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 language | English |
|---|---|
| Pages (from-to) | 3233-3236 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 55 |
| Issue number | 10 |
| Publication status | Published - 1990 |
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ASJC Scopus subject areas
- Organic Chemistry
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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 journal › Article
}
TY - JOUR
T1 - Autoxidation of trimethylamine in aqueous solutions
AU - Chen, Michael J.
AU - Linehan, John
AU - Rathke, Jerome W.
PY - 1990
Y1 - 1990
N2 - 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.
AB - 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.
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M3 - Article
AN - SCOPUS:0006566345
VL - 55
SP - 3233
EP - 3236
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 10
ER -