Hydrolysis of amides to amines

Abstract

Abstract A PROCESS FOR THE HYDROLYSIS OF AMIDES TO AMINES USING LARGE AMOUNTS OF A LOWER ALIPHATIC PRIMARY ALCOHOL AS A MUTUAL SOLVENT TO HOLD BOTH THE CAUSTIC AND THE AMIDE IN WATER SOLUTION, SO AS TO OBTAIN AN HOMOGENEOUS SYSTEM. HERETOFORE AMIDES HAVE BEEN HYDROLIZED TO AMINES WITH AQUEOUS CAUSTIC. SUCH PROCESSES ARE ECONOMICALLY UNATTRACTIVE AS THEY ARE SLOW AND REQUIRE LONG REACTION TIMES. U.S. 2,587,043 SHOWS THAT THE REACTION CAN BE SPEEDED UP USING AN ORGANIC COSOLVENT AND INCREASING THE REACTION TEMPERATURES. THAT REACTION STILL GENERALLY REQUIRES SEVERAL HOURS TO REACH COMPLETION AND THE HYDROLIZING MEDIUM MUST BE REPLACED. FURTHER, THE CRUDE PRODUCT OBTAINED IS GENERALLY DARK IN COLOR AND MUST BE PURIFIED BY DISTILLATION. U.S. 2,281,879 SHOWS A METHOD OF PREPARING AN ORGANIC NITROGEN BASE BY REACTING AN INORGANIC SALT OF THE BASE WITH AN ALKALI-FORMING METAL HYDROXIDE IN AN ANHYDROUS WATER-SOLUBLE ALCOHOL AND REMOVING THE INSOLUBLE ALKALI METAL SALT THUS FORMED. ALTHOUGH THIS PATENT ALLEGES THAT VARIOUS AMINES MAY BE PREPARED THEREBY, NO SPECIFIC EXAMPLES OF SUCH PREPARATION ARE GIVEN. FURTHER, THE PRODUCT IS AN ALKALI METAL SALT, AND ADDITIONAL PURIFICATION WOULD BE NECESSARY TO DERIVE THE AMINE. ALSO, THE PROCESS IS TIME CONSUMING, AND THE MEDIUM MUST BE KEPT SUBSTANTIALLY ANHYDROUS.

Inventors

• 👤 Ralph H Potts
• 👤 Joseph S Stalioraitis

Bibliographic Details