N,N'-Diphenyl-P-Phenylenediamine → Sulfoethyl methacrylate

Participants

Reaction Steps

To the reactor containing the concentrated isethionic acid solution of Example 1 is added 95.2 Kg. (209.5 lbs.) of MAA to achieve a MAA/ITA molar ratio of about 5:1 along with 14 grams of N,N' diphenyl-p-phenylene diamine and 140 grams of monomethyl ether hydroquinone, both serving as polymerization inhibitors. The mixture is heated for about 6 hours under a vacuum of about 90 mm. Hg. at a temperature of about 80° C. to form sulfoethyl methacrylate according to the reaction: ##STR9## with water of reaction and residual water from the oxidation reaction being continuously removed by azeotropic distillation of a water/MAA mixture under vacuum. At the completion of the reaction, as shown by the cessation of the azeotropic distillation and an increase in the pot temperature, any remaining MAA is removed by vacuum distillation at a pressure of about 10 mm. Hg. The resultant product is sulfoethyl methacrylate having a purity of about 90-95% with methacrylic acid as the major impurity.

Provenance & Evidence