Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 4, Issue 11, Pages 6200-6207Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.6b02020
Keywords
1-Ethyl-3-methylimidazolium acetate; Ionic liquid; Cellulose; Dissolution; Organic electrolyte solutions (OESs); Reference-interaction site model (RISM); gamma-Butyrolactone; gamma-Valerolactone
Categories
Funding
- UK Engineering and Physical Sciences Research Council (EPSRC) via the EPSRC Doctoral Training Centre in Sustainable Chemical Technologies, University of Bath [EP/G03768X/1]
- British Council
- Sao Paulo Research Foundation (FAPESP) [CEPID 2013/08293-7, 2014/10448-1, 2015/25031-1]
- Engineering and Physical Sciences Research Council [1223162] Funding Source: researchfish
- The British Council [GII105] Funding Source: researchfish
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [15/25031-1] Funding Source: FAPESP
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Cellulose is an abundant, cheap, renewable, yet recalcitrant, material, which, if dissolved, may be formed into a wide range of materials, composites, and mixtures. Much attention has recently been focused on the use of mixtures of ionic liquids and some solvents (so-called organic electrolyte solutions, OESs) as efficient cellulose dissolution solvents, but many of the cosolvents used lack green credentials a perennial problem where dipolar aprotic solvents are the solvents of choice. We present a rational approach, based on definition of ranges of solvent parameters gathered together in recently published databases, to find greener cosolvents for OES formation. Thus, gamma-butyrolactone is identified as a suitable OES former for dissolution of microcrystalline cellulose and biobased gamma-valerolactone as a marginally less efficient, but significantly safer, alternative. Comparison of cosolvent efficiency reveals that previous use of measures of mass, or concentration, of cellulose dissolved may have masked the similarities between 1-methylimidazole, dimethyl sulfoxide (DMSO), N,N-dimethylformamide, N-N'-dimethylimidazolidinone, NN-dimethylacetamide, N-methylpyrrolidinone, and sulfolane (seldom considered), while comparison on a molar basis reveals that the molar volume of the solvent is an important factor. Reference-interaction site model (RISM) calculations for the DMSO/1-ethyl-3-methylimidazolium acetate OES suggest competition between DMSO and the acetate anion and preferential solvation of cellulose by the ionic liquid.
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