In:
Rubber Chemistry and Technology, Rubber Division, ACS, Vol. 19, No. 1 ( 1946-03-01), p. 34-35
Abstract:
By analogy with hydrogen halides and hydrogen sulfide it is reasonable to expect thiocyanic acid to react with olefins, and it has been reported by Kharasch, May, and Mayo that it will add to isobutylene at room temperature to give a mixture of tert.-butyl thiocyanate and isothiocyanate. Under similar conditions in the present work, the only product that was obtained from cyclohexene and thiocyanic acid was a small quantity of an amorphous powder, probably mainly a perthiocyanic acid, formed by elimination of hydrogen cyanide from three molecules of thiocyanic acid. This tendency towards decomposition of the reagent prevented the use of elevated temperatures, and when methyl thiocyanate (a potential source of SCN and Me radicals by thermal decomposition) was heated at 170° with 1-methylcyclohexene and a little benzoyl peroxide (as catalyst), it underwent but slight reaction, the drop or two of product giving analytical values which suggested that it might be an impure adduct. Attempts to catalyze the addition of thiocyanic acid to, rubber included the use of ultraviolet irradiation, and of aluminum chloride or ferric chloride as catalyst. The most successful of these attempts was with ultraviolet light, but even then the product contained only 1.95% of sulfur, which represented 6% addition to the double bonds of rubber.
Type of Medium:
Online Resource
ISSN:
1943-4804
,
0035-9475
Language:
English
Publisher:
Rubber Division, ACS
Publication Date:
1946
Permalink
