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1 Supporting Information Selective Propene Oligomerization with Nickel(II)-Based Metal-Organic Frameworks Anton N. Mlinar, a,+ Benjamin K. Keitz, b,+ David Gygi, b Eric D. Bloch, b Jeffrey R. Long,*,b Alexis T. Bell*,a a Department of Chemical and Biomolecular Engineering, University of California, Berkeley, CA , USA b Department of Chemistry, University of California, Berkeley, CA 94720, USA * bell@cchem.berkeley.edu, jrlong@berkeley.edu
2 General Information: All reagents were obtained from commercial vendors and used without further purification. The synthesis and activation of Ni 2 (dobdc) was performed according to previously reported procedures. 1 Following activation, metal-organic frameworks were handled in a nitrogen filled dry box until immediately prior to their placement in the reactor. Powder X-ray diffraction data were collected with a Bruker D8 Advance diffractometer using Cu Kα radiation (λ = Å). Elemental analyses for C, H, and N were performed at the Microanalytical Laboratory of the University of California, Berkeley. Data analysis and plotting were performed with OriginPro 8.1. Low-Pressure Gas Adsorption: Gas adsorption isotherms in the range bar were measured volumetrically using a Micromeritics ASAP2020 or ASAP2420 instrument. All gases were % purity or higher. Isotherms at 77 K were measured using liquid nitrogen baths. BET surface areas of both Ni 2 (dobdc) and Ni 2 (dobpdc) were consistent with literature reports. 1 Preparation of Ni 2 (dobpdc): To a 20-ml glass scintillation vial, H 4 dobpdc (41.1 mg, 0.15mmol), Ni(NO 3 ) 2 6 H 2 O (109 mg, mmol), and 15 ml of mixed solvent (1:1:1 H 2 O:DMF:EtOH) were added. The vial was sealed with a teflon lined cap and placed in a 2 cm deep well plate on a 393 K hot plate. After 36 h a green powder formed on the bottom of the vial. The reaction mixture was then decanted and the remaining powder was soaked in DMF at 343 K for 12 hours, after which the solvent was decanted and replaced with fresh DMF. This process was repeated 6 times over the course of 3 days, after which the solvent was switched to MeOH and the process repeated until the DMF amide stretch was no longer visible by IR. The solid was then collected by filtration and fully desolvated by heating under dynamic vacuum (<10 µbar) at 523 K (0.2 K/min) for 24 h to afford 39.3 mg (0.101 mmol) 68% of Ni 2 (dobpdc). Anal. Calc for C 14 H 6 O 6 Ni 2 : C, 43.39; H, Found: C, 43.09; H, 1.24.
3 Figure S1. Comparison of oligomerization activity for ethene (red) and propene (blue) with Ni 2 (dobdc) at 453 K, 5 bar propene pressure, and WHSV = 64 h -1. Figure S2. Powder X-ray diffraction pattern of DMF-solvated Ni 2 (dobpdc).
4 Figure S3. Linear BET plot for Ni 2 (dobpdc) used to ensure that the BET calculations were done correctly and in the right pressure range.
5 Figure S4. Powder X-ray diffraction patterns of Ni 2 (dobdc) before (black) and after (purple) catalysis. Note that the metal-organic framework is mixed with silica gel prior to catalysis, resulting in the amorphous feature in the purple pattern. Table S1. Relative amounts of propene dimer and trimer during propene oligomerization reaction with Ni 2 (dobdc). Time on Stream (min) C6 (mol %) C9 (mol %) Conversion (%)
6 Table S2. Detailed hydrocarbon analysis of propene dimers formed from oligomerization of propene using Ni 2 dobdc, Ni 2 dobpdc, and Ni-Na-X. Component % C6 Ni 2 (dobdc) Ni 2 (dobpdc) Ni-Na-X 1-hexene cis-2-hexene trans-2-hexene cis-3-hexene trans-3-hexene methyl-1-pentene methyl-2-pentene cis-3-methyl-2-pentene methyl-1-pentene cis-4-methyl-2-pentene trans-4-methyl-2-pentene ,3-dimethyl-1-butene References: (1) Dietzel, P.D.C; Panella, B.; Hirscher, M.; Biom, R.; Fjellvåg, H. Chem. Commun. 2006, 1,
Heterogeneous nickel aluminosilicate materials have been
pubs.acs.org/acscatalysis Selective Propene Oligomerization with Nickel(II)-Based Metal Organic Frameworks Anton N. Mlinar,, Benjamin K. Keitz,, David Gygi, Eric D. Bloch, Jeffrey R. Long,*, and Alexis
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