Nucleophilic chemistry of X-type Faujasite zeolites with 2-chloroethyl ethyl sulfide (CEES), a simulant of common mustard gas

Previous work shows that X Faujasite zeolite in a dried condition exhibits nucleophilic character in which the nucleophilic supercage oxygens are not appreciably hydrogen bonded to water and in which the leaving anion-assisting cations are not appreciably coordinated by water. Dry X Faujasite zeolites adsorb and remove chloride ion from 2-chloroethyl ethyl sulfide (CEES) at 1–3 molecules per supercage in the low adsorption limit to form a framework bound ethoxy ethyl sulfide in yields to over 80%. The chemistry with amounts of water near stoichiometric with respect to CEES was examined. Upon subsequent addition of water, 2-hydroxyethyl ethyl sulfide (HEES) is formed in small amounts from hydrolysis of the framework species. When water in the same amount is added to NaX before exposure to CEES, the yields of both framework species and HEES hydrolysis products are reduced. No chemistry of the kind reported in hydrolytic decontamination experiments in solution by Yang et al. [Y. Yang, L.L. Szafraniec, W.T. Beaudry, J.R. Ward, J. Org. Chem. 53 (1988) 3293] was observed under these water sparse, nucleophilic conditions.