An example of lipophiloselectivity: The preferred oxidation, in water, of hydrophobic 2-alkanols catalyzed by a cross-linked polyethyleneimine- polyoxometalate catalyst assembly

Adina Haimov, Ronny Neumann

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67 Citations (Scopus)

Abstract

A cross-linked polyethyleneimine polymer containing the [ZnWZn 2(H2O)2(ZnW9O34) 2]12- polyoxometalate was prepared from branched polyethyleneimine (Mw = 600), the polyoxometalate, and a n-octylamine-epichlorohydrin cross-linking reagent. This catalytic assembly was active for the selective oxidation of 2-alkanols to 2-alkanones with aqueous H2O2 with reactions presumably occurring at a hydrophobic domain. Most importantly, the catalyst showed distinctive lipophiloselectivity, that is selectivity as a function of the lipophilic nature of a reaction substrate. The lipophiloselectivity was proportional to the relative partition coefficient (1-octanol/water) of the substrates.

Original languageEnglish
Pages (from-to)15697-15700
Number of pages4
JournalJournal of the American Chemical Society
Volume128
Issue number49
DOIs
Publication statusPublished - Dec 13 2006

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Polyethyleneimine
Epichlorohydrin
Cross-Linking Reagents
1-Octanol
Oxidation
Catalysts
Water
Catalyst selectivity
Substrates
Polymers
polyoxometalate I
octylamine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "An example of lipophiloselectivity: The preferred oxidation, in water, of hydrophobic 2-alkanols catalyzed by a cross-linked polyethyleneimine- polyoxometalate catalyst assembly",
abstract = "A cross-linked polyethyleneimine polymer containing the [ZnWZn 2(H2O)2(ZnW9O34) 2]12- polyoxometalate was prepared from branched polyethyleneimine (Mw = 600), the polyoxometalate, and a n-octylamine-epichlorohydrin cross-linking reagent. This catalytic assembly was active for the selective oxidation of 2-alkanols to 2-alkanones with aqueous H2O2 with reactions presumably occurring at a hydrophobic domain. Most importantly, the catalyst showed distinctive lipophiloselectivity, that is selectivity as a function of the lipophilic nature of a reaction substrate. The lipophiloselectivity was proportional to the relative partition coefficient (1-octanol/water) of the substrates.",
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AB - A cross-linked polyethyleneimine polymer containing the [ZnWZn 2(H2O)2(ZnW9O34) 2]12- polyoxometalate was prepared from branched polyethyleneimine (Mw = 600), the polyoxometalate, and a n-octylamine-epichlorohydrin cross-linking reagent. This catalytic assembly was active for the selective oxidation of 2-alkanols to 2-alkanones with aqueous H2O2 with reactions presumably occurring at a hydrophobic domain. Most importantly, the catalyst showed distinctive lipophiloselectivity, that is selectivity as a function of the lipophilic nature of a reaction substrate. The lipophiloselectivity was proportional to the relative partition coefficient (1-octanol/water) of the substrates.

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