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Deep eutectic solvents (DESs) for cellulose dissolution: a mini-review

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Abstract

Deep eutectic solvents (DESs), which are a novel class of sustainable designer solvents, have attracted considerable attentions in the field of cellulose chemistry. Due to their low cost and analogous physico-chemical properties to ionic liquids, DESs are expected to be alternative solvents for dissolving cellulose. However, at present, the solubility of cellulose in DESs is much lower than in most ionic liquids. In this mini-review, we briefly summarize the current state of knowledge about cellulose dissolution in DESs. By comparing with similar solvents, it was found that the components of current DESs are usually involved in hydrogen bond interaction making difficult their interaction with the hydrogen bond network of cellulose. Accordingly, we propose a strategy that the components which have good hydrogen bond accepting ability, such as Cl-, OAc-, HCOO-, (MeO)2PO2-, morpholine and imidazole, are promising choices to form DESs for cellulose dissolution. Ultrasound-assisted treatment and adding a surfactant are effective ways to promote cellulose solubility by enhancing the permeability of DESs.

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References

  • Abbott AP, Capper G, Davies DL, Munro HL, Rasheed RK, Tambyrajah V (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem Commun 19:2010

    Article  CAS  Google Scholar 

  • Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun 1:70–71

    Article  CAS  Google Scholar 

  • Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004a) Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. J Am Chem Soc 126:9142–9147

    Article  CAS  PubMed  Google Scholar 

  • Abbott AP, Capper G, Davies DL, Rasheed R (2004b) Ionic liquids based upon metal halide/substituted quaternary ammonium salt mixtures. Inorg Chem 43:3447–3452

    Article  CAS  PubMed  Google Scholar 

  • Abbott AP, Alhaji AI, Ryder KS, Horne M, Rodopoulos T (2016) Electrodeposition of copper–tin alloys using deep eutectic solvents. Trans Inst Met Finish 94:104–113

    Article  CAS  Google Scholar 

  • Abe M, Fukaya Y, Ohno H (2010) Extraction of polysaccharides from bran with phosphonate or phosphinate-derived ionic liquids under short mixing time and low temperature. Green Chem 12:1274–1280

    Article  CAS  Google Scholar 

  • Adorjan I, Sjoberg J, Rosenau T, Hofinger A, Kosma P (2004) Kinetic and chemical studies on the isomerization of monosaccharides in N-methylmorpholine-N-oxide (NMMO) under Lyocell conditions. Carbohyd Res 339:1899–1906

    Article  CAS  Google Scholar 

  • Dai YT, van Spronsen J, Witkamp GJ, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68

    Article  CAS  PubMed  Google Scholar 

  • Ding SY, Himmel ME (2006) The maize primary cell wall microfibril: a new model derived from direct visualization. J Agric Food Chem 54:597–606

    Article  CAS  PubMed  Google Scholar 

  • Ding SY, Liu YS, Zeng Y, Himmel ME, Baker JO, Bayer EA (2012) How does plant cell wall nanoscale architecture correlate with enzymatic digestibility? Science 338(6110):1055–1060

    Article  CAS  Google Scholar 

  • Ek M (ed) (2009) Pulping chemistry and technology, vol 2. Walter de Gruyter, Berlin

    Google Scholar 

  • Eyckens DJ, Demir B, Walsh TR, Welton T, Henderson LC (2016) Determination of Kamlet–Taft parameters for selected solvate ionic liquids. Phys Chem Chem Phys 18:13153–13157

    Article  CAS  PubMed  Google Scholar 

  • Francisco M, van den Bruinhorst A, Kroon MC (2012) New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing. Green Chem 14:2153–2157

    Article  CAS  Google Scholar 

  • Ghasemi M, Alexandridis P, Tsianou M (2017) Cellulose dissolution: insights on the contributions of solvent-induced decrystallization and chain disentanglement. Cellulose 24:571–590

    Article  CAS  Google Scholar 

  • Gross AS, Bell AT, Chu JW (2013) Preferential interactions between lithium chloride and glucan chains in N, N-dimethylacetamide drive cellulose dissolution. J Phys Chem B 117:3280–3286

    Article  CAS  PubMed  Google Scholar 

  • Heinze T, Koschella A (2005) Solvents applied in the field of cellulose chemistry: a mini review. Polímeros 15:84–90

    Article  CAS  Google Scholar 

  • Hertel M, Bommarius A, Realff M, Kang Y (2012) Deep eutectic solvent systems and methods. Patent, WO2012/145522

  • Imran M, El-Fahmy S, Revol-Junelles AM, Desobry S (2010) Cellulose derivative based active coatings: Effects of nisin and plasticizer on physico-chemical and antimicrobial properties of hydroxypropyl methylcellulose films. Carbohyd Polym 81:219–225

    Article  CAS  Google Scholar 

  • Itoh T (2014) Design of ionic liquids for cellulose dissolution. In: Fang Z, Smith R Jr, Qi X (eds) Production of biofuels and chemicals with ionic liquids. Springer, Dordrecht, pp 91–106

    Chapter  Google Scholar 

  • Jørgensen H, Kristensen JB, Felby C (2007) Enzymatic conversion of lignocelluloses into fermentable sugars: challenges and opportunities. Biofuels Bioprod Biorefin 1:119–134

    Article  CAS  Google Scholar 

  • Kamlet MJ, Taft RW (1976) The solvatochromic comparison method. I. The beta-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 98:377–383

    Article  CAS  Google Scholar 

  • Kongruang S (2008) Bacterial cellulose production by Acetobacter xylinum strains from agricultural waste products. Appl Biochem Biotechnol 148:245–256

    Article  CAS  PubMed  Google Scholar 

  • Kosan B, Michels C, Meister F (2008) Dissolution and forming of cellulose with ionic liquids. Cellulose 15:59–66

    Article  CAS  Google Scholar 

  • Lan W, Liu CF, Yue FX, Sun RC, Kennedy JF (2011) Ultrasound-assisted dissolution of cellulose in ionic liquid. Carbohyd Polym 86(2):672–677

    Article  CAS  Google Scholar 

  • Lindman B, Karlstr MG, Stigsson L (2010) On the mechanism of dissolution of cellulose. J Mol Liq 156:76–81

    Article  CAS  Google Scholar 

  • Liu JJ, Zhang JM, Zhang BQ, Zhang XY, Xu LL, Zhang J, He JS, Liu CY (2016) Determination of intrinsic viscosity-molecular weight relationship for cellulose in BmimAc/DMSO solutions. Cellulose 23:2341–2348

    Article  CAS  Google Scholar 

  • Lu BL, Xu AR, Wang JJ (2014) Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids. Green Chem 16:1326–1335

    Article  CAS  Google Scholar 

  • Lynam JG, Kumar N, Wong MJ (2017) Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. Biores Technol 238:684–689

    Article  CAS  Google Scholar 

  • Malaeke H, Housaindokht MR, Monhemi H, Izadyar M (2018) Deep eutectic solvent as an efficient molecular liquid for lignin solubilization and wood delignification. J Mol Liq 263:193–199

    Article  CAS  Google Scholar 

  • Miller RF (2011) Deep eutectic solvents and applications. Patent, US8022014

  • Ohno H, Fukaya Y (2009) Task specific ionic liquids for cellulose technology. Chem Lett 38:2–7

    Article  CAS  Google Scholar 

  • Pan M, Zhao G, Ding C, Wu B, Lian Z, Lian H (2017) Physicochemical transformation of rice straw after pretreatment with a deep eutectic solvent of choline chloride/urea. Carbohyd Polym 176:307–314

    Article  CAS  Google Scholar 

  • Parviainen A, Wahlstrom R, Liimatainen U, Liitia T, Rovio S, Helminen JKJ, Hyvakko U, King AWT, Suurnakki A, Kilpelainen I (2015) Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo 4.3.0 non-5-enium acetate: a batch simulation of the IONCELL-F process. RSC Adv 5:69728–69737

    Article  CAS  Google Scholar 

  • Ren Q, Wu J, Zhang J, He J, Guo M (2003) Synthesis of 1-allyl,3-methylimidazolium-based room-temperature ionic liquid and preliminary study of its dissolving cellulose. Acta Polym Sin 1:448–451

    Google Scholar 

  • Ren HW, Chen CM, Wang QH, Zhao DS, Guo SH (2016a) The properties of choline chloride-based deep eutectic solvents and their performance in the dissolution of cellulose. BioResources 11:5435–5451

    CAS  Google Scholar 

  • Ren HW, Chen CM, Guo SH, Zhao DS, Wang QH (2016b) Synthesis of a novel allyl-functionalized deep eutectic solvent to promote dissolution of cellulose. BioResources 11:8457–8469

    CAS  Google Scholar 

  • Rosenau T, Potthast A, Sixta H, Kosma P (2001) The chemistry of side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process). Prog Polym Sci 26:1763–1837

    Article  CAS  Google Scholar 

  • Satlewal A, Agrawal R, Bhagia S, Sangoro J, Ragauskas AJ (2018) Natural deep eutectic solvents for lignocellulosic biomass pretreatment: recent developments, challenges and novel opportunities. Biotechnol Adv. https://doi.org/10.1016/j.biotechadv.2018.08.009

    Article  PubMed  Google Scholar 

  • Sen S, Martin JD, Argyropoulos DS (2013) Review of cellulose non-derivatizing solvent interactions with emphasis on activity in inorganic molten salt hydrates. ACS Sustain Chem Eng 1:858–870

    Article  CAS  Google Scholar 

  • Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114:11060–11082

    Article  CAS  PubMed  Google Scholar 

  • Sun N, Rodríguez H, Rahman M, Rogers RD (2011) Where are ionic liquid strategies most suited in the pursuit of chemicals and energy from lignocellulosic biomass? Chem Commun 47:1405–1421

    Article  CAS  Google Scholar 

  • Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellose with ionic liquids. J Am Chem Soc 124:4974–4975

    Article  CAS  PubMed  Google Scholar 

  • Tang X, Zuo M, Li Z, Liu H, Xiong CX, Zeng XH, Sun Y, Hu L, Liu SJ, Lei TZ, Lin L (2017) Green processing of lignocellulosic biomass and its derivatives in deep eutectic solvents. ChemSusChem 10:2696–2706

    Article  CAS  PubMed  Google Scholar 

  • Tenhunen T-M, Lewandowska AE, Orelma H, Johansson L-S, Virtanen T, Harlin A, Österberg M, Eichhorn SJ, Tammelin T (2017) Understanding the interactions of cellulose fibres and deep eutectic solvent of choline chloride and urea. Cellulose 25:137–150

    Article  CAS  Google Scholar 

  • Trygg J, Fardim P (2011) Enhancement of cellulose dissolution in water-based solvent via ethanol-hydrochloric acid pretreatment. Cellulose 18:987–994

    Article  CAS  Google Scholar 

  • Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537

    Article  CAS  PubMed  Google Scholar 

  • Wang S, Lu A, Zhang LN (2016) Recent advances in regenerated cellulose materials. Prog Polym Sci 53:169–206

    Article  CAS  Google Scholar 

  • Werner S, Haumann M, Wasserscheid P (2010) Ionic liquids in chemical engineering. Annu Rev Chem Biomol Eng 1:203–230

    Article  CAS  PubMed  Google Scholar 

  • Zdanowicz M, Wilpiszewska K, Spychaj T (2018) Deep eutectic solvents for polysaccharides processing. A review. Carbohyd Polym 200:361–380

    Article  CAS  Google Scholar 

  • Zhang QH, Vigier KD, Royer S, Jerome F (2012a) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41:7108–7146

    Article  CAS  PubMed  Google Scholar 

  • Zhang QH, Benoit M, Vigier KD, Barrault J, Jerome F (2012b) Green and inexpensive choline-derived solvents for cellulose decrystallization. Chem Eur J 18:1043–1046

    Article  CAS  PubMed  Google Scholar 

  • Zhao H (2003) Current studies on some physical properties of ionic liquids. Phys Chem Liq 41(6):545–557

    Article  CAS  Google Scholar 

  • Zhou E, Liu H (2014) A novel deep eutectic solvents synthesized by solid organic compounds and its application on dissolution for cellulose. Asian J Chem 26:3626–3630

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We thank the National Key R&D Program of China (2017YFD0601004) for financial support.

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Authors and Affiliations

  1. Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, Beijing, 100083, China

    Yang-Lei Chen, Xun Zhang, Ting-Ting You & Feng Xu

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  1. Yang-Lei Chen
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  2. Xun Zhang
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  3. Ting-Ting You
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  4. Feng Xu
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Correspondence to Xun Zhang or Feng Xu.

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Chen, YL., Zhang, X., You, TT. et al. Deep eutectic solvents (DESs) for cellulose dissolution: a mini-review. Cellulose 26, 205–213 (2019). https://doi.org/10.1007/s10570-018-2130-7

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