Supplementary Figures

Similar documents
Synthesis of ethanol from paraformaldehyde, CO 2 and H 2

Near Infrared Electrochromism in Electropolymerized Films of Biscyclometallated Ruthenium Complex Bridged by 1,2,4,5-Tetra(2-pyridyl)benzene

Supplementary Materials for

Supporting Information. Silylated Organometals: A Family of Recyclable. Homogeneous Catalysts

Supporting Information

Supporting information for Mesoporous Nitrogen-Doped Carbons with High Nitrogen Content and

Supporting Information

Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure

Electronic Supplementary Information (ESI)

Amphiphilic diselenide-containing supramolecular polymers

Electronic Supplementary Information (ESI) Tunable Phase and Visible-Light Photocatalytic Activity

Supporting Information Chemicals Synthesis Phenyl-C61-butyric acid Phenyl-C61-buryric acid 1H, 1H-Pentadecafluoro-1-octyl ester (F-PCBM)

Supporting Information

Electronic Supplementary Information

A Highly efficient Iron doped BaTiO 3 nanocatalyst for the catalytic reduction of nitrobenzene to azoxybenzene

Supplementary Information

Extracting organic molecules out of water using the metal-organic framework

*Correspondence to:

Sub-10-nm Au-Pt-Pd Alloy Trimetallic Nanoparticles with. High Oxidation-Resistant Property as Efficient and Durable

Supplementary Information

Selective aerobic oxidation of biomass-derived HMF to 2,5- diformylfuran using a MOF-derived magnetic hollow Fe-Co

Supplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni

Supporting Information for

Supplementary Figure 1. Characterization of immobilized cobalt protoporphyrin electrode. The cyclic voltammogram of: (a) pyrolytic graphite

Selective total encapsulation of the sulfate anion by neutral nano-jars

Electronic Supplementary Information

Supporting Information for

Novel Tri-Block Copolymer of Poly (acrylic acid)-b-poly (2,2,3,3,4,4,4- hexafluorobutyl acrylate)-b-poly (acrylic acid) Prepared via Two-Step

Supporting Information

Study on the Selective Hydrogenation of Nitroaromatics to N-aryl hydroxylamines using a Supported Pt nanoparticle Catalyst

Controllable Growth of Bulk Cubic-Phase CH 3 NH 3 PbI 3 Single Crystal with Exciting Room-Temperature Stability

Supporting Information for

Supporting Information

SUPPORTING INFORMATION

Electronic Supplementary Material

Supplementary Information. ZIF-8 Immobilized Ni(0) Nanoparticles: Highly Effective Catalysts for Hydrogen Generation from Hydrolysis of Ammonia Borane

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

4023 Synthesis of cyclopentanone-2-carboxylic acid ethyl ester from adipic acid diethyl ester

Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles

Visible-light Driven Plasmonic Photocatalyst Helical Chiral TiO 2 Nanofibers

Supplementary Information

Electronic Supporting Information

Supporting information for:

structure and paramagnetic character R. Kakavandi, S-A. Savu, A. Caneschi, T. Chassé, M. B. Casu Electronic Supporting Information

Xiufang Chen, Jinshui Zhang, Xianzhi Fu, Markus Antonietti, and Xinchen Wang*

Biomimetic material - poly(n-vinylimidazole)-zinc complex for CO 2 separation

Supporting Information. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes

Supporting Information. CdS/mesoporous ZnS core/shell particles for efficient and stable photocatalytic hydrogen evolution under visible light

Ligand-free coupling of phenols and alcohols with aryl halides by a recyclable heterogeneous copper catalyst

Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)

Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012

Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3

Critical role of surface hydration on the dynamics of serum adsorption studied with monoethylene glycol adlayers on gold

Supplementary Information. Low volume shrinkage polymers by photo Polymerization of 1,1- Bis(ethoxycarbonyl)-2-vinylcyclopropanes

Dendritic Star Polymer of Polyacrylamide Based on β-cyclodextrin Trimer: A. Flocculant and Drug Vehicle

Supporting Information

Hydrogen-Induced Structural Transformation of AuCu Nanoalloys Probed by Synchrotron X-ray Diffraction Techniques

Synthesis of 2 ) Structures by Small Molecule-Assisted Nucleation for Plasmon-Enhanced Photocatalytic Activity

Supporting Information Reagents. Physical methods. Synthesis of ligands and nickel complexes.

Supporting Information for. an Equatorial Diadduct: Evidence for an Electrophilic Carbanion

Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts

Influence of anellation in N-heterocyclic carbenes: Detection of novel quinoxalineanellated NHC by trapping as transition metal complexes

Supporting Information Water-soluble 1,2,4-Triazole with Diethylene Glycol Monoethyl Ether

Aziridine in Polymers: A Strategy to Functionalize Polymers by Ring- Opening Reaction of Aziridine

Supporting information

Supporting Information. Rhodium, iridium and nickel complexes with a. 1,3,5-triphenylbenzene tris-mic ligand. Study of

Supplementary Figure 1. Temperature profile of self-seeding method for polymer single crystal preparation in dilute solution.

Supporting Information

Facile and selective hydrogenolysis of β-o-4 linkages in lignin catalyzed by Pd-Ni bimetallic nanoparticles supported on ZrO 2

Materials and Instrumentation. Preparation of ferrofluid [1] Preparation of polymer magnetic nanoparticles. Preparation of NHC ligand [2]

10 Marking scheme: End-of-chapter test

Supporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source

Alexander S. Münch and Florian O. R. L. Mertens

with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15

Supporting Information For:

Supporting Information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

4) protons experience a net magnetic field strength that is smaller than the applied magnetic field.

Supporting Information

Supporting Information

Supporting Information

Supplementary information

Supporting Information

Disubstituted Imidazolium-2-Carboxylates as Efficient Precursors to N-Heterocylic Carbene Complexes of Rh, Ir and Pd

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Vitamin E-Labeled Polyethylenimine for in vitro and in vivo Gene Delivery

Supporting Information

Transformations: New Approach to Sampagine derivatives. and Polycyclic Aromatic Amides

Understanding Aqueous Dispersibility of Graphene Oxide and Reduced Graphene Oxide through pka Measurements

Supporting Information

CHAPTER 8 ISOLATION AND CHARACTERIZATION OF PHYTOCONSTITUENTS BY COLUMN CHROMATOGRAPHY

Figure S1 - Enzymatic titration of HNE and GS-HNE.

Unusual ph-dependent Surface Adsorption and Aggregation Behavior of a series of Asymmetric Gemini Amino-acid Surfactants

5-Hydroxymethylcytosine-selective oxidation with peroxotungstate

Supporting Information. Graphene Oxide-Palladium Modified Ag-AgBr: A Novel Visible-Light- Responsive Photocatalyst for the Suzuki Coupling Reaction**

Supplementary Information Supplementary Figures

Supporting Information

Supporting information High density monodispersed cobalt nanoparticles filled into multi-walled carbon nanotubes

[(NHC)Au I ]-Catalyzed Acid Free Hydration of Alkynes at Part-Per-Million Catalyst Loadings

Transcription:

Supplementary Figures Supplementary Fig. 1. The GC traces of the products of methanol hydrocarboxylation. (a) liquid sample (toluene as internal standard), (b) gaseous sample. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 12 mmol MeOH, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. Notes: (1) The determined mole response factors of H 2, CO and CH 4 are 6.32, 0.97 and 3.51 times of that of CO 2. (2) The weak air peaks was caused by sampling and injecting operation. 1 / 10

Supplementary Fig. 2. The GC traces of the products of CO hydrogenation without imidazole. (a) liquid sample, (b) gaseous sample. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 3 mmol LiI, 2 ml DMI, 4 MPa CO and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. 2 / 10

Supplementary Fig. 3. The GC traces of the products of CO hydrogenation with imidazole. (a) liquid sample, (b) gaseous sample. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 4 MPa CO and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. 3 / 10

Supplementary Fig. 4. The GC traces of the products of CO 2 hydrogenation without imidazole. (a) liquid sample (toluene as internal standard), (b) gaseous sample. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 3 mmol LiI, 2 ml DMI, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. 4 / 10

Supplementary Fig. 5. The GC traces of the products of CO 2 hydrogenation with imidazole. (a) liquid sample (toluene as internal standard), (b) gaseous sample. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. 5 / 10

Supplementary Fig. 6. The results of XPS analysis. (a) imidazole, (b) imidazole-ru 3 (CO) 12 compound, (c) imidazole-rh 2 (OAc) 4 compound. Notes: X-ray photoelectron spectroscopy (XPS) data were obtained with an ESCALab220i-XL electron spectrometer from VG Scientific using 300W AlKα radiation. The base pressure was about 3 10-9 mbar. The binding energies were referenced to the C1s line at 284.8 ev from adventitious carbon. The preparation of imidazole-ru 3 (CO) 12 compound was conducted at room temperature. In the experiment, 0.0085 g Ru 3 (CO) 12 (40 µmol Ru) was dissolved in 20 ml dioxane, 0.05 g imidazole (750 µmol) was dissolved in 20 ml methanol. The above solutions were mixed and stirred for 5 h, then 40 ml diethyl ether was added to precipitate the target compound. The compound was washed with additional 40 ml diethyl ether for 2 times and dried in vacuum before the XPS analysis. The preparation of imidazole-rh 2 (OAc) 4 compound was conducted at room temperature. In the experiment, 0.0088 g Rh 2 (OAc) 4 (40 µmol Rh) and 0.05 g imidazole (750 µmol) was dissolved in 20 ml methanol respectively. The above solutions were mixed and stirred for 5 h, and then 40 ml diethyl ether was added to precipitate the target compound. The compound was washed with additional 40 ml diethyl ether for 2 times and dried in vacuum before the XPS analysis. 6 / 10

Supplementary Fig. 7. The GC-MS spectra of reaction solution using CH 3 OD instead of methanol. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 12 mmol CH 3 OD, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. Note: The molecular weight of acetic acid generated in the reaction was still 60 Daltons. This result supports three deductions. 1. The CH 3 and OD group broke away during the reaction. Otherwise, the molecular weight of acetic acid should be 61 Daltons. 2. The CO 2 directly participated in the reaction. If methanol carbonylation with CO dominated in the reaction, the OD group generated in situ would take part in the formation of acetic acid with the CH 3 CORh*I intermediate and the molecular weight of acetic acid should be 61 Daltons. The mechanism of rhodium catalyzed methanol carbonylation was reported elsewhere (Ref 3). 3. H atom in the COOH group of acetic acid was from the reactant H 2. Otherwise, the molecular weight of acetic acid should be 61 Daltons. 7 / 10

Supplementary Fig. 8. The GC-MS spectra of reaction solution using CH 18 3 OH instead of methanol. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 12 mmol CH 18 3 OH, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. Note: The molecular weight of acetic acid synthesized was still 60 Daltons. This result supports two deductions. 1. The CH 3 and 18 OH group broke away during the reaction. Otherwise, the molecular weight of acetic acid should be 62 Daltons. 2. The CO 2 directly participated in the reaction. If methanol carbonylation with CO dominated in the reaction, the 18 OH group generated in situ would take part in the formation of acetic acid with the CH 3 CORh*I intermediate and the molecular weight of acetic acid should be 62 Daltons. The mechanism of rhodium catalyzed methanol carbonylation was reported elsewhere (Ref 3). 8 / 10

Supplementary Fig. 9. The GC-MS spectra of reaction solution using 13 CH 3 OH instead of methanol. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 12 mmol 13 CH 3 OH, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. Note: The molecular weight of acetic acid formed in the reaction was 61 Daltons. This demonstrates that the two C atoms in the acetic acid product were from 13 C of 13 CH 3 OH and C of CO 2 respectively. 9 / 10

Supplementary Fig. 10. The NMR spectra of reaction solution using 13 CH 3 OH instead of methanol. (a) 1 H NMR, (b) 13 C NMR. Condition: 40 μmol Ru 3 (CO) 12 and 40 μmol Rh 2 (OAc) 4 (based on metals), 0.75 mmol imidazole, 3 mmol LiI, 2 ml DMI, 12 mmol 13 CH 3 OH, 4 MPa CO 2 and 4 MPa H 2 (at room temperature), 200 o C, and 12 h. Note: In the 1 H NMR spectrum, the proton signal of 13 CH 3 group on the acetic acid molecule splits into two peaks by the coupling with 13 C atom. In the 13 C NMR spectrum, the signal of carbonyl group became weaker and splits into dual peaks, which is caused by the coupling with the adjacent 13 C atom in the 13 CH 3 group. Both 1 H NMR and 13 C NMR spectra confirmed that the CH 3 group in acetic acid molecule is from methanol, i.e., CH 3 group of CH 3 OH is transferred into the acetic acid product in the reaction. 10 / 10