Table 1.
Entry | Substituent (Cell-OR) | DS a | ILs b | Comments c | Ref. |
---|---|---|---|---|---|
carbamates | |||||
1 | phenyl carbamate | 0.5–3.0 | BMIMCl | [36] | |
0.3–3.0 | BMIMCl | - derivatization of bacterial cellulose | [37] | ||
2 | 3-(triethoxysilyl)propyl carbamete | 0.43, 2.95 | BMIMCl | - hydrolysis of ethoxysilyl groups directly after synthesis | [38] |
carboxylic acid esters | |||||
3 | acetate | 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 | propionate/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 | benzoates | 1.0–3.0 | AMIMCl | [46] | |
6 | fuorate | 0.5–3.0 | BMIMCl | - activation of carboxylic acid with N,N’-carbonyldiimidazole (partly) | [47] |
7 | laurate | 0.3–1.5 | BMIMCl | - phase separation with increasing DS | [36] |
8 | stearate | 2.2–2.6 | BMIMCl | [48] | |
9 | pivalate, adamantate, trimethylbenzoate | 0.9–1.4 | AMIMCl | - comparison with DMA/LiCl and DMSO/TBAF | [49] |
10 | succinate, phthalate | 0.2–2.5 | AMIMCl, BMIMCl | - derivatization of cellulose from sugarcane bagasse- catalysts applied - co-solvents utilized (partly) | [50,51,52,53] |
11 | glutarate | 0.3–1.2 | BMIMCl | - ultrasound irradiation | [54] |
12 | carboxylates containing amino groups | 0.1-1.2 | BMIMCl | - tosyl chloride used to form reactive intermediates- co-solvents utilized | [55,56] |
13 | oxy-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 | 2-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 | dehydroabiatate | 1.4–1.9 | BMIMBr | - catalyst applied | [62] |
16 | pyro-pheophorbide | 0.07 | AMIMCl | - activation of acid with N,N'-carbonyldiimidazole | [63] |
ethers | |||||
17 | hydroxethyl/hydroxypropyl | 0.1–2.2 | BMIMCl, BDMIMCl, BDTAC, EMIMAc | - co-solvents utilized | [64,65] |
18 | trityl/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 | carboxymethyl | 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 | trimethylsilyl | 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 | sulfate | 0.1–1.5 | AMIMCl, BMIMCl, EMIMCl | - co-solvents utilized | [71,72] |
1.3–1.7 | BMIMCl | - co-solvents utilized | [73] | ||
22 | tosylate | 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 | chloro-deoxy | 0.8–1.l | BMIMCl | - co-solvent utilized- strong polymer degradation | [75] |
grafts | |||||
24 | graft-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 | graft-poly(acrylic acid) | n.a. | BMIMCl | - initiation by persulfate - microwave irradiation | [77] |
26 | graft-poly(N-isopropylacrylamide) | n.a. | BMIMCl | - initiation by γ-ray irradiation | [78] |
27 | graft-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.