Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry
Within the “compartmentalised smart factory” approach of the ONE-FLOW project the implementation of different catalysts in “compartments” provided by Pickering emulsions and their application in continuous flow is targeted. We present here the development of heterogeneous Pd catalysts that are ready...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.52 |
| _version_ | 1818619648007995392 |
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| author | Katharina Hiebler Georg J. Lichtenegger Manuel C. Maier Eun Sung Park Renie Gonzales-Groom Bernard P. Binks Heidrun Gruber-Woelfler |
| author_facet | Katharina Hiebler Georg J. Lichtenegger Manuel C. Maier Eun Sung Park Renie Gonzales-Groom Bernard P. Binks Heidrun Gruber-Woelfler |
| author_sort | Katharina Hiebler |
| collection | DOAJ |
| description | Within the “compartmentalised smart factory” approach of the ONE-FLOW project the implementation of different catalysts in “compartments” provided by Pickering emulsions and their application in continuous flow is targeted. We present here the development of heterogeneous Pd catalysts that are ready to be used in combination with biocatalysts for catalytic cascade synthesis of active pharmaceutical ingredients (APIs). In particular, we focus on the application of the catalytic systems for Suzuki–Miyaura cross-coupling reactions, which is the key step in the synthesis of the targeted APIs valsartan and sacubitril. An immobilised enzyme will accomplish the final product formation via hydrolysis. In order to create a large interfacial area for the catalytic reactions and to keep the reagents separated until required, the catalyst particles are used to stabilise Pickering emulsions of oil and water. A set of Ce–Sn–Pd oxides with the molecular formula Ce0.99−xSnxPd0.01O2−δ (x = 0–0.99) has been prepared utilising a simple single-step solution combustion method. The high applicability of the catalysts for different functional groups and their minimal leaching behaviour is demonstrated with various Suzuki–Miyaura cross-coupling reactions in batch as well as in continuous flow employing the so-called “plug & play reactor”. Finally, we demonstrate the use of these particles as the sole emulsifier of oil–water emulsions for a range of oils. |
| first_indexed | 2024-12-16T17:40:49Z |
| format | Article |
| id | doaj.art-d4018dd420b542068a1b87f29ecfe595 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T17:40:49Z |
| publishDate | 2018-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-d4018dd420b542068a1b87f29ecfe5952022-12-21T22:22:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-03-0114164865810.3762/bjoc.14.521860-5397-14-52Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistryKatharina Hiebler0Georg J. Lichtenegger1Manuel C. Maier2Eun Sung Park3Renie Gonzales-Groom4Bernard P. Binks5Heidrun Gruber-Woelfler6Institute of Process and Particle Engineering, Graz University of Technology, Inffeldgasse 13/III, 8010 Graz, AustriaInstitute of Process and Particle Engineering, Graz University of Technology, Inffeldgasse 13/III, 8010 Graz, AustriaInstitute of Process and Particle Engineering, Graz University of Technology, Inffeldgasse 13/III, 8010 Graz, AustriaSchool of Mathematics and Physical Sciences, University of Hull, Hull HU6 7RX, UKSchool of Mathematics and Physical Sciences, University of Hull, Hull HU6 7RX, UKSchool of Mathematics and Physical Sciences, University of Hull, Hull HU6 7RX, UKInstitute of Process and Particle Engineering, Graz University of Technology, Inffeldgasse 13/III, 8010 Graz, AustriaWithin the “compartmentalised smart factory” approach of the ONE-FLOW project the implementation of different catalysts in “compartments” provided by Pickering emulsions and their application in continuous flow is targeted. We present here the development of heterogeneous Pd catalysts that are ready to be used in combination with biocatalysts for catalytic cascade synthesis of active pharmaceutical ingredients (APIs). In particular, we focus on the application of the catalytic systems for Suzuki–Miyaura cross-coupling reactions, which is the key step in the synthesis of the targeted APIs valsartan and sacubitril. An immobilised enzyme will accomplish the final product formation via hydrolysis. In order to create a large interfacial area for the catalytic reactions and to keep the reagents separated until required, the catalyst particles are used to stabilise Pickering emulsions of oil and water. A set of Ce–Sn–Pd oxides with the molecular formula Ce0.99−xSnxPd0.01O2−δ (x = 0–0.99) has been prepared utilising a simple single-step solution combustion method. The high applicability of the catalysts for different functional groups and their minimal leaching behaviour is demonstrated with various Suzuki–Miyaura cross-coupling reactions in batch as well as in continuous flow employing the so-called “plug & play reactor”. Finally, we demonstrate the use of these particles as the sole emulsifier of oil–water emulsions for a range of oils.https://doi.org/10.3762/bjoc.14.52compartmentalisationheterogeneous catalysismultistep flow chemistrypalladiumPickering emulsions |
| spellingShingle | Katharina Hiebler Georg J. Lichtenegger Manuel C. Maier Eun Sung Park Renie Gonzales-Groom Bernard P. Binks Heidrun Gruber-Woelfler Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry Beilstein Journal of Organic Chemistry compartmentalisation heterogeneous catalysis multistep flow chemistry palladium Pickering emulsions |
| title | Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry |
| title_full | Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry |
| title_fullStr | Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry |
| title_full_unstemmed | Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry |
| title_short | Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry |
| title_sort | heterogeneous pd catalysts as emulsifiers in pickering emulsions for integrated multistep synthesis in flow chemistry |
| topic | compartmentalisation heterogeneous catalysis multistep flow chemistry palladium Pickering emulsions |
| url | https://doi.org/10.3762/bjoc.14.52 |
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