Suche in Google Scholar PubMed
10. D. Glas, C. Van Doorslaer, D. Depuydt, F. Liebner, T. Rosenau, K. Binnemans, D. E. De Vos, J. Chem. Technol. Biotechnol. 90 (2015) 1821.10.1002/jctb.4492Suche in Google Scholar
11. W. E. S. Hart, J. B. Harper, L. Aldous, Green Chem. 17 (2015) 214.10.1039/C4GC01888ESuche in Google Scholar
12. N. Sun, M. Rahman, Y. Qin, M. L. Maxim, H. Rodríguez, R. D. Rogers, Green Chem. 11 (2009) 646.10.1039/b822702kSuche in Google Scholar
13. A. Brandt, J. Gräsvik, J. P. Hallett, T. Welton, Green Chem. 15 (2013) 550.10.1039/c2gc36364jSuche in Google Scholar
14. E. Reichert, R. Wintringer, D. A. Volmer, R. Hempelmann, Phys. Chem. Chem. Phys. 14 (2012) 5214.10.1039/c2cp23596jSuche in Google Scholar PubMed
15. T. K. F. Dier, D. Rauber, D. Durneata, R. Hempelmann, D. A. Volmer, Sci. Rep. 7 (2017) 5041.10.1038/s41598-017-05316-xSuche in Google Scholar PubMed PubMed Central
16. S. Stiefel, A. Schmitz, J. Peters, D. Di Marino, M. Wessling, Green Chem. 18 (2016) 4999.10.1039/C6GC00878JSuche in Google Scholar
17. O. Movil-Cabrera, A. Rodriguez-Silva, C. Arroyo-Torres, J. A. Staser, Biomass Bioenergy 88 (2016) 89.10.1016/j.biombioe.2016.03.014Suche in Google Scholar
18. S. K. Hanson, R. T. Baker, Acc. Chem. Res. 48 (2015) 2037.10.1021/acs.accounts.5b00104Suche in Google Scholar PubMed
19. S. Trasatti, Electrochim. Acta. 45 (2000) 2377.10.1016/S0013-4686(00)00338-8Suche in Google Scholar
20. H. Zhu, L. Wang, Y. Chen, G. Li, H. Li, Y. Tang, P. Wan, RSC Adv. 4 (2014) 29917.10.1039/C4RA03793FSuche in Google Scholar
21. E. C. Achinivu, R. M. Howard, G. Li, H. Gracz, W. A. Henderson, Green Chem. 16 (2014) 1114.10.1039/C3GC42306ASuche in Google Scholar
22. X. Lu, G. Burrell, F. Separovic, C. Zhao, J. Phys. Chem. B. 116 (2012) 9160.10.1021/jp304735pSuche in Google Scholar PubMed
23. T. L. Greaves, C. J. Drummond, Chem. Rev. 115 (2015) 11379.10.1021/acs.chemrev.5b00158Suche in Google Scholar PubMed
24. M. M. Hossain, L. Aldous, Aust. J. Chem. 65 (2012) 1465.10.1071/CH12324Suche in Google Scholar
25. D. J. G. P. van Osch, L. J. B. M. Kollau, A. van den Bruinhorst, S. Asikainen, M. A. A. Rocha, M. C. Kroon, Phys. Chem. Chem. Phys. 19 (2017) 2636.10.1039/C6CP07499ESuche in Google Scholar PubMed
26. M. V. Galkin, J. S. M. Samec, ChemSusChem. 9 (2016) 1544.10.1002/cssc.201600237Suche in Google Scholar PubMed
27. R. Rinaldi, R. Jastrzebski, M. T. Clough, J. Ralph, M. Kennema, P. C. A. Bruijnincx, B. M. Weckhuysen, Angew. Chemie Int. Ed. 55 (2016) 8164.10.1002/anie.201510351Suche in Google Scholar PubMed PubMed Central
28. G. Chatel, R. D. Rogers, ACS Sustain. Chem. Eng. 2 (2014) 322.10.1021/sc4004086Suche in Google Scholar
29. T. K. F. Dier, D. Rauber, J. Jauch, R. Hempelmann, D. A. Volmer, ChemistrySelect. 2 (2017) 779.10.1002/slct.201601673Suche in Google Scholar
30. D. Schmitt, C. Regenbrecht, M. Hartmer, F. Stecker, S. R. Waldvogel, Beilstein J. Org. Chem. 11 (2015) 473.10.3762/bjoc.11.53Suche in Google Scholar PubMed PubMed Central
31. D. Schmitt, C. Regenbrecht, M. Schubert, D. Schollmeyer, S. R. Waldvogel, Holzforschung 71 (2017) 35.10.1515/hf-2015-0210Suche in Google Scholar
32. D. Schmitt, N. Beiser, C. Regenbrecht, M. Zirbes, S. R. Waldvogel, Sep. Purif. Technol. 181 (2017) 8.10.1016/j.seppur.2017.03.004Suche in Google Scholar
33. R. Behling, S. Valange, G. Chatel, Green Chem. 18 (2016) 1839.10.1039/C5GC03061GSuche in Google Scholar
34. G. F. De Gregorio, C. C. Weber, J. Gräsvik, T. Welton, A. Brandt, J. P. Hallett, Green Chem. 18 (2016) 5456.10.1039/C6GC01295GSuche in Google Scholar
35. T. K. F. Dier, K. Egele, V. Fossog, R. Hempelmann, D. A. Volmer, Anal. Chem. 88 (2016) 1328.10.1021/acs.analchem.5b03790Suche in Google Scholar PubMed
36. Y. Qi, R. Hempelmann, D. A. Volmer, Anal. Bioanal. Chem. 408 (2016) 4835.10.1007/s00216-016-9598-5Suche in Google Scholar PubMed PubMed Central
37. Y. Qi, R. Hempelmann, D. A. Volmer, Anal. Bioanal. Chem. 408 (2016) 8203.10.1007/s00216-016-9928-7Suche in Google Scholar PubMed
38. R. Chen, V. Trieu, H. Natter, K. Stöwe, W. F. Maier, R. Hempelmann, A. Bulan, J. Kintrup, R. Weber, Chem. Mater. 22 (2010) 6215.10.1021/cm102414nSuche in Google Scholar
©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Isomer Identification in Flames with Double-Imaging Photoelectron/Photoion Coincidence Spectroscopy (i2PEPICO) using Measured and Calculated Reference Photoelectron Spectra
- Electrochemical Lignin Degradation in Ionic Liquids on Ternary Mixed Metal Electrodes
- Novel Design, Preparation, Characterization and Antimicrobial Activity of Silver Nanoparticles during Oak Acorns Bark Retrograde
- Mn(II) Catalyzed Oxidation of Atenolol by Cerium(IV) in Aqueous Sulfuric Acid Medium: A Spectrophotometer Aided Kinetic, Mechanistic and Thermodynamic Study
- Synthesis of Nanostructured Tin Oxide by Sol–Gel and Sonochemical Approaches in an Ionic Liquid
- Solubility and Preferential Solvation of Piroxicam in Neat Solvents and Binary Systems
- Study on Host-Guest Inclusion Complexation of a Drug in Cucurbit [6]uril
- Discovery of a Unique Sinusoidal Frequency for the Effective Magnetic Treatment of Brackish Water
Artikel in diesem Heft
- Frontmatter
- Isomer Identification in Flames with Double-Imaging Photoelectron/Photoion Coincidence Spectroscopy (i2PEPICO) using Measured and Calculated Reference Photoelectron Spectra
- Electrochemical Lignin Degradation in Ionic Liquids on Ternary Mixed Metal Electrodes
- Novel Design, Preparation, Characterization and Antimicrobial Activity of Silver Nanoparticles during Oak Acorns Bark Retrograde
- Mn(II) Catalyzed Oxidation of Atenolol by Cerium(IV) in Aqueous Sulfuric Acid Medium: A Spectrophotometer Aided Kinetic, Mechanistic and Thermodynamic Study
- Synthesis of Nanostructured Tin Oxide by Sol–Gel and Sonochemical Approaches in an Ionic Liquid
- Solubility and Preferential Solvation of Piroxicam in Neat Solvents and Binary Systems
- Study on Host-Guest Inclusion Complexation of a Drug in Cucurbit [6]uril
- Discovery of a Unique Sinusoidal Frequency for the Effective Magnetic Treatment of Brackish Water
