Hydrodechlorination of Aryl Chlorides Under Biocompatible Conditions

Abstract

Developing nonenzymatic chemistry that is nontoxic to microbial organisms creates the potential to integrate synthetic chemistry with metabolism and offers new remediation strategies. Chlorinated organic compounds known to bioaccumulate and cause harmful environmental impact can be converted into less damaging derivatives through hydrodehalogenation. The hydrodechlorination of substituted aryl chlorides using Pd/C and ammonium formate in biological media under physiological conditions (neutral pH, moderate temperature, and ambient pressure) is reported. The reaction conditions were successful for a range of aryl chlorides with electron-donating and -withdrawing groups, limited by the solubility of substrates in aqueous media. Soluble substrates gave good yields (60–98%) of the reduction product within 48 h. The relative toxicities of each reaction component were tested separately and together against bacteria, and the reaction proceeded in bacterial cultures containing an aryl chloride with robust cell growth. This work offers an initial step toward the removal of aryl chlorides from waste streams that currently use bacterial degradation to remove pollutants.

Rational Design and Structural Regulation of Robust Catalysts for Electrocatalytic Hydrodechlorination: From Nanostructures to Single Atoms

“…11,12 In addition to policy and legal source control, the research and development of detoxification technology for existing halogenated organic pollutants (especially chlorine-containing organics) in water bodies have also attracted extensive attention. The current treatment technologies for chlorinecontaining organics include adsorption and enrichment, microbial degradation, 13,14 advanced oxidation, 4,15 and chemical reduction. 16,17 Among these methods, chemical reduction achieves faster dechlorination by adding elemental iron (Fe 0 ) 18,19 or hydrogen (H 2 ) 20,21 and has better performances.…”

“…In addition to policy and legal source control, the research and development of detoxification technology for existing halogenated organic pollutants (especially chlorine-containing organics) in water bodies have also attracted extensive attention. The current treatment technologies for chlorine-containing organics include adsorption and enrichment, microbial degradation, , advanced oxidation, , and chemical reduction. , Among these methods, chemical reduction achieves faster dechlorination by adding elemental iron (Fe 0 ) , or hydrogen (H 2 ) , and has better performances. Fe provides electrons to react with C–Cl bonds directly or to react with water to generate active atomic hydrogen H* to substitute Cl, and chlorinated organics are thus converted into nonchlorinated counterparts, and the toxicity is thus significantly reduced; the Fe 2+ produced by the reaction can also participate in flocculation and precipitation to remove the pollutants.…”