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Synthesis of N-oxyethylene substituted imidazolium-based zwitterions as a recyclable solvent for cellulose dissolution

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Abstract

Cellulose is a readily available, renewable, and natural biomaterial that has the potential to replace synthetic fibres. However, their processing to shaped materials such as fibre or film is still complex and restricted due to its insolubility in most conventional solvents. Herein, we present the synthesis and cellulose dissolution characteristics of a new class of recyclable zwitterions composed of tethered N-oxyethylene substituted imidazolium cation and alkyl carboxylate anion. Investigations on cellulose dissolution showed that increasing the alkyl chain length of carboxylate anion and introduction of oxyethylene unit on imidazolium ring led to better cellulose dissolution ability, and up to 12% (w/w) cellulose could be dissolved in aqueous zwitterions at 105 °C. The thermal behavior of zwitterions and their cellulose solutions was characterized by TGA and found to be more stable than the NMMO and Lyocell solutions. Rheological characterization of cellulose solutions revealed viscoelastic behavior and zero shear viscosity of 6–12% (w/w) cellulose solution in hexanoate containing aqueous zwitterion was 555 to 5900 Pa.s at 120 °C. The characteristics of cellulose solution indicate its potential for processing to cellulose fibre by extrusion through a tiny spinneret. Physico-chemical analysis of regenerated cellulose indicates that zwitterions cause no adverse effect on cellulose structure and morphology during dissolution. The zwitterions are recovered after the cellulose regeneration process, and the recovery was found to be 99.6% after purification using the ion-exchange method.

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Acknowledgments

This work has been accomplished under the industrial Ph.D. program of ABSTCPL. The authors would like to thank the analytical team of ABSTCPL and CSIR-National Chemical Laboratory for help with all characterization facilities.

Funding

There is no specific funding for this work. This work is under industrial Ph.D. programme from Aditya Birla Science and Technology Company Pvt Ltd.

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SJ: Methodology, validation, formal analysis, investigation, writing-original draft, visualization. VG: Conceptualization, methodology, visualization, supervision, writing-review, and editing. MKS: conceptualization, methodology, supervision, validation, investigation, resources, visualization, writing-review, and editing. KS: Conceptualization, methodology, supervision, validation, investigation, resources, visualization, writing-review, and editing.

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Correspondence to Madan Kumar Singh or Kadhiravan Shanmuganathan.

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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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All ethical guidelines were followed, and no human or animal experimentation were executed.

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The original online version of this article was revised: One of the affiliations of authors S. Jadhav and K. Shanmuganathan are updated.

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Jadhav, S., Ganvir, V., Singh, M.K. et al. Synthesis of N-oxyethylene substituted imidazolium-based zwitterions as a recyclable solvent for cellulose dissolution. Cellulose 30, 87–109 (2023). https://doi.org/10.1007/s10570-022-04883-1

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  • DOI: https://doi.org/10.1007/s10570-022-04883-1

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