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PreprintCC BYChemRxiv

Expanding the Cygnet Class of Solvents: Development of a Series of Bio-based Polar Aprotic High Boiling Solvents

  • Cicely M. Warne1,2
  • Giacomo Lombardo3
  • Chiara Siracusa2
  • James Sherwood4,5
  • Kristina Ivanova6
  • Eva Ramon6
  • Tzanko Tzanov6
  • Georg M. Guebitz1,2
  • Con R. McElroy4,5,7
  • Alessandro Pellis3
7 affiliations
  1. 1ACIB GmbH, Konrad-Lorenz-Strasse 20, Tulln an der Donau, Austria, 3430
  2. 2Institute of Environmental Biotechnology, Agricultural Sciences, Konrad-Lorenz-Strasse 20, Tulln an der Donau, Austria, 3430
  3. 3Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, Genova, GE, Italy, 16146
  4. 4Department of Chemistry
  5. 5University of York
  6. 6Grup de Biotecnologia Molecular i Industrial, Department of Chemical Engineering, Universitat Politècnica de Catalunya (UPC-BarcelonaTech, Rambla Sant Nebridi 22, Terrassa, Spain, 08222
  7. 7University of Lincoln
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Abstract

Polar aprotic solvents have many applications in organic chemistry, but there are few bio-based substitutes available. As legislation becomes more restrictive due to health and safety concerns, the need for safer and more sustainable solvents has become ever more pressing. Here, we have built on previous works to synthesise several derivatives of the cellulose-derived Cyrene through an environmentally friendly ketalisation reaction, resulting in a class of solvents called the Cygnets. Diol reagents were selected based on their bio-based origin, and four novel solvent structures were synthesised and comprehensively characterised using NMR, ( 1 H and 13 C), GC-FID, and HPLC-ESI-MS. The solvents were also shown to be non-toxic to skin cell lines HaCaT and BJ-5ta, presenting a viability above 70%. Finally, the presented structures show differing properties depending on the structure of the secondary ring formed. The presence of longer side chains results in a solvent with a lower boiling point, allowing it to be used in a wider range of reactions, and presents the interesting possibility to tune the final properties by modifying the used diol reagent.

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Cite

BibTeXRIS
BibTeX
@misc{warne2026expanding,
  title = {{Expanding the Cygnet Class of Solvents: Development of a Series of Bio-based Polar Aprotic High Boiling Solvents}},
  author = {Cicely M. Warne and Giacomo Lombardo and Chiara Siracusa and James Sherwood and Kristina Ivanova and Eva Ramon and Tzanko Tzanov and Georg M. Guebitz and Con R. McElroy and Alessandro Pellis},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008385/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008385/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Expanding the Cygnet Class of Solvents: Development of a Series of Bio-based Polar Aprotic High Boiling Solvents
AU  - Cicely M. Warne
AU  - Giacomo Lombardo
AU  - Chiara Siracusa
AU  - James Sherwood
AU  - Kristina Ivanova
AU  - Eva Ramon
AU  - Tzanko Tzanov
AU  - Georg M. Guebitz
AU  - Con R. McElroy
AU  - Alessandro Pellis
PY  - 2026
DA  - 2026/09/07
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008385/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008385/v1
AB  - Polar aprotic solvents have many applications in organic chemistry, but there are few bio-based substitutes available. As legislation becomes more restrictive due to health and safety concerns, the need for safer and more sustainable solvents has become ever more pressing. Here, we have built on previous works to synthesise several derivatives of the cellulose-derived Cyrene through an environmentally friendly ketalisation reaction, resulting in a class of solvents called the Cygnets. Diol reagents were selected based on their bio-based origin, and four novel solvent structures were synthesised and comprehensively characterised using NMR, ( 1 H and 13 C), GC-FID, and HPLC-ESI-MS. The solvents were also shown to be non-toxic to skin cell lines HaCaT and BJ-5ta, presenting a viability above 70%. Finally, the presented structures show differing properties depending on the structure of the secondary ring formed. The presence of longer side chains results in a solvent with a lower boiling point, allowing it to be used in a wider range of reactions, and presents the interesting possibility to tune the final properties by modifying the used diol reagent.
ER  -