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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16 Citations (Scopus)

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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Epoxidation
Aldehydes
Oxidation
Ionization
Mass spectrometry
Byproducts
Desorption
Zinc
Nuclear magnetic resonance
Hydroxyl Radical
Catalysts
Lasers
Temperature
dimethyldioxirane
polyisobutylene

Keywords

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

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

Cite this

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title = "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",
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.",
keywords = "Characterization, Dimethyldioxirane (DMD), Epoxidation, Kinetics (polym.), MALDI, Polyisobutylene (PIB), Synthesis",
author = "S{\'a}ndor K{\'e}ki and Mikl{\'o}s Nagy and Gy{\"o}rgy De{\'a}k and Albert L{\'e}vai and Mikl{\'o}s Zsuga",
year = "2002",
month = "11",
day = "15",
doi = "10.1002/pola.10455",
language = "English",
volume = "40",
pages = "3974--3986",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
issn = "0887-624X",
publisher = "John Wiley and Sons Inc.",
number = "22",

}

TY - JOUR

T1 - Dimethyldioxirane as a new and effective oxidation agent for the epoxidation of α,ω-di(isobutenyl)polyisobutylene

T2 - A convenient synthesis of α,ω-di(2-methyl-3-hydroxypropyl)-polyisobutylene

AU - Kéki, Sándor

AU - Nagy, Miklós

AU - Deák, György

AU - Lévai, Albert

AU - Zsuga, Miklós

PY - 2002/11/15

Y1 - 2002/11/15

N2 - 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.

AB - 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.

KW - Characterization

KW - Dimethyldioxirane (DMD)

KW - Epoxidation

KW - Kinetics (polym.)

KW - MALDI

KW - Polyisobutylene (PIB)

KW - Synthesis

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U2 - 10.1002/pola.10455

DO - 10.1002/pola.10455

M3 - Article

VL - 40

SP - 3974

EP - 3986

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

IS - 22

ER -