Main > ENVIRONMENTAL > HydroChloroCarbons (HCC) > Methylene Chloride (CH2Cl2) > Air Sensing System. > Org.: USA. U (MacroCyclic Amine) > Research Description

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Macrocyclic amine snags and holds CH2Cl2

A macrocyclic amine has been found to attack methylene chloride (CH2Cl2) with unprecedented high reactivity to form a quaternary ammonium salt (shown) and effectively trap the widely used volatile organic solvent. The discovery could lead to air-sensing systems for protecting industrial workers from CH2Cl2, which is listed by EPA as a probable human carcinogen. Authors were investigating the reaction of tertiary amines with CH2Cl2 when they observed that the macrocyclic amine reacts with a half-life of about two minutes at room temperature. This rate compares with half-lives of weeks to months for linear tertiary amines or small cyclic amines. The researchers believe one of CH2Cl2 s chlorine atoms first associates with the macrocycle s NH groups, and CH2Cl2 s two hydrogen atoms interact with the macrocycle s ether oxygen atoms via weak hydrogen bonds. The macrocyclic nitrogen then attacks CH2Cl2 s carbon atom, a carbon-chlorine bond breaks, and the chloride leaving group remains associated with the macrocycle as a counterion.



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