Process for the preparation of diacetone acrylamide
AssigneeAmerican Cyanamid Company
InventorHenry Richmond
Life of this patent
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Abstract
A process is disclosed whereby acrylonitrile and diacetone alcohol are reacted in at least 93% sulfuric acid to form a novel intermediate reaction product which is recovered as a crystalline solid, washed with an organic solvent to remove colored oily impurities along with sulfuric acid, and hydrolyzed to produce diacetone acrylamide, a reactive monomer useful for preparing polymeric components of photographic films and adhesives. The intermediate reaction product is identified as 5,6-dihydro-6-hydroxy-4,4,6-trimethyl-2-vinyl-1,3(4H)-oxazine sulfate (1:1).
Claims5
A process for preparing N-(1,1-dimethyl-3-oxobutyl)acrylamide comprising:
- reacting acrylonitrile and 4-hydroxy-4-methyl-2-pentanone in the presence of at least 93% sulfuric acid to form a reaction mixture;
- contacting said reaction mixture with water and with a suitable water-immiscible organic solvent to form a liquid two-phase mixture consisting of an aqueous phase and an organic phase;
- neutralizing or alkalizing the aqueous phase with an alkalizing agent;
- separating the neutralized or alkalized aqueous phase;
- and
- recovering N-(1,1-dimethyl-3-oxobutyl)acrylamide from the organic phase,
- the improvement comprising, between the reaction step and the contacting step:
- cooling the reaction mixture to about 15.degree. C. and adding a suitable organic solvent thereto, while maintaining the temperature at about 15.degree.-20.degree. C., to precipitate a crystalline intermediate reaction product from said reaction mixture having the formula ##STR5## and washing said intermediate reaction product with a suitable organic solvent to remove oily impurities and sulfuric acid therefrom.
Dependencies are inferred from the claim text.