Phosphorus 5 oxychloride

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.

All chemicals, except for phosphoric acid esters, were purchased from commercial sources and used without further purification: zinc acetate dihydrate (99%, Merck KGaA), zinc oxide (≥99%, Merck KGaA), sodium hydroxide (pure, POCh Gliwice), phosphorus(V) oxychloride (99%, Sigma-Aldrich), benzyltriethylammonium chloride (99%, Sigma-Aldrich), 4-nitrophenol (≥99%, Merck Schuchardt OHG), 4-methoxyphenol (≥99%, Merck Schuchardt OHG), ethyl 4-hydroxybenzoate (99%, Sigma-Aldrich), and methyl-terminated polydimethylsiloxane (PDMS100; POLSIL®OM 100, viscosity 1 × 10 -4 m 2 s -1 at 25 °C, Chemical Plant "Silikony Polskie" Ltd). Before use, PDMS100 was vacuum-dried (1.33 × 10 -6 mbar) at 120 °C for 10 h.