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

D. Szabó, Ana Maria Bonto, István Kövesdi, A. Gömöry, J. 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)641-652
Number of pages12
JournalJournal of Fluorine Chemistry
Volume126
Issue number4
DOIs
Publication statusPublished - Apr 2005

Fingerprint

Ethers
Hydrates
ether
hydrates
alcohol
ethers
alcohols
Alcohols
tert-Butyl Alcohol
synthesis
products
Freezing
Fatty Alcohols
melting points
Fluorocarbons
1-Propanol
Distillation
Boiling point
methylidyne
fluorocarbon

Keywords

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

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics

Cite this

@article{baca0fa9a5304f69af755e83e9368fd2,
title = "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",
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.",
keywords = "Boiling point, Cohesion parameters, Fluorophilicity, Ideal separation, Melting point, Mitsunobu ether synthesis, Solubility, Steam distillation, Structure-property correlation",
author = "D. Szab{\'o} and Bonto, {Ana Maria} and Istv{\'a}n K{\"o}vesdi and A. G{\"o}m{\"o}ry and J. R{\'a}bai",
year = "2005",
month = "4",
doi = "10.1016/j.jfluchem.2005.01.017",
language = "English",
volume = "126",
pages = "641--652",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier BV",
number = "4",

}

TY - JOUR

T1 - Synthesis of novel lipophilic and/or fluorophilic ethers of perfluoro-tert-butyl alcohol, perfluoropinacol and hexafluoroacetone hydrate via a Mitsunobu reaction

T2 - Typical cases of ideal product separation

AU - Szabó, D.

AU - Bonto, Ana Maria

AU - Kövesdi, István

AU - Gömöry, A.

AU - Rábai, J.

PY - 2005/4

Y1 - 2005/4

N2 - 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.

AB - 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.

KW - Boiling point

KW - Cohesion parameters

KW - Fluorophilicity

KW - Ideal separation

KW - Melting point

KW - Mitsunobu ether synthesis

KW - Solubility

KW - Steam distillation

KW - Structure-property correlation

UR - http://www.scopus.com/inward/record.url?scp=23344447517&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=23344447517&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2005.01.017

DO - 10.1016/j.jfluchem.2005.01.017

M3 - Article

AN - SCOPUS:23344447517

VL - 126

SP - 641

EP - 652

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

IS - 4

ER -