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Molecules 2017, 22, 403 12 of 21 should be extracted with polar solvents or with the addition of medium polarity co-solvents into non-polar solvents. Rothermel et al. applied the methods by Grützke et al. for the extraction of electrolytes and the subsequently effect on the graphite anode recycling efficiency [127]. Therefore, they applied three different approaches for their investigations: (i) thermal evaporation of volatile electrolyte components; (ii) electrolyte extraction with subcritical CO2 and acetonitrile (ACN); and (iii) electrolyte extraction with supercritical CO2. It should be noted that they replaced the term liquid CO2 with subcritical CO2 due to the fact that the used parameters were in fact subcritical and not liquid conditions for the CO2. However, they concluded that the application of the supercritical carbon dioxide extraction method was unfavorable for the resulting crystallinity size of the graphite particles and therefore had an adverse impact on the electrochemical performance. In comparison, the electrolyte extraction using subcritical carbon dioxide was considered to be the “best” recycling method, as the recycled graphite showed the best electrochemical performance and the electrolyte was recovered by 90% including the conductive salt. In general, with the help of analytical and electrochemical characterization techniques it was shown that graphite originating from a previously electrochemically aged commercial cell subjected to a subcritical carbon dioxide assisted electrolyte in combination with a thermal treatment demonstrated the best electrochemical characteristics outperforming even fresh commercial synthetic graphite TIMREX® SLP50 which was used as benchmark (Table 2). Table 2. Overview of the discharge capacities and associated Coulombic efficiencies obtained from electrochemical charge/discharge cycling experiments. SubCO2: subcritical carbon dioxide. It was reprinted with permission from reference [127], Copyright John Wiley & Sons, 2016. Sample (State of Health (SOH) thermal (100%) thermal (70%) subCO2 (100%) subCO2 (70%) scCO2 (100%) scCO2 (70%) benchmark Coulombic Efficiency/% Discharge Capacity 50th Cycle/mAh·g−1 332.7 ± 0.3 346.8 ± 7.8 372.7 ± 2.5 379.9 ± 4.4 348.8 ± 1.9 375.0 ± 1.0 357.6 ± 1.4 1st Cycle 56.1 ± 1.8 85.4 ± 0.5 81.6 ± 3.1 82.9 ± 0.9 78.7 ± 1.2 82.0 ± 1.4 84.8 ± 0.8 2nd Cycle 91.8 ± 0.4 97.8 ± 0.3 96.3 ± 1.2 97.6 ± 0.1 96.2 ± 0.4 97.2 ± 0.3 97.3 ± 0.2 3rd Cycle 94.7 ± 0.3 98.5 ± 0.3 97.6 ± 0.8 98.5 ± 0.1 97.4 ± 0.4 98.2 ± 0.2 98.2 ± 0.2 50th Cycle 99.8 ± 0.1 99.9 ± 0.1 99.9 ± 0.1 99.9 ± 0.1 99.9 ± 0.1 99.9 ± 0.1 99.9 ± 0.1 7. Application of Subcritical and Supercritical CO2 as a Sample Preparation Tool Besides minor aging investigations after supercritical or subcritical extraction (presented by Grützke et al. [19,104,163]) and the influence of the extraction method on the recyclability of graphite (reported by Rothermel et al. [127]), there is a recent study which focused primarily on aging investigations [165]. The aging experiments were conducted on commercial 18,650-type state-of-the-art cells to determine the influence of temperature during electrochemical cycling on the aging behavior of the different cell components. The cells, based on the Li(Ni0.5Co0.2Mn0.3)O2/graphite chemistry, were aged at 20 °C and 45 °C to different states of health. The electrolyte was extracted based on the methods by Grützke et al. [19,163]. With the help of electrolyte aging analysis by GC-MS, it was shown, that temperature dependent cycling leads to differences in SEI composition. The electrolyte samples which were extracted with supercritical CO2 from fresh and aged cells and revealed the following composition: the electrolyte of the fresh cell consisted of DMC and EC and PC as solvents, whereas fluoroethylene carbonate (FEC) [166] and succinonitrile [167] were identified as electrolyte additives in significant amounts. Furthermore, traces of vinylene carbonate (VC) [75] and 1,3-propane sultone [168] were detected in the electrolyte (Figure 13). The cell aged at 45 °C shows traces of FEC in the electrolyte after more than 1000 cycles. In contrast, the additive FEC was no longer detected in the cells cycled at 20 °C. With the help of the supercritical CO2 extraction, which made even traces of electrolyte additives and decomposition products available, they could conclude that after FECPDF Image | CO2 for Recycling and Sample Preparation of Lithium Ion Battery
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