SYSTEMS AND METHODS FOR PRODUCING NITRILES
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 . A method comprising:
a first reacting a molecule comprising at least one of a carboxylic acid, an ester of a carboxylic acid, or an anhydride with ammonia to form a nitrile, wherein:
the first reacting is catalyzed using a metal oxide catalyst excluding TiO 2 .
2 . The method of claim 1 , wherein the molecule comprises at least one of acetic acid, lactic acid, or 3-hydroxyproprionic acid.
3 . The method of claim 1 , wherein the molecule comprises at least one of methyl acetate, ethyl lactate, or ethyl 3-hydroxypropanoate.
4 . The method of claim 1 , wherein the anhydride is acetic anhydride.
5 . The method of claim 1 , 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.
6 . The method of claim 5 , wherein R 1 is a vinyl group and the nitrile is acrylonitrile.
7 . The method of claim 5 , wherein R 1 is a methyl group and the nitrile is acetonitrile.
8 . The method of claim 1 , 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.
9 . The method of claim 1 , wherein the metal oxide catalyst comprises at least one of AlPO 4 , SiO 2 , Al 2 O 3 , NbO 2 , or NbO 5 .
10 . A method comprising:
esterifying a carboxylic acid with an alcohol to produce an ester and water; and
nitrilating the ester to produce a nitrile, the alcohol, and water, wherein:
the nitrilating is performed by reacting the ester with ammonia over a metal oxide catalyst excluding TiO 2 .
11 . The method of claim 10 , wherein the nitrilating is performed with both the ester and the ammonia in the gas phase.
12 . The method of claim 10 , wherein the esterifying is performed by contacting the carboxylic acid and the alcohol with a mineral acid.
13 . The method of claim 10 , wherein the nitrilating is performed at an ester to ammonia molar ratio between 1:1 and 10:1.
14 . The method of claim 10 , further comprising:
after the esterifying, dehydrating a hydroxylated ester to produce an unsaturated ester, wherein:
the carboxylic acid is hydroxylated,
the ester is the hydroxylated ester, and
the nitrile comprises an alkenyl group.
15 . The method of claim 14 , wherein the dehydrating and the nitrilating are performed at substantially the same time.
16 . The method of claim 10 , wherein the metal oxide catalyst comprises at least one of AlPO 4 , SiO 2 , Al 2 O 3 , NbO 2 , or NbO 5 .
17 . 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 a metal oxide catalyst, and
the molecule is at least partially bioderived as determined by ASTM-D6866.
18 . The nitrile of claim 17 . wherein the metal oxide catalyst comprises at least one of TiO 2 , AlPO 4 , SiO 2 , Al 2 O 3 , NbO 2 , or NbO 5 .