Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium
Bernhard LM, Gröger H (2024)
ChemSusChem : e202400073.
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Abstract / Bemerkung
The multi-10.000 tons scale manufactured chemical epsilon-caprolactone attracts high industrial interest due to its favorable biodegradability properties. However, besides being of petrochemical origin yet, its industrial production has a conceptual limitation that is the difficult extraction of this highly water-soluble monomer from the water phase resulting from the aqueous solution of H2O2 applied as reagent. In this contribution, we report a chemoenzymatic cascade starting from bio-based phenol, which makes use of O2 instead of H2O2 and runs in pure organic medium, thus requiring only simply decantation and distillation as work-up. In a first step, phenol is hydrogenated quantitatively to cyclohexanol under solvent-free conditions with a Ru-catalyst. After simple removal of the heterogenous catalyst, cyclohexanol is converted to epsilon-caprolactone in a biocatalytic double oxidation with very high yields just requiring O2 as reagent. This biocatalytic process proceeds in pure organic medium, thus avoiding tedious extraction to isolate the highly water-soluble epsilon-caprolactone and enabling a dramatically simplified work-up by only centrifugal separation of lyophilized whole cells and solvent removal. This oxidation is accomplished using a tailor-made recombinant whole-cell catalyst containing an alcohol dehydrogenase and a cyclohexanone monooxygenase mutant. © 2024 Wiley‐VCH GmbH.
Erscheinungsjahr
2024
Zeitschriftentitel
ChemSusChem
Art.-Nr.
e202400073
eISSN
1864-564X
Page URI
https://pub.uni-bielefeld.de/record/2990610
Zitieren
Bernhard LM, Gröger H. Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium. ChemSusChem . 2024: e202400073.
Bernhard, L. M., & Gröger, H. (2024). Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium. ChemSusChem , e202400073. https://doi.org/10.1002/cssc.202400073
Bernhard, Laura Maria, and Gröger, Harald. 2024. “Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium”. ChemSusChem : e202400073.
Bernhard, L. M., and Gröger, H. (2024). Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium. ChemSusChem :e202400073.
Bernhard, L.M., & Gröger, H., 2024. Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium. ChemSusChem , : e202400073.
L.M. Bernhard and H. Gröger, “Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium”, ChemSusChem , 2024, : e202400073.
Bernhard, L.M., Gröger, H.: Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium. ChemSusChem . : e202400073 (2024).
Bernhard, Laura Maria, and Gröger, Harald. “Overcoming a Conceptual Limitation of Industrial epsilon-Caprolactone Production via Chemoenzymatic Synthesis in Organic Medium”. ChemSusChem (2024): e202400073.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
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PMID: 38856824
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