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research article

Reactions of aliphatic amines with ozone: Kinetics and mechanisms

Lim, Sungeun
•
McArdell, Christa S.
•
von Gunten, Urs  
June 15, 2019
Water Research

Aliphatic amines are common constituents in micropollutants and dissolved organic matter and present in elevated concentrations in wastewater-impacted source waters. Due to high reactivity, reactions of aliphatic amines with ozone are likely to occur during ozonation in water and wastewater treatment. We investigated the kinetics and mechanisms of the reactions of ozone with ethylamine, diethylamine, and triethylamine as model nitrogenous compounds. Species-specific second-order rate constants for the neutral parent amines ranged from 9.3 x 10(4) to 2.2 x 10(6)M(-1)s(-1) and the apparent second-order rate constants at pH 7 for potential or identified transformation products were 6.8 x 10(5) M(-1)s(-1) for N,N-diethylhydroxylamine, similar to 10(5) M(-1)s(-1) for N-ethylhydroxylamine, 1.9 x 10(3) M(-1)s(-1) for N-ethylethanimine oxide, and 3.4M(-1)s(-1) for nitroethane. Product analyses revealed that all amines were transformed to products containing a nitrogen-oxygen bond (e.g., triethylamine N-oxide and nitroethane) with high yields, i.e., 64-100% with regard to the abated target amines. These findings could be confirmed by measurements of singlet oxygen and hydroxyl radical which are formed during the amine-ozone reactions. Based on the high yields of nitroethane from ethylamine and diethylamine, a significant formation of nitroalkanes can be expected during ozonation of waters containing high levels of dissolved organic nitrogen, as expected in wastewaters or wastewater-impaired source waters. This may pose adverse effects on the aquatic environment and human health. (C) 2019 Elsevier Ltd. All rights reserved.

  • Details
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Type
research article
DOI
10.1016/j.watres.2019.03.089
Web of Science ID

WOS:000468253500049

Author(s)
Lim, Sungeun
McArdell, Christa S.
von Gunten, Urs  
Date Issued

2019-06-15

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Published in
Water Research
Volume

157

Start page

514

End page

528

Subjects

Engineering, Environmental

•

Environmental Sciences

•

Water Resources

•

Engineering

•

Environmental Sciences & Ecology

•

Water Resources

•

aliphatic amines

•

ozone

•

reaction kinetics

•

reaction mechanisms

•

transformation products

•

nitroalkanes

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disinfection by-products

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waste-water

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drinking-water

•

transformation products

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aqueous-solution

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inorganic-compounds

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hydroxyl radicals

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organic-compounds

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rate constants

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ozonation

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LTQE  
Available on Infoscience
June 18, 2019
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/157231
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