Functionalized Polyisobutylene and Liquid/Liquid Separations as a Method for Scavenging Transition Metals from Homogeneously Catalyzed Reactions
Ethanedithiol-functionalized polyisobutylene was prepared in one step by a photoinitiated thiol-ene “click” reaction starting from ethanedithiol and polyisobutylene (PIB). The functionalized oligomer product was then used as a soluble sequestrant for transition metals. This PIB-b...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018-12-01
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| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | http://www.mdpi.com/2076-3417/9/1/120 |
| Summary: | Ethanedithiol-functionalized polyisobutylene was prepared in one step by a photoinitiated thiol-ene “click” reaction starting from ethanedithiol and polyisobutylene (PIB). The functionalized oligomer product was then used as a soluble sequestrant for transition metals. This PIB-bound thioether-thiol ligand is phase selectively soluble in alkanes and it quantitatively sequesters common transition metals like Cu2+ and Pd2+ into an alkane phase, separating them from polar solvents in a biphasic liquid/liquid separation. The chelating thioether-thiol ligand was also successfully used to remove Cu and Pd transition metal catalyst residues from products in crude reaction mixtures in both azide/alkyne click reactions and cross-coupling reactions using a liquid/liquid extraction. Separation efficiencies exceeding 95% and in many cases 99% were achieved. |
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| ISSN: | 2076-3417 |