Systems and methods for producing nitriles

Patent metadata

Field	Value
Publication number	US-12286390-B2
Application number	US-202117244172-A
Country	US
Kind code	B2
Filing date	Apr 29, 2021
Priority date	Feb 19, 2016
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

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.

First claim

What is claimed is:

1. A method 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 acrylonitrile, wherein:
the 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 lactic acid or 3-hydroxypropionic acid.

3. The method of claim 1 , wherein the molecule comprises at least one of ethyl lactate or ethyl 3-hydroxypropanoate.

4. 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 Nb 2 O 5 .

5. A method comprising:
esterifying a carboxylic acid with an alcohol to produce an ester and water; and
nitrilating the ester to produce acrylonitrile, the alcohol, and water, wherein:
the nitrilating is performed by reacting the ester with ammonia over a metal oxide catalyst excluding TiO 2 .

6. The method of claim 5 , wherein the nitrilating is performed with both the ester and the ammonia in a gas phase.

7. The method of claim 5 , wherein the esterifying is performed by contacting the carboxylic acid and the alcohol with a mineral acid.

8. The method of claim 5 , wherein the nitrilating is performed at a molar ratio of the ester to the ammonia between 1:1 and 10:1.

9. The method of claim 5 , further comprising,
after the esterifying, dehydrating the ester to produce an unsaturated ester.

10. The method of claim 9 , wherein the dehydrating and the nitrilating are performed at substantially the same time.

11. The method of claim 5 , wherein the metal oxide catalyst comprises at least one of AlPO 4 , SiO 2 , Al 2 O 3 , NbO 2 , or Nb 2 O 5 .

Assignees

• Alliance Sustainable Energy

Inventors

• Karp Eric M
• Beckham Gregg Tyler
• Vardon Derek Richard
• Eaton Todd R

Classifications

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title

• B01D15/08

  Selective adsorption, e.g. chromatography · CPC title

• B01D3/009

  in combination with chemical reactions · CPC title

• B01J27/16

  containing oxygen {, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr} · CPC title

• B01J23/20

  Vanadium, niobium or tantalum · CPC title