Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride

Mari Granström; Jari Kavakka; Alistair King; Johanna Majoinen; Valtteri Mäkelä; Juho Helaja; Sami Hietala; Tommi Virtanen; Sirkka Liisa Maunu; Dimitris S. Argyropoulos; Ilkka Kilpeläinen

doi:10.1007/s10570-008-9197-5

Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride

Mari Granström, Jari Kavakka, Alistair King, Johanna Majoinen, Valtteri Mäkelä, Juho Helaja, Sami Hietala, Tommi Virtanen, Sirkka Liisa Maunu, Dimitris S. Argyropoulos, Ilkka Kilpeläinen^* (Corresponding Author)

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Tosylation and acylation of cellulose were performed under mild reaction conditions using imidazolium based ionic liquids (ILs) as solvents. The non-degradative nature, lower viscosity, as well as higher solubility of cellulose in [amim]Cl encouraged us to carry out the reactions in this media. The reactions described here were optimised for this particular solvent in order to obtain different cellulose derivatives with high yields, homogeneity and degree of substitution (DS). Two reagents employed for the in situ activation of carboxylic acids were N,N′-carbonyldiimidazole (CDI) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI). Final products were characterised by solution and solid-state NMR techniques.

Original language	English
Pages (from-to)	481-488
Number of pages	8
Journal	Cellulose
Volume	15
Issue number	3
DOIs	https://doi.org/10.1007/s10570-008-9197-5
Publication status	Published - 1 Jun 2008
MoE publication type	Not Eligible

Funding

Acknowledgements This research was supported by the University of Helsinki research grant. We would like to thank Dr. Reijo Aksela and Dr. Vesa Myllymäki from Kemira Oyj, Finland.

Keywords

1-Allyl-3-methylimidazolium chloride
Cellulose
Cellulose modification
Ionic liquid
Synthesis of cellulose derivatives

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abstract = "Tosylation and acylation of cellulose were performed under mild reaction conditions using imidazolium based ionic liquids (ILs) as solvents. The non-degradative nature, lower viscosity, as well as higher solubility of cellulose in [amim]Cl encouraged us to carry out the reactions in this media. The reactions described here were optimised for this particular solvent in order to obtain different cellulose derivatives with high yields, homogeneity and degree of substitution (DS). Two reagents employed for the in situ activation of carboxylic acids were N,N′-carbonyldiimidazole (CDI) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI). Final products were characterised by solution and solid-state NMR techniques.",

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AU - Granström, Mari

AU - Kavakka, Jari

AU - King, Alistair

AU - Majoinen, Johanna

AU - Mäkelä, Valtteri

AU - Helaja, Juho

AU - Hietala, Sami

AU - Virtanen, Tommi

AU - Maunu, Sirkka Liisa

AU - Argyropoulos, Dimitris S.

AU - Kilpeläinen, Ilkka

PY - 2008/6/1

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N2 - Tosylation and acylation of cellulose were performed under mild reaction conditions using imidazolium based ionic liquids (ILs) as solvents. The non-degradative nature, lower viscosity, as well as higher solubility of cellulose in [amim]Cl encouraged us to carry out the reactions in this media. The reactions described here were optimised for this particular solvent in order to obtain different cellulose derivatives with high yields, homogeneity and degree of substitution (DS). Two reagents employed for the in situ activation of carboxylic acids were N,N′-carbonyldiimidazole (CDI) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI). Final products were characterised by solution and solid-state NMR techniques.

AB - Tosylation and acylation of cellulose were performed under mild reaction conditions using imidazolium based ionic liquids (ILs) as solvents. The non-degradative nature, lower viscosity, as well as higher solubility of cellulose in [amim]Cl encouraged us to carry out the reactions in this media. The reactions described here were optimised for this particular solvent in order to obtain different cellulose derivatives with high yields, homogeneity and degree of substitution (DS). Two reagents employed for the in situ activation of carboxylic acids were N,N′-carbonyldiimidazole (CDI) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI). Final products were characterised by solution and solid-state NMR techniques.

KW - 1-Allyl-3-methylimidazolium chloride

KW - Cellulose

KW - Cellulose modification

KW - Ionic liquid

KW - Synthesis of cellulose derivatives

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Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride

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