The ability to detect, separate and quantitate trace amounts of sulfur mustards and their decomposition by-products in aqueous solution is of relevance and potential use in environmental studies as well as in general analytical methodology.
Sulfur mustards currently are analyzed by calorimetry using 4-(p-nitrobenzylpyridine (I)' according to the following reaction:
This is a general test and gives positive results for practically all alkylating agents and false positives for some acylating agents. In addition, this test cannot be used for the decomposition by-products.
Gas chromatography (GC) has also been employedZ. However, water samples cannot be analyzed directly by GC but must undergo a lengthy extraction and workup procedure before analysis can be performed.
The sulfur mustards and their by-products do not absorb or fluoresce in the ultraviolet (UV) or visible spectral range. Thus, they are not amenable by themselves to high-performance liquid chromatography (HPLC) analysis using a UV or fluorescent detector.
The arenesulfonylsulfilimines were discovered shortly after World War I by Mann and Pope3. It was shown then that bis-(2-chloroethyl)suhide (mustard gas) (II) was swiftly converted in aqueous solution to crystalline .and innocuous S-bis-(2-chloroethyl)-N-tolylsulfonylsulfilimine (III) by treatment with sodium toluenesulfochloramide (chloramine-T) (IV) according to the following reaction: