A morpholinium ionic liquid for cellulose dissolution

Dilip G. Raut; Ola Sundman; Su Weiqing; Pasi Virtanen; Yasuhito Sugano; Krisztian Kordas; Jyri-Pekka Mikkola

doi:10.1016/j.carbpol.2015.04.032

A morpholinium ionic liquid for cellulose dissolution

Dilip G. Raut, Ola Sundman, Su Weiqing, Pasi Virtanen, Yasuhito Sugano, Krisztian Kordas, Jyri-Pekka Mikkola

Laboratory of Industrial Chemistry and Reaction Engineering

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

87 Citations (Scopus)

Abstract

A series of substituted morpholinium ionic salts and allyl ammonium acetates were prepared. Amongst those, N-allyl-N-methylmorpholinium acetate ([AMMorp][OAc]) was found to dissolve cellulose readily without any pre-processing of native cellulose. At 120 °C, [AMMorp][OAc] could dissolve 30 wt%, 28 wt% and 25 wt% of cellulose with degree of polymerization (DP_n) – 789, 1644 and 2082 respectively, in 20 min. Importantly, SEC analysis indicated that no discernible changes occurred in terms of the degree of polymerization of the different celluloses after regeneration. Furthermore, when comparing the cellulose dissolution capability of these newly synthesized ionic liquids, it is evident that the combination of all three constituents – the morpholinium cation, the existence of an allyl group and choosing the acetate anion are essential for efficient cellulose dissolution. The structure and morphology of the regenerated cellulosic materials were characterized by SEM, XRD, TGA, CP/MAS ¹³C NMR and FTIR, respectively.

Original language	Undefined/Unknown
Pages (from-to)	18–25
Journal	Carbohydrate Polymers
Volume	130
DOIs	https://doi.org/10.1016/j.carbpol.2015.04.032
Publication status	Published - 2015
MoE publication type	A1 Journal article-refereed

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10.1016/j.carbpol.2015.04.032

Cite this

@article{47bfcfaea2524b20bf41955fe80d0901,

title = "A morpholinium ionic liquid for cellulose dissolution",

abstract = "A series of substituted morpholinium ionic salts and allyl ammonium acetates were prepared. Amongst those, N-allyl-N-methylmorpholinium acetate ([AMMorp][OAc]) was found to dissolve cellulose readily without any pre-processing of native cellulose. At 120 °C, [AMMorp][OAc] could dissolve 30 wt%, 28 wt% and 25 wt% of cellulose with degree of polymerization (DPn) – 789, 1644 and 2082 respectively, in 20 min. Importantly, SEC analysis indicated that no discernible changes occurred in terms of the degree of polymerization of the different celluloses after regeneration. Furthermore, when comparing the cellulose dissolution capability of these newly synthesized ionic liquids, it is evident that the combination of all three constituents – the morpholinium cation, the existence of an allyl group and choosing the acetate anion are essential for efficient cellulose dissolution. The structure and morphology of the regenerated cellulosic materials were characterized by SEM, XRD, TGA, CP/MAS 13C NMR and FTIR, respectively.",

author = "Raut, {Dilip G.} and Ola Sundman and Su Weiqing and Pasi Virtanen and Yasuhito Sugano and Krisztian Kordas and Jyri-Pekka Mikkola",

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TY - JOUR

T1 - A morpholinium ionic liquid for cellulose dissolution

AU - Raut, Dilip G.

AU - Sundman, Ola

AU - Weiqing, Su

AU - Virtanen, Pasi

AU - Sugano, Yasuhito

AU - Kordas, Krisztian

AU - Mikkola, Jyri-Pekka

N1 - tk.

PY - 2015

Y1 - 2015

N2 - A series of substituted morpholinium ionic salts and allyl ammonium acetates were prepared. Amongst those, N-allyl-N-methylmorpholinium acetate ([AMMorp][OAc]) was found to dissolve cellulose readily without any pre-processing of native cellulose. At 120 °C, [AMMorp][OAc] could dissolve 30 wt%, 28 wt% and 25 wt% of cellulose with degree of polymerization (DPn) – 789, 1644 and 2082 respectively, in 20 min. Importantly, SEC analysis indicated that no discernible changes occurred in terms of the degree of polymerization of the different celluloses after regeneration. Furthermore, when comparing the cellulose dissolution capability of these newly synthesized ionic liquids, it is evident that the combination of all three constituents – the morpholinium cation, the existence of an allyl group and choosing the acetate anion are essential for efficient cellulose dissolution. The structure and morphology of the regenerated cellulosic materials were characterized by SEM, XRD, TGA, CP/MAS 13C NMR and FTIR, respectively.

AB - A series of substituted morpholinium ionic salts and allyl ammonium acetates were prepared. Amongst those, N-allyl-N-methylmorpholinium acetate ([AMMorp][OAc]) was found to dissolve cellulose readily without any pre-processing of native cellulose. At 120 °C, [AMMorp][OAc] could dissolve 30 wt%, 28 wt% and 25 wt% of cellulose with degree of polymerization (DPn) – 789, 1644 and 2082 respectively, in 20 min. Importantly, SEC analysis indicated that no discernible changes occurred in terms of the degree of polymerization of the different celluloses after regeneration. Furthermore, when comparing the cellulose dissolution capability of these newly synthesized ionic liquids, it is evident that the combination of all three constituents – the morpholinium cation, the existence of an allyl group and choosing the acetate anion are essential for efficient cellulose dissolution. The structure and morphology of the regenerated cellulosic materials were characterized by SEM, XRD, TGA, CP/MAS 13C NMR and FTIR, respectively.

U2 - 10.1016/j.carbpol.2015.04.032

DO - 10.1016/j.carbpol.2015.04.032

M3 - Artikel

SN - 0144-8617

VL - 130

SP - 18

EP - 25

JO - Carbohydrate Polymers

JF - Carbohydrate Polymers

ER -