Price, Charles C. published the artcileHydrolysis and oxidation of mustard gas and related compounds in aqueous solution, Formula: C4H8Cl2S2, the publication is Journal of Organic Chemistry (1947), 238-48, database is CAplus and MEDLINE.
cf. following abstract The hydrolysis and oxidation of S(CH2CH2Cl)2 (I) are studied to evaluate its hazard as a H2O contaminant. To 400 cc. H2O through which O containing O3 is bubbled, 40 cc. Cellosolve containing 1.6 cc. I is added dropwise over a period of 1 hr. The solution is evaporated to dryness to give 53% OS(CH2CH2Cl)2 (II), m. 105-8°. When to 100 cc. H2O containing 0.25 mol. NaOCl, adjusted to pH 7.5, 25 cc. MeOH containing 2 cc. I is added, 57% II, m. 105-8°, is isolated. I and chloramine-T (III) give 83% N-(p-tolylsulfonyl) – S,S’ – bis(2-chloroethyl) sulfilimine, m. 139-42°. I and Halazone (p-HO2CC6H4SO2NCl2) (IV) give 40% II, m. 104-7°. When II is shaken with NaHCO3, Cl is very slowly split off. II and NaOCl in NaHCO3-buffered solution give 37% O2S(CH2CH2Cl)2 (V), m. 54-6°. To 200 g. II in 7.5 l. H2O, 4.5 l. 0.612 N NaOCl contg: 100 g. NaHCO3 is added with stirring, and the mixture kept overnight and extracted exhaustively with CHCl3. From the residue of the CHCl3 extract (205 g.), 37 g. II, m. 103-7°, is filtered off. The filtrate is subjected to a rapid vacuum distillation, giving a distillate (VI), b1 73-145°, and leaving 30 g. residue from which 9 g. light tan crystals, m. 107-8°, are isolated. VI is fractionally distilled through a 12-in. column and the presence of OS(CH:CH2)2, b16 81°, nD20 1.5100, O2S(CH:CH2)2 (VII), b16 109°, nD20 1.4782, CH2:CHSOCH2CH2Cl, b15 126°, nD20 1.5232, and CH2:CHSO2CH2CH2Cl, b16 143°, nD20 1.4952, is indicated. V, after repeated crystallization from EtOH, m. 55-5.2° and dissolves in H2O to 1.115%. When 10 g. V in 1 l. H2O containing 16.8 g. NaHCO3 is kept overnight and the mixture extracted 16 hrs. with ether, 1.6 g. VII, b17 110°, nD20 1.4750, is isolated. O2S(CH2CH2OH)2 (VIII) could not be prepared according to Gilman and Beaber (C.A. 19, 1850) from S(CH2CH2OH)2 (IX) and H2O2 in AcOH, as distillation of the reaction product gave thioxane sulfone (X), m. 129-30°, b1 130-40°. Following the method of Levin (C.A. 24, 4257), VIII, m. 54-5°, is obtained. Into a solution of 1.6 g. IX in 100 cc. H2O, O containing 2.5% O3 is passed at a rate of 200 cc./min. After 0.02 mol. O3 has been introduced, 95% OS(CH2CH2OH)2 (XI), m. 106-8°, is obtained. On further treatment of XI with O3, VIII, m. 36-43°, is formed. When IX is treated with III, 50% XI, m. 108°, is obtained. IX and IV give 76% XI, m. 106-8°. IX and NaOCl at pH 7 give 60% XI. On treatment of IX with Cl, neutralizing the reaction mixture with NaHCO3, evaporating to dryness in vacuo, and extracting with dioxane, X is obtained in good yield. For the detection of sulfonium salt [(HOCH2CH2)2S+CH2CH2]2S 2Cl– (XII) in H2O, a solution of 26 g. KI and 45 g. HgI2 in 20 cc. H2O is used. Addition of 0.02 cc. of this solution to 2 cc. of a solution of 10 g. XII in 1 l. H2O causes a white cloudiness after 5-10 sec. Oxidation of 20 g. XII with 5.7 g. 30% H2O2 gives [(HOCH2CH2)2S+CH2CH2]2SO 2Cl–, rosettes of needles, m. 63.5-5° (sealed tube). When XII is treated with III, 92% p-toluenesulfonamide, m. 133-4°, is formed. When 20 g. XII is treated with 17 g. 30% H2O2 and the mixture evaporated at room temperature, an oil is obtained which is dried in vacuo over P2O5. The oil does not crystallize and its aqueous solution gives a heavy oily precipitate (XIII) with KHgI3. Assuming the composition of XIII to be XIIIa, the yield of XIII is 97%. Attempts to prepare crystalline salts of XIII with picric acid, etc., failed. When 1 g. IX is shaken with 3,5-(O2N)2C6H3COCl with dropwise addition of 0.7 g. NaOH in 10 cc. H2O, bis[2-(3,5-dinitrobenzoxy)ethyl] sulfide, m. 161-2°, is formed; the corresponding sulfoxide, crystals from BuOH, m. 185-6°. Oxidation of 10 g. IX with an excess of 30% H2O2 according to G. and B. (cf. loc. cit.) and treating the resulting oil with Ac2O give bis(2-hydroxyethyl) sulfone diacetate (XIV), b2 170-5°, in addition to a small amount of X, m. 130°. XIV is readily saponified Distillation of washed Levinstein mustard gas (XV) in vacuo gives 69.5% almost pure I, b1 59°, nD20 1.5281, and 9% fairly pure (ClCH2CH2)2S2 (XVI) in addition to a small amount of dithiane, m. 110-11°. Distillation of 750 g. unwashed XV gives 432 g. I, b0.13 57°, nD20 1.5273-1.5278, of a yellow-brown color, in addition to some higher-boiling material. The decomposition of XV in H2O and the Cl demand of XVI, (ClCH2CH2)2S3, and (ClCH2CH2)2S5 in aqueous solution with III are studied and the results given in tables.
Journal of Organic Chemistry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, Formula: C4H8Cl2S2.
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https://en.wikipedia.org/wiki/Chloride,
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