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7 protocols using 1 methylpyrrolidine

1

Synthesis of Alkyl Halides and Ethers

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All solvents and chemical reagents were purchased from Merck, Darmstadt, Germany and used without any purification. The CAS number, source and grade of the chemicals are as follows: 1-bromobutane (109-65-9, Merck, 99%), 1-methylpyrrolidine (120-94-5, Merck, 98%), 1,4-dibromobutane (110-51-1, Merck, 99%), 2-propanol (67-63-0, Merck, 99.5%) and diethyl ether (60-29-7, Merck, 99.9%).
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2

Activated Carbon from PET Face Shields

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The used PET face shields were employed as the precursor material for synthesising activated carbon. Potassium hydroxide (KOH), sodium sulfate (Na2SO4), Nafion binder, 1-methylpyrrolidine, hydroxyethyl cellulose (HEC) were obtained from Merck. Isopropanol was purchased from VWR chemicals. Hydrochloric acid was obtained from Fisher Scientific. All chemicals were used without further purification.
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3

Synthesis and Characterization of Chitosan-Based CO2 Sorbents

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Chitosan (deacetylation degree 75–85%, viscosity 20–300 mPa·s, Mw 50–190 kDa), glutaraldehyde solution (grade II, 25 wt.% in H2O), 4-vinylbenzyl chloride (90% purity), poly(diallyldimethylammonium chloride) (P[DADMA]Cl) solution (20 wt. % in H2O, viscosity 250–500 mPa·s, average Mw 200,000–350,000 medium molecular weight), 1-methylpyrrolidine (≥ 98.0% purity), triethylamine (≥ 99.5% purity), and anion exchange resin Amberlyst A-26 (OH- form) were supplied by Sigma-Aldrich (St. Louis, MO, USA). 2,2′-Azobis(2-methylpropionitrile) (AIBN) was purchased from Glentham Life Sciences (Corsham, UK). Glacial acetic acid and absolute ethanol (EtOH) were both purchased from VWR (Radnor, PA, USA). NaOH (98% purity) was purchased from Panreac (Barcelona, Spain). DMSO-d6 was purchased from Euriso-top (Saint-Aubin, France). Water was purified using reverse osmosis (resistivity > 18 MΩ.cm, Milli-Q, Millipore®, Madrid, Spain). Carbon dioxide (99.8% purity) was supplied by Nippon Gases (Madrid, Spain). He 4.6 and CO2 4.5, supplied by Linde Portugal, were used in thermogravimetric analysis (TGA) and CO2 capture experiments. All chemicals were used without further purification.
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4

Synthesis and Characterization of ILs

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Materials TMOP and TEOP have been synthesized using phosphorus(V) oxychloride (99% purity, Sigma Aldrich) and respective alcohol triethylene glycol monomethyl ether (95% purity, Sigma Aldrich) and di(ethylene glycol) ethyl ether (99% purity, Sigma Aldrich). 1-Methylpyrrolidine (98% purity, Sigma Aldrich) 1,2dimethylimidazole (99% purity, Sigma Aldrich), 1-methylimidazole (98% purity, Sigma Aldrich), sodium sulfate (99% purity, Sigma Aldrich), ethyl acetate (99.5% purity, Sigma Aldrich) and hexane (99% purity, Sigma Aldrich) were used without further purification. All the synthesized ILs were kept in a vacuum oven at 90 1C for at least 3 days until the water content was less than 100 ppm (Table S4, ESI †), as determined by the Karl-Fischer titration using a 917 coulometer (Metrohm) placed inside a glovebox with water and oxygen contents less than 1 ppm. Multi-walled carbon nanotubes (Sigma Aldrich, 95% carbon, O.D.  L 6-9 nm  5 mm), activated charcoal (Sigma Aldrich, 100 mesh size), polyvinyl alcohol (Merck, M W 72 000) and glass microfiber filters (Whatman s ) were used as received.
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5

Synthesis of Polymer Electrolyte Membrane

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Poly(2,6-dimethyl-1,4-phenylene oxide) powder (PPO), 1-methylpyrrolidine (≥98%), and manganese (IV) oxide (5 μm, 99.99%) were supplied by Sigma-Aldrich (St. Louis, MO, USA). N-bromosuccinimide (NBS) for synthesis, benzoyl peroxide (BPO, with 25% H2O), and chlorobenzene were purchased from Merck Millipore. 1-methyl-2-pyrrolidinone (NMP), ethanol, methanol, and toluene all with Grade AR were purchased from QRëC (New Zealand). N,N-dimethylformamide (DMF) (LOBA Chemie, Grade AR, Mumbai, India), trimethylamine (TCI, ca. 25% in methanol), 1-methylimidazole (TCI, ≥99%), chloroform (BDH Chemicals, UK), and KOH plates (Kemaus, Australia) were used as received without further purification. Nickel (Ni) foam as cathode current collector with a purity of 99.97%, 100 pores per inch (PPI), and 1 mm thick was purchased from Qijing Trading Co., Ltd. (Wenzhou, China). Carbon black (Vulcan® XC-72, Cabot Corporation, Boston, MA, USA), BP-2000 (BLACK PEARLS® 2000, Cabot Corporation), and zinc plate (0.1 mm thick 99.99%, Shandong Yr Electronic Co., Ltd., Shandong, China) were used as received. Poly (styrene-co-butadiene) (Sigma-Aldrich, butadiene 4 wt%) was used to prepare binder for the cathode. Poly(vinyl acetate) (PVAc) from TOA Paint Public Co., Ltd. (Samut Prakarn, Thailand) and No. 4 Whatman filter paper (Sigma-Aldrich) were used to prepare the benchmark separator.
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6

Characterization of Ionic Liquid Samples

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All chemicals used in the syntheses were
of reagent grade obtained from commercial sources and used as received.
1-Methylimidazole, 1-methylpyrrolidine, and 2-chloroethyl methyl sulfide
were purchased from Sigma-Aldrich. Lithium bis(trifluoromethylsulfonyl)imide
was obtained from IoLiTec, Inc. Dimethyl sulfoxide-d6 was purchased from Cambridge Isotope Laboratories. 1H and 13C NMR spectra were recorded on a Bruker
400 MHz NMR spectrometer with Topspin software.
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7

Synthesis of Ionic Liquids and Solvents

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1-methylimidazole (>99%), 1-methylpyrrolidine (>98%), pyridine (>99%), 1-bromooctane
lithium bis(trifluoromethane)sulfonylimide (99.95>%) sodium hexafluoroantimonate (V) (technical grade), acetonitrile, ethyl acetate, dichloromethane and methanol were purchased from Sigma Aldrich (Steinheim, Germany). All chemical products were used without additional purification.
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