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Molecules 2017, 22, 403 2 of 21 electrical and electronic equipment needs to be collected by the EU members. The reuse and recovery rate for end of life vehicles is set to at least 85% regarding both the weight per vehicle and the calendar year. Furthermore, the Battery Directive 2006/66/EC was instituted as the most advanced battery recycling legislation worldwide. Each EU member state has to meet a collection rate of 45% and at least a recycling efficiency of 50 wt % for non-lead-acid and non-nickel-cadmium batteries [11–13]. With regard to upcoming pilot processes and plants, the LIB aging has to be taken into account. New or only lightly used LIBs from electric vehicles are not the focus of recycling strategies. Foremost, damaged batteries or batteries that have achieved the end of life (EOL), i.e., strongly aged batteries, are in the focus of recycling. Aging is one of the main performance deteriorations of LIBs as aging leads to capacity loss, resistance increase, power and energy loss and therefore to a reduced lifetime [14,15]. Aging may also be responsible for safety changes of batteries [16]. However, there is no “universal aging mechanism”; in fact, numerous aging mechanisms occur and they can affect each other. Reports in the literature usually focused on the individual parts of the LIB cell such as the reactions between the electrolyte and the anode, solid electrolyte interphase (SEI) growth, the decomposition of cathode and anode, or lithium metal deposition on the anode [17–29] or on the interaction between the different materials [30]. Additionally, the operating conditions have a great influence of the degradation behavior [31–33]. However, the decomposition of the electrolyte is challenging to investigate due to its complex composition. Because of the sensitivity towards water and thermal influence, the literature reveals numerous reports about aging products and mechanisms. The variety of decomposition products includes HF [34–40], inorganic and organic (fluoro)phosphates (OPs) [41–48], CO2 [49,50], dicarboxylates and oligocarbonate based products [51–53], diols [54] and alkyl fluorides [36,45,50]. Furthermore, the applied analysis methods and corresponding reaction mechanisms have been intensively discussed in literature and new reports are constantly added [55,56]. Especially, the fluorinated decomposition compounds and, in particular HF, are in special focus with regard to pilot processes and plants, since, due their chemically aggressive nature and their toxicity, they can seriously hamper or damage the industrial recycling approaches. Therefore, these compounds need to be removed before the recycling process. However, aged LIBs, where the liquid electrolyte is partially decomposed into solid and gaseous products, often appear as “dry”. During operation, the electrolyte immobilizes into the deeper layers of the electrode and into the solid electrolyte decomposition products and can therefore not easily be recovered either for simple removal or subsequent analysis. Sub- and supercritical CO2 are attractive extraction tools for overcoming both challenges. While it is still a young research field, the usage of CO2 as a recycling or sample preparation tool for the recovery and analysis of materials is repeatedly found in the literature in the last years. 2. Lithium Ion Batteries Electrolytes Lithium ion batteries consist of a carbon/graphite based anode, a lithium transition metal oxide cathode and an electrolyte soaked polyolefin-based separator [57,58]. The electrolyte inside a lithium ion battery has to fulfill several requirements: wide electrochemical stability window, high ionic conductivity and redox stability are some of the desired requirements [59]. Additionally, the chemical and electrochemical compatibility with the other cell constituents should be ensured; furthermore, the electrolyte should be non-toxic, safe, environmentally friendly and cost efficient [60,61]. In order to meet these requirements, the electrolyte system typically consists of a conducting salt (1 M), dissolved in a mixture of different linear carbonates, e.g., dimethyl carbonate (DMC), ethyl methyl carbonate (EMC) or dimethyl carbonate (DEC), and a cyclic carbonate such as propylene carbonate (PC) or ethylene carbonate (EC) [62–64] (Figure 1). The most commercially applied conducting is lithium hexafluorophosphate (LiPF6) (Figure 1) while alternatives such as lithium tetraborate (LIBF4), lithium bis-(oxalato)borate (LiBOB) or ionic liquids (ILs) are possible [62,65–70]. Electrolyte additives are used up to 5%, either by weight or by volume [71]. Due to the application of additives, the electrolyte properties can be influenced: improvement of the flammability, enabling overcharge protection [71–73] or the SEI formation [25,74–78]. The SEI is formed during the first charge/dischargePDF Image | CO2 for Recycling and Sample Preparation of Lithium Ion Battery
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