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Catalysts 2019, 9, 413 9 of 12 to minimize junction potentials. The error associated with the potential values was less than 5 mV. The ohmic drop can be one of the main sources of error when ILs are used as solvents, since they are more resistive media than polar aprotic solvents with 0.10 M concentration of supporting electrolytes. Due to the low conductivity and larger viscosity of RTILs (Room Temperature Ionic Liquids), in order to facilitate the direct comparison between the cyclic voltammograms in the different media, the current values obtained were first normalized by the concentration and the scan rate (Ip/cv1/2). Later, those values were also normalized and the relationship between the four solvents can be expressed by a total normalization coefficient. This coefficient can be expressed as a ratio between DMF/[EMIM]TFSI, DMF/[PP13]TFSI, DMF/[N1114]TFSI, and DMF/[BMPyr]TFSI 3.0, 1.7, 6.0, and 2.7, respectively. For electrolysis experiments, the disc working electrodes were replaced by a graphite carbon bar and a silver foil. The counter (Pt bar) and reference (SCE) electrodes were separated from the electrochemical solution by a salt bridge filled by the electrolyte solution. The salt bridge ended with a frit, which was made of a ceramic material, avoiding appreciable contamination. Compounds were electrolyzed at a negative potential of 0.10 V more negative than the Epc potential value under nitrogen- or carbon-saturated solutions. When the reaction was completed, the mixture was extracted into water/ether mixtures. The organic layer was dried with Na2SO4 and evaporated to yield a residue. All products obtained were characterized by Proton Nuclear Magnetic Resonance (1H-NMR) and Gas Chromatography (GC) by comparison with their respective pure commercially available analogues. 3.3. Determination of the CO2 Concentration in ILs A thermal mass flow meter of modular construction with a ‘laboratory style’ pc-board housing (EL-FLOW® Mass Flow Meter/Controller, Bronkhorst Hi-Tec, Ruurlo, Netherlands) was used to monitor the CO2 concentrations in the solution [28]. Control valves are integrated to measure and control a gas flow from the lowest range of 0.2–10 mL/min. 4. Conclusions This manuscript describes a new “environmentally-friendly” electrochemical approach for producing highly valuable compounds using CO2 as a building block in ILs. The selection of the solvent and the nature of the cathode material are crucial, since it helps to overcome the main drawbacks associated with previous processes reported in the literature, in which organic solvents, redox mediators and large quantities of supporting electrolytes are employed. The use of silver instead of carbon cathodes enables p-cyanobenzoic acid to be obtained from the electrochemical reduction of 4-iodobenzonitrile under mild experimental conditions with moderate yields and conversion rates under a CO2 atmosphere. The use of non-acidic ILs also makes the electrocarboxylation process more environmentally friendly, since it is not only able to avoid the use of organic solvents and large quantities of supporting electrolytes, but also the solvation process of 1− appears to be more effective. Hence, the use of ILs (high concentration of cations) instead of tetrabutylammonium salts at low concentrations (0.1 M TBABF4 in DMF) enables the electrochemical potential applied to be also reduced. This study opens the door to develop new strategies for the synthesis of similar derivatives, such as phthalates, by following this “greener” route. Author Contributions: G.G. conceived and designed the experiments; S.M. performed the experiments and analyzed the data. G.G. and I.G. wrote the paper and approved the final version for its publication. Funding: This research was funded by MINECO/FEDER (project CTQ2015-65439-R). Acknowledgments: This work was supported by project CTQ2015-65439-R from the MINECO/FEDER. S.M. thanks the Universitat Autònoma de Barcelona for pre-doctoral PIF fellowships. Conflicts of Interest: The authors declare no conflict of interests.PDF Image | Electrocatalytic Processes for the Valorization of CO2
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