Catalytic efficiency and stability of tertiary amines in oxidation of methyl 4-deoxy-β-L-threo-hex-4-enopyranosiduronic acid by hypochlorous acid

Ghazaleh Afsahi*, Carlo Bertinetto, Michael Hummel, Kavindra Kumar Kesari, Tapani Vuorinen

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Tertiary amines efficiently catalyze oxidation of unsaturated organic substances by hypochlorous acid (HOCl). However, the quaternary chloroammonium cation, formed spontaneously as the reactive species, often undergoes parallel self-decomposition that increases the catalyst dosage required. Thus, an otherwise potential industrial catalyst, 1,4-diazabicyclo[2.2.2]octane (DABCO), decomposes in a few seconds in the presence of HOCl. In this paper, we show that substituting one of the amino groups of DABCO with an alkyl group, in this case with carboxymethyl group, fully stabilizes the polycyclic chloroammonium cation towards self-decomposition. The catalytic efficiency of N-carboxymethyl-1,4-diazabicyclo[2.2.2]octane was similar to, or only slightly lower than that of DABCO, under mild acid conditions (pH 3-6). Although we studied oxidation of methyl 4-deoxy-β-L-threo-hex-4-enopyranosiduronic acid only, the main conclusions on the effect N-alkylation on the catalyst stability and activity should be transferable to catalytic conversion of any other substrate by HOCl.

Original languageEnglish
Article number110413
JournalMolecular Catalysis
Volume474
DOIs
Publication statusPublished - 1 Sep 2019
MoE publication typeA1 Journal article-refereed

Keywords

  • 4-deoxy-β-L-threo-hex-4-enopyranosiduronic acid
  • Catalyst
  • Chemometry
  • Hypochlorous acid
  • Kinetic model
  • N-carboxymethyl-1,4-diazabicyclo[2.2.2]octane

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