Systems and methods for producing nitriles

Patent metadata

Field	Value
Publication number	US-11046642-B2
Application number	US-201715775632-A
Country	US
Kind code	B2
Filing date	Feb 17, 2017
Priority date	Feb 19, 2016
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

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:
a first reacting of a molecule consisting of at least one of lactic acid, 3-hydroxypropionic acid, ethyl lactate, ethyl 3-hydroxypropanoate, or acetic anhydride with ammonia to form a nitrile, wherein:
the first reacting is catalyzed using a catalyst comprising TiO 2 .

2. The method of claim 1 , further comprising:
prior to the first reacting, an initial reacting of at least one of lactic acid or 3-hydroxypropionic acid with an alcohol to produce at least one of ethyl lactate or ethyl 3-hydroxypropanoate and water, wherein:
the first reacting regenerates the alcohol.

3. The method of claim 1 , wherein the first reacting is performed with both the molecule and the ammonia in a gas phase.

4. The method of claim 2 , wherein the initial reacting is performed by contacting the at least one of lactic acid or 3-hydroxypropionic acid and the alcohol with a mineral acid.

5. The method of claim 1 , wherein the first reacting is performed at a molar ratio of the molecule to the ammonia between 1:1 and 10:1.

6. A method comprising:
reacting an anhydride with ammonia to form a nitrile, wherein:
the reacting is catalyzed using a catalyst comprising TiO 2 ,
the nitrile consists of

and
R 1 consists of 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.

7. The method of claim 6 , wherein the nitrile is acrylonitrile.

8. The method of claim 6 , wherein the nitrile is acetonitrile.

Assignees

• Alliance Sustainable Energy

Inventors

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

Classifications

• 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

• B01J21/08

  Silica · CPC title

• B01J21/04

  Alumina · CPC title

• C07C253/22 Primary

  by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups · CPC title