Carbocationic Polymerization in Supercritical Co2. V.* Synthesis of Phenol-Terminated Polyisobutylene

G. Deák, Tibor Pemecker, Joseph P. Kennedy

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The convenient synthesis of well-defined phenol-ended polyisobutylene (PIB): of Mn-2000 in supercritical carbon dioxide (SC.C02) at 140 bar and 32.5 °C has been accomplished. The synthesis involves two steps, both carried out in SC*C02:1. The preparation of tert-CI ended PIB prepolymer (PIB-Cl1) and 2. The quantitative para alkylation of phenol by the prepolymer in the presence of BF3OEt2. The synthesis conditions were developed by studying the model alkylation of phenol by 2-chloro-2,4,4-trlmethylpentane (TMPCI) in SC*C02, giving rise to: According to quantitative ‘H-NMR analysis we conclude that phenol has been quantitatively alkylated by the model compound and by the PIB-Cl2. This is the first time electrophilic aromatic alkylations carried out In SC*C02 solvent are described. Phenol was found to be readily soluble in SC*C02. Efforts to alkylate 2-bromoethylbenzene (BrEtBz) by PIB-Cl2 in the presence of various Friedel-Crafts halides in SC•C02 remained unsuccessful. Evidently, ill-defined side-reactions (cracking, etc.) overwhelm the desired p-alkylation at the relatively high reaction temperatures employed (>31 °C).

Original languageEnglish
Pages (from-to)979-984
Number of pages6
JournalJournal of Macromolecular Science - Pure and Applied Chemistry
Volume32
Issue number7
DOIs
Publication statusPublished - 1995

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Phenol
Phenols
Alkylation
Polymerization
Carbon Dioxide
Carbon dioxide
Nuclear magnetic resonance
polyisobutylene
Temperature

ASJC Scopus subject areas

  • Chemistry(all)
  • Ceramics and Composites
  • Materials Chemistry
  • Polymers and Plastics

Cite this

Carbocationic Polymerization in Supercritical Co2. V.* Synthesis of Phenol-Terminated Polyisobutylene. / Deák, G.; Pemecker, Tibor; Kennedy, Joseph P.

In: Journal of Macromolecular Science - Pure and Applied Chemistry, Vol. 32, No. 7, 1995, p. 979-984.

Research output: Contribution to journalArticle

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