Functionalized polyisobutylene and liquid/liquid separations as a method for scavenging transition metals from homogeneously catalyzed reactions

Dalila Chouikhi, Ihor Kulai, David E. Bergbreiter, Mohammed Al-Hashimi, Hassan S. Bazzi

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Article number120
JournalApplied Sciences (Switzerland)
Volume9
Issue number1
DOIs
Publication statusPublished - 31 Dec 2018

Fingerprint

polyisobutylene
Scavenging
scavenging
Transition metals
transition metals
Sulfhydryl Compounds
thiols
Alkanes
Liquids
Sulfides
liquids
Paraffins
alkanes
Ligands
ligands
Alkynes
Azides
cross coupling
alkynes
products

Keywords

  • Chelation
  • Green chemistry
  • Homogeneous catalysis
  • Polyisobutylene
  • Sequestrant

ASJC Scopus subject areas

  • Materials Science(all)
  • Instrumentation
  • Engineering(all)
  • Process Chemistry and Technology
  • Computer Science Applications
  • Fluid Flow and Transfer Processes

Cite this

Functionalized polyisobutylene and liquid/liquid separations as a method for scavenging transition metals from homogeneously catalyzed reactions. / Chouikhi, Dalila; Kulai, Ihor; Bergbreiter, David E.; Al-Hashimi, Mohammed; Bazzi, Hassan S.

In: Applied Sciences (Switzerland), Vol. 9, No. 1, 120, 31.12.2018.

Research output: Contribution to journalArticle

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