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Molecules 2017, 22, 403 8 of 21 CO2 phase. This results in decreasing density of the helium head pressure carbon dioxide with reduced dissolving power towards aromatic analytes [160]. Nonetheless, compared to liquid solvent extraction, subcritical and supercritical CO2 extraction offers unique advantages. The extraction is fast, highly selective and efficient. Furthermore, pre- or post-concentration or cleanup steps are not necessary [161]. 6. Application of Subcritical and Supercritical CO2 for Recycling of LIB Electrolytes The use of CO2 as an extraction medium was first mentioned in a patent by Sloop et al. Typical for a patent, the details about conditions and parameters as well as influence of the processing on the battery materials were not disclosed [115]. There are no further reports about any application of the patented process. The first application of supercritical CO2 for the extraction of LIB electrolytes was reported by Grützke et al., 2014 [19]. They applied supercritical helium head pressure carbon dioxide (scHHPCO2) in an autoclave and investigated the extraction behavior with a set of two different separators and electrolytes (Figure 6). The extracts were analyzed by gas chromatography–mass spectrometry and ion chromatography–electrospray ionization–mass spectrometry to determine the recovery rate and the nature of the obtained electrolyte composition. It was stated that the recovery rates and extract compositions were strongly depending on the material of which the electrolyte was extracted. The highest achieved recovery rate was 73.5 ± 3.6 wt %. Figure 6. Schematic setup of the applied extraction procedure by Grützke et al. It was reproduced from reference [19] with permission from Elsevier, 2014. After these proof-of-principle-experiments, commercial 18,650 cells were investigated as real samples. In addition to a reference cell, which was opened and extracted after formation, i.e., as supplied, LIB cells were electrochemically aged at 20 °C and 45 °C for post-mortem studies. The extracts were again analyzed by both mentioned techniques. Beside the electrolyte constituents, the following aging products were found and characterized: dimethyl-2,5-dioxahexane dicarboxylate (DMDOHC), ethylmethyl-2,5-dioxahexane dicarboxylate (EMDOHC) and diethyl-2,5-dioxahexane dicarboxylate (DEDOHC). In all experiments, they showed the applicability of the CO2 extraction. Furthermore, besides the application as a recycling tool, they showed the usefulness of the method for aging investigations on electrochemically treated cells. However, due to the obtained recovery rate, flow-through experiments with additional co-solvents were proposed in order to optimize the recovery rate. Dai et al. described an alternative approach for the recovery of LIB electrolytes from separators with a commercial extraction system [162] (Figure 7). Fourier transform infrared spectroscopy (FT-IR), gas chromatography—mass spectrometry (GC-MS), 19F- and 31P-NMR and inductivelyPDF Image | CO2 for Recycling and Sample Preparation of Lithium Ion Battery
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