Chloroacetaldehyde → 2,4,6-tris(chloromethyl)-1,3,5-trithiane

One typical example of the method for producing an episulfide compound of the invention, 2,4,6-tris(epithiomethylthiomethyl)-1,3,5-trithiane (a compound of the general formula (1) wherein n is 0), is shown as Scheme 1 mentioned below. An aqueous 40 wt. % chloroacetaldehyde solution is dissolved in 70 wt. % sulfuric acid, and hydrogen sulfide is introduced thereinto at −20 to 40° C. for 2 to 100 hours to give 2,4,6-tris(chloromethyl)-1,3,5-trithiane. Alternatives to sulfuric acid as the acidic solvent include any of 60/40 (v/v) 95 wt. % sulfuric acid-acetic acid, or hydrogen sulfide-saturated acetic acid, ether, or 95 wt. % ethanol. To the resulting methanol solution of the thus-formed chlorine compound is added potassium hydroxide with which the chlorine compound is processed at −10 to 40° C. for 0.5 to 10 hours for removal of hydrogen chloride from it to give 2,4,6-trimethylene-1,3,5-trithiane. This is thermally reacted with 3-mercaptopropene sulfide at 0 to 100° C. for 6 to 100 hours in the presence of a radical generator (described below), to obtain the intended product, 2,4,6-tris(epithiomethylthiomethyl)-1,3,5-trithiane.

1. additionis introduced

ORD record

ord-5a393e29f0c84327889c39e60e86f9b3

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696540B2