Transformation of 1,2-diols over perfluorinated resinsulfonic acids (Nafion-H)

I. Bucsi, Árpád Molnár, M. Bartók, George A. Olah

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The transformations of 1,2-diols over perfluorinated resinsulfonic acids (Nafion-H) were studied, and correlation were examined between the structures of the investigated diols, the possible dehydration routes and the catalytic properties of Nafion-H. Comparisons were also made between the catalytic properties of Nafion-H and NaHX zeolite. Because of its stronger acidity, Nafion-H functions at temperatures considerably lower than those for the usual dehydrating catalysts, e.g. the zeolites. As is well established for other solid electrophilic catalysts, the dehydration of 1,2-diols mainly proceeds via the pinacol rearrangement. The lower temperatures and the stronger acidity of Nafion-H strongly favour the pinacol rearrangement versus 1,2-elimination. The reaction conditions are also advantageous for the formation of substituted 1,3-dioxolanes in a secondary condenstion between the unreacted diol and the primarily formed carbonyl compounds. Nafion-H gradually deactivates during long use, but it can be partially reactivated by washing with acetone.

Original languageEnglish
Pages (from-to)8195-8202
Number of pages8
JournalTetrahedron
Volume50
Issue number27
DOIs
Publication statusPublished - 1994

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Acids
Zeolites
Dehydration
Acidity
Carbonyl compounds
Catalysts
Temperature
Acetone
Washing
perfluorosulfonic acid
2'-disulfonic acid 1-amino-8-nephthol-2

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Transformation of 1,2-diols over perfluorinated resinsulfonic acids (Nafion-H). / Bucsi, I.; Molnár, Árpád; Bartók, M.; A. Olah, George.

In: Tetrahedron, Vol. 50, No. 27, 1994, p. 8195-8202.

Research output: Contribution to journalArticle

Bucsi, I. ; Molnár, Árpád ; Bartók, M. ; A. Olah, George. / Transformation of 1,2-diols over perfluorinated resinsulfonic acids (Nafion-H). In: Tetrahedron. 1994 ; Vol. 50, No. 27. pp. 8195-8202.
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