Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid
For the industrially relevant hydroformylation of but‑1-ene the concept of supported ionic liquid phase (SILP) has been applied previously. In this work, we have studied the influence of the type of ionic liquid (imidazolium and phosphonium based cations, various anions) on the solubility of the thr...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Journal of Ionic Liquids |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772422023000137 |
| _version_ | 1797454313996419072 |
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| author | Markus Schörner Andreas Schönweiz Stefanie Vignesh Liudmila Mokrushina Matthias Thommes Robert Franke Marco Haumann |
| author_facet | Markus Schörner Andreas Schönweiz Stefanie Vignesh Liudmila Mokrushina Matthias Thommes Robert Franke Marco Haumann |
| author_sort | Markus Schörner |
| collection | DOAJ |
| description | For the industrially relevant hydroformylation of but‑1-ene the concept of supported ionic liquid phase (SILP) has been applied previously. In this work, we have studied the influence of the type of ionic liquid (imidazolium and phosphonium based cations, various anions) on the solubility of the three reagents but‑1-ene, carbon monoxide and hydrogen. For the olefin, the predicted solubility values were determined using the COSMO-RS software tool. These data were compared to the experimentally determined values. A correlation between the predicted solubility and the observed activity within similar ILs could be observed. The highest activity could be obtained with the IL [N1888][NTf2]. A variation of the olefin chain length supported the observed correlation between solubility and activity. With increasing chain length, the activity of the SILP catalyst also increased. For the undesired consecutive reaction leading to aldols it was found that the substrate solubility does not significantly influence the activity or hydrocarbon accumulation under the used reaction conditions. The anion had a more pronounced effect on the accumulation of aldols, with hydrophilic Cl− and [EtOSO3]− showing lowest accumulation as well as aldol formation activity, while [NTf2]− showed highest values for both accumulation and formation activity. It was shown that the Kamlet-Taft-parameter β is a suitable value to be correlated with activity and accumulation for different ILs. |
| first_indexed | 2024-03-09T15:35:31Z |
| format | Article |
| id | doaj.art-ddcc3b6d999d4d59aa2ac16d43dd447d |
| institution | Directory Open Access Journal |
| issn | 2772-4220 |
| language | English |
| last_indexed | 2024-03-09T15:35:31Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Ionic Liquids |
| spelling | doaj.art-ddcc3b6d999d4d59aa2ac16d43dd447d2023-11-26T05:14:33ZengElsevierJournal of Ionic Liquids2772-42202023-12-0132100061Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquidMarkus Schörner0Andreas Schönweiz1Stefanie Vignesh2Liudmila Mokrushina3Matthias Thommes4Robert Franke5Marco Haumann6Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Chemische Reaktionstechnik (CRT), Egerlandstr. 3, Erlangen 91058, Germany; Helmholtz Institute Erlangen-Nürnberg for Renewable Energy (IEK-11), Forschungszentrum Jülich GmbH, Cauerstraße 1, Erlangen 91058, GermanyFriedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Chemische Reaktionstechnik (CRT), Egerlandstr. 3, Erlangen 91058, GermanyFriedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Chemische Reaktionstechnik (CRT), Egerlandstr. 3, Erlangen 91058, GermanyFriedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Thermische Verfahrenstechnik (TVT), Egerlandstr. 3, Erlangen 91058, GermanyFriedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Thermische Verfahrenstechnik (TVT), Egerlandstr. 3, Erlangen 91058, GermanyEvonik Operations GmbH, Paul-Baumann-Str. 1, Marl D-45772, Germany; Ruhr-Universität Bochum, Lehrstuhl für Theoretische Chemie, Universitätsstr. 150, Bochum D-44780, GermanyFriedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Lehrstuhl für Chemische Reaktionstechnik (CRT), Egerlandstr. 3, Erlangen 91058, Germany; Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa; Corresponding author.For the industrially relevant hydroformylation of but‑1-ene the concept of supported ionic liquid phase (SILP) has been applied previously. In this work, we have studied the influence of the type of ionic liquid (imidazolium and phosphonium based cations, various anions) on the solubility of the three reagents but‑1-ene, carbon monoxide and hydrogen. For the olefin, the predicted solubility values were determined using the COSMO-RS software tool. These data were compared to the experimentally determined values. A correlation between the predicted solubility and the observed activity within similar ILs could be observed. The highest activity could be obtained with the IL [N1888][NTf2]. A variation of the olefin chain length supported the observed correlation between solubility and activity. With increasing chain length, the activity of the SILP catalyst also increased. For the undesired consecutive reaction leading to aldols it was found that the substrate solubility does not significantly influence the activity or hydrocarbon accumulation under the used reaction conditions. The anion had a more pronounced effect on the accumulation of aldols, with hydrophilic Cl− and [EtOSO3]− showing lowest accumulation as well as aldol formation activity, while [NTf2]− showed highest values for both accumulation and formation activity. It was shown that the Kamlet-Taft-parameter β is a suitable value to be correlated with activity and accumulation for different ILs.http://www.sciencedirect.com/science/article/pii/S2772422023000137Supported ionic liquid phase (SILP)HydroformylationSolubilityRhodiumAldol condensationKamlet-Taft-parameter |
| spellingShingle | Markus Schörner Andreas Schönweiz Stefanie Vignesh Liudmila Mokrushina Matthias Thommes Robert Franke Marco Haumann Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid Journal of Ionic Liquids Supported ionic liquid phase (SILP) Hydroformylation Solubility Rhodium Aldol condensation Kamlet-Taft-parameter |
| title | Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid |
| title_full | Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid |
| title_fullStr | Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid |
| title_full_unstemmed | Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid |
| title_short | Tuning catalyst performance in the SILP-catalyzed gas-phase hydroformylation of but-1-ene by choice of the ionic liquid |
| title_sort | tuning catalyst performance in the silp catalyzed gas phase hydroformylation of but 1 ene by choice of the ionic liquid |
| topic | Supported ionic liquid phase (SILP) Hydroformylation Solubility Rhodium Aldol condensation Kamlet-Taft-parameter |
| url | http://www.sciencedirect.com/science/article/pii/S2772422023000137 |
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