AI assisted cyclic carbonate monomer synthesis

Patent metadata

Field	Value
Publication number	US-12110280-B2
Application number	US-202117349998-A
Country	US
Kind code	B2
Filing date	Jun 17, 2021
Priority date	Jun 17, 2021
Publication date	Oct 8, 2024
Grant date	Oct 8, 2024

Abstract

A method for synthesizing cyclic carbonate monomers using carbon dioxide (CO2) is provided. The method also includes combining reagents to synthesize the cyclic carbonate monomer, the reagents including a substrate that is a 1,X-diol, where X is between 2 and 5, a base that is a tertiary amine, a promoter that is a multidentate, bis-tertiary amine base where nitrogens are separated by 2 to 4 carbon atoms, a solvent, and CO2.

First claim

What is claimed is:

1. A method for synthesizing a cyclic carbonate monomer using carbon dioxide (CO 2 ), the method comprising:
combining reagents to synthesize the cyclic carbonate monomer, the reagents including
a substrate that is a 1,X-diol, where X is between 2 and 5,
a first base that is a tertiary amine,
a promoter that is a second base that is a multidentate, bis-tertiary amine where nitrogens are separated by 2 to 4 carbon atoms, the second base being different than the first base,
a solvent,
at least one of TsCl and MsCl, and CO 2 ,

wherein the substrate includes a reactive functional group, and the method further comprises reacting the substrate with the first base to promote generation of a functionalized diol monomer that is selected from the group consisting of

2. The method of claim 1 , wherein the first base is at least one of triethylamine and diisopropylethyl amine.

3. The method of claim 1 , wherein the promoter is selected from the group consisting of

4. The method of claim 1 , wherein the solvent includes at least one selected from the group consisting of acetonitrile, ethyl acetate, tetrahydrofuran, dimethylformamide, and dimethyl sulfoxide.

5. The method of claim 1 , wherein an amount of the first base relative to the substrate is between 200-350 mol %.

6. The method of claim 1 , wherein an amount of the promoter relative to the substrate is between 10-100 mol %.

7. The method of claim 1 , wherein a concentration of the diol is between 0.15-0.25 M.

8. The method of claim 1 , wherein a reaction temperature is between −20-22° C.

9. The method of claim 1 , further comprising identifying a cyclic carbonate monomer to synthesize based on input from an artificial intelligence (AI) agent, wherein combining the reagents further includes using the input from the AI agent to influence an order of addition of the reagents to affect at least one of conversion, yield, and byproduct formation for the cyclic carbonate monomer synthesis.

10. A computer implemented method for training an AI agent for cyclic carbonate monomer synthesis from carbon dioxide, comprising:
pretraining a synthesis model with an AI agent based on historical monomer synthesis data;
selecting, based on the synthesis model, reagents to synthesize a cyclic carbonate monomer, the reagents including
a substrate that is a 1,X-diol, where X is between 2 and 5,
a first base that is a tertiary amine,
a promoter that is a second base that is a multidentate, bis-tertiary amine where nitrogens are separated by 2 to 4 carbon atoms, the second base being different than the first base,
a solvent,
at least one of TsCl and MsCl, and
CO 2 ;

identifying, based on the synthesis model, an experimental synthesis protocol;
selecting, based on the synthesis model, process operations for the cyclic carbonate monomer synthesis;
executing the experimental synthesis protocol to generate the cyclic carbonate monomer; and
collecting characterization data of results of the cyclic carbonate monomer synthesis for retraining of the synthesis model,
wherein the substrate includes a reactive functional group, and the method further comprises reacting the substrate with the first base to promote generation of a functionalized diol monomer that selected from the group consisting of

11. The method of claim 10 , further comprising retraining the synthesis model based on the characterization data.

12. The method of claim 10 , wherein the first base is at least one of triethylamine and diisopropylethyl amine.

13. The method of claim 10 , wherein the promoter is selected from the group consisting of

14. The method of claim 10 , wherein the solvent includes at least one selected from the group consisting of acetonitrile, ethyl acetate, tetrahydrofuran, dimethylformamide, and dimethyl sulfoxide.

15. The method of claim 10 , wherein executing the experimental synthesis protocol includes using input from the synthesis model to influence an order of addition of the reagents to affect at least one of conversion, yield, and byproduct formation for the cyclic carbonate monomer synthesis.

Assignees

• IBM

Inventors

• Park Nathaniel H
• Piunova Victoria A
• Zubarev Dmitry
• Erdmann Tim
• Arrechea Pedro
• Hedrick James L

Classifications

• C08G64/1641

  containing nitrogen · CPC title

• C07D273/02

  having two nitrogen atoms and only one oxygen atom · CPC title

• C08G64/0208

  saturated · CPC title

• C08G64/0241

  containing nitrogen · CPC title

• C08G64/30

  using carbonates · CPC title