Ir al menú de navegación principal Ir al contenido principal Ir al pie de página del sitio

Vol. 15 Núm. 1 (2024)
Vol 15, Núm.1 (2024): Enero-Junio

Artículos de investigación / Research papers

Celulosa sulfonada como catalizador para la conversión eficiente de ácido levulínico en levulinato de etilo

https://doi.org/10.19053/01217488.v15.n1.2024.16871

Publicado 2024-04-09

  • Rodrigo Reynoso
    • ,
  • Gustavo A. Pasquale
    • ,
  • Diego M. Ruiz
    • ,
  • Luis A. Páez
    • ,
  • José J. Martinez
    • ,
  • Gustavo P. Romanelli

Rodrigo Reynoso
Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Centro de Investigaciónes en Sanidad Vegetal (CISaV)

Gustavo A. Pasquale
Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Centro de Investigaciónes en Sanidad Vegetal (CISaV

Diego M. Ruiz
Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Centro de Investigaciónes en Sanidad Vegetal (CISaV)

Luis A. Páez
Fundación Universitaria Juan de Castellanos

José J. Martinez
Universidad Pedagógica y Tecnológica de Colombia UPTC

Gustavo P. Romanelli
Centro de Investigación en Ciencias Aplicadas “Jorge Ronco” (CINDECA). CONICET-Univesidad Nacional de La Plata

Resumen

Este estudio destaca el uso de ácido sulfúrico de celulosa como catalizador heterogéneo y reutilizable derivado de biomasa (Cortaderia Selloana) para sintetizar levulinato de etilo mediante esterificación catalítica de ácido levulínico con etanol. Se estudiaron los efectos de la temperatura, la carga del catalizador y la relación molar de etanol:ácido levulínico sobre el rendimiento de levulinato de etilo para optimizar la producción. Se logró un rendimiento del 95% a las 16 horas, 80 °C y una relación molar de 3:1 de etanol:ácido levulínico. Estos resultados demuestran que es factible obtener altos rendimientos de levulinato de etilo utilizando un catalizador derivado de biomasa.

Palabras clave

ácido sulfúrico de celulosa; levulinato de etilo; Esterificación del ácido levulínico

Referencias

  • R. Rinaldi, F. Schuth, "Design of solid catalysts for the conversion of biomass" Energy & Environmental Science vol. 2, pp. 610-626, 2009.
  • P. Drożyner, P. Rejmer, P. Starowicz, A. Klasa, K.A. Skibniewska, "Biomass as a renewable source of energy". Technical Sciences vol. 16(3), pp. 211-220, 2013.
  • M.L. Savaliya, B.Z. Dholakiya, "Chemical transformation of triglycerides of fatty acid of Pongamia pinnata seed to fatty acid methyl esters by microwave irradiation", Chemical Sciences Journal vol. 4, pp. 67, 2013,
  • D.J. Hayes, "An examination of biorefining processes, catalysts and challenges", Catalysis Today vol. 145, pp. 138-151, 2009.
  • J.J. Bozell, L. Moens, D.C. Elliott, Y. Wang, G.G. Neuenscwander, S.W. Fitzpatrick, "Production of levulinic acid and use as a platform chemical for derived products. Resources, Conservation and Recycling" vol. 28, pp. 227-239, 2000.
  • J.C. Serrano-Ruiz, A. Pineda, A.M. Balu, R. Luque, J.M. Campelo, A.A. Romero, "Catalytic transformations of biomass-derived acids into advanced biofuels", Catalysis Today vol. 195, pp. 162-168, 2012.
  • F.M.A Geilen, E. Barthel, H. Andreas, M. Wolfgang, K. Jürgen, W.L. Leitner "Selective and Flexible Transformation of Biomass‐Derived Platform Chemicals by a Multifunctional Catalytic System", Angewandte Chemie International Edition vol. 49, pp. 5510-5514, 2010.
  • C.S.K. Lin, L.A. Pfaltzgraff, L. Herrero-Davila, E.B. Mubofu, S. Abderrahim, J.H. Clark, "Food waste as a valuable resource for the production of chemicals, materials and fuels. Current situation and global perspective", Energy & Environmental Science vol. 6, pp. 426-464, 2013.
  • A. Corma, S. Iborra, A. Velty, "Chemical Routes for the Transformation of Biomass into Chemicals", Chemical Reviews vol. 107, pp. 2411-2502, 2007.
  • J.N. Chheda, G.W. Huber, J.A. Dumesic, "Liquid‐Phase Catalytic Processing of Biomass‐Derived Oxygenated Hydrocarbons to Fuels and Chemicals", Angewandte Chemie International Edition vol. 46, 7164-7183, 2007.
  • E. Christensen, A. Williams, S. Paul, S. Burton, R.L. McCormick, "Properties and Performance of Levulinate Esters as Diesel Blend Components", Energy & Fuels vol. 25, pp. 5422-5428, 2011.
  • A.G. Zavozin, N.E. Kravchenko, N.V. Ignat’ev, S.G. Zlotin, "Variation in the regioselectivity of levulinic acid bromination in ionic liquids", Tetrahedron Letters vol. 51, 545-547, 2010.
  • J. Hegner, K.C. Pereira, B. DeBoef, B.L. Lucht, "Conversion of cellulose to glucose and levulinic acid via solid-supported acid catalysis", Tetrahedron Letters vol. 51, pp. 2356-2358, 2010.
  • D. Unlu, O. Ilgen, N.D. Hilmioglu, "Biodiesel additive ethyl levulinate synthesis by catalytic membrane: SO4−2/ZrO2 loaded hydroxyethyl cellulose", Chemical Engineering Journal vol. 302, pp. 260-268, 2016.
  • T. Lei, Z. Wang, Y. Li, Z. Li, X. He, J. Zhu, "Performance of a Diesel Engine with Ethyl Levulinate-Diesel Blends: A Study using Grey Relational Analysis", BioResources vol. 8(2), pp. 2696-2707, 2013.
  • G. Pasquale, P. Vázquez, G. Romanelli, G. Baronetti, "Catalytic upgrading of levulinic acid to ethyl levulinate using reusable silica-included Wells-Dawson heteropolyacid as catalyst", Catalysis Communications vol. 18, pp. 115-120, 2012.
  • F.D. Pileidis, M. Tabassum, S. Coutts, M-M. Titirici, "Esterification of levulinic acid into ethyl levulinate catalysed by sulfonated hydrothermal carbons", Chinese Journal of Catalysis vol. 35, 929-936, 2014.
  • F.G. Cirujano, A. Corma, F.X. Llabrés i Xamena, "Conversion of levulinic acid into chemicals: Synthesis of biomass derived levulinate esters over Zr-containing MOFs", Chemical Engineering Science vol. 124, pp. 52-60, 2015.
  • K.Y. Nandiwale, S.K. Yadava, V.V Bokade, "Production of octyl levulinate biolubricant over modified H-ZSM-5: Optimization by response surface methodology", Journal of Energy Chemistry vol. 23, pp. 535-541, 2014.
  • Y. Kuwahara, T. Fujitani, H. Yamashita, "Esterification of levulinic acid with ethanol over sulfated mesoporous zirconosilicates: Influences of the preparation conditions on the structural properties and catalytic performances", Catalysis Today vol. 237, pp. 18-28, 2014.
  • M. Popova, P. Shestakova, H. Lazarova, M. Dimitrov, D. Kovacheva, A. Szegedi, "Efficient solid acid catalysts based on sulfated tin oxides for liquid phase esterification of levulinic acid with ethanol", Applied Catalysis A: General vol. 560, pp. 119-131, 2018.
  • I. Ogino, Y. Suzuki, S.R. Mukai, "Esterification of levulinic acid with ethanol catalyzed by sulfonated carbon catalysts: Promotional effects of additional functional groups", Catalysis Today vol. 314, pp. 62-69, 2018.
  • D.R. Fernandes, A.S. Rocha, E.F. Mai, C.J.A. Mota, V. Teixeira da Silva, "Levulinic acid esterification with ethanol to ethyl levulinate production over solid acid catalysts", Applied Catalysis A: General vol. 425-426, pp. 199-204, 2012.
  • M.A. Tejero, E. Ramírez, C. Fité, J. Tejero, F. Cunill, "Esterification of levulinic acid with butanol over ion exchange resins", Applied Catalysis A: General vol. 517, pp. 56-66, 2016.
  • D. Song, S. An, Y. Sun, Y. Guo, "Efficient conversion of levulinic acid or furfuryl alcohol into alkyl levulinates catalyzed by heteropoly acid and ZrO2 bifunctionalized organosilica nanotubes", Journal of Catalysis vol. 333, pp. 184-199, 2016.
  • S. Dharne, V.V. Bokade, "Esterification of levulinic acid to n-butyl levulinate over heteropolyacid supported on acid-treated clay", Journal of Natural Gas Chemistry vol. 20, pp. 18-24, 2011.
  • Y. Kuwahara, W. Kaburagi, K. Nemoto, T. Fujitani, "Esterification of levulinic acid with ethanol over sulfated Si-doped ZrO2 solid acid catalyst: Study of the structure–activity relationships" Applied Catalysis A: General vol. 476, pp. 186-196, 2014.
  • J.A. Melero, G. Morales, J. Iglesias, M. Paniagua, B. Hernández, S. Penedo, "Efficient conversion of levulinic acid into alkyl levulinates catalyzed by sulfonic mesostructured silicas", Applied Catalysis A: General vol. 466, pp. 116-122, 2013.
  • A. Sai, S. Daiyu, L. Bo, Y. Xia, G. Yi‐Hang, "Morphology Tailoring of Sulfonic Acid Functionalized Organosilica Nanohybrids for the Synthesis of Biomass‐Derived Alkyl Levulinates", Chemistry – A European Journal vol. 21, pp. 10786-10798, 2015.
  • B.L. Oliveira, V. Teixeira da Silva, "Sulfonated carbon nanotubes as catalysts for the conversion of levulinic acid into ethyl levulinate", Catalysis Today vol. 234, pp. 257-263, 2014.
  • V.L. Budarin, J.H. Clark, R. Luque, D.J. Macquarrie, "Versatile mesoporous carbonaceous materials for acid catalysis", Chemical Communications vol. 2007, pp. 634-636, 2007.
  • R. Breslow, "Biomimetic control of chemical selectivity", Accounts of Chemical Research vol. 13, pp. 170-177, 1980.
  • W-L. Wei, H-Y. Zhu, C-L- Zhao, M-Y. Huang, Y-Y. Jiang, "Asymmetric hydrogenation of furfuryl alcohol catalyzed by a biopolymer–metal complex, silica-supported alginic acid–amino acid–Pt complex", Reactive and Functional Polymers vol. 59, pp. 33-39, 2004.
  • C. Crecchio, P. Ruggiero, M.D. Pizzigallo, "Polyphenoloxidases immobilized in organic gels: Properties and applications in the detoxification of aromatic compounds", Biotechnology and Bioengineering vol. 48, pp. 585-591, 1995.
  • K. Huang, L. Xue, Y-C. Hu, M-Y. Huang, Y-Y. Jiang, "Catalytic behaviors of silica-supported starch–polysulfosiloxane–Pt complexes in asymmetric hydrogenation of 4-methyl-2-pentanone", Reactive and Functional Polymers vol. 50, pp. 199-203, 2002.
  • E. Guibal, "Heterogeneous catalysis on chitosan-based materials: a review", Progress in Polymer Science vol. 30, pp. 71-109, 2005.
  • D. Klemm, B. Heublein, H.P. Fink, A. Bohn, "Cellulose: Fascinating Biopolymer and Sustainable Raw Material", Angewandte Chemie International Edition vol. 44, pp. 3358-3393, 2005.
  • A. Shaabani, A. Maleki, "Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the one-pot three-component synthesis of α-amino nitriles", Applied Catalysis A: General vol. 331, pp. 149-151, 2007.
  • A. Shaabani, A. Maleki, J. Moghimi Rad, E. Soleimani, "Cellulose Sulfuric Acid Catalyzed One-Pot Three-Component Synthesis of Imidazoazines", Chemical and Pharmaceutical Bulletin vol. 55, pp. 957-958, 2007.
  • J. Venu Madhav, Y. Thirupathi Reddy, P. Narsimha Reddy, M. Nikhil Reddy, S. Kuarm, P.A. Crooks PA, "Cellulose sulfuric acid: An efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a.j]xanthenes under solvent-free conditions" Journal of Molecular Catalysis A: Chemical vol. 304, 85-87, 2009.
  • A. Shaabani, A. Rahmati, Z. Badri, "Sulfonated cellulose and starch: New biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines", Catalysis Communications vol. 9, pp. 13-16, 2008.
  • J. Safari, S.H. Banitaba, S.D. Khalili, "Cellulose sulfuric acid catalyzed multicomponent reaction for efficient synthesis of 1,4-dihydropyridines via unsymmetrical Hantzsch reaction in aqueous media", Journal of Molecular Catalysis A: Chemical vol. 335, pp. 46-50, 2011.
  • P.N. Reddy, Y.T. Reddy, M.N. Reddy, B. Rajitha, P.A. Crooks, "Cellulose Sulfuric Acid: An Efficient Biodegradable and Recyclable Solid Acid Catalyst for the One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones", Synthetic Communications vol. 39, pp. 1257-1263, 2009.
  • M.L. Savaliya, B.Z. Dholakiya, "Cellulose Sulfuric Acid Catalyzed Esterification of Biodiesel Derived Raw Glycerol to Medium Chain Triglyceride: The Dual Advantage", Catalysis Letters vol. 144, pp. 1399-1406, 2014.
  • A. Jordá-Vilaplana, A. Carbonell-Verdú, M.D. Samper, A. Pop, D. Garcia-Sanoguera, "Development and characterization of a new natural fiber reinforced thermoplastic (NFRP) with Cortaderia selloana (Pampa grass) short fibers", Composites Science and Technology vol. 145, pp. 1-9, 2017.
  • B. Liu, Z. Zhang, K. Huang, "Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the synthesis of 5-hydroxymethylfurfural and 5-ethoxymethylfurfural from fructose", Cellulose vol. 20, pp. 2081-2089, 2013.
  • C-K. Shu, B.M. Lawrence, "Formation of 4-Alkoxy-.gamma.-valerolactones from Levulinic Acid and Alcohols during Storage at Room Temperature", Journal of Agricultural and Food Chemistry vol. 43, pp. 782-784, 1995.
  • R. Aafaqi, A.R. Mohamed, S. Bhatia, "Kinetics of esterification of palmitic acid with isopropanol using p-toluene sulfonic acid and zinc ethanoate supported over silica gel as catalysts", Journal of Chemical Technology & Biotechnology vol. 79, pp. 1127-1134, 2004.
  • E. Siva Sankar, V. Mohan, M. Suresh, G. Saidulu, B. David Raju, K.S. Rama Rao , "Vapor phase esterification of levulinic acid over ZrO2/SBA-15 catalyst", Catalysis Communications vol. 75, pp.1-5, 2016.

Descargas

Los datos de descargas todavía no están disponibles.

Artículos similares

<< < 1 2 3 4 

También puede Iniciar una búsqueda de similitud avanzada para este artículo.