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Molecules 2018, 23(3), 511; https://doi.org/10.3390/molecules23030511

Recent Advances in Solvents for the Dissolution, Shaping and Derivatization of Cellulose: Quaternary Ammonium Electrolytes and their Solutions in Water and Molecular Solvents

1
Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508-000 São Paulo, SP, Brazil
2
Bio-based Fibres, Swerea IVF, P.O. Box 104, SE-431 22 Mölndal, Sweden
3
Centre of Excellence for Polysaccharide Research, Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University of Jena, Humboldtstraße 10, 07743 Jena, Germany
*
Author to whom correspondence should be addressed.
Received: 15 December 2017 / Revised: 6 February 2018 / Accepted: 14 February 2018 / Published: 25 February 2018
(This article belongs to the Special Issue Cellulose Chemical Modifications—Towards Sustainable Materials)
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Abstract

There is a sustained interest in developing solvents for physically dissolving cellulose, i.e., without covalent bond formation. The use of ionic liquids, ILs, has generated much interest because of their structural versatility that results in efficiency as cellulose solvents. Despite some limitations, imidazole-based ILs have received most of the scientific community’s attention. The objective of the present review is to show the advantages of using quaternary ammonium electrolytes, QAEs, including salts of super bases, as solvents for cellulose dissolution, shaping, and derivatization, and as a result, increase the interest in further investigation of these important solvents. QAEs share with ILs structural versatility; many are liquids at room temperature or are soluble in water and molecular solvents (MSs), in particular dimethyl sulfoxide. In this review we first give a historical background on the use of QAEs in cellulose chemistry, and then discuss the common, relatively simple strategies for their synthesis. We discuss the mechanism of cellulose dissolution by QAEs, neat or as solutions in MSs and water, with emphasis on the relevance to cellulose dissolution efficiency of the charge and structure of the cation and. We then discuss the use of cellulose solutions in these solvents for its derivatization under homogeneous and heterogeneous conditions. The products of interest are cellulose esters and ethers; our emphasis is on the role of solvent and possible side reactions. The final part is concerned with the use of cellulose dopes in these solvents for its shaping as fibers, a field with potential commercial application. View Full-Text
Keywords: quaternary ammonium electrolytes; molecular solvents; super bases; cellulose dissolution mechanism; cellulose derivatization; cellulose shaping; biomass conversion quaternary ammonium electrolytes; molecular solvents; super bases; cellulose dissolution mechanism; cellulose derivatization; cellulose shaping; biomass conversion
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kostag, M.; Jedvert, K.; Achtel, C.; Heinze, T.; El Seoud, O.A. Recent Advances in Solvents for the Dissolution, Shaping and Derivatization of Cellulose: Quaternary Ammonium Electrolytes and their Solutions in Water and Molecular Solvents. Molecules 2018, 23, 511.

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