Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass
Abstract
:1. Introduction
2. Dissolution of Cellulose in ILs
2.1. ILs
2.2. Mechanism of Cellulose Dissolution
2.3. Hydrogen Bond Basicity of Cellulose Dissolving ILs
2.4. Viscosity of Concentrated Cellulose Solutions in ILs
2.5. Water Effect on the Anion Interaction with Cellulose
3. Industrial Cellulose Derivative Production Methods
3.1. Esterification
3.2. Etherification
4. Cellulose Precipitation
5. Recycling of ILs after Cellulose Processing
6. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
Abbreviations
[Amim]Cl | 1-Allyl-3-methylimidazolium chloride |
[Bmim]BF4 | 1-Butyl-3-methylimidazolium tetrafluoroborate |
[Emim]HCO2 | 1-Ethyl-3-methylimidazolium formate |
[Bmim]PF6 | 1-Butyl-3-methylimidazolium hexafluorophosphate |
[Prmim]HCO2 | 1-Propyl-3-methylimidazolium formate |
[Emim]MeOSO3 | 1-ethyl-3-methylimidazolium methylsulfate |
[Amim]HCO2 | 1-Allyl-3-methylimidazolium formate |
[Emim]MeSO3 | 1-Ethyl-3-methylimidazolium methanesulfonate |
[Bmim]OAc | 1-Butyl-3-methylimidazolium acetate |
[Emim]CF3CO2 | 1-Ethyl-3-methylimidazolium trifluoroacetate |
[Bmim]Cl] | 1-Butyl-3-methylimidazolium chloride |
[Emim]SCN | 1-Ethyl-3-methylimidazolium thiocyanate |
[Bmim]HCO2 | 1-Butyl-3-methylimidazolium formate |
[Emim]BF4 | 1-Ethyl-3-methylimidazolium tetrafluoroborate |
[Emim](MeO)2PO2 | 1-Ethyl-3-methylimidazolium dimethylphosphate |
[Emim]N(CN)2 | 1-Ethyl-3-methylimidazolium dicyanamide |
[Emim](MeO)HPO2 | 1-Ethyl-3-methylimidazolium methylphosphonate |
[Emim]I | 1-Ethyl-3-methylimidazolium iodide |
[Emim](MeO)MePO2 | 1-Ethyl-3-methylimidazolium methyl methylphosphonate |
[Emim]PF6 | 1-Ethyl-3-methylimidazolium hexafluorophosphate |
[Emim](EtO)2PO2 | 1-Ethyl-3-methylimidazolium diethylphosphate |
[Bmim]CH3SO3 | 1-Butyl-3-methylimidazolium methanesulfonate |
[Emim]Cl | 1-Ethyl-3-methylimidazolium chloride |
[Bmim]Br | 1-Butyl-3-methylimidazolium bromide |
[Emim]H2PO2 | 1-Ethyl-3-methylimidazolium dyhidrogenphosphate |
[Amim](MeO)HPO2 | 1-Allyl-3-methylimidazolium methylphosphonate |
[Prmim](MeO)HPO2 | 1-Propyl-3-methylimidazolium methylphosphonate |
[Bmim](MeO)HPO2 | 1-Butyl-3-methylimidazolium methylphosphonate |
[Emim]OAc | 1-Ethyl-3-methylimidazolium acetate |
ECOENG 41M | 1-Butyl-3-methylimidazolium 2-(2-methoxyethoxy)-ethylsulfate |
[Emim]CH3SO3 | 1-Ethyl-3-methylimidazolium methanesulfonate |
[Emim]CF3SO3 | 1-Ethyl-3-methylimidazolium: trifluoromethanesulfonate |
[Emim]Tos | 1-Ethyl-3-methylimidazolium tosylate |
[Emim]EtSO4 | 1-Ethyl-3-methylimidazolium ethylsulfate |
[Empy]EtSO4 | 1-Ethyl-3-methylpyridinium ethylsulfate |
[Epy]EtSO4 | 1-Ethylpyridinium ethylsulfate |
[EEpy]EtSO4 | 1,2-Diethylpyridinium ethylsulfate |
[Mpy]CH3SO4 | 1-methylpyridinium methylsulfate |
[MMpy]CH3SO4 | 1,3-Dimethylpyridinium methylsulfate |
[EMpy]CH3SO4 | 2-ethyl-1-methylpyridinium methylsulfate |
[Bmpyr]OAc | 1-Butyl-1-methylpyrrolidinium acetate |
[Bmpyr]CF3SO3 | 1-Butyl-1-methylpyrrolidinium trifluoromethanesulfonate |
[Bmpyr](BtO)HPO2 | 1-Butyl-1-methylpyrrolidinium butylphosphonate |
[Empyr](EtO)HPO2 | 1-Ethyl-1-methylpyrrolidinium ethylphosphonate |
[DBNH]OAc | 1,5-diaza-bicyclo[4.3.0]non-5-enium acetate |
[Emim]DEP | 1-Ethyl-3-methylimidazolium diethylphosphate |
[Bdmim]Cl | 1-Butyl-2,3-methylimidazolium chloride |
[Admim]Br | 1-Allyl-2,3-methylimidazolium bromide |
[Bmim]OPr | 1-butyl-3-methylimidazolium propionate |
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ILs (Cellulose Solubility > 1%) 1,2 | η (mPa·s) | Tm (°C) | Tdec (°C) | Kamlet–Taft Parameters 3 | Ref. | ILs (Cellulose Solubility < 1%) | β | Ref. | ||
---|---|---|---|---|---|---|---|---|---|---|
β | α | π* | ||||||||
[Amim]Cl | 2090 | 256 | 0.83 | 0.46 | 1.17 | [87] | [Bmim]BF4 | 0.38 | [86] | |
[Emim]HCO2 | 52 | 212 | [87] | [Bmim]PF6 | 0.21 | [86] | ||||
[Prmim]HCO2 | 117 | 0.99 | 0.48 | 1.08 | [87] | [Emim]MeOSO3 | 0.61 | [89] | ||
[Amim]HCO2 | 66 | 205 | 0.99 | 0.48 | 1.08 | [87] | [Emim]MeSO3 | 0.70 | [89] | |
[Bmim]OAc | 1.09 | 0.55 | 0.99 | [88] | [Emim]CF3CO2 | 0.74 | [91] 4 | |||
[Bmim]Cl | 66 | 254 | 0.95 | 0.47 | 1.10 | [91] | [Emim]SCN | 0.71 | [91] | |
[Bmim]HCO2 | 1.01 | 0.56 | 1.03 | [88] | [Emim]BF4 | 0.55 | [91,92] 5 | |||
[Emim](MeO)2PO2 | 265 | 21 | 289 | 1.00 | 0.51 | 1.06 | [89] | [Emim]N(CN)2 | 0.64 | [91] |
[Emim](MeO)HPO2 | 107 | 275 | 1.00 | 0.52 | 1.06 | [89] | [Emim]I | 0.75 | [91] | |
[Emim](MeO)MePO2 | 510 | 262 | 1.07 | 0.50 | 1.04 | [89] | [Emim]PF6 | 0.44 | [91] | |
[Emim](EtO)2PO2 | 1.00 | [89] | [Bmim]CH3SO3 | 0.85 | [91] | |||||
[Emim]Cl | 89 | 285 | [92] | [Bmim]Br | 0.87 | [91] | ||||
[Emim]H2PO2 | 17 | 260 | 0.97 | 0.52 | 1.09 | [93] | ||||
[Amim](MeO)HPO2 | 123 | 265 | 0.99 | 0.51 | 1.06 | [93] | ||||
[Prmim](MeO)HPO2 | 219 | 277 | 1.00 | 0.54 | 1.02 | [93] | ||||
[Bmim](MeO)HPO2 | 287 | 277 | 1.02 | 0.52 | 1.01 | [93] | ||||
[Emim]OAc 6,7 | 162 | 0.95 | 0.40 | 1.09 | [94,95] | |||||
|
IL 1 | T (°C) | η (mPa·s) | ρ (kg/m3) | Water (wt %) 2 | Ref. |
---|---|---|---|---|---|
Methylimidazolium | |||||
[Bmim]OAc | 20 | 646 | 1.100 | [103] | |
ECOENG 41M | 20 | 1676 | 0.083 | [103] | |
[Bmim]OAc | 20 | 429 | 1055 | 0.085 | [104] |
[Bmim]Cl | 25 | 1080 | 0.220 | [105] | |
[Amim]Cl | 25 | 821 | 1166 | 0.180 | [106] |
[Emim]OAc | 20 | 202 | 1102 | 0.124 | [107] |
[Emim](MeO)HPO2 | 20 | 286 | 1212 | 0.078 | [107] |
[Emim]CH3SO3 | 20 | 232 | 1246 | 0.029 | [107] |
[Emim]CF3SO3 | 20 | 52 | 1390 | 0.002 | [107] |
[Emim]Tos | 30 | 1417 | 1223 | 0.056 | [107] |
[Emim](MeO)2PO2 | 30 | 193 | 1214 | 0.014 | [107] |
[Emim]EtSO4 | 20 | 125 | 1240 | 0.105 | [108] |
Pyridinium | |||||
[Empy]EtSO4 | 20 | 204 | 0.026 | [103] | |
[Epy]EtSO4 | 20 | 183 | 0.068 | [103] | |
[EEpy]EtSO4 | 25 | 325 | 1220 | <0.08 | [109] |
[Mpy]CH3SO4 | 25 | 116 | 1345 | <0.06 | [109] |
[MMpy]CH3SO4 | 25 | 129 | 1302 | <0.06 | [109] |
[EMpy]CH3SO4 | 25 | 456 | 1285 | <0.08 | [109] |
Pyrrolidinium | |||||
[Bmpyr]OAc | 25 | 107 | 1021 | 0.070 | [104] |
[Bmpyr]CF3SO3 | 20 | 222 | 1256 | 0.072 | [100] |
[Bmpyr](BtO)HPO2 | 25 | 321 | 1082 | 0.025 | [110] |
[Empyr](EtO)HPO2 | 25 | 320 | 1123 | 0.021 | [110] |
|
Fiber/Solvent 1 | Cross-Section Shape | Tenacity Cond. (cN/tex) | Elongation Cond. (%) | Commercial/Experimental Fiber | Ref. |
---|---|---|---|---|---|
Viscose | Lobate | 22 | com. | [156] | |
NMMO | Round | 40.2 | 13.0 | com. | [157] |
[Emim]Cl | Round | 43.0 | 9.6 | exp. | [157] |
[Bmim]Cl | Round | 50.1 | 9.3 | exp. | [157] |
[Emim]OAc | Round | 44.7 | 10.4 | exp. | [157] |
1 N-methylmorpholine-N-oxide, NMMO;
|
IL 1 | Co-Solvent 2 | Catalyst | Base | wt % 3 | Reagent | Conditions 4 | DS 5 | Ref. |
---|---|---|---|---|---|---|---|---|
[Amim]Cl | DMAP | 4 | Propionic anhydride, butyric anhydride | 1:1–5:1; 2–180 min; 20–100 °C | Prop: 0.89–2.89, But: 0.91–2.76 | [168] | ||
[Amim]Cl | 4 | Propionic anhydride, acetic anhydride, butyric anhydride | 5:1, 9:1, 13:1; 60–300 min; 80–100 °C | Prop: 0.93–2.46, But: 0.86–2.07 | [170] | |||
[Bmim]Cl | Py | 11 | Acetyl chloride | 3:1, 5:1, 10:1; 2 h; 80 °C | Ac < 3.00 | [171] | ||
[Amim]Cl | Py/Et3N | 10 | Acetic anhydride, tosyl chloride | 3:1, 8:1; 48 h, r.t. | Ac: 2.99, Tos: 0.84 | [172] | ||
[Emim]OAc | IM | 3 | Tosyl chloride | 2:1; 300 min; 7 °C | Tos: 0.55 | [173] | ||
[Bmim]Cl | DMI | Py, BIM | 11 | Tosyl chloride | 1:1–5:1; 1–48 h; 25 °C | Tos: 1.14, Cl: 0.16 | [174] | |
[Bmim]Cl | Py | 11 | 2-furoyl chloride | 1:1, 3:1, 5:1; 0.5–17 h; 65 °C | 0.46–3.00 | [175] | ||
[Bmim]Cl [Emim]Cl [Bdmim]Cl [Admim]Br | Py | 11 | Acetyl chloride Phenyl isocyanate | 3:1, 5:1, 10:1; 15–120 min; 80 °C | Ac: 2.81–3.0 Carb:0.26–3.0 | [176] | ||
[Bmim]Cl | 6 | Phenyl isocyanate Acetic anhydride | 1:1–10:1; 120–240 min; 80 °C | Carb: 0.29–3.0 Ac: 0.69–3.0 | [177] | |||
[Bmim]Cl | 3 | Chloroacetyl chloride | 3:1, 5:1; 60–300 min; 30–50 °C | 0.33–1.87 | [178] | |||
[Amim]Cl | DMF | 4 | 2-bromopropionyl bromide | 5:1; 480 min; r.t. | 0.7 | [179] | ||
[Amim]Cl | 3–7 | Benzoyl chloride, 4-toluoyl chloride, 4-chlorobenzoyl chloride, 4-nitrobenzoyl chloride | 2:1–10:1; 60–240 min; 40–100 °C | 1–3.0 | [180] | |||
[Bmim]Cl | Py | 10–12 | Acetic anhydride, Propionic anhydride, Butyric anhydride, Pentanoic anhydride, Hexanoic anhydride | 1:1, 3:1, 5:1; 2 h; 80 °C | 0.4–3.0 | [181] | ||
[Bmim]Cl, [Amim]Cl, [Emim]OAc | DMF | 11 | Sulfur trioxide, chlorosulfonic acid | 1.3:1–3:1; 120–240 min; 25 °C | 0.22–0.89 | [182] | ||
[Bmim]Cl | 2.35 | Phthalic anhydride | 2:1–10:1; 20–120 min; 85–105 °C | 0.12–2.54 | [183] | |||
[Bmim]Cl | 2 | Succinic anhydride | 1:1–12:1; 5–120 min; 85–105 °C | 0.037–0.53 | [184] | |||
[Bmim]Cl | DMSO | NBS | 2 | Succinic anhydride | 4:1; 30–240 min; 90–120 °C | 0.24–2.31 | [185] | |
[Bmim]Cl | DMAP | 2 | Succinic anhydride | 4:1; 30–120 min; 60–110 °C | 0.24–2.34 | [186] | ||
[Bmim]Cl | Iodine | Succinic anhydride | 4:1; 30–120 min; 85–110 °C | 0.56–1.54 | [187] | |||
[Bmim]Oac [Bmim]Cl [Bmim]OPr | Carboxylic anhydrides, carboxylic acid halides, diketene, or acetoacetic acid esters | <0.2 (molar ratio) | 0.1–3.0 | [188] | ||||
6 | Ci to C20 straight- or branched-chain alkyl or aryl carboxylic anhydrides, carboxylic acid halides, diketene, or acetoacetic acid esters | 0.1–3.0 | [189] | |||||
7 | Acetic anhydride, Propionic anhydride, Butyric anhydride, 2-ethylhexanoic anhydride, Nonanoic anhydride | ≤3.0 | [190] | |||||
6 | 0.1–50 | Thionyl chloride, Methanesulfonyl chloride, Chlorodimethyliminium chloride, Phosphoryl chloride, Tosyl chloride | 30–150 °C | 0.5–3.0 | [191] | |||
6 | Py | 5–10 | Chlorosulfonic acid, Sulfur trioxide, Sulphuric acid, Sulfamic acid | 1:1–6:1; 1–720 min; 130 °C | 0.05–2.5 | [192] | ||
|
IL1 | Co-Solvent 2 | Base | Cellulose (wt %) 3 | Reagent | Conditions 4 | DS 5 | Ref. |
---|---|---|---|---|---|---|---|
[Emim]OAc [Emim]Cl | DMSO/DMA | Hexamethyldisilazane | 3:1, 5:1, 8:1; 1 h; 80 °C | 1.6–2.9 | [181] | ||
[Emim]Cl [Bmim]Cl [Emim]Oac [Bmim]OAc [Bmim]PrO | 10 | Hexamethyldisilazane | 1.8:1–9.2:1; 16 h, 80–120 °C | 1.2–2.9 | [196] | ||
[Bmim]Cl | Py | 11 | Trityl chloride | 1–14 h, 100 °C | 0.80–1.37 | [197] | |
[Amim]Cl | Py | 4-methoxytrityl chloride | 3:1, 6 h, 60 °C | ~2 | [198] | ||
[Amim]Cl | Py/BIM | 10 | Trityl chloride | 3:1, 6:1; 1–20 h; 90 °C | 0.02–0.95 | [199] | |
[Emim]OAc | DMSO | 4–11.5 | Propylene oxide, ethylene oxide | 5:1–50:1; 19 h; 80 °C | 0.09–1.34 | [200] | |
[Emim]OAc, [Bmim]Cl | H2O, DMSO, DMF, DME, CHCl3 | Propylene oxide, ethylene oxide, 1-allyloxy-2,3-epoxypropane, 2,3-epoxypropyl isopropyl, etherepichlorohydrine, 2,3-epoxypropyltrimethylammonium chloride, phenylglycidyether, 2,3-epoxypropyl isopropyl ether | 5:1, 10:1, 30:1; 3–72 h; 21–100 °C | 0.09–2.16 6 | [201] | ||
|
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Lopes, J.M.; Bermejo, M.D.; Martín, Á.; Cocero, M.J. Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass. ChemEngineering 2017, 1, 10. https://doi.org/10.3390/chemengineering1020010
Lopes JM, Bermejo MD, Martín Á, Cocero MJ. Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass. ChemEngineering. 2017; 1(2):10. https://doi.org/10.3390/chemengineering1020010
Chicago/Turabian StyleLopes, Joana Maria, María Dolores Bermejo, Ángel Martín, and María José Cocero. 2017. "Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass" ChemEngineering 1, no. 2: 10. https://doi.org/10.3390/chemengineering1020010
APA StyleLopes, J. M., Bermejo, M. D., Martín, Á., & Cocero, M. J. (2017). Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass. ChemEngineering, 1(2), 10. https://doi.org/10.3390/chemengineering1020010