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Enhancing the Stability of Ionic Liquid Media for Cellulose Processing: Acetal Protection Cite This: Green Chem., 2016, 18, 3758 Or Carbene Suppression?†

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Enhancing the Stability of Ionic Liquid Media for Cellulose Processing: Acetal Protection Cite This: Green Chem., 2016, 18, 3758 Or Carbene Suppression?† Green Chemistry View Article Online PAPER View Journal | View Issue Enhancing the stability of ionic liquid media for cellulose processing: acetal protection Cite this: Green Chem., 2016, 18, 3758 or carbene suppression?† Matthew T. Clough,a,b Jeraime A. Griffith,a Olga Kuzminaa and Tom Welton*a Although excellent candidate solvents for cellulose, capable of dissolving ≥20 wt% of the carbohydrate for electrospinning processes, dialkylimidazolium carboxylate ionic liquids undergo undesirable side reac- tions with the reducing end of saccharides, terminating in an equilibrium concentration of a 2-(hydroxy- methyl)-substituted imidazolium ‘adduct’. The addition of small molar quantities of a benign, non-toxic and inexpensive co-solvent, e.g. glycerol, reduces the rate of adduct accumulation, thereby enhancing the long-term thermal stability and recyclability of the expensive ionic liquid component. NMR, UV-vis and mass spectrometry experiments reveal that the improved stability is likely attributable to suppression of the transient dialkylimidazol-2-ylidene carbene, via hydrogen-donation by the protic co-solvent, rather Creative Commons Attribution 3.0 Unported Licence. than by cyclic acetal protection of the carbohydrate. The incorporation of (up to) 10 wt% of glycerol into Received 5th January 2016, the solvent mixture does not exacerbate the rate of cellulose depolymerisation compared to in the neat Accepted 4th April 2016 ionic liquid, and high solubility of cellulose is maintained. Furthermore, a colourimetric comparison of the DOI: 10.1039/c6gc00027d recovered solvents, following cellulose re-precipitation, demonstrates that glycerol does not increase the www.rsc.org/greenchem concentration of contaminant reducing sugars in the organic electrolyte. This article is licensed under a Introduction lose fibres by initially dissolving crude cellulose in an IL, and then ‘electrospinning’ the viscous solution into an anti-solvent – In view of the rapidly depleting planetary fossil fuel reserves, pool (e.g. water).8 12 Open Access Article. Published on 04 April 2016. Downloaded 2/7/2021 5:20:00 PM. accompanied by a fast-growing global population, there is a However, there is the need for an informed selection of the mounting imperative to identify and to exploit renewable incorporated IL ions; both the anion and the cation4 play a resources in order to meet heightening energy and material critical role in dismantling the extensive inter-/intra-molecular demands. Lignocellulosic biomass is one excellent candidate hydrogen-bonding framework of crystalline cellulose. Accord- renewable resource; the separation and subsequent decon- ingly, the pairing of strongly hydrogen-bond basic13,14 anions 15 − − − struction/reprocessing of the three major biopolymer com- (high β, e.g. Cl , [OAc] or [(CH3)2PO4] ) with cations that ponents (cellulose, hemicellulose and lignin) affords a broad offer a hydrogen-bond acidity within a suitable range16 and spectrum of textiles, fuels and commodity chemicals, poten- that contribute to thermodynamically-favourable dissolution17 1–3 + tially alleviating the reliance on petrochemical sources. (e.g. 1-ethyl-3-methylimidazolium, ‘[C2C1im] ’)affords ILs that Ionic Liquids (ILs), salts that are molten at (or just above) are effective cellulose-dissolving solvents. Furthermore, a room temperature, are increasingly finding favour as solvents certain degree of research attention has been devoted to the for cellulose, which accounts for 35–50% of the weight of dry so-called ‘organic electrolyte solutions’, mixtures of an ionic biomass and is the most abundant bio-renewable resource on species with a polar aprotic organic solvent (for example 4–7 18–20 21 earth. It is possible to prepare high-quality crystalline cellu- DMSO, (CH3)2CO ). LiCl in dimethylacetamide (DMA) is the archetypal organic electrolyte for cellulose dissolution, described first by Spange et al.22 The application of LiCl/DMA for solvation of cellulose is restricted by the toxicity of DMA; aDepartment of Chemistry, Imperial College London, London, SW7 2AZ, UK. nevertheless, this report22 was the first to identify that basicity E-mail: [email protected] is a primary criterion for effective cellulose dissolution. Con- b Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim- temporary organic electrolyte solvent systems have the poten- an-der-Ruhr, Germany 18–20 †Electronic supplementary information (ESI) available. See DOI: 10.1039/ tial to maintain (or even to improve on ) moderate-to-high c6gc00027d cellulose solubility, whilst simultaneously minimising difficul- 3758 | Green Chem.,2016,18,3758–3766 This journal is © The Royal Society of Chemistry 2016 View Article Online Green Chemistry Paper ties associated with handling highly viscous solutions of cellu- lose in neat ILs. Employing ILs for the dissolution of cellulose has the potential to circumvent profound limitations associated with contemporary industrial technologies; the Lyocell process is restricted by the limited thermal stability of the solvent, N-methylmorpholine-N-oxide (NMMO)23 and the modern Viscose process employs toxic, volatile, highly flammable 24 25 CS2. ILs are not intrinsically expensive. However, when using comparatively costly cellulose-dissolving ILs of the form − Fig. 1 Structures of the ionic liquids (1, 2), carbohydrates (3–5) and co- [CnC1im][X] (where n is typically 2 or 4 and [X] is commonly − − − solvents/additives (6–12) employed in this investigation. Cl , [OAc] or [(CH3)2PO4] ), there is a necessity for ready and continuous recycling of the IL component. Recycling of the pure IL, following one cellulose reprocessing cycle, may be hin- dered via several pathways: (i) inherent thermal degradation of wt% of cellulose, strategies for enhancing the stability of the 26,27 28 the IL; (ii) volatilisation of the intact IL ions (expected to mixture via a structural modification of the IL ions appear be a minimal contribution for dialkylimidazolium carboxylate unfeasible; this observation motivated our research group to 29,30 ILs on account of their high vaporisation enthalpies ), and; investigate alternative approaches. (iii) direct reaction between the IL and the cellulose solute. We proposed that it might be possible, instead, to suppress 31 32 Previously, Liebert and Heinze and Ebner et al. demon- the sequence of IL-carbohydrate degradation mechanisms by strated the ambient-temperature reaction of the cellulose- inclusion of a covalent protecting group at the reducing end of 2 dissolving IL [C4C1im][OAc], at the imidazolium C position, with cellulose, thereby leaving the cellulose backbone unchanged Creative Commons Attribution 3.0 Unported Licence. the reducing (aldehyde) end of either D-(+)-glucose or cellulose and retaining the beneficial high biopolymer solubility in the itself. Reaction occurs via a transient N-Heterocyclic Carbene IL. The conversion of an aldehyde (e.g., the open form of the (NHC) intermediate, facilitated by the basicity of the IL anion, cellulose reducing end) or ketone into a hemi-acetal or acetal 31–33 to yield a hydroxyalkylated adduct species. is one of the best-known organic protection strategies. In the Recently, we further examined this reactivity by exposing circumstance that the aldehyde functionality can be protected mixtures of the IL [C2C1im][OAc] with carbohydrates to temp- in situ, in the form of a cyclic acetal, undesirable side reaction eratures analogous to those of industrial cellulose reprocessing of the IL with cellulose could be suppressed. Investigations protocols (100–120 °C), for extended periods of time (up to were undertaken to evaluate the feasibility of this protecting 24 h); the mixtures underwent a sequence of decomposition group strategy for cellulose dissolved in carboxylate ILs. The This article is licensed under a reactions, terminating in an equilibrium concentration of the structures of all ILs (1, 2), carbohydrates (3–5) and co-solvents ‘C1 adduct’ compound, 1-ethyl-2-(hydroxymethyl)-3-methyl- (6–12) employed in this investigation are displayed in Fig. 1. 2 34 imidazolium acetate, [C2C1(HO)C1 im][OAc]. Evaluation of Syntheses of 1 and 2 are described in the ESI,† and experi- Open Access Article. Published on 04 April 2016. Downloaded 2/7/2021 5:20:00 PM. the equilibrium concentration of this C1 adduct, and the rate mental procedures are outlined below. at which maximum adduct concentration is reached, rep- resents a useful proxy for assessing cellulose (or carbohydrate model compound) degradation when dissolved in ILs. Experimental This observed sequence of degradation steps represents an – undesired side-reaction between the IL and cellulose, hinder- Solvent carbohydrate mixtures: preparation & analysis ing recycling of the solvent and, furthermore, damaging the A sample of carbohydrate (D-(+)-glucose 3, D-(+)-cellobiose 4,or carbohydrate fibres. Considering these reactive dialkylimid- cellulose 5) (0.050 ± 0.001 g) was carefully weighed into a 5 ml azolium carboxylate ILs, on initial inspection, blocking the C2–H single-necked round-bottomed flask, fitted with an adapter substituent (e.g. methylation) will prevent the formation of an for Schlenk apparatus and a magnetic stirrer bar. Where NHC intermediate and therefore suppress reactivity with cellu- employed, a co-solvent/additive (ethane-1,2-diol, 6, 2,3-di- lose. However, this substitution yields a salt with higher methylbutane-2,3-diol (pinacol), 7, glycerol, 8, trans-cyclo- melting point and a smaller stable liquid range.35
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