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CO2 can be confirmed since the peak current value was directly linked to the CO2 concentration, as it can be seen in Figure 4b. In the case of using silver as a working electrode, the electrochemical processes and their associated reactivity were easily controlled by the applied potential. Note that in this case, since the electrochemical reduction of CO2 occurred prior to the benzonitrile reduction, no electrocatalytic processes were observed related to the role of benzonitrile as a redox mediator Catalysts 2019, 9, 413 7 of 12 (Scheme 4). Scheme 4. Mechanism proposal for the electrochemical reduction of 1 using an Ag electrode under a CO2 atmosphere. Scheme 4. Mechanism proposal for the electrochemical reduction of 1 using an Ag electrode under a 2.3. Electrochemicarboxylation of 4-Iodobenzonitrile Once the electrochemical reduction mechanism was disclosed, electrocarboxylation processes CO2 atmosphere. The same general electrochemical trend was observed when DMF was replaced by [PP13]TFSI were performed using a carbon graphite rod and a silver foil electrode after its first reduction wave (ca. under a N2 and a CO2 atmosphere at the GC and silver electrodes. However, when using [EMIM]TFSI, −1.9 V) under a CO2 atmosphere. The results are summarized in Table 2. It is important to note that, the electrochemical reduction of benzonitrile was not detected in any of the cases due to the fact that when silver was used as a cathode, the electrochemical potential required was 0.5 V lower. A closer the reduction of the imidazolium cation appeared at less negative potentials either in inert or CO2 look at the data when carbon electrode was used indicates that when the electrocarboxylation process atmospheres [44]. was performed in [EMIM]TFSI, there was a loss of efficiency and no electrocarboxylation products were obtained (entry 1). Those facts can be easily explained by taking into account the IL electrochemical 2.3. Electrochemicarboxylation of 4-Iodobenzonitrile window and the acidity of the C2–H of the imidazolium moiety. The replacement of the carbon cathode for silver allowed the efficiency of the electrosynthesis to increase, since the reduction potential applied Once the electrochemical reduction mechanism was disclosed, electrocarboxylation processes was less negative, although no electrocarboxylated product was observed, again due to the acidity of were performed using a carbon graphite rod and a silver foil electrode after its first reduction wave the IL cation (entry 4). (ca. −1.9 V) under a CO2 atmosphere. The results are summarized in Table 2. It is important to note that, when silver was used as a cathode, the electrochemical potential required was 0.5 V lower. A Table 2. Results of the electrocarboxylation of 1. closer look at the data when carbon electrode was used indicates that when the electrocarboxylation process was performed in [EMIM]TFSI, there was a loss of efficiency and no electrocarboxylation products were obtained (entry 1). Those facts can be easily explained by taking into account the IL the carbon cathode for silver allowed the efficiency of the electrosynthesis to increase, since the Yield Entries Solvent Cathode Electrochemical Conditions Electrocarboxylated Ar-H electrochemical window and the acidity of the C2–H of the imidazolium moiety. The replacement of Products (Conversion Rate) Eapplied (V) F (C mol−1) 3 4 2 reduction potential applied was less negative, although no electrocarboxylated product was 1 [EMIM]TFSI Carbon −1.9 3.3 observed, again due to the acidity of the IL cation (entry 4). - 45% 2% (19%) 33% 12% (21%) 44% -- 95% 2 [PP13]TFSI Carbon 3 [PP13]TFSI Carbon −1.9 2.0 −1.9 3.0 −1.4 1.5 −1.4 1.0 −1.4 2.5 −1.4 3.0 −1.4 1.0 −1.4 2.4 - 8% (19%) - 4 [EMIM]TFSI 5 [PP13]TFSI 6 [PP13]TFSI 7 [PP13]TFSI 8 [BMPyr]TFSI 9 [N1114]TFSI Silver Silver Silver Silver Silver Silver 5% (10%) 26% (29%) 30% (30%) 10% (33%) 29% (38%) - 45% - 66% 70% 20% 48% The use of an IL composed of non-acidic cations enabled electrocarboxylated products to be obtained. When [PP13]TFSI was used, around 10% of electrocarboxylated products (p-cyanobenzoic acid (3) and benzoic acid (4)) were obtained using carbon electrodes (Scheme 5, entries 2 and 3). The use of a high reduction potential value caused the appearance of an unexpected carboxylation product, 4, which should be related to the further electrochemical reactions of compound 3 that take place under these electrochemical conditions. Note that when the charge passed to the system increased, the onlyPDF Image | Electrocatalytic Processes for the Valorization of CO2
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