Chemical oxidation of bis(2-chloroethyl) ether in the Fenton process: Kinetics, pathways and toxicity assessment.

Chemosphere

State Environmental Protection Key Laboratory of Soil Environmental Management and Pollution Control, Nanjing Institute of Environmental Sciences, Ministry of Environmental Protection of China, Nanjing, 210042, China.

Published: August 2017

Bis(2-chloroethyl) ether (BCEE) is a common chemical material and a frequently detected contaminant in groundwater. It has a strong toxicity and some other chemicals such as poly(vinyl chloride-co-isobutyl vinyl ether) contain similar chloroaliphatic ether structure. So the effective degradation method and transformation pathways for BCEE need to be learned. The present study compared the degradation rate of BCEE by Fenton's reagent and other common oxidation methods, and optimized the reaction conditions. Oxidation intermediates and pathways were also proposed and toxicities of the intermediates were investigated. Results showed that Fenton was highly effective to degrade BCEE. pH, Fe and HO concentration all affected the oxidation rate, among which Fe was the most significant variable. A total of twelve chlorinated intermediates were detected. Three main reaction pathways involved cleavage of the ether bond, hydroxyl substitution for hydrogen, and radical coupling. The pathways could be well interpreted and supported by theoretical calculations. The reaction mixture showed a decreasing trend in TOC concentration and toxicity until totally harmless to Vibrio fischeri after 15 min, but it was noteworthy that toxicities of some dimeric intermediates were stronger than BCEE by calculation.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.chemosphere.2017.03.104DOI Listing

Publication Analysis

Top Keywords

bis2-chloroethyl ether
8
ether
5
pathways
5
bcee
5
chemical oxidation
4
oxidation bis2-chloroethyl
4
ether fenton
4
fenton process
4
process kinetics
4
kinetics pathways
4

Similar Publications

Heteropolyacid Ligands in Two-Dimensional Channels Enable Lithium Separation from Monovalent Cations.

ACS Nano

January 2025

Institute of Molecular Plus, Department of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China.

Extracting lithium from salt lakes requires ion-selective membranes with customizable nanochannels. However, it remains a major challenge to separate alkali cations due to their same valences and similar ionic radius. Inspired by the K channel of KcsA K, significant progress has been made in adjusting nanochannel size to control the ion selectivity dominated by alkali cations dehydration.

View Article and Find Full Text PDF

Herein, we present an efficient and practical method for multicomponent carbo-heterofunctionalization of alkenes radical-polar crossover photoredox catalysis. Employing geminal bromonitroalkanes as redox-active reagents with a wide range of O-centered nucleophiles allows rapid access to various 1,3-difunctionalized nitro compounds, including β-nitro ketones, 1,3-nitro alcohols, 1,3-nitro ethers as well as cyclic molecules.

View Article and Find Full Text PDF

The proton bond is a pivotal chemical motif in many areas of science and technology. Its quantum chemical description is remarkably challenged by nuclear and charge delocalization effects and the fluxional perturbation that it induces on molecular substrates. This work seeks insights into proton bonding at sub-kelvin temperatures.

View Article and Find Full Text PDF

Crown ethers (CEs), macrocyclic polyethers, have attracted significant attention in supramolecular chemistry. It is known that they have many isomers due to their flexibility. It is challenging to select some exact conformation and tune the following self-assembly structure of CEs, and it has rarely been reported to date.

View Article and Find Full Text PDF

Photocatalyzed Azidofunctionalization of Alkenes via Radical-Polar Crossover.

Angew Chem Int Ed Engl

January 2025

Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, CH-1015, Lausanne, Switzerland.

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range of alkenes, including vinyl arenes, enamides, enol ethers, vinyl sulfides, and dehydroamino esters, were regioselectively functionalized with an azide and nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric acids, oximes, and phenols. The method led to a more efficient synthesis of 1,2-azidofunctionalized pharmaceutical intermediates when compared to previous approaches, resulting in both reduction of step count and increase in overall yield.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!