Selective Hydrogenation of Cinnamaldehyde over Co-based. Intermetallic Compounds Derived from Layered Double Hydroxides
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1 Supporting Informtion Selective Hydrogention of Cinnmldehyde over Co-bsed Intermetllic Compounds Derived from Lyered Double Hydroxides Yusen Yng, 1 Deming Ro, 1,2 Yudi Chen, 3 Siyun Dong, 1 Bin Wng, 4 Xin Zhng,* 1 Min Wei* 1 1 Stte Key Lbortory of Chemicl Resource Engineering, Beijing Advnced Innovtion Center for Soft Mtter Science nd Engineering, Beijing University of Chemicl Technology, Beijing , P. R. Chin 2 Institute of Science nd technology strtegy, Jingxi cdemy of science, Nnchng , P. R. Chin 3 Beijing Center for Physicl & Chemicl Anlysis, Beijing , P. R. Chin 4 Beijing Reserch Institute of Chemicl Industry, Sinopec Group, Beijing , P. R. Chin * Corresponding uthors. Tel: ; Fx: E-mil ddresses: zhngxin@mil.buct.edu.cn (X. Zhng); weimin@mil.buct.edu.cn (M. Wei). S1
2 Figure S1. SEM imges of the s-synthesized LDH precursors: (A) CoMgAl-LDH, (B) CoInMgAl-LDH, nd (C) CoGMgAl-LDH, respectively. Figure S2. H2-TPR profiles for () CoMgAl-LDH, (b) CoInMgAl-LDH, nd (c) CoGMgAl-LDH, respectively. S2
3 Figure S3. (A) HAADF-STEM imge of Co, nd EELS spectr collected t Bem: (B) Co L-edge, (C) O K-edge. (D) HAADF-STEM imge of CoIn3, nd EELS spectr collected t Bem: (E) Co L-edge, (F) In M-edge. (G) HAADF-STEM imge of CoG3, nd EELS spectr collected t Bem: (H) Co L-edge, (I) G L-edge. Tble S1. Element contents of vrious ctlysts determined by inductively coupled plsm tomic emission spectroscopy (ICP AES) Entry Ctlyst Co content (wt.%) In content (wt.%) G content (wt.%) 1 Co/MgO Al 2O CoIn 3/MgO Al 2O CoG 3/MgO Al 2O Element content ws determined by inductively coupled plsm tomic emission spectroscopy (ICP AES). S3
4 Tble S2. XRD, curve-fitting of Co K-edge EXAFS spectr nd DFT clcultion results of Co, CoIn3 nd CoG3 R(Å) R(Å) R(Å) CN CN CN Smple Shell Δσ 2 (Å) g XRD CF b DFT c XRD d CF e DFT f Co Co Co CoIn 3 Co Co Co In Co Co CoG 3 Co G Distnce between bsorber nd bcksctter tom, determined by XRD. b Distnce between bsorber nd bcksctter tom, determined by curve fitting. c Distnce between bsorber nd bcksctter tom, determined by DFT clcultion. d Coordintion number, determined by XRD. e Coordintion number, determined by curve fitting. f Coordintion number, determined by DFT clcultion. g Chnge in the Debye-Wller fctor vlue reltive to the reference smple. Figure S4. XPS spectr of Co 2p of Co. S4
5 Tble S3. Bder chrge nlysis of Co, CoIn3 nd CoG3 Smple Atom Chrge Co Co 9 Co 9.43 CoIn 3 In In In Co 9.57 CoG 3 Three In toms of CoIn 3 IMC. G1 b 2.81 G2 b 2.81 G3 b 2.81 b Three G toms of CoG 3 IMC. Figure S5. Structurl models Co-bsed IMCs with lbels of Co nd In (or G) toms: (A) CoIn3, nd (B) CoG3. Co: blue bll; In: ornge bll; G: brown bll. Figure S6. In situ Fourier-trnsformed infrred spectr of CO dsorption over () Co, (b) CoIn3, nd (c) CoG3, respectively. S5
6 Figure S7. Correltion between ctlytic performnce of CoG3 smple nd rection conditions: (A) CAL conversion s function of H2 pressure or rection temperture; (B) COL selectivity s function of H2 pressure or rection temperture. Tble S4. Comprison of ctlytic performnce for selective hydrogention of CAL over vrious ctlysts Entry Ctlyst Conversion Selectivity Rection Rte Ref. (%) (%) (mmol g 1 h 1 ) 1 Co/MgO Al 2O This work 2 CoIn 3/MgO Al 2O This work 3 CoG 3/MgO Al 2O This work 4 Co/ZSM Co/SiO Pt/SiO Co-Pt/SiO Au/ZnO-CP Au/Fe 2O 3-CP Pt/CoAl-MMO Pt/ZnAl-MMO Ni-Co/GRA Ni-Co/MWCNT Pt@UiO-66-NH Rection rte is clculted on the bsis of tngent slope of the conversion-rection time plot within 20 40% conversion of CAL. S6
7 Figure S8. First-order kinetic plots for CAL hydrogention over: () Co, (b) CoIn3, nd (c) CoG3, respectively. Tble S5. First-order rte constnt for CAL hydrogention over vrious ctlysts Entry Ctlyst Rection Time (h) First-Order Rte Constnt k (h 1 ) 1 Co/MgO Al 2O CoIn 3/MgO Al 2O CoG 3/MgO Al 2O First-order rte constnt (k, h 1 ) is clculted on the bsis of the slope of first-order kinetic plots for CAL hydrogention. Tble S6. Ctlytic performnce for CAL hydrogention with or without ctlyst Entry Ctlyst Rection Time Solvent Conversion Selectivity (h) (%) (%) 1 Co/MgO Al 2O 3 8 Isopropnol CoIn 3/MgO Al 2O 3 8 Isopropnol CoG 3/MgO Al 2O 3 8 Isopropnol Isopropnol 1 0 Rection conditions: CAL/Co = 58 (molr rtio); CAL: 1.0 ml; iso-proh: 30 ml; temperture: 100 C; H 2 pressure: 2 MP, rection time: 8 h. S7
8 Figure S9. (A) XRD ptterns of the used ctlysts fter 5 cycles: () Co, (b) CoIn3, (c) CoG3. XRD stndrd crds for Co nd Co-bsed IMCs re shown in the lower prt of the pnels: Co- PDF# , CoIn3-PDF# , nd CoG3-PDF# TEM imges of the used ctlysts fter 5 cycles: (B) Co, (C) CoIn3, (D) CoG3. Tble S7. Ctlytic performnce for hydrogention of different kinds of unsturted ldehydes over Co nd CoG3 IMC Entry Substrte Product Co CoG 3 Con. Sel. Con. Sel. 1 97% 0 45% 44% 2 100% 0.4% 42% 36% 3 98% 1.0% 57% 82% 4 76% 0.8% 23% 61% Rection conditions: CAL/Co = 58 (molr rtio); CAL: 1.0 ml; iso-proh: 30 ml; temperture: 100 C; H 2 pressure: 2 MP, rection time: 8 h. S8
9 Figure S10. H2-TPD profiles of () Co, (b) CoIn3, nd (c) CoG3, respectively. Figure S11. First-order kinetic plots for CAL hydrogention over CoG3 t different H2 pressure: () 1 MP, (b) 2 MP, (c) 3 MP, nd (d) 4 MP, respectively Tble S8. First-order rte constnt for CAL hydrogention over CoG3 t different H2 pressure Entry Ctlyst H 2 pressure (MP) Rection Time (h) First-Order Rte Constnt k (h 1 ) 1 CoG 3/MgO Al 2O CoG 3/MgO Al 2O CoG 3/MgO Al 2O CoG 3/MgO Al 2O First-order rte constnt (k, h 1 ) is clculted on the bsis of the slope of first-order kinetic plots for CAL hydrogention. S9
10 Figure S12. FT-IR spectr of the rection progress of CAL over CoG3 smple recorded in cm 1 by flowing H2. From curve to curve f: 0 s, 40 s, 80 s, 160 s, 640 s nd 900 s, respectively. Figure S13. Density of sttes of Co, CoIn3 nd CoG3, respectively. Figure S14. Adsorption structures nd dsorption energies of crolein on different sites of CoG3(221). S10
11 Figure S15. Adsorption structures nd dsorption energies of crolein on the surfce of (A) Co nd (B) CoG3. The white, gry, red, blue nd brown bll represent H, C, O, Co nd G element, respectively; nd this color mode will be used in the full text. Figure S16. Elementry rection steps vi Pth-12, Pth-21, Pth-34 nd Pth-43, respectively. Tble S9. First-order rte constnt for CAL hydrogention over Co nd CoG3 smples t different rection tempertures Entry Ctlyst Rection Temperture ( C) Rection Rte (mmol g 1 h 1 ) First-Order Rte Constnt b 1 Co/MgO Al 2O Co/MgO Al 2O Co/MgO Al 2O CoG 3/MgO Al CoG 3/MgO Al CoG 3/MgO Al Rection rte is clculted on the bsis of tngent slope of the conversion-rection time plot within 20 40% conversion of CAL. b First-order rte constnt (k, h 1 ) is clculted on the bsis of the slope of first-order kinetic plots for CAL hydrogention. S11
12 Figure S17. Apprent ctivtion energy (E) for selective hydrogention of CAL on Co nd CoG3 smples, respectively. Figure S18. Fourier-trnsformed infrred spectr of the hydrogention progress of CAL over CoG3 ctlyst by flowing H2 s rection gs. From curve to curve c in ech pnel: 0 s, 80 s nd 640 s, respectively. Figure S19. Structurl models of Co nd Co-bsed IMCs: (A) Co, (B) CoIn3, nd (C) CoG3. Co: blue bll; In: ornge bll; G: brown bll. S12
13 REFERENCES (1) Zhng, X.; Zhng, Y.; Chen, F.; Xing, Y.; Zhng, B.; Xu, Y.; Zhng, T. Efficient Selective Hydrogention of Cinnmldehyde over Zeolite Supported Coblt Ctlysts in Wter. Rec. Kinet. Mech. Ct. 2015, 115, (2) Zheng, R.; Porosoff, M. D.; Weiner, J. L.; Lu, S.; Zhu, Y.; Chen, J. G. Controlling Hydrogention of C=O nd C=C Bonds in Cinnmldehyde Using Silic Supported Co-Pt nd Cu-Pt Bimetllic Ctlysts. Appl. Ctl., A 2012, 419, (3) Chen, H.; Cullen, D. A.; Lrese, J. Z. Highly Efficient Selective Hydrogention of Cinnmldehyde to Cinnmyl Alcohol over Gold Supported on Zinc Oxide Mterils. J. Phys. Chem. C 2015, 119, (4) Tin, Z.; Li, Q.; Hou, J.; Pei, L.; Li, Y.; Ai. S. Pltinum Nnocrystls Supported on CoAl Mixed Metl Oxide Nnosheets Derived from Lyered Double Hydroxides s Ctlysts for Selective Hydrogention of Cinnmldehyde. J. Ctl. 2015, 331, (5) Mlobel, L. J.; Heveling, J.; Augustyn, W. G.; Cele, L. M. Nickel-Coblt on Crbonceous Supports for the Selective Ctlytic Hydrogention of Cinnmldehyde. Ind. Eng. Chem. Res. 2014, 53, (6) Guo, Z.; Xio, C.; Mligl-Gnesh, R. V.; Zhou, L.; Goh, T. W.; Li, X.; Tesfgber, D.; Thiel, A.; Hung. W. Pt Nnoclusters Confined within Metl Orgnic Frmework Cvities for Chemoselective Cinnmldehyde Hydrogention. ACS Ctl. 2014, 4, S13
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