Efficient epoxidation over dinuclear sites in titanium silicalite-1.
Journal
Nature
ISSN: 1476-4687
Titre abrégé: Nature
Pays: England
ID NLM: 0410462
Informations de publication
Date de publication:
10 2020
10 2020
Historique:
received:
22
07
2019
accepted:
26
08
2020
entrez:
29
10
2020
pubmed:
30
10
2020
medline:
30
10
2020
Statut:
ppublish
Résumé
Titanium silicalite-1 (TS-1) is a zeolitic material with MFI framework structure, in which 1 to 2 per cent of the silicon atoms are substituted for titanium atoms. It is widely used in industry owing to its ability to catalytically epoxidize olefins with hydrogen peroxide (H
Identifiants
pubmed: 33116285
doi: 10.1038/s41586-020-2826-3
pii: 10.1038/s41586-020-2826-3
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
708-713Commentaires et corrections
Type : CommentIn
Références
Notari, B. in Studies in Surface Science and Catalysis Vol. 60 (eds Inui, T., Namba, S. & Tatsumi T.) 343–352 (Elsevier, 1991).
Teles, J. H., Hermans, I., Franz, G. & Sheldon, R. A. Oxidation in Ullmann’s Encyclopedia of Industrial Chemistry 1–103 (Wiley-VCH, 2015).
Lin, M., Xia, C., Zhu, B., Li, H. & Shu, X. Green and efficient epoxidation of propylene with hydrogen peroxide (HPPO process) catalyzed by hollow TS-1 zeolite: a 1.0 kt/a pilot-scale study. Chem. Eng. J. 295, 370–375 (2016).
Sankar, G. et al. The three-dimensional structure of the titanium-centered active site during steady-state catalytic epoxidation of alkenes. J. Phys. Chem. B 105, 9028–9030 (2001).
Thomas, J. M., Catlow, C. R. A. & Sankar, G. Determining the structure of active sites, transition states and intermediates in heterogeneously catalysed reactions. Chem. Commun. 24, 2921–2925 (2002).
Gamba, A., Tabacchi, G. & Fois, E. TS-1 from first principles. J. Phys. Chem. A 113, 15006–15015 (2009).
pubmed: 19785451
Solans-Monfort, X., Copéret, C. & Eisenstein, O. Theoretical Modeling: An Access to Molecular Understanding of Single-Site Silica Based Heterogeneous Catalysts (American Scientific Publishers, 2009).
Bordiga, S., Lamberti, C., Bonino, F., Travert, A. & Thibault-Starzyk, F. Probing zeolites by vibrational spectroscopies. Chem. Soc. Rev. 44, 7262–7341 (2015).
pubmed: 26435467
Signorile, M. et al. Effect of Ti speciation on catalytic performance of TS-1 in the hydrogen peroxide to propylene oxide reaction. J. Phys. Chem. C 122, 9021–9034 (2018).
Signorile, M. et al. Computational assessment of relative sites stabilities and site-specific adsorptive properties of titanium silicalite-1. J. Phys. Chem. C 122, 1612–1621 (2018).
Bordiga, S. et al. The structure of the peroxo species in the TS-1 catalyst as investigated by resonant Raman spectroscopy. Angew. Chem. Int. Ed. 41, 4734–4737 (2002).
Lin, W. & Frei, H. Photochemical and FT-IR probing of the active site of hydrogen peroxide in Ti silicalite sieve. J. Am. Chem. Soc. 124, 9292–9298 (2002).
pubmed: 12149037
Matsumoto, K., Sawada, Y., Saito, B., Sakai, K. & Katsuki, T. Construction of pseudo-heterochiral and homochiral di-μ-oxotitanium(Schiff base) dimers and enantioselective epoxidation using aqueous hydrogen peroxide. Angew. Chem. Int. Ed. 44, 4935–4939 (2005).
Sawada, Y., Matsumoto, K. & Katsuki, T. Titanium-catalyzed asymmetric epoxidation of non-activated olefins with hydrogen peroxide. Angew. Chem. Int. Ed. 46, 4559–4561 (2007).
Berkessel, A., Günther, T., Wang, Q. & Neudörfl, J.-M. Titanium salalen catalysts based on cis-1,2-diaminocyclohexane: enantioselective epoxidation of terminal non-conjugated olefins with H
Lansing, M., Engler, H., Leuther, T. M., Neudörfl, J.-M. & Berkessel, A. Titanium cis-1,2-diaminocyclohexane salalen catalysts of outstanding activity and enantioselectivity for the asymmetric epoxidation of nonconjugated terminal olefins with hydrogen peroxide. ChemCatChem 8, 3706–3709 (2016).
Lane, B. S. & Burgess, K. Metal-catalyzed epoxidations of alkenes with hydrogen peroxide. Chem. Rev. 103, 2457–2474 (2003).
pubmed: 12848577
Kholdeeva, O. A. Hydrogen peroxide activation over Ti
Takahashi, E. et al. Synthesis and oxidation catalysis of a Ti-substituted phosphotungstate, and identification of the active oxygen species. Catal. Sci. Technol. 5, 4778–4789 (2015).
Ehinger, C., Gordon, C. P. & Copéret, C. Oxygen transfer in electrophilic epoxidation probed by
pubmed: 30842846
Müller, U., Rudolf, P., Krug, G. & Senk, R. Process for the preparation of a titanium zeolite catalyst. WO patent WO2011064191 (2011).
Parvulescu, A.-N. et al. Molding for a hydrophobic zeolitic material and process for its production. WO patent WO2015059171A1 (2015).
Yamamoto, K. et al. Activation of O
Caughlan, C. N., Smith, H. S., Katz, W., Hodgson, W. & Crowe, R. W. Organic compounds of titanium. II. Association of organic titanates in benzene solution. J. Am. Chem. Soc. 73, 5652–5654 (1951).
Lamberti, C. et al. Ti location in the MFI framework of Ti−silicalite-1: a neutron powder diffraction study. J. Am. Chem. Soc. 123, 2204–2212 (2001).
pubmed: 11456866
Langhendries, G., De Vos, D. E., Baron, G. V. & Jacobs, P. A. Quantitative sorption experiments on Ti-zeolites and relation with α-olefin oxidation by H
Shin, S. B. & Chadwick, D. Kinetics of heterogeneous catalytic epoxidation of propene with hydrogen peroxide over titanium silicalite (TS-1). Ind. Eng. Chem. Res. 49, 8125–8134 (2010).
Wells, D. H., Delgass, W. N. & Thomson, K. T. Evidence of defect-promoted reactivity for epoxidation of propylene in titanosilicate (TS-1) catalysts: a DFT study. J. Am. Chem. Soc. 126, 2956–2962 (2004).
pubmed: 14995213
Prileschajew, N. Oxydation ungesättigter Verbindungen mittels organischer Superoxyde. Ber. Dtsch. Chem. Ges. 42, 4811–4815 (1909).
Snyder, B. E. R., Bols, M. L., Schoonheydt, R. A., Sels, B. F. & Solomon, E. I. Iron and copper active sites in zeolites and their correlation to metalloenzymes. Chem. Rev. 118, 2718–2768 (2018).
pubmed: 29256242
O’Dell, L. A. & Schurko, R. W. QCPMG using adiabatic pulses for faster acquisition of ultra-wideline NMR spectra. Chem. Phys. Lett. 464, 97–102 (2008).
Perras, F. A., Widdifield, C. M. & Bryce, D. V. QUEST quadrupolar exact software: a fast graphical program for the exact simulation of NMR and NQR spectra for quadrupolar nuclei. Solid State Nucl. Magn. Reson. 45-46, 36–44 (2012).
pubmed: 22763585
Kresse, G. & Hafner, J. Ab initio molecular dynamics for liquid metals. Phys. Rev. B 47, 558–561 (1993).
Kresse, G. & Hafner, J. Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium. Phys. Rev. B 49, 14251–14269 (1994).
Kresse, G. & Furthmüller, J. Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set. Comput. Mater. Sci. 6, 15–50 (1996).
Blöchl, P. E. Projector augmented-wave method. Phys. Rev. B 50, 17953–17979 (1994).
Hammer, B., Hansen, L. B. & Nørskov, J. K. Improved adsorption energetics within density-functional theory using revised Perdew-Burke-Ernzerhof functionals. Phys. Rev. B 59, 7413–7421 (1999).
Grimme, S., Antony, J., Ehrlich, S. & Krieg, S. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J. Chem. Phys. 132, 154104 (2010).
pubmed: 20423165
Pereira, M. M. et al. Biomass-mediated ZSM-5 zeolite synthesis: when self-assembly allows to cross the Si/Al lower limit. Chem. Sci. 9, 6532–6539 (2018).
pubmed: 30310584
pmcid: 6115686
Gutierrez-Acebo, E., Rey, J., Bouchy, C., Schuurman, Y. & Chizallet, C. Location of the active sites for ethylcyclohexane hydroisomerization by ring contraction and expansion in the EUO zeolitic framework. ACS Catal. 9, 1692–1704 (2019).
Goncalves, T. J., Plessow, P. N. & Studt, F. On the accuracy of density functional theory in zeolite catalysis. ChemCatChem 11, 4368–4376 (2019).
Henkelman, G. & Jónsson, H. A dimer method for finding saddle points on high dimensional potential surfaces using only first derivatives. J. Chem. Phys. 111, 7010–7022 (1999).
te Velde, G. et al. Chemistry with ADF. J. Comput. Chem. 22, 931–967 (2001).
Adamo, C. & Barone, V. Toward reliable density functional methods without adjustable parameters: the PBE0 model. J. Chem. Phys. 110, 6158–6170 (1999).
van Lenthe, E., Baerends, E. J. & Snijders, J. G. Relativistic regular two-component Hamiltonians. J. Chem. Phys. 99, 4597–4610 (1993).
van Lenthe, E., Baerends, E. J. & Snijders, J. G. Relativistic total energy using regular approximations. J. Chem. Phys. 101, 9783–9792 (1994).
van Lenthe, E., Baerends, E. J. & Snijders, J. G. Geometry optimizations in the zero order regular approximation for relativistic effects. J. Chem. Phys. 110, 8943–8953 (1999).
van Lenthe, E., Baerends, E. J. & Snijders, J. G. The zero-order regular approximation for relativistic effects: the effect of spin-orbit coupling in closed shell molecules. J. Chem. Phys. 105, 6505–6516 (1996).
van Lenthe, E., van Leeuwen, R., Baerends, E. J. & Snijders, J. G. Relativistic regular two-component Hamiltonians. Int. J. Quantum Chem. 57, 281–293 (1996).
Frisch, M. J. et al. Gaussian 09, revision D.01 (Gaussian, 2009).
Dunning, T. H. & Hay, P. J. in Methods of Electronic Structure Theory (ed. Schaefer, H. F.) 1–18 (Springer, 1977).
Weigend, F. & Ahlrichs, R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys. Chem. Chem. Phys. 7, 3297–3305 (2005).
pubmed: 16240044