Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose : Effects of alkyl and alkoxy side chains

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Ferreira , D C , Oliveira , M L , Bioni , T A , Nawaz , H , King , A W T , Kilpeläinen , I , Hummel , M , Sixta , H & El Seoud , O A 2019 , ' Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose : Effects of alkyl and alkoxy side chains ' , Carbohydrate Polymers , vol. 212 , pp. 206-214 . https://doi.org/10.1016/j.carbpol.2019.02.024

Title: Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose : Effects of alkyl and alkoxy side chains
Author: Ferreira, Daniela C.; Oliveira, Mayara L.; Bioni, Thais A.; Nawaz, Haq; King, Alistair W. T.; Kilpeläinen, Ilkka; Hummel, Michael; Sixta, Herbert; El Seoud, Omar A.
Contributor: University of Helsinki, Department of Chemistry
University of Helsinki, Department of Chemistry
Date: 2019-05-15
Language: eng
Number of pages: 9
Belongs to series: Carbohydrate Polymers
ISSN: 0144-8617
URI: http://hdl.handle.net/10138/314874
Abstract: The efficiency of mixtures of ionic liquids (ILs) and molecular solvents in cellulose dissolution and derivatization depends on the structures of both components. We investigated the ILs 1-(1-butyl)-3-methylimidazolium acetate (C(4)MeImAc) and 1-(2-methoxyethyl)-3-methylimidazolium acetate (C(3)OMeImAc) and their solutions in dimethyl sulfoxide, DMSO, to assess the effect of presence of an ether linkage in the IL side-chain. Surprisingly, C(4)MeImAc-DMSO was more efficient than C(3)OMeImAc-DMSO for the dissolution and acylation of cellulose. We investigated both solvents using rheology, NMR spectroscopy, and solvatochromism. Mixtures of C(3)OMeImAc-DMSO are more viscous, less basic, and form weaker hydrogen bonds with cellobiose than C(4)MeImAc-DMSO. We attribute the lower efficiency of C(3)OMeImAc to "deactivation" of the ether oxygen and C2-(H) under bar of the imidazolium ring due to intramolecular hydrogen bonding. Using the corresponding ILs with C2-(CH3) under bar instead of C2-(H) under bar, namely, 1-butyl-2,3-dimethylimidazolium acetate (C(4)Me(2)ImAc) and 1-(2-methoxyethyl)-2,3-dimethylimidazolium acetate (C(3)OMe(2)ImAc) increased the concentration of dissolved cellulose; without noticeable effect on biopolymer reactivity.
Subject: Ionic liquid-DMSO
Cellulose dissolution
Solvatochromism
Biopolymer derivatization
Cellulose esters
MICROWAVE-ASSISTED DERIVATIZATION
ACID ANHYDRIDE MIXTURES
DIMETHYL-SULFOXIDE
AQUEOUS-SOLUTIONS
OXIDATION
ACETYLATION
ACYLATION
SOLVATOCHROMISM
DEPENDENCE
CELLOBIOSE
116 Chemical sciences
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