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Synthesis of a cellulose dissolving liquid zwitterion from general and low-cost reagents

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Abstract

A carboxylate-type liquid zwitterion, OE2imC3C, has been recently reported as a unique solvent as a class of ionic liquids with distinctive properties and functions such as cellulose dissolution ability and low toxicity to fermentative microoganisms. Therefore, OE2imC3C first enabled successive conversion of biomass to bioethanol in the same reaction pot. However, the reagent, 1-bromo-2-(2-methoxyethoxy)ethane, used for OE2imC3C synthesis is expensive and sometimes out of production and thus prevents its industrialization. Here we synthesized OE2imC3C from general and low-cost reagents. We also confirmed that the present OE2imC3C maintained the distinctive properties and functions because previous literature indicates synthetic procedures affect the properties. The low toxicity and cellulose dissolution ability of the OE2imC3C synthesized in this study were equivalent to those of conventional OE2imC3C. In addition, OE2imC3C is known to have ability to cryopreserve mammalian cells and the OE2imC3C synthesized in this study exhibited the ability.

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Scheme 1
Scheme 2
Fig. 1

Availability of data and material

Data that support the findings of this study are available upon reasonable request from the corresponding author.

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Acknowledgments

We thank Ms. S. Yamagishi (Hirata Laboratory) for her technical assistance.

Funding

This study was partly supported by ACT-X (for K.K., JPMJAX1915 from Japan Science and Technology Agency), KAKENHI (18K14281 for K.K. and 17K07181 for E.H. from the Japan Society for the Promotion of Science), and the Leading Initiative for Excellent Young Researchers (for K.K., from Ministry of Education, Culture, Sports, Science and Technology-Japan). This research was also partly supported by the COI program "Construction of next-generation infrastructure using innovative materials–Realization of a safe and secure society that can coexist with the Earth for centuries", which is supported by Ministry of Education, Culture, Sports, Science and Technology-Japan and Japan Science and Technology Agency. This research was also partly supported by Kanazawa University SAKIGAKE project 2020.

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Authors and Affiliations

  1. Faculty of Biological Science and Technology, Institute of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

    Gyanendra Sharma, Yui Kato, Ayumi Hachisu, Kenji Takahashi & Kosuke Kuroda

  2. Cancer Research Institute, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

    Kojiro Ishibashi & Eishu Hirata

  3. Institute for Frontier Science Initiative, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

    Kazuaki Ninomiya

  4. Nano Life Science Institute of Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

    Eishu Hirata

  5. NanoMaterials Research Institute, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

    Kosuke Kuroda

Authors
  1. Gyanendra Sharma
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  2. Yui Kato
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  3. Ayumi Hachisu
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  4. Kojiro Ishibashi
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  5. Kazuaki Ninomiya
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  6. Kenji Takahashi
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  7. Eishu Hirata
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  8. Kosuke Kuroda
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Contributions

G.S. and A.H. performed the chemical reactions and physicochemical properties measurements, Y.K., K.I., E.H. and K.K. performed and analyzed most of the biological experiments; G.S., K.K., K.N. and K.T. co-wrote the manuscript with input from all authors. All authors contributed to the interpretation of the results and commented on the final manuscript.

Corresponding author

Correspondence to Kosuke Kuroda.

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Sharma, G., Kato, Y., Hachisu, A. et al. Synthesis of a cellulose dissolving liquid zwitterion from general and low-cost reagents. Cellulose 29, 3017–3024 (2022). https://doi.org/10.1007/s10570-021-04185-y

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  • DOI: https://doi.org/10.1007/s10570-021-04185-y

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