Two dimensional zeolites in catalysis
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1 Topsoe Catalysis Forum, August 27 28, 2015 Two dimensional zeolites in catalysis Jiří Čejka
2 OUTLINE Two dimensional zeolites Synthesis routes Properties Catalytic applications Advantages Disadvantages Synthesis of unfeasible zeolites from lamellas ADOR mechanism
3 Where we are ZEOLITE CONUNDRUM Energy vs. Density 233 zeolites IZA Energies above quartz, up to +30 kj/mol Si Millions of possible structure ~ 15 2D zeolites Energy (kj/mol Si) Traditional Synthesis Vector Density (Si/1000 Å 3 ) Deem MW, J Phys Chem C 2013
4 Where we go 2D ZEOLITES Outline Synthesis Design Top down 15 2D zeolites prepared by different approaches Roth WJ, Nachtigall P, Morris RE, Čejka J, Chem Rev 2014
5 INTEGRATION OF 2D AND 3D ZEOLITES 3-D zeolites FTC Various Layer Architecture and Bonding 2-D Traditional 3-D Framework ABW CAS MWW FAU FER MFI NSI SOD As-synth ed Calcined Conventional 3-D zeolite MCM-49 Direct, c~2.5 MCM-22,-49 c~2.5 Layered precursor Ordered Dis-ordered Unmodified Stabilized Unmodified Stabilized MCM-22P Direct, c>2.6 MCM-22 c~2.5 IEZ-MWW Treat, c>2.6 IEZ-MWW EMM-13,c>2.6 EMM-10P Direct, c>2.6 EMM-10 c~2.5 EMM-12P Treat, c>2.6 EMM-10 c>2.6 Acid-treated MCM-22P/ac +acid, c~2.5 c~2.5 Delaminated MCM-56 Direct, c~2.5 MCM-56 ITQ-2(T) c~2.5 Swollen/ pillared MCM-22P-sw Treat, c >4.5 MCM-36 c >4.5 1-D ZON WJ Roth, Micropor Mesopor Mater (2011)
6 2D ZEOLITES MWW FAMILY HIT and MISS SYNTHESIS Roth WJ, ExxonMobil
7 TWO DIMENSIONAL ZEOLITES OPTIMIZED TEMPLATE STRUCTURE R. Ryoo et al., Nature (2009); ZMPC (2012)
8 3D to 2D HYDROLYSIS Pailaud JL, Science (2004) Corma A, Chem Commun (2004) Conditions ph neutral to acidic water or 0.1 M HCl room temperature 100 C (200) interlayer reflection Intensity (a.u.) IPC-1P UTL Theta A A = 9.0 Å 1 µm
9 3D to 2D SWELLING and PILLARING Swelling 25% C 16 TMA Cl + 40% TPA OH (10:1 w/w) 100 C 1 µm Intensity (a.u.) IPC-1SW IPC-1 calc Pillaring TEOS 100 C SEM image of IPC 1SW IPC-1P Theta IPC 1SW Intensity (a.u.) IPC-1PI Theta IPC-1P IPC 1PI
10 3D to 2D TEXTURAL PROPERTIES Sample Element mol. % Si Ge B Si/Ge Si/B BET (m 2 /g) V micro (cm 3 /g) V meso (cm 3 /g) B-UTL IPC IPC-1SW IPC IPC-1PI IPC 1PI, pillared B UTL IPC 2, stabilized IPC 1SW, swollen IPC 1, hydrolysed a (cm 3 /g) p/p 0
11 Catalysis on 2D zeolites
12 TWO DIMENSIONAL ZEOLITES Synthesis of 2 methyl naphthyl 4 methyl 1,3 dioxolane orange blossom fragrance delaminated ITQ 2 O HO O O + OH H + + H 2 O Yield ratio Beta : MCM 22 : ITQ 2 = 5 : 20 : 63 Activity on External Surface Potential for functionalization Climent A, Corma A, Appl Catal (2004)
13 2D ZEOLITES IMPROVED CATALYTIC PROPERTIES MWW Family Pillared MCM 36 as solid iso butane/olefin (C4) alkylation Delaminated MCM 56 liquid phase short chain aromatic alkylation Delaminated ITQ 2 enhanced processing of larger molecules UZM 8 disordered commecialized zeolite (Zones, MMM, 2011) MFI Single and Multilayer Nanosheets MTG delayed aging extended time between regeneration Enhanced conversions of larger molecules FER Delaminated ITQ 6 Synthesis of diamine diphenyl methane (DADPM) excellent activity, longer catalyst life than conventional zeolites Aminopropyl modified high adsorption efficiency in CO 2 NSI Delaminated ITQ 18 Chance of replacing HCl in synthesis of DADPM
14 N HEXADECANE HYDROCARCKING Isomerization (ITQ 6)x, x = swelling time n Hexadecane conversion vs. T FER Cracking A Corma, Catal Today (2009)
15 MCM 36 C4 ALKYLATION Catalyst MCM-22 MCM-36 Faujasite, EMT HF H 2 SO 4 SiO 2 /Al 2 O 3 <20 > Temp., [ºC] Yield, [wt/wt] C 8, [wt %] Me 3 C 5 /Me 2 C 6 low or poor RON/MON 91, ,97 94,96 Stability, [g alkyl./g cat.] > * E.J.A. Schweitzer and P.F. van dev Oosterkamp, Micro. Mesop. Mat, 20, 393 (1998) based on patent literature
16 METHANOL to OLEFINS Conventional MFI UnilamellarMFI R. Ryoo et al., Nature (2009)
17 MCM 56 LIQUID PHASE BENZENE ALKYLATION WITH ETHYLENE Process for preparing short chain alkyl aromatics US Patent 5,453,554, 1995 Relative activity for Ethylbenzene MCM 22 : MCM 49 : MCM 56 : beta 1:1.2:1.6:2.2 EB Selectivity 5 % higher than beta MCM 56 is obtained by direct hydrothermal synthesis Reaction on the surface WJ Roth, US Patent 5,453,554 (1995)
18 TOLUENE ALKYLATION WITH ISOPROPYL ALCOHOL 1 st step 2 nd step OH + -H 2 O H 3 C + CH 3 CH 3 CH 3 CH 3 Toluene conversion Concentration of sites Channel size Σ cymene p cymene selectivity Size of channels Product selectivity iso /n propyltoluene ratio n propyltoluene selectivity Size of intersections CH 3 Čejka J, Wichterlová B, Catal Rev (2002)
19 TWO DIMENSIONAL ZEOLITES TOLUENE ALKYLATION WITH PROPYLENE Toluene conversion (%) Selectivity to cymenes (%) Iso/n-propyltoluenes ratio T-O-S (min) T-O-S (min) Hexagonally mesostructure 10 R zeolite MFI 1.4 nm MFI nanosheet, 2 pentasil layers Disordered mesostructure 10 R zeolite with 2.1nm thickness Disordered mesostructure 10 R zeolite with 2.7nm thickness P-cymene in cymenes (%) R. Ryoo, J. Čejka, Catal Sci Technol (2013)
20 2D MFI BECKMANN REARRANGEMENT EPOXIDATIONS Aluminosilicate MFI nanosheets Activity Selectivity Long term stability R. Ryoo et al., ACS Catalysis (2011)
21 HYDROXYLATION of PHENOL SEM TEM MTS 2 (MEL type titanosilicate nanosheets) Sample d cryst, μm Conv, % Y ortho, % Y para, % MTS TS TS Wang et al., J Mater Chem A (2015)
22 2D ZEOLITES vs. 3D ZEOLITES vs. MESOPOROUS MOLECULAR SIEVES 2D = 3D = ZSM 5 Mesoporous = Al MCM 41 Kore et al., Chem Eur J (2014)
23 GLUCOSE to FRUCTOSE TRANSFORMATION Sn MFI Sn Self Pillared MFI Glucose (GLU) into fructose (FRU) GLU is first treated in ethanol to a mixture of FRU and ethyl fructoside (FRU ketalization product with ethanol) Hydrolysis of the fructoside yields FRU ME Davis et al., Angew Chem (2015)
24 Synthesis of unfeasible zeolites from lamellas
25 ADOR = Assembly Disassembly Organization Reassembly UTL PCR Assembly UTL with Ge rich D4R A Disassembly Hydrolysis of D4R IPC 1P Roth WJ et al, JACS 2011 D Organization Regular arrangement of neighboring layers O Reassembly Layer condensation PCR Roth WJ et al, Nature Chem 2013 R
26 ADOR Extensions Regular shift of adjacent layers Regular alternation of inter layer pillars IEZ strategy (and more general approach) ADOR extensions No shift of adjacent layers Different lamellar precursors: zeolites with D4R zeolites with D3R other zeolites (?) Encouragement for experimentalists large number of novel zeolites can be prepared from layered zeolite precursors XRD powder pattern of novel materials are provided (useful hints) Trachta, Nachtigall, et al 2014
27 3D to 2D ZEOLITES HYDROLYSIS STUDY water, 0.1M 12M HCl, 95 C calcination IPC-4 (10-8R) fast hydrolysis removing of Ge calcination UTL IPC-6 ( R) calcination IPC-2 (12-10R)
28 STAGED STRUCTURE of IPC nm Optimum acidity and Si/Ge ratio IPC-4 IPC-2 Regular arrangement of IPC 4 and IPC 2 layers Tuneable porosity Unlimited number of combinations from 0 (IPC 4) to 100 % (IPC 2) Wheatley P, Chlubná-Eliášová P, Morris RE, Angew Chem 2014
29 ADOR LANDSCAPE Continuous Porosity IPC 6 BET area (m 2 g -1 ) Micropore Volume (cm 3 g -1 ) IPC 7 IPC 4 0 IPC 4 IPC 6 IPC 2 IPC Molarity ([H ]) 0.00 IPC 2 BET area Micropore volume Wheatley P, Chlubná P, Morris RE, Angew Chem 2014
30 REGULAR SHIFT OF ADJACENT LAYERS Shift of the layers IPC 9 (i) (ii) (iii) (iv) UTL IPC 1P IPC 9P Shift of the layers + Si addition IPC 10 Effect of organics shape and charge choline concentration Mazur M, et al. Nature Chem, accepted
31 Is ADOR APPLICABLE with a SHIFT of the LAYERS? IPC 4 IPC 9 IPC-9 Intensity [a.u.] Critical role of intercalation
32 Is ADOR APPLICABLE WITH a SHIFT of the LAYERS with INTERCALATION? IPC 2 IPC 10 IPC-10 Intensity [a.u.] Critical role of intercalation and silane addition
33 Where we go NEW ZEOLITES Energy vs. Density Energies above quartz, up to +30 kj/mol Si Traditional Synthesis Vector Energy (kj/mol Si) IPC 10 UTL IPC 9 IPC 2 IPC 6 IPC 4 Synthesis of zeolites via ADOR Energetically less favored Odd rings Low chance for solvothermal synthesis Density (Si/1000 Å 3 ) Solution Gel Zeolite Based on Deem MW, J Phys Chem C 2013
34 SUMMARY Two dimensional zeolites Bottom up approach Accidental synthesis Tailored structure directing agents Top down approach Hydrolysis of Ge containing units ADOR mechanism Eliášová P, Nachtigall P, Čejka J, et al, Chem Soc Rev 2015 Transformation to 2D zeolites (extended building units) Intercalation chemistry Synthesis of new zeolites even with odd rings (other materials) Controlling the porosity of zeolites Highly energetic zeolites (not accessible by solvothermal synthesis) Catalysis Activity active sites Stability Selectivity structure of the surface Low rate of deactivation
35 ACKNOWLEDGEMENT J. Heyrovsky Institute, Prague P. Eliášová N. Žilková W.J. Roth A. Zukal M. Mazur M. Shamzhy M. Opanasenko J. Přech Charles University, Prague P. Nachtigall L. Grajciar M. Položij Institute of Organic Chemistry, Prague O. Bludský M. Trachta University of St. Andrews R.E. Morris P. Wheatley W. Zhou ETH Zurich A.B. Pillar L. McCusker Centre of Excellence (Czech Science Foundation) Micromeritics Instrument Award
36
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