Levulinate amidinium protic ionic liquids (PILs) as suitable media for the dissolution and levulination of cellulose

Becherini, Stefano; Mezzetta, Andrea; Chiappe, Cinzia; Guazzelli, Lorenzo

doi:10.1039/c9nj00191c

Cited by 36 publications

(29 citation statements)

References 59 publications

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“…In this framework, fatty acids raised remarkable interest as building blocks for ILs containing natural hydrophobic tails [ 45 , 46 , 47 , 48 , 49 , 50 ] and such materials were investigated in pharmaceutical applications [ 42 , 51 , 52 , 53 , 54 ]. An intriguing subclass of ILs is that of the so-called protic ionic liquids (PILs), which are easily prepared by reacting a Brønsted acid and a Brønsted base [ 55 , 56 ].…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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For topical treatment of skin cancer, the design of pH-responsive nanocarriers able to selectively release the drug in the tumor acidic microenvironment represents a reliable option for targeted delivery. In this context, a series of newly synthesized surface-active fatty acid-protic ionic liquids (FA-PILs), based on tetramethylguanidinium cation and different natural hydrophobic fatty acid carboxylates, have been investigated with the aim of developing a pH-sensitive nanostructured drug delivery system for cutaneous administration in the skin cancer therapy. The capability of FA-PILs to arrange in micelles when combined with each other and with the non-ionic surfactant d-α-Tocopherol polyethylene glycol succinate (vitamin E TPGS) as well as their ability to solubilize imiquimod, an immuno-stimulant drug used for the treatment of skin cancerous lesions, have been demonstrated. The FA-PILs-TPGS mixed micelles showed pH-sensitivity, suggesting that the acidic environment of cancer cells can trigger nanostructures’ swelling and collapse with consequent rapid release of imiquimod and drug cytotoxic potential enhancement. The in vitro permeation/penetration study showed that the micellar formulation produced effective imiquimod concentrations into the skin exposed to acid environment, representing a potential efficacious and selective drug delivery system able to trigger the drug release in the tumor tissues, at lower and less irritating drug concentrations.

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Section: Introductionmentioning

confidence: 99%

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

et al. 2020

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“…Of the ILs known to dissolve cellulose there are two distinct groups: ''aprotic'' ILs (AILs) formed of discreet ionic species such as 1-butyl-3-methylimidazolium chloride ([BMIm][Cl]) (Pinkert et al 2009;Hallett and Welton 2011;Petkovic et al 2011) and ''protic'' ILs (PILs) formed from the proton transfer reaction between a Brønsted acid and base such as 1,1,3,3-tetramethylguanidinium propionate ([TMGH][OPr]). (Walker 2004;King et al 2011;Hauru et al 2012;Greaves and Drummond 2015;Meenatchi et al 2017;Becherini et al 2019). Ionic liquids in mixtures with dipolar aprotic solvents such as dimethyl sulfoxide, c-valerolactone and 1-methylimidazole have also been shown to solubilize cellulose quite readily (Xu et al 2013;Zhao et al 2013;Gale et al 2016;Holding et al 2017), which has greatly enabled the spinning of cellulose fibers using ionic liquids (Hauru et al 2014;Sixta et al 2015;Ma et al 2019).…”

Section: Introductionmentioning

confidence: 99%

Cellulose dissolution and regeneration using a non-aqueous, non-stoichiometric protic ionic liquid system

et al. 2020

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The solubility of cellulose has been studied as a function of composition in the binary mixture of 1,1,3,3-tetramethylguanidine and propionic acid. In amine-rich compositions, greater quantities of cellulose can be dissolved than in the equimolar composition, a.k.a. the protic ionic liquid [TMGH][OPr]. By applying a methodology of a short period of heating followed by cooling, similar concentrations of cellulose can be achieved in a much shorter time period. Finally, regeneration of cellulose from solution can be achieved by altering the acid:amine molar ratio. In comparison to cellulose regenerated from these solutions using water as an antisolvent, cellulose regenerated with propionic acid exhibit a lower crystallinity as inferred from x-ray diffractometry, but a greater average molecular weight as inferred from gel permeation chromatography.

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“…Additionally, a new class of distillable acid–base conjugated ILs was successfully attempted to dissolve cellulose [ 143 , 144 , 145 ]. Combinations of superbases, including 1,1,3,3-tetra-methylguanidine (TMG), 1,5-diazabicyclo-[4.3.0]non-5-ene (DBN) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with different organic acids [ 146 , 147 , 148 , 149 , 150 , 151 ], were used to synthesize protic ionic liquids (PILs), which were tested for dissolution of eucalyptus cellulose pulp fibers. For instance, TMG-based ILs achieved 13 wt% cellulose solubility [ 151 ].…”

Section: Cellulosementioning

confidence: 99%

“…Combinations of superbases, including 1,1,3,3-tetra-methylguanidine (TMG), 1,5-diazabicyclo-[4.3.0]non-5-ene (DBN) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with different organic acids [ 146 , 147 , 148 , 149 , 150 , 151 ], were used to synthesize protic ionic liquids (PILs), which were tested for dissolution of eucalyptus cellulose pulp fibers. For instance, TMG-based ILs achieved 13 wt% cellulose solubility [ 151 ]. These PILs not only showed a strong ability for cellulose dissolution but also demonstrated to be easily recovered by distillation.…”

Section: Cellulosementioning

confidence: 99%

Use of Ionic Liquids and Deep Eutectic Solvents in Polysaccharides Dissolution and Extraction Processes towards Sustainable Biomass Valorization

et al. 2020

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A shift to a bioeconomy development model has been evolving, conducting the scientific community to investigate new ways of producing chemicals, materials and fuels from renewable resources, i.e., biomass. Specifically, technologies that provide high performance and maximal use of biomass feedstocks into commodities with reduced environmental impact have been highly pursued. A key example comprises the extraction and/or dissolution of polysaccharides, one of the most abundant fractions of biomass, which still need to be improved regarding these processes’ efficiency and selectivity parameters. In this context, the use of alternative solvents and the application of less energy-intensive processes in the extraction of polysaccharides might play an important role to reach higher efficiency and sustainability in biomass valorization. This review debates the latest achievements in sustainable processes for the extraction of polysaccharides from a myriad of biomass resources, including lignocellulosic materials and food residues. Particularly, the ability of ionic liquids (ILs) and deep eutectic solvents (DESs) to dissolve and extract the most abundant polysaccharides from natural sources, namely cellulose, chitin, starch, hemicelluloses and pectins, is scrutinized and the efficiencies between solvents are compared. The interaction mechanisms between solvent and polysaccharide are described, paving the way for the design of selective extraction processes. A detailed discussion of the work developed for each polysaccharide as well as the innovation degree and the development stage of dissolution and extraction technologies is presented. Their advantages and disadvantages are also identified, and possible synergies by integrating microwave- and ultrasound-assisted extraction (MAE and UAE) or a combination of both (UMAE) are briefly described. Overall, this review provides key information towards the design of more efficient, selective and sustainable extraction and dissolution processes of polysaccharides from biomass.

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Levulinate amidinium protic ionic liquids (PILs) as suitable media for the dissolution and levulination of cellulose

Abstract: Levulinate protic ionic liquids allow for the dissolution and the levulination of their parent polysaccharide.

Cited by 36 publications

References 59 publications

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

pH-Responsive Nanostructures Based on Surface Active Fatty Acid-Protic Ionic Liquids for Imiquimod Delivery in Skin Cancer Topical Therapy

Cellulose dissolution and regeneration using a non-aqueous, non-stoichiometric protic ionic liquid system

Use of Ionic Liquids and Deep Eutectic Solvents in Polysaccharides Dissolution and Extraction Processes towards Sustainable Biomass Valorization

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