Chloroethyl Chlorosulfonate and 2-Chloroethoxy trichlorosilane

Submitted by Donald R. Martin, John F. Suttle,f and Harold Simmons Booth J 

One hundred sixty milliliters of sulfuryl chloride (2.0 mols) is placed in a 500-ml. three-necked flask. The flask 

The reactor is placed in an ice bath, and its contents are stirred vigorously while the ethylene chlorohydrin is added dropwise at a rate of approximately 2 ml./min. (hood). The reaction mixture is maintained at 0° until the addition is completed. Stirring is continued for 45 minutes after all the ethylene chlorohydrin has been added, while the reaction mixture is allowed to warm slowly to room temperature. 

The apparatus originally attached to the three necks of the flask is quickly replaced with two glass stoppers and a Vigreux fractionating column adapted for vacuum distillation. The pressure within the distillation apparatus is cautiously reduced to about 25 mm. After the dissolved hydrogen chloride and other volatile compounds cease to be evolved, the reaction products are heated slowly to about 100°. All the distillate which is removed below 100° is discarded. The clear product is collected between 100 and 101°. The yield is 196 ml. (85%). Anal. Calcd. for C1C2-H4OSO2CI Cl, 39.61 S, 17.91. Found Cl, 38.57 S, 17.02. 

The procedure for the preparation of (2-chloroethoxy)-trichlorosilane is the same as that given in part A above, with a few modifications. The reaction is carried out in a 1-1. flask rather than in the 500-ml. flask described above the rest of the apparatus is the same as in part A. 

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