Autoxidation of trimethylamine in aqueous solutions

Michael J. Chen, John Linehan, Jerome W. Rathke

Research output: Contribution to journalArticle

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Abstract

The autoxidation of trimethylamine in aqueous solutions has been studied at 100°C and at O2 pressures up to 153 atm. Trimethylamine N-oxide is a major product. Its yield accounts for as much as, but never in excess of 50%, the balance being Me2NH and HCONMe2. The reaction follows second-order kinetics, -d[Me3N]/dt = k[Me3N]Po2, where k = 8.7 × 10-7 atm-1 s-1. In solutions buffered with 0.1 N NaOH, the yield of Me3NO is reduced. These results are interpreted in terms of a rate-limiting electron-transfer reaction between Me3N and dioxygen, followed by reactions dictated by the radical ions, Me3N.+ and O2 .-, thus generated. It is noted that only one oxygen atom in the O2 molecule is incorporated into Me3NO, the other being used in the sacrificial oxidations to give other products.

Original languageEnglish
Pages (from-to)3233-3236
Number of pages4
JournalJournal of Organic Chemistry
Volume55
Issue number10
Publication statusPublished - 1990

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Oxygen
Ions
Atoms
Oxidation
Molecules
Kinetics
Electrons
trimethylamine
trimethyloxamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Autoxidation of trimethylamine in aqueous solutions. / Chen, Michael J.; Linehan, John; Rathke, Jerome W.

In: Journal of Organic Chemistry, Vol. 55, No. 10, 1990, p. 3233-3236.

Research output: Contribution to journalArticle

Chen, MJ, Linehan, J & Rathke, JW 1990, 'Autoxidation of trimethylamine in aqueous solutions', Journal of Organic Chemistry, vol. 55, no. 10, pp. 3233-3236.
Chen, Michael J. ; Linehan, John ; Rathke, Jerome W. / Autoxidation of trimethylamine in aqueous solutions. In: Journal of Organic Chemistry. 1990 ; Vol. 55, No. 10. pp. 3233-3236.
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