Propylene Oxide → 1,3-Bis(2-hydroxypropyl)-5,5-dimethyl-2,4-imidazolidinedione

Participants

Reaction Conditions

Reaction Steps

A mixture of 217 g of 5,5-dimethylhydantoin (1.695 mols) 3.61 g of lithium chloride (5 mol percent) and 560 ml of dimethylformamide is stirred at 50° C. 230 g of propene oxide (propylene oxide) (3.955 mols) are added dropwise to the clear solution over the course of 4 hours, 50°-55° C. The reaction is slightly exothermic. After the dropwise addition, the temperature is slowly raised to 90° C. After 5 hours at 90° C. the dimethylformamide is distilled off in a waterpump vacuum and thereafter the product is dried to constant weight at 100° C. and 0.1 mm Hg. 415 g of a pale yellow highly viscous oil (100% of theory) are obtained. The crude product is distilled at 0.1 to 0.2 mm Hg and 170°-172° C.: 386.0 g yield of pure material (93.5% of theory). On cooling the 1,3-di(β-hydroxy-n-propyl)- 5,5-dimethylhydantoin solidifies to give white crystals of melting point 65°-67° C. The elementary analysis shows 11.81% N (calculated, 11.47% N), and the molecular weight was determined by vapour pressure osmometry to be 247 (theory 244). The infrared spectrum shows the absence of N-H-amide frequencies at 3.1 to 3.2μ and the presence of C--OH frequencies at 2.90μ.

Provenance & Evidence