Preparation And Characterization Of The N-alkoxyl Methacrylamide Compounds

In this paper, four kinds of different N-(alkoxymethyl)acrylamide and N-(alkoxymethyl)methacrylamide compounds were synthesized by "one pot" method, using acrylamide (or methacrylamide), paraformaldehyde, and different alcohols as the starting materials. They were N-(n-butoxymethyl)acryamide, N-(i-butoxymethyl)acryamide, N-(benzyloxymethyl)acryamide and N-(methoxymethyl)methacryamide. The influence of the method of getting rid of water on the yield of products was researched, and a new method(blowing air to the reactor) to take out the water was selected. Also different inhibitors were used to prevent polymerizing and hydroquinone monomethyl ether and anhydrous CuSO₄ was selected which was the best one. Furthermore the influence factors of processes such as the reaction time and the ratio of alcohols and acrylamide(or methacrylamide) were discussed, and the optimal reaction conditions were obtained by experiments. The optimal reaction conditions and best yields were: reaction time 5h, n(n-butanol): n(acrylamide)= 4:1, N-(n-butoxymethyl)acryamide 94.8%; reaction time 5h, n(i-butanol): n(acrylamide)=:4:1, N-(i-butoxymethyl)acryamide 74.3%; reaction time 6h, n(benzylol): n(acrylamide)= 5:1, N-(benzyloxymethyl)acryamide 57.5%; reaction time 5h, n(methanol): n(methacrylamide)= 7:1, N-(methoxymethyl)methacryamide 91.8% .In order to get high-grade products, HPLC was used to analyse the crude products, and column chromatography was used to purify them, finally products which have single peak in HPLC were obtained. Then the products were characterized by IR,¹HNMR and MS technics.