Bulky diarylammonium arenesulfonates as selective esterification catalysts

Kazuaki Ishihara, Shoko Nakagawa, Akira Sakakura

Research output: Contribution to journalArticle

97 Citations (Scopus)

Abstract

More environmentally benign alternatives to current chemical processes, especially large-scale, fundamental reactions such as ester condensations, are highly desirable for many reactions. Bulky diarylammonium pentafluorobenzenesulfonates and tosylates serve as extremely active dehydration catalysts for the ester condensation reaction of carboxylic acids with equimolar amounts of sterically demanding alcohols and acid-sensitive alcohols. Typically, the esterification reaction is performed in heptane by heating at 80 °C in the presence of 1 mol % of the catalyst without removing water. Esterification with primary alcohols proceeds without solvents even at room temperature. Furthermore, 4-(N-mesitylamino)polystyrene resin-bound pentafluorobenzenesulfonate can be recycled more than 10 times without activity loss.

Original languageEnglish
Pages (from-to)4168-4169
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number12
DOIs
Publication statusPublished - Mar 30 2005
Externally publishedYes

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Esterification
Alcohols
Catalysts
Esters
Chemical Phenomena
Heptanes
Condensation reactions
Polystyrenes
Heptane
Carboxylic Acids
Dehydration
Carboxylic acids
Heating
Condensation
Resins
Temperature
Acids
Water

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Bulky diarylammonium arenesulfonates as selective esterification catalysts. / Ishihara, Kazuaki; Nakagawa, Shoko; Sakakura, Akira.

In: Journal of the American Chemical Society, Vol. 127, No. 12, 30.03.2005, p. 4168-4169.

Research output: Contribution to journalArticle

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