Chloroethyl Mercaptan

A mixture of /3-hydroxyethyl mercaptan and 3 times its volume of concentrated hydrochloric acid is heated to boiling under a reflux condenser. Reflux temperature is maintained for 5 minutes. The precipitated oil is separated quickly, washed once with water, and dried over sodium sulfate. The crude /3-chloroethyl mercaptan obtained in this manner amounts to a 90% yield. Distillation of the dried crude product gives a 30-45% yield of pure mercaptan, boiling at 125-126°. Considerable polymerization occurs during distillation. 

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Chloroethyl mercaptan should be handled with extreme care, since it has a powerful vesicant action. 

CjHsClOjS, Ethanesulfonyl chloride.. 141 CjHsClS, -Chloroethyl mercaptan... 78... 

A mixture of monoisopropyl methylphosphonate, l,l,2-trifluoro-2-chloroethyl mercaptan, and abs. benzene stirred 3 hrs. at room temp., calcined KF added to the soln. to remove HF, and allowed to stand overnight fluorochloro-thioacetyl isopropyl methylphosphonate. Y 85%. F. e. s. A. V. Fokin, Y. N. Studnev, and A. A. Skladnev, 33, 3366 (1963) G. A. 60, 4176d. 

This type is produced from di-2-chloroethyl formal with a small percentage of 1,2,3-trichloropropane to provide a branch point for improving the cure state obtainable, and hence compression set. A much lower molecular weight polymer, ca. 80,000, is produced with predominantly mercaptan (SH) end groups. The sulphur content of the resultant polymer is 37%. 

Polysulfide rubber manufacturing processes are described in more detail by Bertozzi [26]. Briefly, the processes involve preparation of sodium polysulfide (S + NaOH), and reaction with bis(2-chloroethyl)formal along with 2% of a branching agent such as 1,2,3-trichloropropane to give a mercaptan terminated polymer of MW approximately 80,000 similar to that described in Preparation 2-2, Method A. 

Magnesium acetylacetonate Manganese acetylacetonate N-Nitrosodiethylamine N-Nitrosodimethylamine Octyl acrylate, t-Octyl mercaptan Oleyl palmitamide 3-(n-Pentadecyl) phenol Phenol a-Pinene Tetrabutyltin Titanium acetylacetonate 0,0,0-Tri butyl phosphorothioate 1,3,5-Trichlorobenzene Triisooctyl phosphite 0,0,0-Triisooctyl phosphorothioate Triisopropyl phosphite 3,5,5-Trimethylhexan-l-ol Tripropylene Tris 2-chloroethyl, phosphite... 

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