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. 2012 Jun 15;17(6):7458–7502. doi: 10.3390/molecules17067458

Table 1.

Overview over cellulose derivatives, in ionic liquids (ILs).

Entry Substituent (Cell-OR) DS a ILs b Comments c Ref.
carbamates
1 Inline graphicphenyl carbamate 0.5–3.0 BMIMCl [36]
0.3–3.0 BMIMCl - derivatization of bacterial cellulose [37]
2 Inline graphic3-(triethoxysilyl)propyl carbamete 0.43, 2.95 BMIMCl - hydrolysis of ethoxysilyl groups directly after synthesis [38]
carboxylic acid esters
3 Inline graphicacetate 0.9–2.8 AMIMCl [39,40]
1.9–3.0 BMIMCl, EMIMCl, BDMIMCl, ADMIMBr [36,41]
0.7–3.0 BMIMCl - derivatization of bacterial cellulose [37]
4 Inline graphicpropionate/butyrate/… and mixed esters ≈0.5–2.9 ABIMCl, BMIMAc, DOHMIMAc, HMIMAc, MOEMIMAc - cellulose esters and mixed esters prepared- microwave irradiation (partly)- also pentanoates and hexanoates prepared [42,43,44]
1.4–2.7(DSoverall) AMIMCl - acetate-butyrates and acetate-propionates prepared- derivatization of cellulose from sugarcane bagasse [45]
0.5–2.9(DSoverall) BMIMAc, BMIMCl, BMIMDMP, BMIMPr, EMIMAc, TBMADMP - cellulose esters and mixed esters prepared- co-solvents applied (partly)- also mixed esters with benzoate prepared [16,17,18,19,20]
0.2–2.5 BMIMCl, EMIMAc - heterogeneous conversion with gaseous ketenes- acetates, propionates, and pentanoates prepared [21]
5 Inline graphicbenzoates 1.0–3.0 AMIMCl [46]
6 Inline graphicfuorate 0.5–3.0 BMIMCl - activation of carboxylic acid with N,N’-carbonyldiimidazole (partly) [47]
7 Inline graphiclaurate 0.3–1.5 BMIMCl - phase separation with increasing DS [36]
8 Inline graphicstearate 2.2–2.6 BMIMCl [48]
9 Inline graphicpivalate, adamantate, trimethylbenzoate 0.9–1.4 AMIMCl - comparison with DMA/LiCl and DMSO/TBAF [49]
10 Inline graphicsuccinate, phthalate 0.2–2.5 AMIMCl, BMIMCl - derivatization of cellulose from sugarcane bagasse- catalysts applied - co-solvents utilized (partly) [50,51,52,53]
11 Inline graphicglutarate 0.3–1.2 BMIMCl - ultrasound irradiation [54]
12 Inline graphiccarboxylates containing amino groups 0.1-1.2 BMIMCl - tosyl chloride used to form reactive intermediates- co-solvents utilized [55,56]
13 Inline graphicoxy-carboxylic acid esters 0.1–3.0 AMIMCl, BMIMCl, EMIMCl - activation of oxy-carbonic acid with N,N’-carbonyldiimidazole- derivatization of bacterial cellulose (partly) [57]
14 Inline graphic2-halo carboxylate macro-initiators 0.6–1.0 AMIMCl - co-solvents utilized- bromo compounds utilized [58,59,60]
0.3–1.9 BMIMCl - chloro compounds utilized [61]
15 Inline graphicdehydroabiatate 1.4–1.9 BMIMBr - catalyst applied [62]
16 Inline graphicpyro-pheophorbide 0.07 AMIMCl - activation of acid with N,N'-carbonyldiimidazole [63]
ethers
17 Inline graphichydroxethyl/hydroxypropyl 0.1–2.2 BMIMCl, BDMIMCl, BDTAC, EMIMAc - co-solvents utilized [64,65]
18 Inline graphictrityl/methoxytrityl 0.8, 1.8 AMIMCl - pyridine utilized as base and co-solvent [66]
0.8–1.4 BMIMCl - pyridine utilized as base and co-solvent [67]
19 Inline graphiccarboxymethyl 0.49 BMIMCl - co-solvents utilized- heterogeneous (solid NaOH used as base)- gel-like system formed [36]
n.a. BMIMCl - heterogeneous (solid NaOH used as base) [68]
20 Inline graphictrimethylsilyl 0.4–2.9 BMIMCl, EMIMAc - co-solvents utilized [69]
0.2–3.0 BMIMCl, BMIMAc, BMIMBz, BMIMPr, EMIMAc, EMIMDEP - heterogeneous derivatization (polar and non-polar liquid phase) [70]
sulfuric/sulfonic acid esters
21 Inline graphicsulfate 0.1–1.5 AMIMCl, BMIMCl, EMIMCl - co-solvents utilized [71,72]
1.3–1.7 BMIMCl - co-solvents utilized [73]
22 Inline graphictosylate 0.1–1.1 AMIMCl, BMIMCl - co-solvents utilized, reaction at 25 °C [74]
0.84 AMIMCl - reaction at 10 °C [63]
deoxy cellulose derivatives
23 Inline graphicchloro-deoxy 0.8–1.l BMIMCl - co-solvent utilized- strong polymer degradation [75]
grafts
24 Inline graphicgraft-poly(L-lactide) 0.7–2.7(1.4–4.5) d AMIMCl - grafting by ring-opening of L-lactide- 4-dimethylamino pyridine applied as catalyst [76]
25 Inline graphicgraft-poly(acrylic acid) n.a. BMIMCl - initiation by persulfate - microwave irradiation [77]
26 Inline graphicgraft-poly(N-isopropylacrylamide) n.a. BMIMCl - initiation by γ-ray irradiation [78]
27 Inline graphicgraft-poly(methyl methacrylate) 0.3–1.9 BMIMCl - derived from 14 by atom transfer radical polymerization [61]

a Range of degrees of substitution (DS), n.a.: no information available; b Cations: ABIM+: 1-allyl-3-butylimidazolium, ADMIM+: 1-allyl-2,3-dimethylimidazolium, AMIM+: 1-allyl-3-methylimidazolium, BDMIM+: 1-butyl-2,3-dimethylimidazolium, BMIM+: 1-butyl-3-methylimidazolium, BDMTA+: benzyldimethyltetradecylammonium, DOHMIM+: 1-(3,6-dioxa-(1-heptyl))-3-methylimidazolium, EDMIM+: 1-ethyl-2,3-dimethylimidazolium, EMIM+: 1-ethyl-3-methylimidazolium, EMPIP+: 1-ethyl-1-methylpiperidinium, HEMIM+: 1-hydroxyethyl-3-methylimidazolium, HMIM+: 1-hexyl-3-methylimidazolium, MOEMIM+: 1-(2-methoxyethyl)-3-methylimidazolium, TBMA+: tributylmethylammonium, TEMA+: triethtylmethylammonium, anions: Ac: acetate, Br: bromide, Bz: benzoate, Cl: chloride, DEP-:diethylposphate, DEP: dimethylposphate, Fo: formate, MPo: methylphosphonate, Pr: propionate; c Completely homogeneous conversion, if not noted otherwise; d Values in braces represent degree of polymerization of the grafted chain.