Graphene from Alginate Pyrolysis as a Metal-Free Catalyst for Hydrogenation of Nitro Compounds
Mihaela-Mirela Trandafir
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorMihaela Florea
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorFlorentina Neaţu
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorDr. Ana Primo
Instituto Universitario de Tecnología Química CSIC-UPV, Universitat Politécnica de Valencia, Av. de los Naranjos s/n, 46022 Valencia, Spain
Search for more papers by this authorCorresponding Author
Prof. Vasile I. Parvulescu
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorCorresponding Author
Prof. Hermenegildo García
Instituto Universitario de Tecnología Química CSIC-UPV, Universitat Politécnica de Valencia, Av. de los Naranjos s/n, 46022 Valencia, Spain
Search for more papers by this authorMihaela-Mirela Trandafir
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorMihaela Florea
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorFlorentina Neaţu
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorDr. Ana Primo
Instituto Universitario de Tecnología Química CSIC-UPV, Universitat Politécnica de Valencia, Av. de los Naranjos s/n, 46022 Valencia, Spain
Search for more papers by this authorCorresponding Author
Prof. Vasile I. Parvulescu
Department of Organic Chemistry, Biochemistry and Catalysis, University of Bucharest, B-dul Regina Elisabeta 4-12, Bucharest, Romania
Search for more papers by this authorCorresponding Author
Prof. Hermenegildo García
Instituto Universitario de Tecnología Química CSIC-UPV, Universitat Politécnica de Valencia, Av. de los Naranjos s/n, 46022 Valencia, Spain
Search for more papers by this authorGraphical Abstract
Graphene catalysis: Graphene, obtained by pyrolysis of natural polysaccharide alginate and subsequent exfoliation of the turbostratic graphitic residue, promotes hydrogenation of nitro groups at higher, but similar, rates to carbon–carbon multiple bonds. Aromatic, conjugated, and aliphatic nitro groups undergo hydrogenation in the presence of graphene as metal-free catalyst, the reactivity depending on the substrate.
Abstract
Graphene obtained by pyrolysis of alginate at 900 °C under inert atmosphere and exfoliation is used as a metal-free catalyst for reduction of nitro to amino groups with hydrogen as a reagent. The process is general for aromatic and aliphatic, conjugated and isolated nitro groups, and occurs with low selectivity over hydrogenation of carbon–carbon double bonds.
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References
- 1N. Zhang, M.-Q. Yang, S. Liu, Y. Sun, Y.-J. Xu, Chem. Rev. 2015, 115, 10307–10377.
- 2N. Zhang, Y. Zhang, Y.-J. Xu, Nanoscale 2012, 4, 5792–5813.
- 3S. Navalon, A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Coord. Chem. Rev. 2016, 312, 99–148.
- 4D. R. Dreyer, C. W. Bielawski, Chem. Sci. 2011, 2, 1233–1240.
- 5J. J. Mousseau, A. B. Charette, Acc. Chem. Res. 2013, 46, 412–424.
- 6S. Navalon, A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Chem. Rev. 2014, 114, 6179–6212.
- 7D. S. Su, S. Perathoner, G. Centi, Chem. Rev. 2013, 113, 5782–5816.
- 8D. S. Su, J. Zhang, B. Frank, A. Thomas, X. Wang, J. Paraknowitsch, R. Schlögl, ChemSusChem 2010, 3, 169–180.
- 9S.-i. Fujita, H. Watanabe, A. Katagiri, H. Yoshida, M. Arai, J. Mol. Catal. A 2014, 393, 257–262.
- 10A. Primo, F. Neatu, M. Florea, V. Parvulescu, H. Garcia, Nat. Commun. 2014, 5, 5291.
- 11M. Boronat, P. Concepcion, A. Corma, S. Gonzalez, F. Illas, P. Serna, J. Am. Chem. Soc. 2007, 129, 16230–16237.
- 12A. Corma, P. Serna, Science 2006, 313, 332–334.
- 13A. Corma, P. Serna, P. Concepcion, J. Juan Calvino, J. Am. Chem. Soc. 2008, 130, 8748–8753.
- 14Y. Lin, S. Wu, W. Shi, B. Zhang, J. Wang, Y. A. Kim, M. Endo, D. S. Su, Chem. Commun. 2015, 51, 13086–13089.
- 15H.-C. Wang, B.-L. Li, Y.-J. Zheng, W.-Y. Wang, Bull. Korean Chem. Soc. 2012, 33, 2961–2965.
- 16S. Wu, G. Wen, J. Wang, J. Rong, B. Zong, R. Schloegl, D. S. Su, Catal. Sci. Technol. 2014, 4, 4183–4187.
- 17Y. Gao, D. Ma, C. Wang, J. Guan, X. Bao, Chem. Commun. 2011, 47, 2432–2434.
- 18S. Wu, G. Wen, J. Wang, J. Rong, B. Zong, R. Schlogl, D. S. Su, Catal. Sci. Technol. 2014, 4, 4183–4187.
- 19H. Hu, J. H. Xin, H. Hu, X. Wang, Nano Res. 2015, 8, 3992–4006.
- 20C. Feng, H.-Y. Zhang, N.-Z. Shang, S.-T. Gao, C. Wang, Chin. Chem. Lett. 2013, 24, 539–541.
- 21P. S. Kumbhar, J. Sanchez-Valente, J. M. M. Millet, F. Figueras, J. Catal. 2000, 191, 467–473.
- 22A. Dhakshinamoorthy, S. Navalon, D. Sempere, M. Alvaro, H. Garcia, Chem. Commun. 2013, 49, 2359–2361.
- 23A. Dhakshinamoorthy, K. Pitchumani, Tetrahedron Lett. 2008, 49, 1818–1823.
- 24A. Dhakshinamoorthy, M. Alvaro, H. Garcia, Adv. Synth. Catal. 2009, 351, 2271–2276.
- 25A. Primo, P. Atienzar, E. Sanchez, J. Maria Delgado, H. Garcia, Chem. Commun. 2012, 48, 9254–9256.
- 26S. J. Geier, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 3476–3477.
- 27T. A. Rokob, A. Hamza, I. Papai, J. Am. Chem. Soc. 2009, 131, 10701–10710.
- 28D. W. Stephan, Dalton Trans. 2009, 3129–3136.
- 29A. Stirling, A. Hamza, T. A. Rokob, I. Papai, Chem. Commun. 2008, 3148–3150.
- 30A. Primo, E. Sanchez, J. M. Delgado, H. Garcia, Carbon 2014, 68, 777–783.
- 31W. S. Hummers, R. E. Offeman, J. Am. Chem. Soc. 1958, 80, 1339–1339.
- 32M. Latorre-Sánchez, C. Lavorato, M. Puche, V. Fornés, R. Molinari, H. Garcia, Chem. Eur. J. 2012, 18, 16774–16783.
