Systems and methods for producing nitriles

Abstract

An aspect of the present disclosure is a method that includes a first reacting a molecule from at least one of a carboxylic acid, an ester of a carboxylic acid, and/or an anhydride with ammonia to form a nitrile, where the first reacting is catalyzed using an acid catalyst. In some embodiments of the present disclosure, the molecule may include at least one of acetic acid, lactic acid, and/or 3-hydroxyproprionic acid (3-HPA). In some embodiments of the present disclosure, the molecule may include at least one of methyl acetate, ethyl lactate, and/or ethyl 3-hydroxypropanoate (ethyl 3-HP). In some embodiments of the present disclosure, the anhydride may be acetic anhydride.

1 - 24 . (canceled) 
     
     
         25 . A nitrile produced by a process comprising:
 reacting a molecule comprising at least one of a carboxylic acid, an ester of a carboxylic acid, or an anhydride with ammonia to form the nitrile, wherein:   the reacting is catalyzed using an acid catalyst, and   the molecule is at least partially bioderived.   
     
     
         26 . The nitrile of  claim 25 , wherein the molecule comprises at least one of acetic acid, lactic acid, or 3-hydroxyproprionic acid. 
     
     
         27 . The nitrile of  claim 25 , wherein the molecule comprises at least one of methyl acetate, ethyl lactate, or ethyl 3-hydroxypropanoate. 
     
     
         28 . The nitrile of  claim 25 , wherein the anhydride is acetic anhydride. 
     
     
         29 . The nitrile of  claim 25 , wherein:
 the nitrile comprises   
       
         
           
           
               
               
           
         
       
       and
 R 1  comprises at least one of an alkyl group, an alkenyl group, an alkynyl group, a phenyl group, a carbonyl group, an aldehyde group, a carbonate group, a carboxylic acid group, or an ester group. 
 
     
     
         30 . The nitrile of  claim 29 , wherein R 1  is a vinyl group and the nitrile is acrylonitrile. 
     
     
         31 . The nitrile of  claim 29 , wherein R 1  is a methyl group and the nitrile is acetonitrile. 
     
     
         32 . The nitrile of  claim 25 , wherein:
 the molecule is the ester of a carboxylic acid,   prior to the first reacting, a second reacting of the carboxylic acid with an alcohol to produce the molecule and water, and   the second reacting regenerates the alcohol.   
     
     
         33 . The nitrile of  claim 25 , wherein the nitrile is acrylonitrile. 
     
     
         35 . The nitrile of  claim 25 , wherein the nitrile is acetonitrile. 
     
     
         36 . The nitrile of  claim 25 , wherein the acid catalyst comprises TiO 2 .