Epichlorohydrin → Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) ester

Participants

Reaction Conditions

Reaction Steps

4163 g of epichlorhydrin, 693 g of hexahydrophthalic acid anhydride and 105 g of distilled water were weighed into a 6-liter four-necked flask, equipped with a reflux condenser, gas inlet pipe and dropping funnel, and heated with stirring to 90°C. A gentle stream of nitrogen was passed over the reaction mixture. After 2.5 hours, 15 g of K2HPO4 (secondary o-potassium phosphate) were added and the mixture was kept for about another 4 hours at 90°C. Thereafter, the product had an acid number of 0. It was cooled to approximately 20°C, followed by the dropwise addition over a period of 1 to 2 hours of 882 g of 45% by weight of NaOH. The sump temperature should not exceed 30°C during the addition. A water jet vacuum was then applied, and water together with excess epichlorhydrin (substantially quantitative) was distilled off. After the sump temperature had reached 90°C and the vacuum settled at approximately 20 mm, the product was taken up with 1000 g of toluene and washed with water until salt-free.

Provenance & Evidence