IP Library Granted Patent US 11,046,642
Granted Patent B2
US 11,046,642 · App. 15/775,632 · Granted Jun 29, 2021

Systems and methods for producing nitriles

Inventors: Eric M. Karp (Denver, CO); Gregg Tyler Beckham (Golden, CO); Derek Richard Vardon (Lakewood, CO); Todd R. Eaton (Denver, CO)
Assignee: Alliance for Sustainable Energy, LLC
C07C253/22B01D3/009B01D15/08B01J21/063
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,046,642
App. No.
15/775,632
Granted
Jun 29, 2021
Kind
B2
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.

Claims (17)

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.

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded Mar 24, 2022
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 059497/0046 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 13, 2018
From: KARP, ERIC M.; BECKHAM, GREGG TYLER; VARDON, DEREK RICHARD; EATON, TODD R.
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 046629/0720 →