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One-Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds

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One-Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds

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Vidal, JD.; Climent Olmedo, MJ.; Corma Canós, A.; Concepción Heydorn, P.; Iborra Chornet, S. (2017). One-Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds. ChemSusChem. 10(1):119-128. https://doi.org/10.1002/cssc.201601333

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/111644

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Título: One-Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds
Autor: Vidal, Juan D Climent Olmedo, María José Corma Canós, Avelino Concepción Heydorn, Patricia Iborra Chornet, Sara
Entidad UPV: Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Universitat Politècnica de València. Departamento de Química - Departament de Química
Fecha difusión:
Resumen:
[EN] N-substituted 5-methyl-2-pyrrolidones were prepared in a one-pot process starting from ethyl levulinate and nitro compounds in the presence of a nanosized Pt-based catalyst. Pt supported on TiO2 nanotubes (Pt/TiO2-NT) ...[+]
Palabras clave: Ethyl levulinate , Nitro compounds , Platinum , Pyrrolidones , Reductive amination
Derechos de uso: Reserva de todos los derechos
Fuente:
ChemSusChem. (issn: 1864-5631 )
DOI: 10.1002/cssc.201601333
Editorial:
John Wiley & Sons
Versión del editor: http://doi.org/10.1002/cssc.201601333
Código del Proyecto:
info:eu-repo/grantAgreement/MINECO//SEV-2012-0267/
info:eu-repo/grantAgreement/MINECO//CTQ2015-67592-P/ES/VALORIZACION DE COMPUESTO OXIGENADOS PRESENTES EN FRACCIONES ACUOSAS DERIVADAS DE BIOMASA EN COMBUSTIBLES Y PRODUCTOS QUIMICOS/
info:eu-repo/grantAgreement/GVA//PROMETEOII%2F2013%2F011/ES/Catalizadores moleculares y supramoleculares altamente selectivos, estables y energéticamente eficientes en reacciones químicas (PROMETEO)/
Descripción: This is the peer reviewed version of the following article: Vidal, Juan D, Climent Olmedo, María José, Corma Canós, Avelino, Concepción Heydorn, Patricia, Iborra Chornet, Sara. (2017). One-Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds .ChemSusChem, 10, 1, 119-128, which has been published in final form at http://doi.org/10.1002/cssc.201601333. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Agradecimientos:
Financial support by Consolider-Ingenio 2010 (Project Multicat), Spanish MICINN Project (CTQ-2015-67592-P), Generalitat Valenciana (Prometeo Program) and Program Severo Ochoa is gratefully acknowledged.
Tipo: Artículo

References

Vispute, T. P., Zhang, H., Sanna, A., Xiao, R., & Huber, G. W. (2010). Renewable Chemical Commodity Feedstocks from Integrated Catalytic Processing of Pyrolysis Oils. Science, 330(6008), 1222-1227. doi:10.1126/science.1194218

Climent, M. J., Corma, A., & Iborra, S. (2014). Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels. Green Chemistry, 16(2), 516. doi:10.1039/c3gc41492b

Corma, A., Iborra, S., & Velty, A. (2007). Chemical Routes for the Transformation of Biomass into Chemicals. Chemical Reviews, 107(6), 2411-2502. doi:10.1021/cr050989d [+]
Vispute, T. P., Zhang, H., Sanna, A., Xiao, R., & Huber, G. W. (2010). Renewable Chemical Commodity Feedstocks from Integrated Catalytic Processing of Pyrolysis Oils. Science, 330(6008), 1222-1227. doi:10.1126/science.1194218

Climent, M. J., Corma, A., & Iborra, S. (2014). Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels. Green Chemistry, 16(2), 516. doi:10.1039/c3gc41492b

Corma, A., Iborra, S., & Velty, A. (2007). Chemical Routes for the Transformation of Biomass into Chemicals. Chemical Reviews, 107(6), 2411-2502. doi:10.1021/cr050989d

Climent, M. J., Corma, A., & Iborra, S. (2011). Converting carbohydrates to bulk chemicals and fine chemicals over heterogeneous catalysts. Green Chemistry, 13(3), 520. doi:10.1039/c0gc00639d

Gallezot, P. (2012). Conversion of biomass to selected chemical products. Chem. Soc. Rev., 41(4), 1538-1558. doi:10.1039/c1cs15147a

Top Value Added Chemicals from Biomass. Results of Screening for Potential Candidates from Sugars and Synthesis Gas, Vol. 1 2004 http://www.nrel.gov/docs/fy04osti/35523.pdf

Bozell, J. J., & Petersen, G. R. (2010). Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s «Top 10» revisited. Green Chemistry, 12(4), 539. doi:10.1039/b922014c

Gürbüz, E. I., Alonso, D. M., Bond, J. Q., & Dumesic, J. A. (2011). Reactive Extraction of Levulinate Esters and Conversion to γ-Valerolactone for Production of Liquid Fuels. ChemSusChem, 4(3), 357-361. doi:10.1002/cssc.201000396

L. E. Manzer E. I. Du Ponte De Nemours And Company US6743819B1 2004

L. E. Manzer US20060247443A1 2006

Wei, Y., Wang, C., Jiang, X., Xue, D., Li, J., & Xiao, J. (2013). Highly efficient transformation of levulinic acid into pyrrolidinones by iridium catalysed transfer hydrogenation. Chemical Communications, 49(47), 5408. doi:10.1039/c3cc41661e

Huang, Y.-B., Dai, J.-J., Deng, X.-J., Qu, Y.-C., Guo, Q.-X., & Fu, Y. (2011). Ruthenium-Catalyzed Conversion of Levulinic Acid to Pyrrolidines by Reductive Amination. ChemSusChem, 4(11), 1578-1581. doi:10.1002/cssc.201100344

Ortiz-Cervantes, C., Flores-Alamo, M., & García, J. J. (2016). Synthesis of pyrrolidones and quinolines from the known biomass feedstock levulinic acid and amines. Tetrahedron Letters, 57(7), 766-771. doi:10.1016/j.tetlet.2016.01.018

Du, X.-L., He, L., Zhao, S., Liu, Y.-M., Cao, Y., He, H.-Y., & Fan, K.-N. (2011). Hydrogen-Independent Reductive Transformation of Carbohydrate Biomass into γ-Valerolactone and Pyrrolidone Derivatives with Supported Gold Catalysts. Angewandte Chemie International Edition, 50(34), 7815-7819. doi:10.1002/anie.201100102

Du, X.-L., He, L., Zhao, S., Liu, Y.-M., Cao, Y., He, H.-Y., & Fan, K.-N. (2011). Hydrogen-Independent Reductive Transformation of Carbohydrate Biomass into γ-Valerolactone and Pyrrolidone Derivatives with Supported Gold Catalysts. Angewandte Chemie, 123(34), 7961-7965. doi:10.1002/ange.201100102

Wei, Y., Wang, C., Jiang, X., Xue, D., Liu, Z.-T., & Xiao, J. (2014). Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid. Green Chem., 16(3), 1093-1096. doi:10.1039/c3gc42125b

Ledoux, A., Sandjong Kuigwa, L., Framery, E., & Andrioletti, B. (2015). A highly sustainable route to pyrrolidone derivatives – direct access to biosourced solvents. Green Chem., 17(6), 3251-3254. doi:10.1039/c5gc00417a

L. E. Manzer E. I. Du Pont De Nemours And Company US7129362B2 2006

L. E. Manzer US20060247444A1 2006

Chieffi, G., Braun, M., & Esposito, D. (2015). Continuous Reductive Amination of Biomass-Derived Molecules over Carbonized Filter Paper-Supported FeNi Alloy. ChemSusChem, 8(21), 3590-3594. doi:10.1002/cssc.201500804

Touchy, A. S., Hakim Siddiki, S. M. A., Kon, K., & Shimizu, K. (2014). Heterogeneous Pt Catalysts for Reductive Amination of Levulinic Acid to Pyrrolidones. ACS Catalysis, 4(9), 3045-3050. doi:10.1021/cs500757k

Vidal, J. D., Climent, M. J., Concepcion, P., Corma, A., Iborra, S., & Sabater, M. J. (2015). Chemicals from Biomass: Chemoselective Reductive Amination of Ethyl Levulinate with Amines. ACS Catalysis, 5(10), 5812-5821. doi:10.1021/acscatal.5b01113

ChemCatChem 2016 10.1002/cctc.201600739

Climent, M. J., Corma, A., & Iborra, S. (2011). Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals. Chemical Reviews, 111(2), 1072-1133. doi:10.1021/cr1002084

José Climent, M., Corma, A., & Iborra, S. (2012). Homogeneous and heterogeneous catalysts for multicomponent reactions. RSC Adv., 2(1), 16-58. doi:10.1039/c1ra00807b

Yoshida, H., Igarashi, N., Fujita, S., Panpranot, J., & Arai, M. (2014). Influence of Crystallite Size of TiO2 Supports on the Activity of Dispersed Pt Catalysts in Liquid-Phase Selective Hydrogenation of 3-Nitrostyrene, Nitrobenzene, and Styrene. Catalysis Letters, 145(2), 606-611. doi:10.1007/s10562-014-1404-4

L. E. Manzer E. I. Du Pont De Nemours And Company US6855731B2 2005

L. E. Manzer E. I. Du Pont De Nemours And Company US6818593B2 2004

Yang, X., Yu, X., Long, L., Wang, T., Ma, L., Wu, L., … Liao, S. (2014). Pt nanoparticles entrapped in titanate nanotubes (TNT) for phenol hydrogenation: the confinement effect of TNT. Chemical Communications, 50(21), 2794. doi:10.1039/c3cc49331h

Hsu, C.-Y., Chiu, T.-C., Shih, M.-H., Tsai, W.-J., Chen, W.-Y., & Lin, C.-H. (2010). Effect of Electron Density of Pt Catalysts Supported on Alkali Titanate Nanotubes in Cinnamaldehyde Hydrogenation. The Journal of Physical Chemistry C, 114(10), 4502-4510. doi:10.1021/jp9095198

Chiu, T.-C., Lee, H.-Y., Li, P.-H., Chao, J.-H., & Lin, C.-H. (2013). Effects of interfacial charge and the particle size of titanate nanotube-supported Pt nanoparticles on the hydrogenation of cinnamaldehyde. Nanotechnology, 24(11), 115601. doi:10.1088/0957-4484/24/11/115601

Zhu, B., Li, K., Wang, S., Zhang, S., Wu, S., & Huang, W. (2008). Influences of the H2PtCl6Solution’s pH on the Photocatalytic Activities of Platinum-Loaded TiO2Nanotubes. Journal of Dispersion Science and Technology, 29(10), 1408-1411. doi:10.1080/01932690802313311

XIAO-JING, H., BAO-LIN, Z., JIAN-XUN, D., WEI-LING, Z., SHU-RONG, W., SHOU-MIN, Z., & WEI-PING, H. (2012). THE INFLUENCE OF PLATINUM ON THE STRUCTURE AND PHOTOCATALYTIC PERFORMANCE OF HYDROGEN TITANATE NANOTUBES. Journal of the Chilean Chemical Society, 57(1), 1008-1011. doi:10.4067/s0717-97072012000100012

Kubo, T., Nagata, H., Takeuchi, M., Matsuoka, M., Anpo, M., & Nakahira, A. (2008). Structural evaluation and photocatalytic properties of Pt-supported titanate nanotubes. Research on Chemical Intermediates, 34(4), 339-346. doi:10.1163/156856708784040605

Hadjiivanov, K. I. (1998). IR study of CO and H2O coadsorption on Ptn+/TiO2 and Pt/TiO2 samples. Journal of the Chemical Society, Faraday Transactions, 94(13), 1901-1904. doi:10.1039/a801892h

Shen, S., Wang, X., Ding, Q., Jin, S., Feng, Z., & Li, C. (2014). Effect of Pt cocatalyst in Pt/TiO2 studied by in situ FTIR of CO adsorption. Chinese Journal of Catalysis, 35(11), 1900-1906. doi:10.1016/s1872-2067(14)60172-8

Greenler, R. G., Burch, K. D., Kretzschmar, K., Klauser, R., Bradshaw, A. M., & Hayden, B. E. (1985). Stepped single-crystal surfaces as models for small catalyst particles. Surface Science, 152-153, 338-345. doi:10.1016/0039-6028(85)90163-3

Jiang, F., Zeng, L., Li, S., Liu, G., Wang, S., & Gong, J. (2014). Propane Dehydrogenation over Pt/TiO2–Al2O3 Catalysts. ACS Catalysis, 5(1), 438-447. doi:10.1021/cs501279v

Serna, P., López-Haro, M., Calvino, J. J., & Corma, A. (2009). Selective hydrogenation of nitrocyclohexane to cyclohexanone oxime with H2 on decorated Pt nanoparticles. Journal of Catalysis, 263(2), 328-334. doi:10.1016/j.jcat.2009.02.025

Climent, M. J., Corma, A., Iborra, S., & Santos, L. L. (2009). Multisite Solid Catalyst for Cascade Reactions: The Direct Synthesis of Benzodiazepines from Nitro Compounds. Chemistry - A European Journal, 15(35), 8834-8841. doi:10.1002/chem.200900492

Climent, M. J., Corma, A., Iborra, S., & Martí, L. (2014). Process Intensification with Bifunctional Heterogeneous Catalysts: Selective One-Pot Synthesis of 2′-Aminochalcones. ACS Catalysis, 5(1), 157-166. doi:10.1021/cs5011713

Corma, A., Concepción, P., & Serna, P. (2007). A Different Reaction Pathway for the Reduction of Aromatic Nitro Compounds on Gold Catalysts. Angewandte Chemie International Edition, 46(38), 7266-7269. doi:10.1002/anie.200700823

Corma, A., Concepción, P., & Serna, P. (2007). A Different Reaction Pathway for the Reduction of Aromatic Nitro Compounds on Gold Catalysts. Angewandte Chemie, 119(38), 7404-7407. doi:10.1002/ange.200700823

Corma, A., Serna, P., Concepción, P., & Calvino, J. J. (2008). Transforming Nonselective into Chemoselective Metal Catalysts for the Hydrogenation of Substituted Nitroaromatics. Journal of the American Chemical Society, 130(27), 8748-8753. doi:10.1021/ja800959g

Kasuga, T., Hiramatsu, M., Hoson, A., Sekino, T., & Niihara, K. (1998). Formation of Titanium Oxide Nanotube. Langmuir, 14(12), 3160-3163. doi:10.1021/la9713816

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