Functionalization of carbon black for Ru complexation towards the oxidative cleavage of oleic acid
•Heterogenization of ru through polydopamine and bipyridine on carbon black.•Functionalized carbon Ru-catalysts active in the oxidative cleavage of oleic acid.•Total conversion and 95% of yields after 7 h of stirring at room temperature.•High catalytic activity of carbon black-polydopamine-Ru up to...
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| Vydané v: | Molecular catalysis Ročník 541; s. 113097 |
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| Hlavní autori: | , , , |
| Médium: | Journal Article |
| Jazyk: | English |
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Elsevier B.V
15.04.2023
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| ISSN: | 2468-8231, 2468-8231 |
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| Abstract | •Heterogenization of ru through polydopamine and bipyridine on carbon black.•Functionalized carbon Ru-catalysts active in the oxidative cleavage of oleic acid.•Total conversion and 95% of yields after 7 h of stirring at room temperature.•High catalytic activity of carbon black-polydopamine-Ru up to 5 recycling tests.
Macroporous oxidized carbon black (CBO) have been functionalized with 4,4′-diamino-2,2′-bipyridine (NH2-bpy) and polydopamine (PDA) allowing the complexation of Ru for the catalytic valorization of oleic acid through its oxidative cleavage. This reaction produces azelaic and pelargonic acids which are highly demanded in pharmacology. Conventional bpy is a well-known chelating agent for Ru and the aim of this work is directed to assess its suitability along with polydopamine in building a stable catalyst in the oxidative cleavage reaction. NH2-bpy was covalently bonded to COOH groups on CBO surface by amidation through an acylation and cross-linking(NHS/EDC). On its side, dopamine was self-polymerized in contact with CBO. The success of the deposition of NH2-bpy and PDA was confirmed by FTIR, TGA, and N2 physisorption, while Ru complexation was determined by ICP and XPS analyses. Among the three catalysts, the catalyst based on PDA was the most promising one, reaching a complete conversion of oleic acid with yields of pelargonic and azelaic acids around 95%. Although hot-filtration tests confirmed the presence of Ru species in the reaction medium, the PDA catalyst remained active even after five runs. Actually, post-catalysis characterization of the solid revealed that catechol groups of PDA re-adsorb Ru species once the reaction ends thereby ensuring the reusability of the heterogeneous catalyst.
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| AbstractList | •Heterogenization of ru through polydopamine and bipyridine on carbon black.•Functionalized carbon Ru-catalysts active in the oxidative cleavage of oleic acid.•Total conversion and 95% of yields after 7 h of stirring at room temperature.•High catalytic activity of carbon black-polydopamine-Ru up to 5 recycling tests.
Macroporous oxidized carbon black (CBO) have been functionalized with 4,4′-diamino-2,2′-bipyridine (NH2-bpy) and polydopamine (PDA) allowing the complexation of Ru for the catalytic valorization of oleic acid through its oxidative cleavage. This reaction produces azelaic and pelargonic acids which are highly demanded in pharmacology. Conventional bpy is a well-known chelating agent for Ru and the aim of this work is directed to assess its suitability along with polydopamine in building a stable catalyst in the oxidative cleavage reaction. NH2-bpy was covalently bonded to COOH groups on CBO surface by amidation through an acylation and cross-linking(NHS/EDC). On its side, dopamine was self-polymerized in contact with CBO. The success of the deposition of NH2-bpy and PDA was confirmed by FTIR, TGA, and N2 physisorption, while Ru complexation was determined by ICP and XPS analyses. Among the three catalysts, the catalyst based on PDA was the most promising one, reaching a complete conversion of oleic acid with yields of pelargonic and azelaic acids around 95%. Although hot-filtration tests confirmed the presence of Ru species in the reaction medium, the PDA catalyst remained active even after five runs. Actually, post-catalysis characterization of the solid revealed that catechol groups of PDA re-adsorb Ru species once the reaction ends thereby ensuring the reusability of the heterogeneous catalyst.
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| ArticleNumber | 113097 |
| Author | de la Torre, Ernesto Magerat, Alixandre Gaigneaux, Eric M. Gámez, Sebastián |
| Author_xml | – sequence: 1 givenname: Sebastián orcidid: 0000-0002-8850-8604 surname: Gámez fullname: Gámez, Sebastián email: sebastian.gamez@uclouvain.be organization: Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Pasteur 1, L4.01.09, Louvain-la-Neuve 1348, Belgium – sequence: 2 givenname: Alixandre orcidid: 0000-0001-9480-3549 surname: Magerat fullname: Magerat, Alixandre organization: Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Pasteur 1, L4.01.09, Louvain-la-Neuve 1348, Belgium – sequence: 3 givenname: Ernesto surname: de la Torre fullname: de la Torre, Ernesto organization: Department of Extractive Metallurgy, Escuela Politécnica Nacional, Ladron de Guevera E11-253, Quito 170517, Ecuador – sequence: 4 givenname: Eric M. orcidid: 0000-0003-2239-4306 surname: Gaigneaux fullname: Gaigneaux, Eric M. organization: Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Pasteur 1, L4.01.09, Louvain-la-Neuve 1348, Belgium |
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| Keywords | Polydopamine Heterogeneous catalysis Fatty acids Bipyridine Oxidative cleavage |
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