FHI Lecture Series Modern Methods in Heterogeneous Catalysis: Transient Infrared Spectroscopy

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1 FHI Lecture Series Modern Methods in Heterogeneous Catalysis: Transient Infrared Spectroscopy Prof. Guido Mul University of Twente Thanks to : Dr. Gerben Hamminga (now BASF) Dr. Dirk Renckens (now ASML) Prof. Michiel Kreutzer (Delft University of Technology) Prof. Heinz Frei (Berkeley)

2 Contents General Introduction ATR-IR to Study Liquid Phase Catalysis Slow transients (min) Commercially Available Equipment Reaction monitoring (Comparing with Raman) Fast transients (s) Rapid Scan Spectroscopy Sorption studied in Microreactors Faster transients (ms) Rapid Scan Spectroscopy Light induced processes 2

3 Infrared spectroscopy Vibrations that change dipole moment of a molecule active vibration for infrared absorption inactive vibration for infrared absorption I d dq 2 Q: vibrational coordinates 3

4 Infrared spectroscopy Applications: In-situ and operando Catalyst characterisation direct measurement of catalyst IR spectrum measurement of interaction with probe molecules: NH 3, pyridine: acidity C, N: nature of active sites (e.g. Fe in zeolites) Mechanistic studies adsorbed species, reaction intermediates deactivation by strongly adsorbing species Analysis of reactants and products

5 IR-spectroscopy Transmission solids, liquids Diffuse Reflectance Gas-solid interactions Attenuated Total Reflection solids, liquids Specular reflectance Reflection absorbance flat surfaces 5

6 Transmission Pellets or gas/liquid chambers Quantification Lambert Beer (Absorbance Concentration) A = b c = molar extinction coefficient, b = pathlength, c=concentration

7 powders Infrared FT Spectroscopy (DRIFTS) Quantification Kubelka Munk vs. Absorption Reflectance Strong absorption Weak absorption 7

8 ATR-IR principle d p Reflected radiation n 2 n 1 ZnSe Sample Incident radiation Layer thickness ~ 1-2 m 8

9 Penetration Depth dependent on d p n n21 2 n (sin ) n n d p ( m) For n 1 = 1.5, = 45 ZnSe (n 2 = 4) Ge (n 2 = 2.4) n = refractive index = angle of incidence Wavenumber (cm -1 ) ANALYTICAL CHEMISTRY

10 Case 1: Minute scale transients 10

11 Transient - Sampling catalyst : volume ratio changes in time C 1 W exp 1 t C0 2 V0 V0 Error in k = t 2V 0 kt Alternatives? 11

12 Experimental Set-Up Conditions: 180 o C, 50 bar H 2 Reaction volume: 0.2 l Stirring speed 1500 min -1 Reactor medium IR in ATR crystal IR out 12

13 Selective hydrogenation +2H 2-2H 2 γ-butyrolactone (GBL) 1,4-Butanediol (BD) 13

14 Cu/Zn catalysed hydrogenation 1060 cm cm cm cm -1 Results 14

15 Kinetics 15

16 Catalyst bserved? 16

17 Mechanism 17

18 Catalyst observations? Silica--R Silica in n-decane (solvent) with hexanoic acid and octanol 18

19 Combined Raman-Infrared G.M. Hamminga et al. Applied Spectrosc. 61 (2007)

20 State of the art Not much literature available Variables Stirring Pressure Catalyst Particles Effect Process variables on Intensity 20

21 945 cm -1 band intensity [-] Stirring Speed Dioxolane 1,3-Dioxolane (B) Stirrer speed [RPM] G.M. Hamminga et al. Appl. Spectrosc. (2007) 21

22 Bubble formation. 500 rpm 22

23 Bubble formation. 750 rpm 23

24 Bubble formation rpm 1500 rpm 24

25 Bubble formation.scattering Collection Fiber (200 μm) Long-pass Mirror Probe housing Safire window Excitation Fiber (100 μm) Band-pass Dichroic Extension sleeve Laser path Scattering path Common path 1500 rpm 25

26 945 cm -1 band intensity [-] (B) Pressure (at 1500 rpm) Longer Gas Hold-up Smaller bubble size Shrinking bubble size Pressure [MPa] G.M. Hamminga et al. Appl. Spectrosc. (2007) 26

27 Catalyst Particles Collection Fiber (200 μm) Long-pass Mirror Probe housing Safire window Excitation Fiber (100 μm) Band-pass Dichroic Extension sleeve Laser path Scattering path Common path Scattering + Absorption 27

28 945 cm -1 band intensity [-] Catalyst Particles (B) Catalyst concentration [g/l] G.M. Hamminga et al. Appl. Spectrosc. (2007) 28

29 Conclusions ATR for monitoring Transients in minute time resolution easily obtained High accuracy in kinetic data Intermediates can be observed Catalyst reaction medium interactions difficult to observe, but leaching observed Raman less suitable due to probing principle (focal point inside reaction volume) 29

30 ATR interesting for catalysis Probe depth ~1-2 µm, so local conditions are measured d p Simultaneous measurement of bulk and adsorbed species on catalyst coated on crystal 30

31 Transient analysis of catalyst behavior Theory Berger et al. App. Cat. A 342, p (2008) January 31,

32 Experimental setup Flow cell (4 ml) 1000 x lower volume Microfluidic device (4 μl) IR illumination area: ~10 times less Catalyst: ~10 times less Consequence: signal-to-noise ratio 1 mm 5 cm 32 January 31,

33 Considerations. Device fabrication Solvent resistant soft lithography Liquid phase adsorption/desorption Show that dynamics on surface can be probed

34 ATR Crystals are expensive Soft lithography for ATR Bonding of glass, silica, etc requires heat that changes the catalyst Clamp PDMS (a soft elastomer) on the crystal, but PDMS swell and is not solvent-resistant

35 SIFEL: solvent resistant, but issues Swelling: Solvent PDMS SIFEL Diisopropylamine 113% 7% Triethylamine 58% 7% Chloroform 39% 7% Hexane 35% 3% Toluene 31% 3% Si CF 2 CF CF 3 n Si Maltezos - Lab Chip (2007)

36 ptimized recipe for SIFEL Cover layer of PDMS provides strength, but is never in contact with fluids in the channel SIFEL solution can be used for adhesive purposes As fast and simple as PDMS

37 bubble device Protect the incoming step change from dispersion with a single bubble, introduced in a 6-way valve vercome the Taylor dispersion limit

38 verview of the flowcell Coating from suspension, cell clamped Slits control direct incoming light into channel

39 Absorption [au] Masked IR beam to scan channel only Position [au]

40 Miniaturization Flow cell Microfluidic device Switching ~10 times faster than best known performance 1 1. Urakawa et al. J Phys Chem B 107, p (2008) Results 40 January 31,

41 Adsorbing compounds Device is capable of switching in ~1 s Interesting compounds: Poisons, inhibitors Interesting catalysts: Photocatalysts (low T, so strong adsorption) Here: amines on Ti 2

42 Catalyst layer 42

43 Adsorption [a.u.] Spectra in Flow cell Heptylamine C-H stretch Heptylamine-Ti 2 NH 3 + group stretch Heptyl-amine Ti 2 (8 min contact) Heptyl-amine Solvent Toluene Wavenumber [cm -1 ]

44 Transient Rapid scan spectroscopy C-H amine 2-site Langmuir model 44

45 Transients C-H amine N-H amine 45

46 Concluding 46

47 Third Example Spectroscopy on the ms time scale Photon induced processes January 31,

48 Rapid Scan (ms) Rapid Scan ATR-FTIR Spectroscopy January 31,

49 Rapid Scan ATR-FTIR Setup Experimental January 31,

50 1 forward/backward scan (1.22 ms) Method V time Experiment duration multiple of scan duration Timing 50

51 Experimental 480 ms Pump Probe 1 2 Average 12 s See papers Frei et al January 31,

52 Hydration of Si 2 supported Structures Weckhuysen et al. J.Phys. Chem Photo-active These intermediate stages? Not Photo-active Absorption Edge (Wavelength) 400 nm January 31, nm

53 Absorbance Spectra 0, Diamond a, layer 0, V H H H Si Si 0, b, evacuated c, H H January 31, 2014 Wavenumbers (cm -1 ) ~ Figure 1

54 Absorbance Continuous Light on 0,016 0,014 0,012 0,010 H V H H Si Si 120 s 0,008 0,006 ads 90 s 0, s 0,002 0, s -0,002-0,004-0,006 - H H -0, Wavenumbers (cm-1) Figure 2 January 31, Intermediates?

55 Absorbance Transients (ms) H H ms H V Si Si 995 H V Si Si ms H H H V 1015 Si Si Wavenumbers (cm -1 ) January 31,

56 Absorbance H H V H Si Si s 6.5 s H H H V Si Si 995 H V Si Si 9.3 s Wavenumbers (cm - 1 ) Adsorbed H 2 January 31,

57 Cyclohexene oxidation over vanadia January 31,

58 Conclusions Vanadia Photocatalysis Partially hydrated Vanadia catalysts photoactive with visible light Selective oxidation of cyclohexene yields cyclohexenone Time resolved ATR studies have revealed changes in molecular state of the vanadyl center Hydrated site is final (deactivated) state January 31,

59 General Conclusions ATR systems are very suitable for reaction monitoring Applying coating on ATR crystals, and using microchannels is very valuable for analysis of liquid phase sorption Time resolved studies (ms) possible to determine short lived intermediates (fast transient in stimulus necessary) January 31,

60 Thank you! Questions? 60

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