a.CAS Key Laboratory of Engineering Plastics, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, the Chinese Academy of Sciences, Beijing 100190, China
b.University of Chinese Academy of Sciences, Beijing 100049, China
zhangbq@iccas.ac.cn (B.Q.Z.)
liucy@iccas.ac.cn (C.Y.L.)
收稿:2022-04-13,
修回:2022-5-9,
录用:2022-5-16,
网络首发:2022-09-05,
纸质出版:2023-01-01
Scan QR Code
Xu, K. J.; Zhang, B. Q.; Qiao, X.; Liu, C. Y. Cellulose solubility in deep eutectic solvents: inspecting quantitative hydrogen-bonding analysis. Chinese J. Polym. Sci. 2023, 41, 75–83
Kuang-Jie Xu, Bao-Qing Zhang, Xin Qiao, et al. Cellulose Solubility in Deep Eutectic Solvents: Inspecting Quantitative Hydrogen-Bonding Analysis[J]. Chinese Journal of Polymer Science, 2023, 41(1): 75-83.
Xu, K. J.; Zhang, B. Q.; Qiao, X.; Liu, C. Y. Cellulose solubility in deep eutectic solvents: inspecting quantitative hydrogen-bonding analysis. Chinese J. Polym. Sci. 2023, 41, 75–83 DOI: 10.1007/s10118-022-2801-6.
Kuang-Jie Xu, Bao-Qing Zhang, Xin Qiao, et al. Cellulose Solubility in Deep Eutectic Solvents: Inspecting Quantitative Hydrogen-Bonding Analysis[J]. Chinese Journal of Polymer Science, 2023, 41(1): 75-83. DOI: 10.1007/s10118-022-2801-6.
The potential deep eutectic solvents (DESs) for cellulose dissolution and regeneration must be hydrogen-bond basic DESs that satisfy the criterion of Δ
α
Δ
β
<
0.
According to the Kamlet-Abraham-Taft (KAT) polarity parameters (
α
β
π
*
)
polymers and solvents can be categorized as hydrogen-bond (H-bond) acidic (
α
>
β
) or H-bond basic (
α
<
β
). Recently
we proposed a quantitative hydrogen bonding (QHB) analysis to predict the solubility of polymers in ionic liquids (ILs) using the product of Δ
α
Δ
β
<
0 as an indicator
where Δ
α
is the difference between the H-bond acidic parameters of the polymer and IL
and Δ
β
is the difference in their basicity
while the prerequisite of the “complementary” principle (
i.e.
that one component is H-bond acidic and the other is basic) is satisfied. Here
the applicability of QHB analysis was first confirmed by testing the solubilities of carefully chosen polymer/deep eutectic solvent (DES) pairs
as the DESs were eutectic mixtures dominated by hydrogen bonding interactions. Then
our attention focused on the solubility of cellulose in DESs. Our testing results as well as the typical published results were summarized
which indicate that the potential DESs for cellulose dissolution and regeneration must be of the H-bond basic type because the “complementary” principle should be satisfied as a prerequisite. However
the H-bond basic DESs investigated in this study do not show the superior solubility of cellulose that has been commonly observed for H-bond basic ILs
even if the criterion of Δ
α
Δ
β
<
0 is satisfied for both DESs and ILs. Possible reasons for this discrepancy are given to understand the varying effectiveness in cellulose dissolution for H-bond basic DESs and ILs.
Brem, A.; Lhost, O.; Tervoort, T. A . Influence of solvent quality and crystallization conditions on the drawability of ultra-high molecular weight polyethylene cast from solution . Macromolecules , 2020 . 53 5957 - 5970 . DOI: 10.1021/acs.macromol.0c00756 http://doi.org/10.1021/acs.macromol.0c00756 .
Pereira, R. F. P.; Brito-Pereira, R.; Goncalves, R.; Silva, M. P.; Costa, C. M.; Silva, M. M.; Bermudez, V. D.; Lanceros-Mendez, S . Silk fibroin separators: a step toward lithium-ion batteries with enhanced sustainability . ACS Appl. Mater. Interfaces , 2018 . 10 5385 - 5394 . DOI: 10.1021/acsami.7b13802 http://doi.org/10.1021/acsami.7b13802 .
Zhang, J. M.; Wu, J.; Yu, J.; Zhang, X. C.; Mi, Q. Y.; Zhang, J . Processing and functionalization of cellulose with ionic liquids . Acta Polymerica Sinica (in Chinese) , 2017 . 1058 - 1072 . DOI: 0.11777/j.issn1000-3304.2017.17066 http://doi.org/0.11777/j.issn1000-3304.2017.17066 .
Flory, P. J., Principles of Polymer Chemistry , Cornell University Press, New York, 1953 .
Hiemenz, P. C.; Lodge, T. P., Chapter 7 in Polymer Chemistry , 2 nd Edition, CRC Press, New York, 2007 .
Yuan, Y. F.; Zhang, J. M.; Zhang, B. Q.; Liu, J. J.; Zhou, Y.; Du, M. X.; Han, L. X.; Xu, K. J.; Qiao, X.; Liu, C. Y . Polymer solubility in ionic liquids: dominated by hydrogen bonding . Phys. Chem. Chem. Phys. , 2021 . 23 21893 - 21900 . DOI: 10.1039/D1CP03193G http://doi.org/10.1039/D1CP03193G .
Kamlet, M. J.; Abboud, J. L. M.; Abraham, M. H.; Taft, R. W. Linear solvation energy relationships. 23 . A comprehensive collection of the solvatochromic parameters π *, α , and β , and some methods for simplifying the generalized solvatochromic equation . J. Org. Chem. , 1983 . 48 2877 - 2887 . DOI: 10.1021/jo00165a018 http://doi.org/10.1021/jo00165a018 .
Abraham, M. H . Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes . Chem. Soc. Rev. , 1993 . 22 73 - 83 . DOI: 10.1039/cs9932200073 http://doi.org/10.1039/cs9932200073 .
Reichardt, C . Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N -phenolate betaine dyes . Green Chem. , 2005 . 7 339 - 351 . DOI: 10.1039/b500106b http://doi.org/10.1039/b500106b .
Spange, S.; Reuter, A.; Vilsmeier, E.; Heinze, T.; Keutel, D.; Linert, W . Determination of empirical polarity parameters of the cellulose solvent N,N -dimethylacetamide/LiCl by means of the solvatochromic technique . J. Polym. Sci.,Part A: Polym. Chem. , 1998 . 36 1945 - 1955 . DOI: 10.1002/(SICI)1099-0518(199808)36:11<1945::AID-POLA30>3.0.CO;2-C http://doi.org/10.1002/(SICI)1099-0518(199808)36:11<1945::AID-POLA30>3.0.CO;2-C .
Ab Rani, M, A.; Brant, A.; Crowhurst, L.; Dolan, A.; Lui, M.; Hassan, N. H.; Hallett, J. P.; Hunt, P. A.; Niedermeyer, H.; Perez-Arlandis, J. M.; Schrems, M.; Welton, T.; Wilding, R . Understanding the polarity of ionic liquids . Phys. Chem. Chem. Phys. , 2011 . 13 16831 - 16840 . DOI: 10.1039/c1cp21262a http://doi.org/10.1039/c1cp21262a .
Florindo, C.; McIntosh, A. J. S.; Welton, T.; Branco, L. C.; Marrucho, I. M . A closer look into deep eutectic solvents: exploring intermolecular interactions using solvatochromic probes . Phys. Chem. Chem. Phys. , 2018 . 20 206 - 213 . DOI: 10.1039/C7CP06471C http://doi.org/10.1039/C7CP06471C .
Smith, E. L.; Abbott, A. P.; Ryder, K. S . Deep eutectic solvents (DESs) and their applications . Chem. Rev. , 2014 . 114 11060 - 11082 . DOI: 10.1021/cr300162p http://doi.org/10.1021/cr300162p .
Hansen, B. B.; Spittle, S.; Chen, B.; Poe, D.; Zhang, Y.; Klein, J. M.; Horton, A.; Adhikari, L.; Zelovich, T.; Doherty, B. W.; Gurkan, B.; Maginn, E. J.; Ragauskas, A.; Dadmun, M.; Zawodzinski, T. A.; Baker, G. A.; Tuckerman, M. E.; Savinell, R. F.; Sangoro, J. R . Deep eutectic solvents: a review of fundamentals and applications . Chem. Rev. , 2021 . 121 1232 - 1285 . DOI: 10.1021/acs.chemrev.0c00385 http://doi.org/10.1021/acs.chemrev.0c00385 .
Ramon, D. J.; Guillena, G., Deep eutectic solvents: synthesis, properties, and applications , Wiley-VCH, Weinheim, Germany, 2020 .
Plotka-Wasylka, J.; de la Guardia, M.; Andruch, V.; Vilkova, M. Deep eutectic solvents vs ionic liquids: similarities and differences. M icrochem. J. 2020 , 159 , 105539.
Jablonsky, M.; Skulcova, A.; Sima, J . Use of deep eutectic solvents in polymer chemistry—a review . Molecules , 2019 . 24 3978 DOI: 10.3390/molecules24213978 http://doi.org/10.3390/molecules24213978 .
Wang, C. G.; Yang, S. Q.; Song, X. B.; Pi, Q. F.; Zhang, Q.; Liu, Q. Y.; Xu, Y.; Chen, L. G.; Ma, L. L . Novel solvent systems for biomass fractionation based on hydrogen-bond interaction: a minireview . Adv. Sustain. Syst. , 2020 . 4 2000085 DOI: 10.1002/adsu.202000085 http://doi.org/10.1002/adsu.202000085 .
Tome, L. C.; Mecerreyes, D . Emerging ionic soft materials based on deep eutectic solvents . J. Phys. Chem. B , 2020 . 124 8465 - 8478 . DOI: 10.1021/acs.jpcb.0c04769 http://doi.org/10.1021/acs.jpcb.0c04769 .
Sosa, F. H. B.; Dias, R. M.; Lopes, A. M. D.; Coutinho, J. A. P.; da Costa, M. C . Fast and efficient method to evaluate the potential of eutectic solvents to dissolve lignocellulosic components . Sustainability , 2020 . 12 3358 DOI: 10.3390/su12083358 http://doi.org/10.3390/su12083358 .
Hakkinen, R.; Abbott, A . Solvation of carbohydrates in five choline chloride-based deep eutectic solvents and the implication for cellulose solubility . Green Chem. , 2019 . 21 4673 - 4682 . DOI: 10.1039/C9GC00559E http://doi.org/10.1039/C9GC00559E .
Alizadeh, V.; Kirchner, B . Molecular level insight into the solvation of cellulose in deep eutectic solvents . J. Chem. Phys. , 2021 . 155 084501 DOI: 10.1063/5.0058333 http://doi.org/10.1063/5.0058333 .
Arunan, E.; Desiraju, G. R.; Klein, R. A.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.; Crabtree, R. H.; Dannenberg, J. J.; Hobza, P.; Kjaergaard, H. G.; Legon, A. C.; Mennucci, B.; Nesbitt, D. J. . Defining the hydrogen bond: an account (IUPAC Technical Report) . Pure Appl. Chem. , 2011 . 83 1619 - 1636 . DOI: 10.1351/PAC-REP-10-01-01 http://doi.org/10.1351/PAC-REP-10-01-01 .
Martins, M. A. R.; Crespo, E. A.; Pontes, P. V. A.; Silva, L. P.; Bulow, M.; Maximo, G. J.; Batista, E. A. C.; Held, C.; Pinho, S. P.; Coutinho, J. A. P . Tunable hydrophobic eutectic solvents based on terpenes and monocarboxylic acids . ACS Sustain. Chem. Eng. , 2018 . 6 8836 - 8846 . DOI: 10.1021/acssuschemeng.8b01203 http://doi.org/10.1021/acssuschemeng.8b01203 .
Shukla, S. K.; Mikkola, J. P . Intermolecular interactions upon carbon dioxide capture in deep-eutectic solvents . Phys. Chem. Chem. Phys. , 2018 . 20 24591 - 24601 . DOI: 10.1039/C8CP03724H http://doi.org/10.1039/C8CP03724H .
Farooq, M. Q.; Odugbesi, G. A.; Abbasi, N. M.; Anderson, J. L . Elucidating the role of hydrogen bond donor and acceptor on solvation in deep eutectic solvents formed by ammonium/phosphonium salts and carboxylic acids . ACS Sustain. Chem. Eng. , 2020 . 8 18286 - 18296 . DOI: 10.1021/acssuschemeng.0c06926 http://doi.org/10.1021/acssuschemeng.0c06926 .
Abbasi, N. M.; Farooq, M. Q.; Anderson, J. L . Investigating the variation in solvation interactions of choline chloride-based deep eutectic solvents formed using different hydrogen bond donors . ACS Sustain. Chem. Eng. , 2021 . 9 11970 - 11980 . DOI: 10.1021/acssuschemeng.1c04375 http://doi.org/10.1021/acssuschemeng.1c04375 .
Abbasi, N. M.; Farooq, M. Q.; Anderson, J. L . Modulating solvation interactions of deep eutectic solvents formed by ammonium salts and carboxylic acids through varying the molar ratio of hydrogen bond donor and acceptor . J. Chromatogr. A , 2021 . 1643 462011 DOI: 10.1016/j.chroma.2021.462011 http://doi.org/10.1016/j.chroma.2021.462011 .
Ghasemi, M.; Tsianou, M.; Alexandridis, P . Assessment of solvents for cellulose dissolution . Bioresour. Technol. , 2017 . 228 330 - 338 . DOI: 10.1016/j.biortech.2016.12.049 http://doi.org/10.1016/j.biortech.2016.12.049 .
Ge, W. J.; Shuai, J. B.; Wang, Y. Y.; Zhou, Y. X.; Wang, X. H . Progress on chemical modification of cellulose in “green” solvents . Polym. Chem. , 2022 . 13 359 - 372 . DOI: 10.1039/D1PY00879J http://doi.org/10.1039/D1PY00879J .
Zhou, Y.; Zhang, X. C.; Zhang, J. M.; Cheng, Y . H.; Wu, J.; Yu, J.; Zhang, J. Molecular weight characterization of cellulose using ionic liquids . Polym. Test , 2021 . 93 106985 DOI: 10.1016/j.polymertesting.2020.106985 http://doi.org/10.1016/j.polymertesting.2020.106985 .
Ren, H. W.; Chen, C. M.; Wang, Q. H.; Zhao, D. S.; Guo, S. H . The properties of choline chloride-based deep eutectic solvents and their performance in the dissolution of cellulose . BioResources , 2016 . 11 5435 - 5451 . .
Chen, YL; Zhang, X; You, T. T.; Xu, F . Deep eutectic solvents (DESs) for cellulose dissolution: a mini-review . Cellulose , 2019 . 26 205 - 213 . DOI: 10.1007/s10570-018-2130-7 http://doi.org/10.1007/s10570-018-2130-7 .
Zhong, Y. L.; Wu, J. W.; Kang, H. L.; Liu, R. G . Choline hydroxide based deep eutectic solvent for dissolving cellulose . Green Chem. , 2022 . 24 2464 - 2475 . DOI: 10.1039/D1GC04130D http://doi.org/10.1039/D1GC04130D .
Liu, Q. L.; Zhao, X. H.; Yu, D. K.; Yu, H. T.; Zhang, Y. B.; Xue, Z. M.; Mu, T. C . Novel deep eutectic solvents with different functional groups towards highly efficient dissolution of lignin . Green Chem. , 2019 . 21 5291 - 5297 . DOI: 10.1039/C9GC02306B http://doi.org/10.1039/C9GC02306B .
Ma, Y.; Xia, Q. Q.; Liu, Y. Z.; Chen, W. S.; Liu, S. X.; Wang, Q. W.; Liu, Y. X.; Li, J.; Yu, H. P . Production of nanocellulose using hydrated deep eutectic solvent combined with ultrasonic treatment . ACS Omega , 2019 . 4 8539 - 8547 . DOI: 10.1021/acsomega.9b00519 http://doi.org/10.1021/acsomega.9b00519 .
Teles, A. R. R.; Capela, E. V.; Carmo, R. S.; Coutinho, J. A. P.; Silvestre, A. J. D.; Freire, M. G. Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids. Fluid Phase Equilib. 2017 , 448 ,15−21.
Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D . Dissolution of cellulose with ionic liquids . J. Am. Chem. Soc. , 2002 . 124 4974 - 4975 . DOI: 10.1021/ja025790m http://doi.org/10.1021/ja025790m .
Zhang J. M.; Xu, L. L.; Yu, J.; Wu, J.; Zhang, X. Y.; He, J. S.; Zhang, J . Understanding cellulose dissolution: effect of the cation and anion structure of ionic liquids on the solubility of cellulose . Sci. China-Chem. , 2016 . 59 1421 - 1429 . DOI: 10.1007/s11426-016-0269-5 http://doi.org/10.1007/s11426-016-0269-5 .
Brehm, M.; Radicke, J.; Pulst, M.; Shaabani, F.; Sebastiani, D.; Kressler, J . Dissolving cellulose in 1,2,3-triazolium- and imidazolium-based ionic liquids with aromatic anions . Molecules , 2020 . 25 3539 DOI: 10.3390/molecules25153539 http://doi.org/10.3390/molecules25153539 .
Liu, F. Y.; Lv, Y. X.; Liu, J. J.; Yan, Z. C.; Zhang, B. Q.; Zhang, J.; He, J. S.; Liu, C. Y . Crystallization and rheology of poly(ethylene oxide) in imidazolium ionic liquids . Macromolecules , 2016 . 49 6106 - 6115 . DOI: 10.1021/acs.macromol.6b01171 http://doi.org/10.1021/acs.macromol.6b01171 .
Colby, R. H . Structure and linear viscoelasticity of flexible polymer solutions: comparison of polyelectrolyte and neutral polymer solutions . Rheol. Acta , 2010 . 49 425 - 442 . DOI: 10.1007/s00397-009-0413-5 http://doi.org/10.1007/s00397-009-0413-5 .
Graessley, W. W . Polymer chain dimensions and the dependence of viscoelastic properties on concentration, molecular weight and solvent power . Polymer , 1980 . 21 258 - 262 . DOI: 10.1016/0032-3861(80)90266-9 http://doi.org/10.1016/0032-3861(80)90266-9 .
Barik, S.; Chakraborty, M.; Mahapatra, A.; Sarkar, M . Choline chloride and ethylene glycol based deep eutectic solvent (DES) versus hydroxyl functionalized room temperature ionic liquids (RTILs): assessing the differences in microscopic behaviour between the DES and RTILs . Phys. Chem. Chem. Phys. , 2022 . 24 7093 - 7106 . DOI: 10.1039/D1CP05010A http://doi.org/10.1039/D1CP05010A .
Kundu, D.; Rao, P. S.; Banerjee, T . First-principles prediction of Kamlet-Taft solvatochromic parameters of deep eutectic solvent using the COSMO-RS Model . Ind. Eng. Chem. Res. , 2020 . 59 11329 - 11339 . DOI: 10.1021/acs.iecr.0c00574 http://doi.org/10.1021/acs.iecr.0c00574 .
0
浏览量
230
Downloads
0
CSCD
关联资源
相关文章
相关作者
相关机构
京公网安备11010802046900号