Heterogeneous catalysis: understanding the fundamentals for catalyst design

[EN] Taking the chemoselective hydrogenation of substituted nitroaromatics as a base case, it will be shown that it is possible to design improved and new catalysts by attacking the problem in a multidisciplinary way. By combining molecular modeling with in situ operando spectroscopy, and with micro-kinetic and isotopic studies, it is possible to determine how and where on the catalysts the reactant molecules interact. Then, materials synthesis methods can be applied to prepare catalysts with the desired surface active sites and their selective interaction with the reactants.This work was funded by the Spanish Government (Severo Ochoa program SEV2012-0267). The support of the European Union by (ERC-AdG-2014-671093 – SynCatMatch) is also acknowledged.Corma Canós, A. (2016). Heterogeneous catalysis: understanding the fundamentals for catalyst design. Faraday Discussions of the Chemical Society. 188:9-20. https://doi.org/10.1039/c6fd00066eS92018

Porous catalysts Separate to accumulate: A sequential templating technique yields bifunctional catalysts with controlled separation of cooperative catalytic functionalities

Corma Canós, A. (2016). Porous catalysts Separate to accumulate: A sequential templating technique yields bifunctional catalysts with controlled separation of cooperative catalytic functionalities. Nature Materials. 15(2):134-136. http://hdl.handle.net/10251/101669S13413615

Isolated metal atoms and clusters for alkane activation: translating knowledge from enzymatic and homogeneous to heterogeneous systems

[EN] Activation of alkanes can be achieved with different types of catalysts, spanning over enzymes, homogeneous and heterogeneous metal catalysts. Though a tremendous amount of knowledge has been accumulated in the literature, the connections between different types of catalysts are rarely discussed due to the differences among the three catalysis fields in terms of catalyst structures, reaction conditions, and catalytic performances. There are also similarities among the various systems in terms of the structural features of the active sites and reaction mechanisms. In this review, we attempt to show the interconnections among the three catalysis fields regarding the nature of active sites and reaction mechanism for metal-catalyzed alkane activation reactions. We will show the lessons obtained from well-defined enzymatic and molecular catalysts developed in bio- and homogeneous catalysis, and how these can be translated into fundamental understanding and further developments of heterogeneous metal catalysts, for practical applications related to alkane activation.We are grateful for the financial supports from the Spanish Government through the "Severo Ochoa Program'' (SEV-2016-SEV-0683).Liu, L.; Corma Canós, A. (2021). Isolated metal atoms and clusters for alkane activation: translating knowledge from enzymatic and homogeneous to heterogeneous systems. Chem. 7(9):2347-2384. https://doi.org/10.1016/j.chempr.2021.04.001S234723847

Confining isolated atoms and clusters in crystalline porous materials for catalysis

[EN] Structure-reactivity relationships for nanoparticle-based catalysts have been greatly influenced by the study of catalytic materials with either supported isolated metal atoms or metal clusters comprising a few atoms. The stability of these metal species is a key challenge because they can sinter into large nanoparticles under harsh reaction conditions. However, stability can be achieved by confining the nanoparticles in crystalline porous materials (such as zeolites and metal-organic frameworks). More importantly, the interaction between the metal species and the porous framework may modulate the geometric and electronic structures of the subnanometric metal species, especially for metal clusters. This confinement effect can induce shape-selective catalysis or different chemoselectivity from that of metal atoms supported on open-structure solid carriers. In this Review, we discuss the structural features, synthesis methodologies, characterization techniques and catalytic applications of subnanometric species confined in zeolites and metal-organic frameworks. We make a critical comparison between confined and non-confined isolated atoms and metal clusters, and provide future perspectives for the field.We are grateful for financial support from the European Research Council (grant ERC-AdG-2014-671093, SynCatMatch) and the Spanish Government through the Severo Ochoa Program (SEV-2016-0683).Liu, L.; Corma Canós, A. (2021). Confining isolated atoms and clusters in crystalline porous materials for catalysis. Nature Reviews Materials. 6(3):244-263. https://doi.org/10.1038/s41578-020-00250-32442636

Catálisis con zeolitas: Desde el laboratorio a su aplicación industrial

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Direct Conversion of Cellulose into Alkyl Glycoside Surfactants

[EN] The one-step production of biodegradable alkyl glycoside (1-dodecyl mono- and oligoglucoside) surfactants from cellulose has been achieved by direct alcoholysis in fatty alcohol media under BrOnsted acid catalysis at near-ambient pressure. The fatty alcohol serves as both solvent and reagent. Addition of small amounts of water prevents dehydration events and thus minimises product and solvent degradation. Furthermore, high initial cellulose loadings and short thermal cycles enable moderate-to-high conversions and selectivities (up to approximate to 70%), and low solvent-to-product ratios.Financial support from the Spanish Government-MINECO through "Severo Ochoa" (SEV 2012-0267) is acknowledged. AVP also thanks the Spanish Government (Agencia Estatal de Investigacion) and the European Union (European Regional Development Fund) for a grant for young researchers (CTQ2015-74138-JIN, AEI/FEDER/UE).Puga, AV.; Corma Canós, A. (2017). Direct Conversion of Cellulose into Alkyl Glycoside Surfactants. ChemistrySelect. 2(8):2495-2498. https://doi.org/10.1002/slct.201700389S249524982

Advances in the synthesis of titanosilicates: From the medium pore TS-1 zeolite to highly-accessible ordered materials

[EN] In the present review, we would like to cover the most fundamental advances achieved in the design of ordered titanosilicates since the earlier discovery of TS-1 reported by EniChem in the mid-eighties. The invention of the medium-pore TS-1 zeolite was a breakthrough, and this material has been applied as efficient catalyst in diverse industrial applications. However, its limited pore size (5 5.5 Å) offers diffusion limitations when working with large molecules. The design and preparation of open titanosilicates, such as large pore molecular sieves, mesoporous ordered materials, or layered-type zeolites will be described. The applicability of these titanosilicates to catalytic oxidation processes requiring bulky organic molecules will also be presented.This work has been supported by the Spanish GovernmentMINECO (MAT2012-37160), Consolider Ingenio 2010-Multicat, and UPV through PAID-06-11 (n.1952). Manuel Moliner also acknowledges to ‘‘Subprograma Ramon y Cajal’’ for the contract RYC-2011-08972. ITQ thanks the ‘‘Program Severo Ochoa’’ for financial support (SEV 2012 0267).Moliner Marin, M.; Corma Canós, A. (2014). Advances in the synthesis of titanosilicates: From the medium pore TS-1 zeolite to highly-accessible ordered materials. Microporous and Mesoporous Materials. 189:31-40. https://doi.org/10.1016/j.micromeso.2013.08.003S314018

What Is Measured When Measuring Acidity in Zeolites with Probe Molecules?

[EN] Based on theoretical calculations of CO, NH3, and pyridine adsorption at different sites in MOR and MFI zeolites, we analyze how confinement effects influence the measurement of acidity based on the interaction of probe molecules with Brönsted acid sites. Weak bases, such as CO, form neutral ZH¿CO adducts with a linear configuration that can be distorted by spatial restrictions associated with the dimensions of the pore, leading to weaker interaction, but can also be stabilized by dispersion forces if a tighter fitting with the channel void is allowed. Strong bases such as NH3 and pyridine are readily protonated on Brönsted acid sites, and the experimentally determined adsorption enthalpies include not only the thermochemistry associated with the proton transfer process itself, but also the stabilization of the Z¿¿BH+ ion pair formed upon protonation by multiple interactions with the surrounding framework oxygen atoms, leading in some cases to a heterogeneity of acidities within the same zeolite structure.This work was supported by the European Union through No. ERC-AdG-2014-671093 (SynCatMatch), and by the Spanish Government-MINECO through "Severo Ochoa" (No. SEV-2016-0683) and No. MAT2017-82288-C2-1-P projects. Red Espanola de Supercomputacion (RES) and Centre de Calcul de la Universitat de Valencia are gratefully acknowledged for computational resources.Boronat Zaragoza, M.; Corma Canós, A. (2019). What Is Measured When Measuring Acidity in Zeolites with Probe Molecules?. ACS Catalysis. 9(2):1539-1548. https://doi.org/10.1021/acscatal.8b04317S1539154892Chen, H.Y. In Urea–SCR Technology for deNOx After Treatment of Diesel Exhausts; Nova, I., Tronconi, E., Eds. Springer: New York, 2014; pp 123–147.Corma, A. (1995). Inorganic Solid Acids and Their Use in Acid-Catalyzed Hydrocarbon Reactions. Chemical Reviews, 95(3), 559-614. doi:10.1021/cr00035a006Corma, A. (1997). From Microporous to Mesoporous Molecular Sieve Materials and Their Use in Catalysis. Chemical Reviews, 97(6), 2373-2420. doi:10.1021/cr960406nClerici, M. G. (2000). Topics in Catalysis, 13(4), 373-386. doi:10.1023/a:1009063106954Haw, J. F., Song, W., Marcus, D. M., & Nicholas, J. B. (2003). The Mechanism of Methanol to Hydrocarbon Catalysis. Accounts of Chemical Research, 36(5), 317-326. doi:10.1021/ar020006oCorma, A. (2003). State of the art and future challenges of zeolites as catalysts. Journal of Catalysis, 216(1-2), 298-312. doi:10.1016/s0021-9517(02)00132-xBhan, A., & Iglesia, E. (2008). A Link between Reactivity and Local Structure in Acid Catalysis on Zeolites. Accounts of Chemical Research, 41(4), 559-567. doi:10.1021/ar700181tWang, W., & Hunger, M. (2008). Reactivity of Surface Alkoxy Species on Acidic Zeolite Catalysts. Accounts of Chemical Research, 41(8), 895-904. doi:10.1021/ar700210fMartínez, C., & Corma, A. (2011). Inorganic molecular sieves: Preparation, modification and industrial application in catalytic processes. Coordination Chemistry Reviews, 255(13-14), 1558-1580. doi:10.1016/j.ccr.2011.03.014Vermeiren, W., & Gilson, J.-P. (2009). Impact of Zeolites on the Petroleum and Petrochemical Industry. Topics in Catalysis, 52(9), 1131-1161. doi:10.1007/s11244-009-9271-8Yilmaz, B., & Müller, U. (2009). Catalytic Applications of Zeolites in Chemical Industry. Topics in Catalysis, 52(6-7), 888-895. doi:10.1007/s11244-009-9226-0Rinaldi, R., & Schüth, F. (2009). Design of solid catalysts for the conversion of biomass. Energy & Environmental Science, 2(6), 610. doi:10.1039/b902668aOlsbye, U., Svelle, S., Lillerud, K. P., Wei, Z. H., Chen, Y. Y., Li, J. F., … Fan, W. B. (2015). The formation and degradation of active species during methanol conversion over protonated zeotype catalysts. Chemical Society Reviews, 44(20), 7155-7176. doi:10.1039/c5cs00304kAbate, S., Barbera, K., Centi, G., Lanzafame, P., & Perathoner, S. (2016). Disruptive catalysis by zeolites. Catalysis Science & Technology, 6(8), 2485-2501. doi:10.1039/c5cy02184gRabo, J. A., & Gajda, G. J. (1990). Acid Function in Zeolites: Recent Progress. NATO ASI Series, 273-297. doi:10.1007/978-1-4684-5787-2_17Sauer, J., Ugliengo, P., Garrone, E., & Saunders, V. R. (1994). Theoretical Study of van der Waals Complexes at Surface Sites in Comparison with the Experiment. Chemical Reviews, 94(7), 2095-2160. doi:10.1021/cr00031a014Van Santen, R. A., & Kramer, G. J. (1995). Reactivity Theory of Zeolitic Broensted Acidic Sites. Chemical Reviews, 95(3), 637-660. doi:10.1021/cr00035a008Gounder, R., & Iglesia, E. (2011). The Roles of Entropy and Enthalpy in Stabilizing Ion-Pairs at Transition States in Zeolite Acid Catalysis. Accounts of Chemical Research, 45(2), 229-238. doi:10.1021/ar200138nJones, A. J., & Iglesia, E. (2015). The Strength of Brønsted Acid Sites in Microporous Aluminosilicates. ACS Catalysis, 5(10), 5741-5755. doi:10.1021/acscatal.5b01133Van Speybroeck, V., Hemelsoet, K., Joos, L., Waroquier, M., Bell, R. G., & Catlow, C. R. A. (2015). Advances in theory and their application within the field of zeolite chemistry. Chemical Society Reviews, 44(20), 7044-7111. doi:10.1039/c5cs00029gBoronat, M., & Corma, A. (2014). Factors Controlling the Acidity of Zeolites. Catalysis Letters, 145(1), 162-172. doi:10.1007/s10562-014-1438-7Farneth, W. E., & Gorte, R. J. (1995). Methods for Characterizing Zeolite Acidity. Chemical Reviews, 95(3), 615-635. doi:10.1021/cr00035a007Lercher, J. A., Gründling, C., & Eder-Mirth, G. (1996). Infrared studies of the surface acidity of oxides and zeolites using adsorbed probe molecules. Catalysis Today, 27(3-4), 353-376. doi:10.1016/0920-5861(95)00248-0SATO, H. (1997). Acidity Control and Catalysis of Pentasil Zeolites. Catalysis Reviews, 39(4), 395-424. doi:10.1080/01614949708007101Garrone, E., & Otero Areán, C. (2005). Variable temperature infrared spectroscopy: A convenient tool for studying the thermodynamics of weak solid–gas interactions. Chemical Society Reviews, 34(10), 846. doi:10.1039/b407049fBusca, G. (2007). Acid Catalysts in Industrial Hydrocarbon Chemistry. Chemical Reviews, 107(11), 5366-5410. doi:10.1021/cr068042eVimont, A., Thibault-Starzyk, F., & Daturi, M. (2010). Analysing and understanding the active site by IR spectroscopy. Chemical Society Reviews, 39(12), 4928. doi:10.1039/b919543mDerouane, E. G., Védrine, J. C., Pinto, R. R., Borges, P. M., Costa, L., Lemos, M. A. N. D. A., … Ribeiro, F. R. (2013). The Acidity of Zeolites: Concepts, Measurements and Relation to Catalysis: A Review on Experimental and Theoretical Methods for the Study of Zeolite Acidity. Catalysis Reviews, 55(4), 454-515. doi:10.1080/01614940.2013.822266Bordiga, S., Lamberti, C., Bonino, F., Travert, A., & Thibault-Starzyk, F. (2015). Probing zeolites by vibrational spectroscopies. Chemical Society Reviews, 44(20), 7262-7341. doi:10.1039/c5cs00396bGorte, R. J., & White, D. (1997). Topics in Catalysis, 4(1/2), 57-69. doi:10.1023/a:1019167601251Zheng, A., Li, S., Liu, S.-B., & Deng, F. (2016). Acidic Properties and Structure–Activity Correlations of Solid Acid Catalysts Revealed by Solid-State NMR Spectroscopy. Accounts of Chemical Research, 49(4), 655-663. doi:10.1021/acs.accounts.6b00007Brand, H. V., Curtiss, L. A., & Iton, L. E. (1992). Computational studies of acid sites in ZSM 5: dependence on cluster size. The Journal of Physical Chemistry, 96(19), 7725-7732. doi:10.1021/j100198a044Brand, H. V., Curtiss, L. A., & Iton, L. E. (1993). Ab initio molecular orbital cluster studies of the zeolite ZSM-5. 1. Proton affinities. The Journal of Physical Chemistry, 97(49), 12773-12782. doi:10.1021/j100151a024Eichler, U., Brändle, M., & Sauer, J. (1997). Predicting Absolute and Site Specific Acidities for Zeolite Catalysts by a Combined Quantum Mechanics/Interatomic Potential Function Approach. The Journal of Physical Chemistry B, 101(48), 10035-10050. doi:10.1021/jp971779aBrändle, M., & Sauer, J. (1998). Acidity Differences between Inorganic Solids Induced by Their Framework Structure. A Combined Quantum Mechanics/Molecular Mechanics ab Initio Study on Zeolites. Journal of the American Chemical Society, 120(7), 1556-1570. doi:10.1021/ja9729037Jones, A. J., Carr, R. T., Zones, S. I., & Iglesia, E. (2014). Acid strength and solvation in catalysis by MFI zeolites and effects of the identity, concentration and location of framework heteroatoms. Journal of Catalysis, 312, 58-68. doi:10.1016/j.jcat.2014.01.007Grajciar, L., Areán, C. O., Pulido, A., & Nachtigall, P. (2010). Periodic DFT investigation of the effect of aluminium content on the properties of the acid zeolite H-FER. Physical Chemistry Chemical Physics, 12(7), 1497. doi:10.1039/b917969kSauer, J., & Sierka, M. (2000). Combining quantum mechanics and interatomic potential functions inab initio studies of extended systems. Journal of Computational Chemistry, 21(16), 1470-1493. doi:10.1002/1096-987x(200012)21:163.0.co;2-lLesthaeghe, D., Van Speybroeck, V., & Waroquier, M. (2009). Theoretical evaluation of zeolite confinement effects on the reactivity of bulky intermediates. Physical Chemistry Chemical Physics, 11(26), 5222. doi:10.1039/b902364jGounder, R., & Iglesia, E. (2013). The catalytic diversity of zeolites: confinement and solvation effects within voids of molecular dimensions. Chemical Communications, 49(34), 3491. doi:10.1039/c3cc40731dDEROUANE, E. (1988). Surface curvature effects in physisorption and catalysis by microporous solids and molecular sieves. Journal of Catalysis, 110(1), 58-73. doi:10.1016/0021-9517(88)90297-7Derouane, E. G. (1998). Zeolites as solid solvents1Paper presented at the International Symposium `Organic Chemistry and Catalysis’ on the occasion of the 65th birthday of Prof. H. van Bekkum, Delft, Netherlands, 2–3 October 1997.1. Journal of Molecular Catalysis A: Chemical, 134(1-3), 29-45. doi:10.1016/s1381-1169(98)00021-1Smit, B., & Maesen, T. L. M. (2008). Molecular Simulations of Zeolites: Adsorption, Diffusion, and Shape Selectivity. Chemical Reviews, 108(10), 4125-4184. doi:10.1021/cr8002642Klimeš, J., & Michaelides, A. (2012). Perspective: Advances and challenges in treating van der Waals dispersion forces in density functional theory. The Journal of Chemical Physics, 137(12), 120901. doi:10.1063/1.4754130Göltl, F., Grüneis, A., Bučko, T., & Hafner, J. (2012). Van der Waals interactions between hydrocarbon molecules and zeolites: Periodic calculations at different levels of theory, from density functional theory to the random phase approximation and Møller-Plesset perturbation theory. The Journal of Chemical Physics, 137(11), 114111. doi:10.1063/1.4750979Gomes, J., Zimmerman, P. M., Head-Gordon, M., & Bell, A. T. (2012). Accurate Prediction of Hydrocarbon Interactions with Zeolites Utilizing Improved Exchange-Correlation Functionals and QM/MM Methods: Benchmark Calculations of Adsorption Enthalpies and Application to Ethene Methylation by Methanol. The Journal of Physical Chemistry C, 116(29), 15406-15414. doi:10.1021/jp303321sGrimme, S. (2004). Accurate description of van der Waals complexes by density functional theory including empirical corrections. Journal of Computational Chemistry, 25(12), 1463-1473. doi:10.1002/jcc.20078Grimme, S. (2006). Semiempirical GGA-type density functional constructed with a long-range dispersion correction. Journal of Computational Chemistry, 27(15), 1787-1799. doi:10.1002/jcc.20495De Moor, B. A., Reyniers, M.-F., Gobin, O. C., Lercher, J. A., & Marin, G. B. (2010). Adsorption of C2−C8 n-Alkanes in Zeolites. The Journal of Physical Chemistry C, 115(4), 1204-1219. doi:10.1021/jp106536mWakabayashi, F., Kondo, J., Wada, A., Domen, K., & Hirose, C. (1993). FT-IR studies of the interaction between zeolitic hydroxyl groups and small molecules. 1. Adsorption of nitrogen on H-mordenite at low temperature. The Journal of Physical Chemistry, 97(41), 10761-10768. doi:10.1021/j100143a040Bordiga, S., Regli, L., Cocina, D., Lamberti, C., Bjørgen, M., & Lillerud, K. P. (2005). Assessing the Acidity of High Silica Chabazite H−SSZ-13 by FTIR Using CO as Molecular Probe:  Comparison with H−SAPO-34. The Journal of Physical Chemistry B, 109(7), 2779-2784. doi:10.1021/jp045498wArean, C. O., Delgado, M. R., Nachtigall, P., Thang, H. V., Rubeš, M., Bulánek, R., & Chlubná-Eliášová, P. (2014). 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Direct synthesis of a titanosilicate molecular sieve containing large and medium pores in its structure

[EN] The direct synthesis of the titanosilicate form of ITQ-39 is reported. This is the first description of the direct preparation of a titanosilicate molecular sieve containing large and medium pores in the same structure. The characterization clearly indicates the presence of Ti atoms in tetrahedral coordination in the framework of ITQ-39 zeolite. This material is very active in the oxidation of lineal and cyclic olefins with H2O2, showing selectivities between TS-1 and Ti-Beta. (C) 2012 Elsevier Inc. All rights reserved.Financial support by the Spanish MEC (Consolider Ingenio 2010-Multicat), Generalitat Valenciana by the PROMETEO program and UPV through PAID-06-11 (n.1952) is acknowledged. Manuel Moliner acknowledges to "Subprograma Ramon y Cajal" for the contract RYC-2011-08972. Jose Gaona is also acknowledged for technical help.Moliner Marin, M.; Corma Canós, A. (2012). Direct synthesis of a titanosilicate molecular sieve containing large and medium pores in its structure. Microporous and Mesoporous Materials. 164:44-48. https://doi.org/10.1016/j.micromeso.2012.06.035S444816

Procedimiento de obtención directa de oxima de ciclohexanona a partir de nitroderivados

La presente patente de invención describe un procedimiento para producir oxima de ciclohexanona directamente a partir de nitroderivados, como por ejemplo nitrobenceno, que se puede llevar a cabo en un mismo “batch” mediante hidrogenación, usando un catalizador con al menos un metal soportado. La invención describe las condiciones de reacción necesarias para conseguir la secuencia reactiva que conduce a oxima de ciclohexanona desde el material de partida.Peer reviewedConsejo Superior de Investigaciones Científicas, Universitat Politecnica de ValenciaR Informe sobre el estado de la técnica publicado separadament