Supplementary Information. Simple Quaternary Ammonium Cations-Templated Syntheses
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1 Supplementary Information Simple Quaternary Ammonium Cations-Templated Syntheses of Extra-Large Pore Germanosilicate Zeolites Risheng Bai, Qiming Sun, Ning Wang, Yongcun Zou, Guanqi Guo, Sara Iborra, Avelino Corma, and Jihong Yu*, State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun, P.R. China Instituto de Tecnología Químicia, UPV-CSIC, Universidad Politénica de Valencia, Avda. de los Naranjos, s/n, Valencia, Spain *Author to whom correspondence should be addressed. S1
2 Table of Contents 1. Experimental section. Reactant agents. Synthesis of the samples. 2. Characterizations. 3. Catalytic tests. 4. Supplementary Figures and Tables Figure S1 High-magnification TEM images. Figure S2 13 C MAS NMR spectra of the as-synthesized samples. Figure S3 19 F MAS NMR spectra of the as-synthesized samples. Figure S4 29 Si MAS NMR spectra of the as-synthesized samples. Figure S5 Thermogravimetric curves of the as-synthesized samples. Figure S6 XRD patterns of the calcined zeolite samples. Figure S7 27 Al MAS NMR spectra of the TPA-NUD-1 sample. Figure S8 NH 3 temperature-programmed desorption of the calcined TPA-NUD-1 sample. Table S1 Compositional analysis of the as-synthesized samples. Table S2 Porous properties of the calcined zeolite samples. Table S3 Catalytic activity in converting bulky substrates with aluminum catalysts. Table S4 Catalytic activity in converting bulky substrates. 5. References S2
3 Experimental section Reactant agents. All reagents were used as purchased commercially without any further purification. Ludox (SiO 2, 40%, Sigma-Aldrich), Tetraethylorthosilicate (TEOS, Tianjin Fuchen Chemical Reagent Factory), GeO 2 (>99.99%, Yunnan Lincang Xinyuan Germanium Industrial Co., Ltd), Al 2O 3 (Beijing Chemical Works), HF (40%, Beijing Chemical Works), Al(OH) 3 (Beijing Chemical Works), tetraethylammonium hydroxide (TEAOH) (35%, Alfa), tetrapropylammonium hydroxide (TPAOH) (40% Alfa), tetrabutylammonium hydroxide (TBAOH) (55%, Alfa). Dodecane was purchased from Beijing Chemical Works. Benzaldehyde (>98.5%), 2-hydroxyacetophenone (99%) were purchased from Aladdin Industrial Co. Heptanal (97%), 2-phenylpropanal (95%), diphenylacetaldehyde (97%) and trimethylorthoformate (98%) were purchased from Energy Chemical Co. Synthesis of zeolite TEA-ITQ-44. As a typical procedure: GeO 2 and Al 2O 3 were added to the solution of SDAOH, stirring for 2 h. Then Ludox (SiO 2, 40%) was added into the mixture solution followed by continuous stirring of 1 h. Finally, HF was added under the continuous stirring. The gel mixture was kept on stirring to evaporate the excess water until getting to the desired water ratio. The desired reaction gel was transferred into a Teflon-lined stainless steel autoclave and heated at 170 C for 3 days under static conditions. The product was washed adequately with deionized water and dried at 80 C overnight. The optimized gel molar composition for the synthesis of TEA-ITQ-44 was x SiO 2: (1-x) GeO 2: y Al 2O 3: 0.25 TEAOH: 0.25 HF: 1 H 2O, where x = and y = Synthesis of zeolites TPA-ITQ-44 and TPA-NUD-1. When using TPAOH as the structure-directing agent, the synthesis procedure and crystallization conditions were the same as the one mentioned above. And the optimal gel molar composition for the synthesis of TPA-ITQ-44 was 0.2 SiO 2: 0.8 GeO 2: x Al 2O 3: 0.25 TPAOH: 0.25 HF: 1 H 2O (x = ). In synthesizing TPA-NUD-1, the optimized gel molar composition was x SiO 2: (1-x) GeO 2: y Al 2O 3: 0.25 TPAOH: 0.25 HF: 1 H 2O, where x = and y = Synthesis of zeolites TBA-ITQ-33 and TBA-NUD-1. TBAOH could also direct the synthesis of the ITQ-33 and NUD-1 zeolite with the typical synthesis procedure mentioned above. And the optimal molar composition in synthesizing TBA-ITQ-33 was x SiO 2: (1-x) GeO 2: y Al 2O 3: 0.25 TBAOH: 0.25 HF: 3 H 2O, where x ranges from 0.5 to 0.8 and y ranges from 0 to The optimized gel molar composition in synthesizing TBA-NUD-1 was x SiO 2: (1-x) GeO 2: y Al 2O 3: 0.25 TBAOH: 0.25 HF: 1 H 2O, where x ranges from 0.5 to 0.8 and y ranges from 0 to Synthesis of conventional ZSM-5. As a typical run, 0.4 g of NaAlO 2, 3.3 ml of TPAOH, and 3.5 ml of TEOS were mixed, followed by addition of 10 ml of water. After stirring at room temperature for 6 h and aging at 100 C for 2 h. The mixture was then transferred into an autoclave for crystallization at 180 C for 3 days. The products were collected by filtration, dried in air and then calcined at 550 C for 6 h to remove the templates. [S1] Characterizations Powder X-ray diffraction analysis of the samples was carried out on a Rigaku D-Max 2550 diffractometer using Cu Kα radiation (λ = Å, 50 KV). Transmission electron microscopy (TEM) images were recorded on a JEM-2200FS electron microscope. Nitrogen adsorption-desorption measurements were carried out on a Micromeritics ASAP 2420 analyzer at 77 K. The testing samples were degassed at S3
4 150 C under vacuum for 10h. Thermogravimetric (TG) analysis was performed with a TA company TGA Q500 in air atmosphere with a heating rate of 10 C minˉ1 from room temperature to 800 C. The elements analysis of C, H, N was performed on a ELEMENTER VARIO MICRO. Chemical compositions were determined with inductively coupled plasma (ICP) analysis performed on a icap 7000 SERIES ICP spectrometer. The temperature-programmed desorption of ammonia (NH 3-TPD) experiments were carried out with a Micromeritics AutoChem II 2920 automated chemisorption analysis unit with a thermal conductivity detector (TCD) under helium flow. 27 Al magic-angle spinning (MAS) NMR spectrum and 29 Si MAS NMR spectra were recorded on a Varian Infinity plus 400 spectrometer at resonance frequencies of MHz and 79.5 MHz with spinning rates of 6 KHz and 4 KHz, respectively. 13 C CP MAS NMR and 19 F MAS NMR spectra were performed on a Bruker AVANCE III 400 WB spectrometer at resonance frequencies of MHz and MHz with a spinning rate of 8 KHz and 20 KHz, respectively. Chemical shifts of 27 Al, 29 Si, 13 C and 19 F are referenced to 1.0 M Al(NO 3) 3, 2,2-dimethyl-2-ilapentane-5-sulfonate sodium salt (DSS), tetramethylsilane (TMS) and CFCl 3, respectively. Catalytic tests Condensation of benzaldehyde with 2-hydroxyacetophenone was carried out in a three-necked round flask equipped with a condenser and a magnetic stirrer. The mixture containing 7 mmol of benzaldehyde, 3.5 mmol of 2-hydroxyacetophenone and 50 mg of the catalyst was heated to 150 C and maintained at that temperature for 15 h. The products were analyzed by Gas chromatography-mass spectrometry (GC-MS, Thermo Fisher Trace ISQ, equipped with TG-5MS column, 60m 320µm 25µm). The reaction conditions of carbonyl compound (heptanal, 2-phenylpropanal, or diphenylacetaldehyde) with trimethylorthoformate (TOF) were as follows: 30 mg of catalyst, 3 mmol of carbonyl compound, 15 mmol of TOF, at 120 C for 6 h. The products were analyzed by Gas chromatography-mass spectrometry (GC-MS, Thermo Fisher Trace ISQ, equipped with TG-5MS column, 60m 320µm 25µm). S4
5 Supplementary Figures and Tables Figure S1. High-magnification TEM images of the as-synthesized (a) TEA-ITQ-44, (b) TPA-ITQ-44, (c) TPA-NUD-1, (d) TBA-ITQ-33 and (e) TBA-NUD-1 samples. S5
6 Figure S2. Solid-state 13 C MAS NMR spectra of the as-synthesized samples with different organic structure-directing agents. All these organic templates remain essentially intact in the structures of TEA-ITQ-44, TPA-ITQ-44, TPA-NUD-1, TBA-ITQ-33, and TBA-NUD-1. S6
7 Figure S3. 19 F MAS NMR spectra of the as-synthesized TEA-ITQ-44 (red), TPA-ITQ-44 (green), TPA-NUD-1 (orange), TBA-ITQ-33 (blue) and TBA-NUD-1 (pink). Figure S4. 29 Si MAS NMR spectra of the as-synthesized TEA-ITQ-44 (red, -100 and -112 ppm), TPA-ITQ-44 (green, -105 and -112 ppm), TPA-NUD-1 (orange, -105 and -112 ppm), TBA-ITQ-33 (blue, -105 and -112 ppm) and TBA-NUD-1 (pink, -105 and -112 ppm). All these bands are attributed to tetrahedral framework silicon atoms. The resonance peak from -100 ppm to -105 ppm can be attributed to Si(OSi) 3(OGe(Al)), and the resonance peak at -112 ppm are generated from the Si(OSi) 4. [S2] S7
8 Figure S5. Thermogravimetric curves of the as-synthesized samples. Figure S6. XRD patterns of the calcined TPA-NUD-1 (red), TBA-ITQ-33 (green), and TBA-NUD-1 (blue) zeolite samples and the corresponding as-made TPA-NUD-1 (purple), TBA-ITQ-33 (olive), and TBA-NUD-1 (black) zeolite samples. S8
9 Figure S7. 27 Al MAS NMR spectrum of the calcined Al-containing TPA-NUD-1 sample with (Si+Ge)/Al=3.13. Figure S8. NH 3 temperature-programmed desorption of the TPA-NUD-1 sample (blue) without aluminum and the Al-containing TPA-NUD-1 sample (red) with (Si+Ge)/Al=3.13. S9
10 Table S1. Compositional and thermal analyses of the as-synthesized samples C (wt.%) H (wt.%) N (wt.%) C/N H 2O weight loss (%) c Template d weight loss Molar composition (%) c TEA-ITQ a (Calc. 73.8) b 16.0 (Calc. 15.4) 10.5 (Calc. 10.8) 8.2 (Calc. 8) H 7.67 (Si 11 Ge Al 7.67 O 104 F 3 ) (C 8 H 20 N) 5.95 (OH) 2.95 TPA-ITQ (Calc. 77) 15.2 (Calc. 15.5) 7.2 (Calc. 7.5) 12.6 (Calc. 12) H 8.16 (Si Ge Al 7.75 O 104 F 3 ) (C 12 H 28 N) 2.60 TPA-NUD (Calc. 77) 15.3 (Calc. 15.5) 7.2 (Calc. 7.5) 12.6 (Calc. 12) H (Si Ge Al O 98 F 3 ) (C 12 H 28 N) 3.04 (OH) 0.04 TBA-ITQ (Calc. 79.3) 15.4 (Calc. 14.9) 6.0 (Calc. 5.8) 15.3 (Calc. 16) H 2.62 (Si Ge Al 1.81 O 92 F 3 ) (C 16 H 36 N) 2.19 TBA-NUD (Calc. 79.3) 14.9 (Calc. 14.9) 6.0 (Calc. 16) 15.4 (Calc. 16) H 5.65 (Si Ge Al 3.78 O 98 F 3 ) (C 16 H 36 N) 1.13 a Elemental analysis was recorded on a C, H, N, S elemental analyser. b The ideal weight percentage of the OSDA molecules calculated in their cations form. c Weight loss were calculated according to the thermogravimetric (TG) analyses. d The molar compositions of the as-synthesized zeolite samples are calculated on the basis of ICP analyses, thermogravimetric analyses, and CHN elemental analyses, as well as crystallographic data of the corresponding zeolite structures. Table S2. Porous properties of the calcined zeolite samples Samples S BET a (m 2 g -1 ) S micro b (m 2 g -1 ) S ext b (m 2 g -1 ) V micro b (cm 3 g -1 ) TPA-NUD TBA-NUD TBA-ITQ a Specific surface area calculated from the nitrogen adsorption isotherm using the BET method. b S micro (micropore area), S ext (external surface area) and V micro (micropore volume) calculated using the t-plot method. S10
11 Table S3. Catalytic activity in converting bulky substrates with aluminum catalysts Selectivity (%) Catalyst Conversion (%) a Flavanone Chalcone Al 2 O Al(OH) 3 32 TPA-NUD-1 b >99% a The conversion was calculated on the 2-hydroxyacetophenone. 47 <1% Table S4. Catalytic activity in converting bulky substrates Samples Si/Al ratio Conversion (%) a Note TPA-NUD b this work ZSM b this work a The conversion was calculated on the heptanal, 2-phenylpropanal, and diphenylacetaldehyde. b This value was the molar ratio of (Si+Ge)/Al, which was calculated according to the inductively coupled plasma (ICP). S11
12 References [S1] F. Liu, T. Willhammar, L. Wang, L. Zhu, Q. Sun, X. Meng, W. Carrillo-Cabrera, X. Zou, F. S. Xiao, J. Am. Chem. Soc. 2012, 134, [S2] Dorset, D. L.; Kennedy, G. J.; Strohmaier, K. G.; Diaz-Cabanas, M. J.; Rey, F.; Corma, A. J. Am. Chem. Soc. 2006, 128, S12
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