Reaction Products and Process of 2-Chloroethyl Ethyl Sulfide in Microemulsion Media

Abstract

GRAPHICAL ABSTRACTCl S +H 2 O S OH S S Cl S S OH S Cl H S OH S Cl +H 2 O _ ECT EHT 2-CEES 2-HEES Abstract The reaction of 2-chloroethyl ethyl sulfide was investigated in several oil-in-water microemulsions. The reaction products were identified by GC/MS, NMR, and LC/MS, and the reaction process was monitored by measuring peak height of reaction products and 2-chloroethyl ethyl sulfide with time by 1 H NMR spectroscopy. The result showed that 2-chloroethyl ethyl sulfide degraded to 2-hydroxyethyl ethyl sulfide, cyclic sulfonium ion, open chain sulfonium chloro ion and sulfonium hydroxyl ion, and the reaction proceeded via a cyclic sulfonium ion intermediate. Based on the NMR results, a pseudoternary model was established for the reaction process of 2-chloroethyl ethyl sulfide in microemulsion.

Detoxification of the Toxic Sulfur Mustard Simulant by a Supramolecular Antidote in Vitro and in Vivo

“…As the widely proposed S N 1 mechanism for mustard degradation, 51 an intermediate ethyl thiiranium 4a is formed first, which further reacts with H 2 O to give 7 or to give 5 or 6 with 7 or CEES (4). 52 The initiate ratio of 5, 6, and 7 depends on the concentration of CEES (4). When the concentration of CEES (4) is 5.0 mM, the initiate ratio of 5, 6, and 7 is 23, 7, and 70%, respectively (Figures 3A and S8).…”

“…CEES ( 4 ) is degradated immediately to three main products in water, which are assigned to sulfonium salts 5 , 6, and 2-(ethylthio)­ethanol 7 (Figure A). As the widely proposed S N 1 mechanism for mustard degradation, an intermediate ethyl thiiranium 4a is formed first, which further reacts with H 2 O to give 7 or to give 5 or 6 with 7 or CEES ( 4 ) . The initiate ratio of 5 , 6, and 7 depends on the concentration of CEES ( 4 ).…”