Extended dissolution studies of cellulose in imidazolium based ionic liquids
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1 Electronic Supplementary Information Extended dissolution studies of cellulose in imidazolium based ionic liquids Jürgen Vitz, a,b Tina Erdmenger, a,b Claudia Haensch, a,b Stephanie Hornig # and Ulrich S. Schubert* a,b,c a Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, P. O. Box 513, NL-5600 MB Eindhoven, The Netherlands, Tel.: , Fax: ; u.s.schubert@tue.nl, b Dutch Polymer Institute (DPI), P.O. Box 902, NL-5600 AX Eindhoven, The Netherlands, Tel.: , Fax: ; c Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, D Jena, Germany, Tel.: +49(0) , Fax:+49(0) ; ulrich.schubert@uni-jena.de # Current address: Kompetenzzentrum Polysaccharidforschung, Friedrich-Schiller-University Jena, Humboldtstr. 10, Jena, Germany Content 1 Analytical data Tables Figures Schemes... 6
2 1 Analytical data 1 H NMR and 13 C NMR spectra were recorded on a Varian Mercury spectrometer (400 MHz) or on a Varian Gemini spectrometer (300 MHz). Chemical shifts are given in ppm downfield from TMS. IR spectra were recorded on a Perkin Elmer 1600 FT-IR ATR spectrometer. Also a Bruker TENSOR 37 equipped with a HTS-XT (High Throughput Screening extension) compartment and a HYPERION 3000 microscope was used. 1 H NMR: chemical shift (multiplicity, number of protons, assignment, coupling constant). [C 2 MIM]F 1-ethyl-3-methylimidazolium fluoride: 1 H NMR: δ H (300 MHz, DMSO) 1.37 (t, 3H, J = 7.2 Hz), 3.81 (s, 3H), 4.14 (q, 2H, J = 7.2 Hz), 7.65 (bs, 2H), (bs, 1H). [C 2 MIM]Br 1-ethyl-3-methylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 1.39 (t, 3H, J = 7.4 Hz), 3.83 (s, 3H), 4.18 (q, 2H, J = 7.4 Hz), 7.69 (s, 1H), 7.78 (s, 1H), 9.15 (s, 1H). FT-IR: ν max /cm (H 2 O), 3144, 3071, 2983, 1628, 1570, 1452, 1336, 1167, 1089, 829, 753. [C 3 MIM]Br 1-methyl-3-propylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.84 (t, 3H, J = 7.4 Hz), 1.79 (dd, 3H, J = 7.3, 14.4 Hz), 3.86 (s, 3H), 4.14 (t, 2H, J = 7.1 Hz), 7.74 (s, 1H), 7.81 (s, 1H), 9.23 (s, 1H). FT-IR: ν max /cm , 3058, 2964, 2876, 1568, 1458, 1386, 1336, 1169, 1090, 753. [C 4 MIM]Br 1-butyl-3-methylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.89 (t, 3H, J = 7.3 Hz), 1.25 (m, 2H), 1.76 (m, 2H), 3.86 (d, 3H, J = 1.7 Hz), 4.18 (t, 2H, J = 7.2 Hz), 7.74 (s, 1H), 7.82 (s, 1H), 9.25 (s, 1H). [C 5 MIM]Br 1-methyl-3-pentylimidazolium bromide: 1 H NMR: δ H (300 MHz, CDCl 3 ) 0.74 (bs, 3H), 1.20 (s, 4H), 1.78 (d, 2H, J = 6.8 Hz), 4.00 (s, 3H), 4.20 (t, 2H, J = 7.3 Hz), 7.47 (s, 1H), 7.62 (s, 1H), (s, 1H). [C 6 MIM]Br 1-hexyl-3-methylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.85 (s, 3H), 1.25 (s, 6H), 1.76 (s, 2H), 3.85 (d, 3H, J = 4.0 Hz), 4.16 (s, 2H), 7.72 (s, 1H), 7.79 (s, 1H), 9.19 (s, 1H). 2
3 [C 7 MIM]Br 1-heptyl-3-methylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.84 (bs, 3H), 1.24 (s, 8H), 1.77 (s, 2H), 3.85 (s, 3H), 4.16 (t, 2H, J = 7.2 Hz), 7.73 (s, 1H), 7.80 (s, 1H), 9.20 (s, 1H). [C 8 MIM]Br 1-methyl-3-octylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.84 (t, 3H, J = 6.7 Hz), 1.24 (s, 10H), 1.76 (s, 2H), 3.84 (s, 3H), 4.15 (t, 2H, J = 7.2 Hz), 7.72 (d, 1H, J = 1.7 Hz), 7.78 (d, 1H, J = 1.7 Hz), 9.17 (s, 1H). [C 9 MIM]Br 1-methyl-3-nonylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.84 (t, 3H, J = 6.7 Hz), 1.23 (s, 12H), 1.76 (s, 2H), 3.84 (s, 3H), 4.15 (t, 2H, J = 7.2 Hz), 7.72 (d, 1H, J = 1.7 Hz), 7.79 (t, 1H, J = 1.8 Hz), 9.19 (s, 1H). [C 10 MIM]Br 1-decyl-3-methylimidazolium bromide: 1 H NMR: δ H (300 MHz, DMSO) 0.83 (s, 3H), 1.23 (s, 14H), 1.76 (s, 2H), 3.85 (s, 2H), 4.15 (s, 3H), 7.72 (s, 1H), 7.79 (s, 1H), 9.20 (s, 1H). [AllylMIM]Br 1-allyl-3-methylimidazolium bromide: 1 H NMR δ H (300 MHz, CDCl 3 ) 4.08 (s, 3H), 4.98 (d, 2H, J = 6.3 Hz), 5.43 (t, 2H, J = 13.0 Hz), 5.99 (d, 1H, J = 6.5 Hz), 7.48 (s, 1H), 7.67 (s, 1H), (s, 1H). FT-IR: ν max /cm , 2959, 2934, 2874, 1568, 1465, 1382, 1253, 1170, 742, 657. [DiMIM]I 1,3-dimethylimidazolium iodide: 1 H NMR δ H (400 MHz, DMSO) 3.84 (s, 6H), 7.66 (s, 2H), 9.02 (s, 1H). [C 4 MIM]I 1-butyl-3-methylimidazolium iodide: 1 H NMR: δ H (300 MHz, CDCl 3 ) 0.91 (t, 3H, J = 8.2 Hz), (m, 2H), (m, 2H), 4.05 (s, 3H), 4.30 (pt, 2H, J = 7.4), 7.51 (pt, 1H, J = 1.7 Hz), 7.59 (pt, 1H, J = 1.7 Hz), 9.92 (s, 1H). FT-IR: ν max /cm (H 2 O), 3140, 3077, 2958, 2933, 2872, 1568, 1462, 1382, 1337, 1165, 820, 749. [DiMIM]Me 2 PO 4 1,3-dimethylimidazolium dimethyl-phosphate: 1 H NMR: δ H (400 MHz, CDCl 3 ) 3.24 (s, 3H), 3.26 (s, 3H), 3.83 (s, 6H), 7.70 (d, 2H, J = 1.6 Hz), 9.31 (s, 1H). FT-IR: ν max /cm , 3068, 2945, 2838, 1575, 1462, 1241, 1179, 1091, 1036, 850, 770, 731. [C 2 MIM]Et 2 PO 4 1-ethyl-3-methylimidazolium diethyl-phosphate: 1 H NMR: δ H (400 MHz, DMSO) 1.04 (t, 6H, J = 7.1 Hz), 1.39 (t, 3H, J = 7.3 Hz), 3.59 (p, 4H, J = 7.0 Hz), 3.84 (s, 3H), 4.18 (q, 2H, J = 7.3 Hz), 7.71 (s, 1H), 7.80 (s, 1H), 9.38 (s, 1H). FT-IR: 3
4 ν max /cm (H 2 O), 3073, 2974, 2934, 2893, 1572, 1232, 1173, 1107, 1082, 1043, 935, 779, 733. [C 4 MIM]Bu 2 PO 4 1-butyl-3-methylimidazolium dibutyl-phosphate: 1 H NMR: δ H (400 MHz, DMSO) 0.85 (m, 9H), (m, 10H), (m, 2H), (m, 4H), 3.84 (s, 3H), 4.15 (t, 2H, J = 7.2 Hz), 7.71 (s, 1H), 7.78 (s, 1H), 9.36 (s, 1H). FT-IR: ν max /cm (H 2 O), 3078, 2959, 2936, 2874, 1570, 1464, 1236, 1173, 1067, 1026, 1005, 974, 889, 820, 797, 733. [C 2 MIM]OAc 1-ethyl-3-methylimidazolium acetate: 1 H NMR: δ H (400 MHz, DMSO) 1.39 (t, 5H, J = 7.3 Hz), 3.84 (s, 3H), 4.19 (q, 3H, J = 7.3 Hz), 7.72 (d, 1H, J = 1.6 Hz), 7.81 (s, 1H), (m, 1H). FT-IR: ν max /cm (H 2 O), 3073, 2981, 1562, 1451, 1427, 1384, 1331, 1172, 907, 759, 701, 667. [C 4 MIM]OAc 1-butyl-3-methylimidazolium acetate: 1 H NMR: δ H (400 MHz, DMSO) 0.87 (t, 3H, J = 8.4 Hz), 1.23 (dq, 2H, J = 7.4, 14.7 Hz), 1.56 (s, 3H), 1.74 (dt, 2H, J = 7.4, 14.8 Hz), 3.85 (s, 4H), (m, 2H), 7.73 (s, 1H), 7.79 (s, 1H), 9.72 (s, 1H). [C 4 MIM]NO 3 1-butyl-3-methylimidazolium nitrate: 1 H NMR: δ H (300 MHz, DMSO) 0.90 (t, 3H, J = 7.3 Hz), 1.26 (dq, 2H, J = 7.3, 14.6 Hz), (m, 2H), 3.85 (s, 3H), 4.16 (t, 2H, J = 7.2 Hz), 7.71 (pt, 1H, J = 1.7 Hz), 7.78 (pt, 1H, J = 1.8 Hz), 9.13 (s, 1H). [C 4 MIM]NTf 2 1-butyl-3-methylimidazolium bis(trifluoro-methylsulfonyl)imide: NMR: δ H (400 MHz, DMSO) (m, 3H), 1.23 (m, 2H), 1.75 (m, 2H), 3.82 (s, 3H), 4.14 (q, 2H, J = 3.6 Hz), 7.68 (s, 1H), 7.75 (s, 1H), 9.08 (s, 1H). FT-IR: ν max /cm (H 2 O), 3017, 2971, 2946, 1738, 1729, 1456, 1435, 1365, 1353, 1229, 1217, 1204, 1183, 1132, 1053, 741, H 4
5 2 Tables Table 1 Synthesized imidazolium based ionic liquids with different side chain lengths. N N 120 C + Br nch 3 microwave n=1-9 N N n CH 3 Br - Ionic liquid Reaction time (min) Conversion (%) b T decomp ( C) c T m ( C) [C 2 MIM]Br 20 >99 a [C 3 MIM]Br 30 >99 a d [C 4 MIM]Br 10 >99 a d [C 5 MIM]Br d [C 6 MIM]Br 10 >99 a d [C 7 MIM]Br 10 >99 a d [C 8 MIM]Br 10 >99 a [C 9 MIM]Br 10 >99 a [C 10 MIM]Br 10 >99 a a No starting material detectable (determined by 1 H NMR). b Temperature of thermal decomposition. c Melting point. d Melting point could not be determined by DSC. Table 2 DP of cellulose samples after processing in [C 4 MIM]Cl under microwave heating. IL Temperature Time DP ( C) (min) Avicel PH a [C 4 MIM]Cl b b b b a Before processing, b after regeneration. 3 Figures Fig. 1 Parallel setup to study the dissolution of cellulose. 5
6 Fig. 2 Dissolution of cellulose in [C 2MIM]Cl under microwave irradiation: a) 6 wt-% of cellulose, 100 C, power between 60 and 140 W, b) 2 10 wt-% of cellulose, 140 C, 80 W, 30 min, c) 2 10 wt-% of cellulose, 160 C, 80 W, 30 min Temperature ( C, line) Power (Watt, dash) Cellulose (wt-%) Time (min) Fig. 3 Heating and power profiles for the dissolution of cellulose in [C 2MIM]Cl at different concentrations under microwave irradiation. 4 Schemes NR 3 OAc - N N Cl - N N OAc - NR 3 Cl - Scheme 1 Schematic representation of the anion exchange with Amberlite IRA-400. Scheme 2 Schematic representation of the reaction scheme and schematic process of the anion exchange with AgF. 6
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