Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose

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dc.contributor Aalto-yliopisto fi
dc.contributor Aalto University en 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. 2019-03-11T15:22:40Z 2019-03-11T15:22:40Z 2019-05-15
dc.identifier.citation 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 . en
dc.identifier.issn 0144-8617
dc.identifier.issn 1879-1344
dc.identifier.other PURE UUID: 6a2a530e-629d-437b-9aa8-5fbcf7ef5e45
dc.identifier.other PURE ITEMURL:
dc.identifier.other PURE LINK:
dc.description.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 bothsolvents 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 of the imidazolium ring due to intramolecular hydrogen bonding. Using the corresponding ILs with C2–CH 3 instead of C2–H, 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. en
dc.format.extent 9
dc.format.extent 206-214
dc.language.iso en en
dc.publisher ELSEVIER SCI LTD
dc.relation.ispartofseries Carbohydrate Polymers en
dc.relation.ispartofseries Volume 212 en
dc.rights embargoedAccess en
dc.subject.other Organic Chemistry en
dc.subject.other Polymers and Plastics en
dc.subject.other Materials Chemistry en
dc.subject.other 216 Materials engineering en
dc.title Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose en
dc.type A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä fi
dc.description.version Peer reviewed en
dc.contributor.department Universidade de Sao Paulo
dc.contributor.department University of Helsinki
dc.contributor.department Department of Bioproducts and Biosystems
dc.subject.keyword Biopolymer derivatization
dc.subject.keyword Cellulose dissolution
dc.subject.keyword Cellulose esters
dc.subject.keyword Ionic liquid-DMSO
dc.subject.keyword Solvatochromism
dc.subject.keyword OXIDATION
dc.subject.keyword AQUEOUS-SOLUTIONS
dc.subject.keyword ACETYLATION
dc.subject.keyword ACYLATION
dc.subject.keyword SOLVATOCHROMISM
dc.subject.keyword ACID ANHYDRIDE MIXTURES
dc.subject.keyword DEPENDENCE
dc.subject.keyword DIMETHYL-SULFOXIDE
dc.subject.keyword CELLOBIOSE
dc.subject.keyword Organic Chemistry
dc.subject.keyword Polymers and Plastics
dc.subject.keyword Materials Chemistry
dc.subject.keyword 216 Materials engineering
dc.identifier.urn URN:NBN:fi:aalto-201903112211
dc.identifier.doi 10.1016/j.carbpol.2019.02.024 info:eu-repo/date/embargoEnd/2020-02-17

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