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

Tutkimustuotos: Lehtiartikkelivertaisarvioitu

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

julkaisussa: Carbohydrate Polymers, Vuosikerta 212, 15.05.2019, s. 206-214.

Tutkimustuotos: Lehtiartikkelivertaisarvioitu

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APA

Ferreira, D. C., Oliveira, M. L., Bioni, T. A., Nawaz, H., King, A. W. T., Kilpeläinen, I., ... 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, 212, 206-214. https://doi.org/10.1016/j.carbpol.2019.02.024

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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. / Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose : Effects of alkyl and alkoxy side chains. Julkaisussa: Carbohydrate Polymers. 2019 ; Vuosikerta 212. Sivut 206-214.

Bibtex - Lataa

@article{6a2a530e629d437b9aa85fbcf7ef5e45,
title = "Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose: Effects of alkyl and alkoxy side chains",
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 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.",
keywords = "Biopolymer derivatization, Cellulose dissolution, Cellulose esters, Ionic liquid-DMSO, Solvatochromism, OXIDATION, AQUEOUS-SOLUTIONS, ACETYLATION, ACYLATION, SOLVATOCHROMISM, ACID ANHYDRIDE MIXTURES, MICROWAVE-ASSISTED DERIVATIZATION, DEPENDENCE, DIMETHYL-SULFOXIDE, CELLOBIOSE",
author = "Ferreira, {Daniela C.} and Oliveira, {Mayara L.} and Bioni, {Thais A.} and Haq Nawaz and King, {Alistair W.T.} and Ilkka Kilpel{\"a}inen and Michael Hummel and Herbert Sixta and {El Seoud}, {Omar A.}",
year = "2019",
month = "5",
day = "15",
doi = "10.1016/j.carbpol.2019.02.024",
language = "English",
volume = "212",
pages = "206--214",
journal = "Carbohydrate Polymers",
issn = "0144-8617",

}

RIS - Lataa

TY - JOUR

T1 - Binary mixtures of ionic liquids-DMSO as solvents for the dissolution and derivatization of cellulose

T2 - Effects of alkyl and alkoxy side chains

AU - Ferreira, Daniela C.

AU - Oliveira, Mayara L.

AU - Bioni, Thais A.

AU - Nawaz, Haq

AU - King, Alistair W.T.

AU - Kilpeläinen, Ilkka

AU - Hummel, Michael

AU - Sixta, Herbert

AU - El Seoud, Omar A.

PY - 2019/5/15

Y1 - 2019/5/15

N2 - 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 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.

AB - 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 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.

KW - Biopolymer derivatization

KW - Cellulose dissolution

KW - Cellulose esters

KW - Ionic liquid-DMSO

KW - Solvatochromism

KW - OXIDATION

KW - AQUEOUS-SOLUTIONS

KW - ACETYLATION

KW - ACYLATION

KW - SOLVATOCHROMISM

KW - ACID ANHYDRIDE MIXTURES

KW - MICROWAVE-ASSISTED DERIVATIZATION

KW - DEPENDENCE

KW - DIMETHYL-SULFOXIDE

KW - CELLOBIOSE

UR - http://www.scopus.com/inward/record.url?scp=85061769510&partnerID=8YFLogxK

U2 - 10.1016/j.carbpol.2019.02.024

DO - 10.1016/j.carbpol.2019.02.024

M3 - Article

VL - 212

SP - 206

EP - 214

JO - Carbohydrate Polymers

JF - Carbohydrate Polymers

SN - 0144-8617

ER -

ID: 32312535