Dithioadipic acid

Bulk Polymerization of Dithioadipic Acid with Biallyl (1,5-Hexadiene). 48... 

To a quartz test tube were added equimolar amounts of dithioadipic acid and biallyl. The tube was stoppered, agitated, and placed under a UV lamp for several hours to give a solid product. The product was isolated by dissolution in chloroform and reprecipitation in methanol. The polymer was filtered, washed with fresh methanol, and dried under reduced pressure to give a 6.3% yield of polymer with inherent viscosity (in chloroform at 25 C) of 0.22... 

In a 100-ml quartz flask are placed 1.76 gm of crude dithioadipic acid, 0.82 gm of biallyl, and approximately 40 ml of purified cyclohexane. All of the acid did not dissolve in the cyclohexane. The flask was stoppered with a cork and placed under the UV lamp (at a distance of about 6 in fi-om a polychromatic source of UV light, Hanovia Type 7420). After 3 hr of exposure, a solid began to form on the wall of the flask. The flask was removed after a total exposure time of 15 hr. When the solid was filtered and dried, it weighed 0.69 gm, a yield of 26.8%. The solid was dissolved in chloroform, the solution was filtered, and the polymer reprecipitated with methanol. The melting point was 91-95°C, and the inherent viscosity 0.13. 

In a 50-ml quartz flask are placed 3.08 gm of crude dithioadipic acid, 1.43 gm of biallyl and 20 ml of dry, thiophene-free benzene. After an exposure time of approximately 18 hr under the UV lamp, a solid weighing 1.74 gm is filtered from the solution. An additional 1.51 gm is obtained by diluting the filtrate with methanol. The total weight of solid polymer is 2.50 gm, a yield of 72%. Both... 

Fig. 1 (A) Polymer from adipoyl chloride and hexamethylenedithiol (B) polymer from biallyl and dithioadipic acid. [Reprinted from C. S. Marvel and A. Kotch, J. Am. Chem. Soc. 73, 1100 (1951). Copyright by the American Chemical Society. Reproduced by permission of the copyright owner.]...

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