Synthesis of novel lipophilic and/or fluorophilic ethers of perfluoro-tert-butyl alcohol, perfluoropinacol and hexafluoroacetone hydrate via a Mitsunobu reaction: Typical cases of ideal product separation

Dénes Szabó, Ana Maria Bonto, István Kövesdi, Ágnes Gömöry, József Rábai

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Fluorophilic ethers having the structure RC(CF3) 2O(CH2)3CnF2n + 1 are obtained in high yields, when F-tert-butyl alcohol (R = CF3), F-acetone hydrate (R = O(CH2)3CnF 2n + 1), F-pinacol (R = C(CF3)2O(CH 2)3CnF2n + 1) are reacted with 3-perfluoroalkyl-1-propanols (CnF2n + 1(CH 2)3OH, n = 4, 6, 8, 10) in a Mitsunobu reaction (Ph 3P/DIAD [i-PrO2CN = NCO2Pr-i]/ether). The parent lipophilic ethers with the structure of (CF3) 3CO(CH2)3CnH2n + 1 were prepared analogously using the corresponding fatty alcohols and F-tert-butyl alcohol. To achieve ideal separations, products were transferred to orthogonal phases relative to the other reaction components using fluorous extraction, fluorous solid-organic liquid filtration, or steam-distillation. Selected physical properties including melting and boiling point, together with fluorous partition coefficients of these ethers were determined and the figures obtained were qualitatively analyzed using relevant thermodynamic theories. Some of these ethers are liquids with rather low freezing points and are miscible with fluorocarbon solvents.

Original languageEnglish
Pages (from-to)639-650
Number of pages12
JournalJournal of Fluorine Chemistry
Volume126
Issue number4
DOIs
Publication statusPublished - Apr 2005

Keywords

  • Boiling point
  • Cohesion parameters
  • Fluorophilicity
  • Ideal separation
  • Melting point
  • Mitsunobu ether synthesis
  • Solubility
  • Steam distillation
  • Structure-property correlation

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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