Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions
<i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diimines (BIANs) have been used to reduce the undesired high viscosity of alkyl magnesium solutions, which are known to form polymeric structures. In order to understand the mechanism...
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/2/489 |
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| author | Julia Felicitas Schwarz Lukas Gadermayr Samuel Redl Thorsten Holtrichter-Rößmann Christian Paulik Clemens Schwarzinger |
| author_facet | Julia Felicitas Schwarz Lukas Gadermayr Samuel Redl Thorsten Holtrichter-Rößmann Christian Paulik Clemens Schwarzinger |
| author_sort | Julia Felicitas Schwarz |
| collection | DOAJ |
| description | <i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diimines (BIANs) have been used to reduce the undesired high viscosity of alkyl magnesium solutions, which are known to form polymeric structures. In order to understand the mechanisms, analyses of the BIAN alkyl magnesium solutions have been carried out under inert conditions with SEC-MS, NMR, and FTIR and were compared to the structures obtained from HPLC-MS, FTIR, and NMR after aqueous workup. While viscosity reduction was shown for all BIAN derivatives used, only the bis (diisopropyl)-substituted BIAN could be clearly assigned to a single reaction product, which also could be reused without loss of efficiency or decomposition. All other derivatives have been shown to behave differently, even under inert conditions, and decompose upon contact with acidic solvents. While the chemical reactions observed after the workup of the used BIANs are dominated by (multiple) alkylation, mainly on the C = N double bond, the observation of viscosity reduction cannot be assigned to this reaction alone, but to the interaction of the nitrogen atoms of BIANs with the Mg of the alkyl magnesium polymers, as could be shown by FTIR and NMR measurements under inert conditions. |
| first_indexed | 2024-03-09T11:36:43Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:36:43Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2149646295d940929e0a37d1debf43522023-11-30T23:40:35ZengMDPI AGMolecules1420-30492023-01-0128248910.3390/molecules28020489Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium SolutionsJulia Felicitas Schwarz0Lukas Gadermayr1Samuel Redl2Thorsten Holtrichter-Rößmann3Christian Paulik4Clemens Schwarzinger5Institute for Chemical Technology of Organic Materials, Johannes Kepler University (JKU), Altenberger Strasse 69, 4040 Linz, AustriaInstitute for Chemical Technology of Organic Materials, Johannes Kepler University (JKU), Altenberger Strasse 69, 4040 Linz, AustriaInstitute of Inorganic Chemistry, Johannes Kepler University (JKU), Altenberger Strasse 69, 4040 Linz, AustriaLanxess Organometallics GmbH, Ernst-Schering-Strasse 14, 59192 Bergkamen, GermanyInstitute for Chemical Technology of Organic Materials, Johannes Kepler University (JKU), Altenberger Strasse 69, 4040 Linz, AustriaInstitute for Chemical Technology of Organic Materials, Johannes Kepler University (JKU), Altenberger Strasse 69, 4040 Linz, Austria<i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diimines (BIANs) have been used to reduce the undesired high viscosity of alkyl magnesium solutions, which are known to form polymeric structures. In order to understand the mechanisms, analyses of the BIAN alkyl magnesium solutions have been carried out under inert conditions with SEC-MS, NMR, and FTIR and were compared to the structures obtained from HPLC-MS, FTIR, and NMR after aqueous workup. While viscosity reduction was shown for all BIAN derivatives used, only the bis (diisopropyl)-substituted BIAN could be clearly assigned to a single reaction product, which also could be reused without loss of efficiency or decomposition. All other derivatives have been shown to behave differently, even under inert conditions, and decompose upon contact with acidic solvents. While the chemical reactions observed after the workup of the used BIANs are dominated by (multiple) alkylation, mainly on the C = N double bond, the observation of viscosity reduction cannot be assigned to this reaction alone, but to the interaction of the nitrogen atoms of BIANs with the Mg of the alkyl magnesium polymers, as could be shown by FTIR and NMR measurements under inert conditions.https://www.mdpi.com/1420-3049/28/2/489magnesium alkylsviscosity reductioninert SEC-MS<i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diiminesstructure elucidationHPLC-MS |
| spellingShingle | Julia Felicitas Schwarz Lukas Gadermayr Samuel Redl Thorsten Holtrichter-Rößmann Christian Paulik Clemens Schwarzinger Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions Molecules magnesium alkyls viscosity reduction inert SEC-MS <i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diimines structure elucidation HPLC-MS |
| title | Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions |
| title_full | Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions |
| title_fullStr | Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions |
| title_full_unstemmed | Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions |
| title_short | Structural Characterization of BIAN Type Molecules Used in Viscosity Reduction of Alkyl Magnesium Solutions |
| title_sort | structural characterization of bian type molecules used in viscosity reduction of alkyl magnesium solutions |
| topic | magnesium alkyls viscosity reduction inert SEC-MS <i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diphenylacenaphthylene-1,2-diimines structure elucidation HPLC-MS |
| url | https://www.mdpi.com/1420-3049/28/2/489 |
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