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4 protocols using 1 bromooctane

1

Synthesis of Ionic Liquids and Catalysts

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Pt/C catalyst (20 wt %,
HiSPEC-3000, Johnson Matthey) was purchased from Alfa Aesar. HClO4 solution (70%) was purchased from Sigma-Aldrich. 1-Ethyl-3-methylimidazolium
bis(trifluomethanesulfonyl)imide ([C2C1im][NTf2]) and lithium bis(trifluomethanesulfonyl)imide
(NTf2) (99%) were purchased from IoLiTec GmbH. 1-Bromobutane
(≥98%) and 1-bromodecane (≥98%) were obtained from Merck.
1-Bromohexane (≥99%) and 1-bromooctane (≥99%) were provided
by Acros Organics. 1-Methylimidazole (99%) was supplied by Solvent
Innovation GmbH. All chemicals were used as received without further
purification.
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2

Synthesis of Ionic Liquids from Alkyl Halides

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The following chemicals were used for the synthesis of ILs: 1-bromobutane (Sigma-Aldrich, 99%), 1-bromooctane (Acros Organics, 99%), 1-bromododecane (Acros Organics, 98%), triethylamine (Acros Organics, 99% pure), 1-methylimidazole, 1-chlorobutane (Sigma Aldrich, 99,5%), diethylether (Lach-Ner, 99%), n-pentane (Penta, p.a.). The 1-methylimidazole was purified by distillation and drying with potassium hydroxide. The other chemicals were used as received.
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3

Synthetic Procedures and Characterization

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N,N-Dimethylethanolamine (99%), ethanol (99.9%), ethyl iodide (98%), 2-propanol (99%), HCl conc. (35%), NaNO2 (99%), phenol (98%) K2CO3 (99.5%), Na2CO3 (99.5%), NaOH (98%), 1-bromododecane (99%), 1-bromoheptane (99%), 1-bromooctane (99%) and 1,6-dibromohexane (99%) were purchased from Acros Organics and used without further purification. Petroleum ether (b.p. 60–90 °C), acetonitrile (99.9%), dichloromethane (99.9%), acetone (99%) and ethyl acetate (99%) were commercial products obtained from Acros Organics. 1H NMR (400 MHz) and 13C NMR (100 MHz) were recorded on a Bruker 400 MHz Ultrashield™ spectrometer. Elemental analysis was performed using a CHN elemental analyser.
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4

Synthesis and Characterization of Novel Polymers

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PEtOx (poly(2-ethyl-2-oxazoline), 50 kDa, Sigma Aldrich, St. Louis, MO, USA), HClaq (hydrochloric acid 37 wt.% in H2O, Acros Organics, Geel, Belgium), NaOH (sodium hydroxide, Chempur, Piekary Śl., Poland), diethyl ether (Chempur, Piekary Śl., Poland), 1,5-dibromopentane (Acros Organics, Geel, Belgium), 1-bromooctane (Acros Organics, Geel, Belgium), methyliodide (Acros Organics, Geel, Belgium), NaHCO3 (sodium bicarbonate, Chempur, Piekary Śl., Poland), anhydrous ethanol (Stanlab, Lublin, Poland), hexane (Chempur, Piekary Śl., Poland), Bis-GMA (bisphenol A glycerolate dimethacrylate, Sigma-Aldrich, St. Louis, MO, USA), TEGDMA (triethylene glycol dimethacrylate, Sigma-Aldrich, St. Louis, MO, USA), CQ (camphorquinone, Sigma-Aldrich, St. Louis, MO, USA), DMAEMA (dimethylaminoethyl methacrylate, Sigma-Aldrich, St. Louis, MO, USA) were used as received.
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