Dimethyldioxirane as a new and effective oxidation agent for the epoxidation of α,ω-di(isobutenyl)polyisobutylene: A convenient synthesis of α,ω-di(2-methyl-3-hydroxypropyl)-polyisobutylene

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Abstract

The synthesis and characterization of α,ω-di(2-methyl-2,3-epoxypropyl)-polyisobutylene are reported. The epoxidation of α,ω-di(isobutenyl)polyisobutylene was achieved at room temperature with dimethyldioxirane, which proved to be a very effective reagent for epoxidation without the formation of byproducts. A very good agreement was found for the conversion determined by 1H NMR and matrix-assisted laser desorption/ionization mass spectrometry (MALDI HMS). The epoxy end groups were converted quantitatively into aldehyde termini with zinc bromide as a catalyst. The aldehyde groups were then reduced with LiAlH4 into primary hydroxyl functions to obtain α,ω-di(2-methyl-3-hydroxylpropyl)polyisobutylene with high efficiency.

Original languageEnglish
Pages (from-to)3974-3986
Number of pages13
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume40
Issue number22
DOIs
Publication statusPublished - Nov 15 2002

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Keywords

  • Characterization
  • Dimethyldioxirane (DMD)
  • Epoxidation
  • Kinetics (polym.)
  • MALDI
  • Polyisobutylene (PIB)
  • Synthesis

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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