Chemo-Enzymatic Baeyer–Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Methods
2.3. Synthetic Procedures
2.3.1. Synthesis of CNTs-CONH (A1)
2.3.2. Synthesis of CNTs-C=N (I1)
2.3.3. Synthesis of CNTs-CONH-HEX-I (A2) and CNTs-C=N-HEX-I (I2)
2.3.4. Synthesis of CNTs-CONH-HEX-N(Tf)2 (A3) and CNTs-C=N-HEX- N(Tf)2 (I3)
2.3.5. Synthesis of CNTs-CONH-HEX-N(CN)2 (A4) and CNTs-C=N-HEX- N(CN)2 (I4)
2.3.6. Synthesis of CNTs-CONH-Oc2PO4 (A5) or CNTs-C=N- Oc2PO4 (I5)
2.3.7. Synthesis of CNTs-CONH-OcSO4 (A6) or CNTs-C=N- OcSO4 (I6)
2.3.8. Synthesis of CNTs-CONH-[bmim][N(Tf)2] and CNTs-C=N-[bmim][N(Tf)2]
2.3.9. Immobilization of the Lipase
2.3.10. General Procedure of the Baeyer–Villiger Oxidation of 2-Adamantanone
2.3.11. Recycle of the Biocatalyst
3. Results and Discussion
3.1. Synthesis and Characterization of Biocatalysts
3.2. SILLP Biocatalysts in Chemo-Enzymatic Baeyer–Villiger Oxidation
3.2.1. Influence of the Structure of SILLP Biocatalyst
3.2.2. Influence of the Amount of SILLP Biocatalyst
3.2.3. Stability of SILLP Biocatalyst
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Material | Content of Functional Groups (wt.%) * | Content of CALB (wt.%) * | Content of CRL (wt.%) * | Content of AOL (wt.%) * |
---|---|---|---|---|
CNTs-COOH | 1.4 | N/A | N/A | N/A |
CNTs-CONH (A1) | 5.8 | N/A | N/A | N/A |
CNTs-CONH-HEX-I (A2) | 6.4 | 2.7 | 7.9 | 5.0 |
CNTs-CONH-HEX-N(Tf)2 (A3) | 9.1 | 2.8 | 1.1 | 6.7 |
CNTs-CONH-HEX-N(CN)2 (A4) | 7.0 | 2.3 | 4.7 | 5.3 |
CNTs-CONH-Oc2PO4 (A5) | 10.9 | 6.4 | 1.2 | 1.9 |
CNTs-CONH-OcSO4 (A6) | 8.3 | 4.1 | 6.5 | 1.6 |
CNTs-CHO | 0.7 | N/A | N/A | N/A |
CNTs-C=N (I1) | 3.2 | N/A | N/A | N/A |
CNTs-C=N-HEX-I (I2) | 4.3 | 5.9 | 3.4 | 7.8 |
CNTs-C=N-HEX-N(Tf)2 (I3) | 7.5 | 0.6 | 9.2 | 4.1 |
CNTs-C=N-HEX-N(CN)2 (I4) | 5.1 | 1.9 | 5.3 | 3.7 |
CNTs-C=N-Oc2PO4 (I5) | 2.7 | 3.1 | 7.1 | 2.6 |
CNTs-C=N-OcSO4 (I6) | 2.6 | 2.6 | 6.2 | 5.0 |
Material | [bmim][N(Tf)2] Content (wt.%) | CALB Content (wt.%) |
---|---|---|
CNTs-CONH-[bmim][NTf2] (MR 1:0.1) | 0.4 | 2.8 |
CNTs-CONH-[bmim][NTf2] (MR 1:0.3) | 1.2 | 4.5 |
CNTs-CONH-[bmim][NTf2] (MR 1:0.5) | 2.2 | 8.0 |
CNTs-CONH-[bmim][NTf2] (MR 1:0.8) | 3.2 | 18.6 |
CNTs-CONH-[bmim][NTf2] (MR 1:1.1) | 3.4 | 19.2 |
CNTs-C=N-[bmim][NTf2] (MR 1:0.1) | 0.1 | 5.1 |
CNTs-C=N-[bmim][NTf2] (MR 1:0.3) | 0.7 | 5.7 |
CNTs-C=N-[bmim][NTf2] (MR 1:0.5) | 1.1 | 6.7 |
CNTs-C=N-[bmim][NTf2] (MR 1:0.8) | 2.2 | 15.6 |
CNTs-C=N-[bmim][NTf2] (MR 1:1.1) | 2.8 | 17.0 |
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Szelwicka, A.; Wolny, A.; Grymel, M.; Jurczyk, S.; Boncel, S.; Chrobok, A. Chemo-Enzymatic Baeyer–Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase. Materials 2021, 14, 3443. https://doi.org/10.3390/ma14133443
Szelwicka A, Wolny A, Grymel M, Jurczyk S, Boncel S, Chrobok A. Chemo-Enzymatic Baeyer–Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase. Materials. 2021; 14(13):3443. https://doi.org/10.3390/ma14133443
Chicago/Turabian StyleSzelwicka, Anna, Anna Wolny, Miroslawa Grymel, Sebastian Jurczyk, Slawomir Boncel, and Anna Chrobok. 2021. "Chemo-Enzymatic Baeyer–Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase" Materials 14, no. 13: 3443. https://doi.org/10.3390/ma14133443